Sensory Properties of Volatile Maillard Reaction Products and Related Compounds

12
Sensory Properties of Volatile Maillard Reaction

Products and Related Compounds
A Literature Review
SUSAN FORS
SIK-The Swedish Food Institute, Box 5401, S-402 29 Göteborg, Sweden
Downloaded by EMORY UNIV on June 19, 2014 | http://pubs.acs.org
Publication Date: April 29, 1983 | doi: 10.1021/bk-1983-0215.ch012
V o l a t i l e c o m p o u n d s f o r m e d by n o n - e n z y m a t i c b r o w n i n g
r e a c t i o n s are of g r e a t i m p o r t a n c e f o r the sensory p r o p e r -
t i e s of h e a t - t r e a t e d f o o d s .
L i t e r a t u r e i n f o r m a t i o n about the sensory p r o p e r t i e s
f o r n e a r l y 450 M a i l l a r d r e a c t i o n p r o d u c t s has b e e n c o m -
p i l e d in a s u r v e y . It i n c l u d e s q u a l i t a t i v e a r o m a and f l a v o r
d e s c r i p t i o n s as w e l l as sensory t h r e s h o l d values in
d i f f e r e n t m e d i a f o r the c o m p o u n d s , c l a s s i f i e d a c c o r d i n g
to t h e i r c h e m i c a l s t r u c t u r e .
In r e c e n t d e c a d e s a l a r g e n u m b e r of papers and r e v i e w s about r e s e a r c h on

f o o d a r o m a and f l a v o r have been p u b l i s h e d , and this r e s e a r c h f i e l d
c o n t i n u e s to e x p a n d . T h e e x p a n s i o n is r e f l e c t e d in the r a p i d i n c r e a s e in
the n u m b e r of v o l a t i l e c o m p o u n d s i d e n t i f i e d in v a r i o u s f o o d s .
N o n - e n z y m a t i c b r o w n i n g r e a c t i o n s play a c e n t r a l role in the
f o r m a t i o n of f o o d a r o m a and f l a v o r , e s p e c i a l l y in h e a t - t r e a t e d f o o d s . T h e
purpose of this work is to present sensory d a t a , s c a t t e r e d in the
l i t e r a t u r e , f o r v o l a t i l e n o n - e n z y m a t i c browning r e a c t i o n p r o d u c t s a n d
r e l a t e d c o m p o u n d s . T h e c o m p i l a t i o n has no p r e t e n s i o n s to c o m p l e t e n e s s
and only a s m a l l p a r t of the e x t e n s i v e p a t e n t l i t e r a t u r e has been c o v e r e d .
A n y h o w , it is f e l t t h a t a c o m p i l a t i o n of this k i n d , w h i c h has not b e e n
a v a i l a b l e h i t h e r t o , w o u l d be u s e f u l to w o r k e r s in the f i e l d .
T h e m a j o r i t y of the c o m p o u n d s in this c o m p i l a t i o n are M a i l l a r d
r e a c t i o n p r o d u c t s and l i k e w i s e r e c o g n i z e d as i m p o r t a n t a r o m a and f l a v o r
s u b s t a n c e s in f o o d s .
T h e sensory p r o p e r t i e s , p r e s e n t e d in t a b u l a r f o r m , i n c l u d e the
following
• T h e q u a l i t a t i v e odor a n d / o r f l a v o r d e s c r i p t i o n of the c o m p o u n d .
T h e c o n c e n t r a t i o n m a y h a v e a s t r o n g i n f l u e n c e on the odor or
f l a v o r q u a l i t y ; one c o m p o u n d s t r o n g l y d i l u t e d w i l l not h a v e the
sensory c h a r a c t e r i s t i c s of the s a m e c o m p o u n d in a m o r e c o n c e n -
trated f o r m .
0097-6156/83/0215-0185$21.20/0
© 1983 American Chemical Society
In The Maillard Reaction in Foods and Nutrition; Waller, G., et al.;

ACS Symposium Series; American Chemical Society: Washington, DC, 1983.
186 MAILLARD REACTIONS
• T h e t h r e s h o l d values d e t e r m i n e d in d i f f e r e n t liquids ( w a t e r , o i l ,
o r a n g e j u i c e , b e e r , sugar s o l u t i o n e t c . ) or less f r e q u e n t l y , in a i r . T h e
m a j o r i t y of the t h r e s h o l d values g i v e n are d e t e c t i o n r a t h e r than
r e c o g n i t i o n t h r e s h o l d s , although in m a n y cases the type of t h r e s h o l d
d e t e r m i n e d is not i n d i c a t e d in the o r i g i n a l p a p e r .
The t h r e s h o l d values g i v e n by d i f f e r e n t i n v e s t i g a t o r s vary c o n s i d e r -

ably depending on the c h o i c e of solvent(s), the m e t h o d used f o r the
d e t e r m i n a t i o n , and the p u r i t y of the c o m p o u n d . T h e r e f o r e , the s a m e
a r o m a or f l a v o r c o m p o u n d may have as many t h r e s h o l d values as t h e r e are
i n v e s t i g a t o r s . C a r e must be e x e r c i s e d when t h r e s h o l d values f r o m the
l i t e r a t u r e are u s e d , and the m e n t i o n e d s o u r c e s of d i s c r e p a n c i e s must
a l w a y s be borne in m i n d . O d o r t h r e s h o l d v a l u e s , e x p r e s s e d as c o n c e n t r a t i o n
in the gaseous p h a s e , have the d i s t i n c t a d v a n t a g e of being independent of
the s o l v e n t used.
M a j o r c l a s s e s of f l a v o r c o m p o u n d s in g e n e r a l
The v o l a t i l e c o m p o u n d s f o r m e d by the M a i l l a r d r e a c t i o n are only one group

of f l a v o r c o m p o u n d s in f o o d s . S c h u t t e (1) presents a b r i e f s u m m a r y of the
m a j o r classes and t h e i r modes of f o r m a t i o n f r o m p r e c u r s o r s . S o m e of t h e m
can be f o r m e d by d i f f e r e n t p a t h w a y s . A n e x a m p l e is the f u r a n s , w h i c h c a n
be f o r m e d by n o n - e n z y m a t i c b r o w n i n g r e a c t i o n but also by b i o t r a n s -
formation.
C l a s s i f i c a t i o n of M a i l l a r d r e a c t i o n p r o d u c t s
S i n c e this c o m p i l a t i o n c o n c e r n s v o l a t i l e M a i l l a r d r e a c t i o n p r o d u c t s , a b r i e f
p r e s e n t a t i o n o f d i f f e r e n t t y p e s of s u b s t a n c e s in this group is j u s t i f i e d . T h e
c l a s s i f i c a t i o n s y s t e m g i v e n by N u r s t e n (1980-1981) (2) has b e e n a v a l u a b l e
t o o l . T h e v o l a t i l e s may be c l a s s i f i e d into t h r e e groups
1) ' S i m p l e ' sugar d e h y d r a t i o n / f r a g m e n t a t i o n p r o d u c t s :

Furans
Pyrones
Cyclopentenes
Carbonyl compounds
Acids
2) 'Simple' amino a c i d degradation products:
Aldehydes
Sulfur compounds
3) V o l a t i l e s p r o d u c e d by f u r t h e r i n t e r a c t i o n s :
Pyrroles
Pyridines
Imidazoles
Pyrazines
Oxazoles
Thiazoles
C o m p o u n d s ex aldol c o n d e n s a t i o n s

12. FORS Sensory Properties: Literature Review 187
A s seen a b o v e , the v o l a t i l e M a i l l a r d c o m p o u n d s h a v e v e r y d i v e r s e
c h e m i c a l s t r u c t u r e s . T h e m o s t i m p o r t a n t groups w i l l now be p r e s e n t e d one
by o n e .
T h e i m p o r t a n c e of h e t e r o c y c l i c c o m p o u n d s
A m o n g the known c o n s t i t u e n t s of f o o d a r o m a , h e t e r o c y c l i c c o m p o u n d s
deserve particular attention. T h e s e are f o r m e d in l a r g e n u m b e r s during
p r e p a r a t i o n of the f o o d , e . g . , by c o o k i n g , baking or r o a s t i n g . O w i n g to
t h e i r c h a r a c t e r i s t i c o d o r s , h e t e r o c y c l e s c o n t r i b u t e s i g n i f i c a n t l y to the
f l a v o r of p r o c e s s e d f o o d s . T h e s e h e t e r o c y c l i c s do not a l w a y s a r i s e by
n o n - e n z y m a t i c M a i l l a r d r e a c t i o n s ; e n z y m a t i c (including m i c r o b i o l o g i c a l )
p r o c e s s e s are also i m p o r t a n t r o u t e s of f o r m a t i o n . D e g r a d a t i o n by p y r o l y s i s
of c e r t a i n c o m p o u n d s (sugars, a m i n o a c i d s , t h i a m i n , t r i g o n e l l i n e , e t c . ) , also
r e l e a s e s a r o m a c o m p o u n d s (3).
A m o n g the h e t e r o c y c l i c s t h e r e is one group w h i c h w i l l be t h o r o u g h l y

e x a m i n e d : the p y r a z i n e s . T h e c o m p o u n d s b e l o n g i n g to this f a m i l y play a
v e r y i m p o r t a n t r o l e as c o n t r i b u t o r s of d e s i r a b l e f o o d f l a v o r p r o p e r t i e s .
S t r u c t u r a l l y , p y r a z i n e s are h e t e r o c y c l i c n i t r o g e n c o m p o u n d s a n d t h e i r
f o r m a t i o n is a quite c o m p l i c a t e d p r o c e s s . M a g a and S i z e r (4) p r e s e n t a
s u m m a r y of these f o r m a t i o n p a t h w a y s .
N o n - h e t e r o c y c l i c compounds
T h e r e are other c o m p o u n d s than h e t e r o c y c l i c s that also d e s e r v e a t t e n t i o n :

S u l f u r c o m p o u n d s and other c l a s s e s of a l i p h a t i c s .
S c h u t t e (1) lists s u b s t a n c e s c o n t a i n i n g s u l f u r and t h e i r m o d e of
f o r m a t i o n . ( N o t e that t h i a z o l e s , t h i o p h e n e s , and o t h e r c y c l i c c o m p o u n d s
c a n be c l a s s i f i e d also in the p r e c e d i n g g r o u p , the h e t e r o c y c l i c s ) .
O t h e r groups of a l i p h a t i c substances ( a l d e h y d e s , k e t o n e s , e s t e r s , e t c . )
m a y also c o n t r i b u t e to a g r e e a b l e f o o d s e n s a t i o n s .
A r o m a and f l a v o r p r o p e r t i e s of i m p o r t a n t s u b s t a n c e groups
T h i s c h a p t e r g i v e s b r i e f g e n e r a l d e s c r i p t i o n s of the sensory p r o p e r t i e s of
the most i m p o r t a n t s u b s t a n c e groups. It is i n t e n d e d as an i n t r o d u c t i o n to
the m o r e d e t a i l e d sensory i n f o r m a t i o n in the f o l l o w i n g t a b l e s .
P y r a n o n e s , f u r a n o n e s , and r e l a t e d c o m p o u n d s (6, 7). Structurally

these s u b s t a n c e s are g e n e r a l l y c y c l i c e t h e r s , m a i n l y f u r a n o i d c o m p o u n d s .
T h e y are found in c o n d e n s a t e s f r o m c a r b o h y d r a t e s t h a t have been s u b -
j e c t e d to browning r e a c t i o n s .
A s a rule f u r a n d e r i v a t i v e s are c o n s i d e r e d i m p o r t a n t a r o m a c o n -
s t i t u e n t s f r o m a sensory point o f v i e w . T h e y are m a i n l y a s s o c i a t e d w i t h
s w e e t , f r u i t y , n u t t y or c a r a m e l - l i k e o d o r - i m p r e s s i o n s . T h e furans h a v e no
m e a t y c h a r a c t e r i s t i c s , but it s e e m s possible that they c o n t r i b u t e to the
o v e r a l l odor of b r o i l e d and r o a s t e d m e a t .
F u r a n d e r i v a t i v e s w i t h s e v e r a l f u n c t i o n a l groups h a v e i n c r e a s e d odor
i n t e n s i t y as c o m p a r e d with l o w e r h o m o l o g u e s .

Pyrroles (5 - 8). About fifty members of this group have

b e e n d e t e c t e d in various f o o d s t u f f s , though it appears t h a t p y r r o l e s are
not present in f r e s h , raw f o o d s . P y r r o l e s have not r e c e i v e d m u c h
a t t e n t i o n as f l a v o r - c o n t r i b u t i n g c o m p o n e n t s , but they s e e m to c o n t r i b u t e
an u n d d e s i r a b l e odor to c o o k e d m e a t .
P y r i d i n e s (6, 9). P y r i d i n e s have been found in c o f f e e , b a r l e y and

r o a s t e d l a m b . T h e i r i m p o r t a n c e as a r o m a c o n s t i t u e n t s is l i m i t e d .
P y r a z i n e s (4, 6, 10, 11). The pyrazines constitute a very

i m p o r t a n t class a m o n g f l a v o r c o m p o u n d s . T h e y have b e e n i d e n t i f i e d in
v a r i o u s f o o d s y s t e m s , and they are a s s o c i a t e d w i t h p l e a s a n t and d e s i r a b l e
f o o d f l a v o r p r o p e r t i e s . A s a r u l e , the a l k y l d e r i v a t i v e s p r o d u c e r o a s t e d -
- n u t l i k e sensory i m p r e s s i o n s . T h e a c e t y l p y r a z i n e s also have an e s s e n t i a l
p l a c e a m o n g f l a v o r i n g a g e n t s . T h e y have a c h a r a c t e r i s t i c r o a s t e d n o t e ,
r e m i n i s c e n t of p o p c o r n .
Sulfur compounds S u l f u r - c o n t a i n i n g v o l a t i l e s c o n t r i b u t e to both

p l e a s a n t and unpleasant o v e r a l l f l a v o r s in m a n y f o o d s .
• T h i o l s (7, 12)
The t r a d i t i o n a l n a m e f o r this group is m e r c a p t a n s ; n o w a d a y s , the t e r m
t h i o l s is m o r e c o m m o n . T h e y have been i d e n t i f i e d in m o r e t h a n s i x t y
different foodstuffs.
M a g a (12) g i v e s an e x p l a n a t i o n f o r t h e i r i m p o r t a n c e as a r o m a and
flavor components:
a) they have o b j e c t i o n a b l e sensory p r o p e r t i e s (although t h e r e a r e e x c e p -
tions)
b) the t h r e s h o l d s f o r most t h i o l s are in the low p a r t s - p e r - m i l l i o n r a n g e
or l o w e r .
• T h i o p h e n e s (13)
The m a j o r i t y of the thiophenes has b e e n i d e n t i f i e d as c o n s t i t u e n t s of
m e a t - b a s e d p r o d u c t s . T h i s group of f l a v o r c o m p o u n d s is r e l a t i v e l y n e w ,
t h e r e f o r e sensory d a t a are s o m e w h a t l a c k i n g .
• O x a z o l e s and O x a z o l i n e s (14, 15)

T h e i r p r e s e n c e has only been r e p o r t e d in a l i m i t e d n u m b e r of f o o d s : c o f f e e ,
c o c o a , m e a t p r o d u c t s , b a r l e y and soy s a u c e . V e r y f e w sensory p r o p e r t i e s
have b e e n r e p o r t e d f o r o x a z o l e s and o x a z o l i n e s .
• T h i a z o l e s (6, 16)
T h i a z o l e s are in a c e r t a i n way unique; they c o n t a i n a h e t e r o c y c l i c r i n g
c o n t a i n i n g b o t h n i t r o g e n and s u l f u r . M o s t of the t h i a z o l e s h a v e b e e n
i s o l a t e d f r o m c o f f e e and m e a t . T h e a l k y l d e r i v a t i v e s a r e most c o m m o n ;
t h e y g e n e r a l l y have g r e e n , n u t t y , and v e g e t a b l e - l i k e o d o r s .

Sensory d a t a f o r c o m p o u n d s
E x p l a n a t o r y notes
N o t a t i o n , s y m b o l s and a b b r e v i a t i o n s used in the f o l l o w i n g t a b l e s :
Names
T h e n o m e n c l a t u r e is i n t e n d e d to f o l l o w I U P A C 1979 R u l e s , " N o m e n c l a t u r e
of O r g a n i c C h e m i s t r y " .
Synonyms
S y n o n y m s are at t i m e s g i v e n , e s p e c i a l l y when a c c e p t e d t r i v i a l n a m e s exist

a n d / o r to a v o i d doubt.
Descriptions
T h e sensory p r o p e r t i e s of e a c h c o m p o u n d s are d e s c r i b e d .
F s i g n i f i e s F l a v o r , i.e. odor and taste t o g e t h e r (the senses of s m e l l and

t a s t e ) , w h i c h is the c a s e when the i t e m is t a k e n into the m o u t h .
Ο s i g n i f i e s O d o r , i.e. a p r o p e r t y p e r c e i v e d through the sense o f s m e l l

only.
L e a v i n g out one or both of these l e t t e r s s i g n i f i e s l a c k of such i n f o r m a t i o n ,

for example: green note, characteristic.
T h r e s h o l d values
T h e s e values are usually e v a l u a t e d through the sense of s m e l l ; they are

m a r k e d w i t h Ο = O d o r t h r e s h o l d v a l u e . S o m e values are e v a l u a t e d through
the sense of t a s t e ;
Τ = T a s t e t h r e s h o l d value
F = F l a v o r t h r e s h o l d v a l u e , i.e. odor and t a s t e t o g e t h e r .
T h e s o l v e n t used is m e n t i o n e d a f t e r the t h r e s h o l d v a l u e :
Examples:
Ο 0.05 p p b / w a t e r the odor threshold of an a r o m a c o m p o u n d
is m e a s u r e d (dissolved) in w a t e r
Τ 150 p p m / w a t e r the t a s t e threshold of a c o m p o u n d in b e e r
* F o r further values, see r e f e r e n c e s N o s . 23, 141, and 142.
Remarks
U n d e r this h e a d i n g , place(s) of o c c u r r e n c e of e a c h c o m p o u n d is g i v e n .
F f o r F o o d s , i.e. the c o m p o u n d s has been i d e n t i f i e d in a f o o d or
b e v e r a g e , such as m e a t , v e g e t a b l e s , c o f f e e , c o c o a , and t e a .
M f o r M o d e l S y s t e m , i.e. the c o m p o u n d has been i d e n t i f i e d in a

non-food milieu. Example: glucose-cysteine model system.
S f o r S y n t h e t i c , i.e. the c o m p o u n d has been s y n t h e s i z e d .

FURANS
NAME / (SYNONYM) R 2 R 3 R^
Furan
2-Methylfuran CH^
C H
2-Ethylfuran 25
2-Propylfuran Π"Ο^Η 7
2-Butylfuran U- C
4 H 9
C H
2-Pentylfuran -" 5 11
2-Vinylfuran CH=CH,
2
(2-Furylethylene)
2-Acetylfuran COChL
(2-Furyl methyl ketone)
2-Furyl-2-propanone CHJiZOCH
(2-Furfuryl methyl ketone)
2-Furfuryl methyl ether ChLOCH

(2-(Methoxymethyl)furan)

R
3 W « 2
2Λ
DESCRIPTION THRESHOLD VALUE REM. REF
O: Peculiar spice-smoky, F,M,S, 17

slightly cinnamon-like
O: Ethereal 18
Ο of GC eluates: Sickly, nasty 19
Ο 4.5 ppm/water 20
O: Ethereal F,M,S, 18
Ο of GC eluates: Sickly 19
Ο 3.5 ppm/water 20
Ο 27 ppm/oil 21
O: Powerful sweet, burnt; F,S 17

when dilute, warm, sweet
F: Caffeine-like
Ο 8 ppm/oil 21
Ο 6 ppm/oil F 21
O: Weak, noncharacteristic F 22
Ο 10 ppm/oil 21
O: Fruity F,S 23
Ο of GC eluates: Green, sweet 19
pungent
O: Sweet, pungent
F in vegetable oil at concentration
up to 10 ppm: Beany, grassy
Ο 6 ppb/water 24
Ο 2 ppm/oil 21
O: Phenolic, coffee-grounds
Ο 1 ppm/oil 22
21
O: Pleasant, ketonic F,M
F: Burning, sweetish 18
O: Powerful balsamic-sweet with a
tobacco-like, almost narcotic 17
pungence. Floral undertones of
balsamic-cinnamic character
F in beer: Almonds, rubber, burnt/ 80 ppm/beer 25
/phenolic, pyrazole
Τ 110 ppm/orange juice 26
F 80 ppm/water 27
O: Mild, sweet, fruity-caramellic, F,S 17

somewhat spicy
F: Sweet, fruity-spicy, slightly nut- like
F: Suggestive of radish 23
O: Rum-like 6
O: Mustard-like 22
C o n t i n u e d on n e x t page

MAILLARD REACTIONS
FURANS (cont.)
NAME / (SYNONYM) R
l R
2 R
3 R
4
2-Furfuryl methyl sulfide CH SCH 2 3
2-Furfuryl acetate CH OCOCH 2 3
2-Furfuryl propionate CH OCOC H 2 2 5
2-Ethyl furoate COOC H 2 5
(2-Furancarboxylic acid, ethyl ester)

2-Furoic acid
(2-Furancarboxylic acid)
COOH
2-Furfuryl alcohol
(2-Furylmethanol,
CH OH
2-(Hydroxymethyl)furan)
2
2-(Hydroxyacetyl)furan COCH OH 2
(2-Furyl hydroxymethyl ketone)
2-Propionylfuran COCJ-L
(Ethyl 2-furyl ketone)
2-Furaldehyde CHO
(Furfural, 2-Furancarbaldehyde)
2,5-Dimethylfuran CH 3 CH 3

O: Coffee-like F,M 28
O: Nut-like F 29
O: Bitter, nut-like F 22
O: Burnt, buttery, vanilla-like F 6

Ο: Stinging
F,M,S 18
F: Sour
Ο: Practically odorless
17
F: Clear acid, mildly caramellic note
O: "Characteristic"
F,M,S 18
F: Bitter
O: Very mild, warm-oily, "burnt"
F: Warm, slightly caramellic, in higher 17
concentration burning, yet some
what creamy
O: Mild sweet 22
F in beer: Sugar cane, woody > 3000 ppm/beer 25
F 5 ppm/water 27
O: Burnt 30
O: None F,M 18
Τ >200 ppm/ orange juice 26

F: Burning, sweetish
F,M 28
O: Sweet, caramellic
O: Pungent, but sweet, bread-like
caramellic, cinnamon-almond-like F,M,S 17
of poor tenacity
Sweet bread-like, caramellic in
proper dilution
O: "Characteristic"
18
F: Sweet
F: Bitter 29
F in beer: Paper, husk 150 ppm/beer 25
F 5 ppm/water 27
Ο 3000 ppb/water 24
O: Ethereal F,M 28

FURANS (cont.)
NAME (SYNONYM)
5-Methyl-2-furaldehyde CHO
(5-Methylfurfural)
5-Hydroxymethyl-2-furaldehyde CHO CH OH
2
(HMF, 5-(Hydroxymethyl)furfural)
2,5-Diformylfuran CHO CHO

(2,5-Furandicarbaldehyde)
2-Acetyl-3-hydroxyfuran COCH 3 OH
(Isomaltol)
2-Acetyl-5-methylfuran COCH, CH 7
2-Butyl-5-methylfuran H CH 7
n-c 94
2-(2-Hydroxybutyl)-5-methylfuran CH CH(OH)C H
2 2 5 CH,
2-(l,2-Dioxopropyl)-5-methylfuran COCOCH^ CH,
2-(2,3-Dioxobutyl)-5-methylfuran CH COCOCH
2 3 CH,
2-Cyano-5-methylfuran CN CH,
(5-Methyl-2-furonitrile)

O: Sweet-spicy, warm and slightly

F,M,S 17
caramellic
F: Sweet-caramellic, warm y
O: Burnt, caramel-like, slightly meaty 6
F in beer: Almonds, burnt/phenolic, 20 ppm/beer 25
pyrazole
10 ppm/orange juice 26
O: None
F,M,S 18
F: Bitter, astringent
O: Warm-herbaceous, winy-ethereal
remotely resembling Hungarian
chamomile (matricaria oil). A 17
natural sweetness common;
similarity to hay, caramel, tobac
co, etc. often perceptible
F: Sweet, herbaceous-hay-like, mildly
tobacco-like
F2 Bitter 29
F in beer: Aldehyde, stale, vegetable 1000 ppm/beer 25
oil
Τ >200 ppm/orange juice 26
F 100 ppm/water 27
F > 100 ppm/water M,S 27
Ο: Burnt, pungent, fruity

F,M,S 18
F: Sour, sweet, fruity
O: Caramellic-sweet, but rather
pungentjof good tenacity
F: First sour, then sweet, caramellic- 17
-fruity, bread-like, depending upon
the concentration used. Sour taste
mostly noticed in high concentration!
of the material.
O: Caramel-like F,M 28
O: Green S 31
O: Green S 31
O: Caramel F 2 ppm/water M,S 27
O: Like roasted rye bread F 22
O: Nut-like, bitter almond-like F 22
Continued on next page

FURANS (cont.)
NAME / (SYNONYM) R x R £ R 3 R 4
2-Methyl-3-furanthiol CH 3 SH
(5-Mercapto-2-methylfuran)
2-Methyl-4-furanthiol CH 3 SH
(4-Mercapto-2-methylfuran)
2,5-Dimethyl-3-furanthiol CH 3 SH CH 3
(3-Mercapto-2,5-dimethylfuran)
S-Methyl 2-thiofuroate COSCH 3
(2-Thiofuroic acid, methyl ester)
5-Methylthio-2-furaldehyde CHO SCH 3
(5-Methylthiofurfural)
2-(Mercaptomethyl)furan CH SH 2
(2-Furylmethanethiol, Furfuryl
mercaptan)
S-2-Furfuryl thioacetate CH SCOCH 2 3
2-Methyl-5-(methylthio)furan CH 3 SCH
(2-Methyl-5-furyl methyl sulfide)
2- ((Methyldithio)methyDfuran CH SSCH 2 3
(Furfuryl methyl disulfide)
2-Furfurylfuran CH ~furan
2
Difurfuryl sulfide CH SCH ~furan

2 2

F: Sweetish, fried meat, beef broth 32
O: Green, meaty, herbaceous 31
F: Strongly roasted meat 32

O: Mercaptan-like F,M 22
O: Cabbage-like 28
O: Meaty F,S 33
O: Extremely powerful and diffusive,

penetrating, only in proper dilution
agreeable, coffee-like, caramellic- F,M,S 17
-burnt, sweet
F: Dilution < 5 ppm: Pronounced cara-
mellic-coffee-like
O: Characteristic, unpleasant 23
O: Strong like roasted coffee 22
F: Coffee 34
0.04 ppb/water
0.04 ppb/2%
protein-hydro- 32
lysate solution
0.003 ppb/skim
milk
O: Coffee-like F 22
O: Very strong sulfurated F,M,S 23
O: Fresh white bread crust 0.04 ppb/water 6,7

O: Roasted bread crust 35
O: Freshly baked bread
36
O: Caramellic F,M
37
O: Toasted F,M
37

4,5-DIHYDROFURANS
NAME / (SYNONYM) R R 2 R 3 R
2-Methyl-4,5-dihydrofuran-3-thiol CH 3 SH
2-Methyltetrahydrofuran-3-ol CH, OH
FURANONES 2<5H> / \
3-Hydroxy-4,5-dimethyl-2(5H)- CH CH 3 CH 3
-furanone
3-Hydroxy-4-ethyl-5-methyl- OH C H 2 $ CH 3
-2(5H)-furanone
3-Hydroxy-4-methyl-5-ethyl- OH C H
3 C
2 5 H
-2(5H)-furanone
4 - Hydroxy - 5 - methyl - 3(2H)- f uranone OH CH,
4-Mercapto-5-methyl-3(2H)-f uranone SH CH,
2,5-Dimethyl-3(2H)-furanone CH, CH 7
2,5-Dimethyl-4-methoxy-3(2H)- CH 3 OCH 3 CH 3
-furanone
4-Hydroxy-2,5-dimethyl-3(2H)- CH 3 OH CH,
-furanone^
(Furaneol )

TETRAHYDROFURANS
O: Roasted meat 31
O: Fatty 31
R R
3\/^ 1
F: Burnt 38
29
O: Typically caramel
29
O: Typically caramel Τ 0.005-0.01 ppm/
water 39
Ο 0.5-1 ppm/water
O: Maple-like, curry-like 38
O: Intense caramel and curry-like 7
O: Caramel-like F,M 40
O: Roasted chicory root 38
O: Reminiscent of roasted chicory root
with an unmistakable undertone of
maple sirup
O: Sweet, meat-like 31
O: Strong odor of freshly baked bread

but not very reminiscent of bread
aroma
O: Reminiscent of sherry 7
Ο 0.03 ppb/water 41
O: Fragrant, fruity, caramel, burnt

pineapple F,M 18
F: Burning, sweet
O: Caramel, burnt sugar-like 30
O: Sweet, cotton-candy 42
O: Caramel-like, burnt pineapple
which turns into a strawberry-
like note as dilution increases
F 1 ppm/water 27
Ο 0.1-0.2 ppm/water
39
Τ 0.03 ppm/water

FURANONES (cont.)
NAME / (SYNONYM) R, R,.
2-Hydroxymethyl-4-hydroxy- CH OH 2 OH CH,
- 5- methyl - 3(2H)- f uranone
2-Ethyl-4-hydroxy-5-methyl- C H
2 5 OH CH,
-3(2H)-furanone
DIHYDROFURAN-3-ONES
4-Hydroxy-5-methyl-2,3-dihydro- OH CH,
furan-3-one
TETRAHYDROFURAN-3-ONES
2-Methyltetrahydrofuran-3-one CH^
4-Mercaptotetrahydrofuran-3-one SH
(4-Mercapto-3-oxotetrahydrofuran)
4-Mercapto-5-methyltetrahydrofuran- SH CH,
-3-one
(4-Mercapto-5-methyl-3-oxotetra-
hydrofuran)

O: Unpleasant odor of charred paper M 42
O: Sweet, reminiscent of shortcake F 7

F: Intensely sweet 38
O: Caramel-like 40
F: Pleasant, maltol-like M 43
Ο: Sweet, roasted F,M 28
O: Green, meaty, "Maggi-like" S 31
O: Meaty, "Maggi-like" S 31

4H-PYRAN-4-ONES
NAME / (SYNONYM) R x R £ R ? R^
2-Methyl-3-hydroxy-4H-pyran-4-one CH, OH
(Maltol)
2-Ethyl-3-hydroxy-4H-pyran-4-one C H,-
? OH
(Ethylmaltol)
2-Methyl-3,5-dihydroxy-4H-pyran- CH 3 OH OH
-4-one
(5-Hydroxymaltol)
2-Ethyl-3-hydroxy-6-methyl-4H- C ^ O H C H
3
-pyran-4-one
Ô
2,3-Dihydro-3,5-dihydroxy-6- H O v ^ \ OH
- methyl-4H-pyran-4-one v
fj j
(5-Hydroxy-5,6-dihydromaltol) ^ J
3 Ό
.OH
3- Hydroxy -2H-py ran-2-one
(3-Hydroxy-2-pyrone) O
I
Methyl 4,5-dimethyl-3,6-dihydro- ^^3\ "
2H-pyran-2-carboxylate
S) c
OOCH 3

DESCRIPTION THRESHOLD VALUE REM. REFE
O: Warm-fruity, caramellic-sweet
with emphasis on the caramellic
note in the dry state, while solu F,M,S 17
tions show a pronounced fruity,
jam-like odor of pineapple, straw
berry type
O: Fragrant, caramel
18
F: Bitter, sweetish
O: Warm, sweet, fruity; jam-like in 23
solution
O: Coffee, malt, caramel 34
20 ppm/water 27
7.1 ppm/water 44
35 ppm/water
13 ppm/water
39
O: Intensely sweet, fruity-bread
like, pleasant, of immense ten
acity
F: Sweet, fruity-jam-like, remini 17
scent of pineapple, strawberry,
vanilla and heavy fruit-preserve
or syrup, depending upon concen
tration
O: Very sweet, caramel-like, of
immense tenacity 23
F: Sweet, fruity with initial bitter-
tart flavor
O: Caramel-like 40
O: Preserved tang boiled down in 7

soy sauce
O: Not reminiscent of maltol 29
O: Odorless F,S 18
Τ > 200 ppm/orange juice 26
Τ 30 ppm/orange juice F 26
Ο: Interesting green note F,S 45

PYRROLES
NAME / (SYNONYM) R± R 2 R 3 R 4
Pyrrole H
1-Methylpyrrole CH 3
(N-Methylpyrrole)
2 - Pyrrolecar baldehy de H CHO

1-Acetonylpyrrole CH COCH 2 3
(l-Pyrrolyl-2-propanone)
2-Acetylpyrrole H COCH 3
(Methyl 2-pyrrolyl ketone)
2-Acetyl-5-chloropyrrole H COCH 3 Cl
2-Acetyl-5-bromopyrrole H COCH 3 Br
2-Formyl-5-methylpyrrole H CHO CH
'3
(5-Methylpyrrole-2-carbaldehyde)
l-Ethyl-2-formylpyrrole C H 2 5 CHO
(N-Ethylpyrrole-2-carbaldehyde)
l-(2-Furfuryl)pyrrole furfuryl
(N-Furfurylpyrrole)
PYRROLIDINES (TETRAHYDROPYRROLES)
Pyrrolidine H
1-Acetylpyrrolidine COCH
1-Pyrroline

O: Sweet and warm-ethereal, slightly F,S 17

burnt-nauseating, resembling that
of chloroform
O: Powerful and penetrating smoky-

-tarry, in extreme dilution sweet, F,S 17
woody-herbaceous, slightly animal.
O: Corny, pungent F,M 37

O: Bready green Ο 10 ppb/water M 46

O: Cookie- or mushroom-like 7
Τ 200 ppm/orange juice F 26
O: Strong almond aroma F,S 47
O: Strong almond aroma F,S 48
Τ 110 ppm/orange juice F,M,S 26

O: Pungent 37
τ 2 ppm/orange juice F,M 26
O: Green, hay-like F 29
Ο 1
O: Penetrating amine-type remini F,S 17

scent of ammonia and piperidine,
nauseating and diffusive, of very
poor tenacity, repulsive
O: Bread-like M 46
O: Corn-like M 49

2,3-DIHYDRO-lH-PYRROLIZINES
NAME / (SYNONYM) R 1 R 2 R 3 R 4
5-Acetyl-2,3-dihydro-lH-pyrrolizine COCH 3
5-Acetyl-6-methyl-2,3-dihydro-lH-
-pyrrolizine COCH 3 CH 3
5-Formyl-6-methyl-2,3-dihydro-lH-
-pyrrolizine CHO CH
TETRAHYDROINDOLIZIN-8-ONES
5,6,7,8-Tetrahydroindolizin-8-one H
2-Methyl-5,6,7,8-tetrahydro-
indolizin-8-one CH 3

*1
O: Smoky, amine-like F,M 30

F: Sweet
O: Smoky, medicine-like M 30
F: Bitter
Ο: Smoky
F,M 30
F: Sweet, cinnamic
r9
Ο: Mild smoky, weak amine-like M 30
Ο: Mild smoky, weak amine-like M 30

PYRIDINES
NAME / (SYNONYM) R^ R 2 R ? R^
Pyridine
3-Methylpyridine CH,
(P -Picoline)
2-Ethylpyridine C H
2 5
3-Ethylpyridine C H 2 5
3-Propylpyridine n-C H 3 ?
2-Isopropylpyridine i-C H3 7
2-Butylpyridine
2 - Isobu tylpy ridine irC H

4 9
2-Pentylpyridine n-C H 5 n
(2-Amylpyridine)
2-Methoxypyridine OCH,
2-Ethoxypyridine OC H 2 5
2-Pyridinecarbaldehyde CHO
(2-Pyridylmethanal)
2-Acetylpyridine COCH,
(Methyl 2-pyridyI ketone)
2-Acetylpyridin-3-ol COCH 3 OH
3,4-Dimethylpyridine CH 3 CH 3

N R
" V 1
R
4^f
O: Burnt, pungent, diamine Ο 21 ppb/air F 50

O: Pungent, penetrating and
diffusive, generally de
scribed as nauseating, but 17
in extreme dilution, warm,
"burnt", smoky, of very poor
tenacity
F: ( * Ί ppm): Rather sharp, burnt
Ο 0.82 ppm/water 51
F: Green F,S 52
F: Green F,S 52
F: Green, smoky 53
F: Tobacco F 23
F; Sweet, musty, beany 53
F: Green, vegetable S 52
F: Sweet, green F,S 52
F: Green pepper S 52
O: Fatty or tallowy-like Ο 0.6 ppb/water F 54
F: Phenolic 52
F: Phenolic 52
Ο: Pungent bitter almond-like, poor

tenacity. In extreme dilution quite 17
pleasant, sweet, bitter almond and
nut-like
O: Popcorn 6
O: Bready 46
O: Tobacco-like 23
O: Cracker-like Ο 19 ppb/water 55
F: Cereal-like 53
F: Green F,S 52

PYRIDINES (cont.)
NAME / (SYNONYM) R R 2 R 3 R 4
4-Ethyl-3-methylpyridine CH^ C
25 H
2- Isobutyl-3-methoxypyridine i-C^H^ OCH^
3- Isobutyl-2-methoxypyridine OCH, i-C-H g

1,4,5,6-TETRAHYDROPYRIDINES
2-Acetyl-l,4,5,6-tetrahydropyridine COCH
PYRIMIDINES
4,6-Dimethylpyrimidine CH 3
4-Acetyl-2-methylpyrimidine CH 3 COCH 3

F: Sweet, nutty S 52
F: Green pepper S 52
Ο: Not very characteristic, but per- Ο 11 ppb/water S 56

haps somewhat camphoraceous
Ο
Ο: Distinct odor of crackers F,S 57

O: Cracker-like Ο 1.6 ppb/water 55
"2
O: Similar to alkyl-substituted F 6
pyrazines (i.e. roasted, nut-like)
Very interesting grilled note F 6

PYRAZINES
NAME / (SYNONYM) Η χ R £ R 3 R^
Pyrazine
2-Methylpyrazine CH^
2-Ethylpyrazine C
2 5 H
2-Propylpyrazine D" 3 7C H
2-Isopropylpyrazine i-C^H^
2-Isobutylpyrazine i-C^H^
2-Pentylpyrazine -" 5 11
C H
2,3-Dimethylpyrazine CH^ CH^

XT
R X^R
3 2
O: Pungent, sweet, in dilution floral

with remote resemblance to helio F,S 17
trope. Very diffusive, poor tenacity
O: Strong, sweet (slightly ammoniacal) 58
Ο: Cornlike with bitter note 70
Ο 50 χ 10 gpb/water 59
F: Roasted hazelnuts Ο 17.5 χ 10 ppb/water 35
F >100 ppm/beer 60
F: Chocolate, roasted peanuts, grilled F,S 35

chicken
Ο: Nutty, roasted 52
Ο: Nutty, green 46
Ο: Strong basic role; in dilution 58
chocolate character
Ο: Grassy 70
10 χ 10 ppb/water 59
105 ppm/water \ 61
27 ppm/oil 1
100 pprn/beer 60
6 χ 10 ppb/water 62
O: Nutty, roasted F,S 52

O: Buttery, rum 65
22 ppm/water 61
17 ppm/oil
6000 ppb/water 62
10 ppm/beer
60
Green, vegetable F,S
52
Green, nutty F,S
52
Green, fruity F,S
400 ppb/water 52
63
1 ppm/water S 61
9 ppm/oil
O: Pungent; in dilution chocolate type F,S 58

O: Nutty, green 52
O: New leather, linseed oil 65
400 ppm/water 59
2500 ppb/water 62
35 ppm/water 64
50 ppm/beer 60

PYRAZINES (cont.)
NAME / (SYNONYM) R ± R £ R 3 R 4
2,5-Dimethylpyrazine CH^ CH 3
2,6-Dimethylpyrazine CH^ CH^
2,3-Diethylpyrazine C
2 5 H C
2 5 H
2.5- Diethylpyrazine ^2^5 ^2^5
2.6- Diethylpyrazine ^2^5 ^2^5
2-Ethyl-3-methyIpyrazine C
2 5 H C
^3
(3-Ethyl-2-methylpyrazine)
2-Ethyl-5-methylpyrazine CH 3
(5-Ethyl-2-methylpyrazine)
2-Ethyl-6-vinylpyrazine C
2 5 H
CH=CH 2
2-Methyl-6-propylpyrazine CH 3 D'^H^

F: Characteristic, reminiscent of F,S 23

potato chips
F: Chocolate, grilled chicken, 35
roasted peanuts
O: Grassy, "cornnuts" 70
O: Roasted Ο 800 ppb/water 66
F in oil: Earthy raw potato Ο 1 ppm/water ι 67
2 ppm/oil '
Ο 2600 ppb/oil 62
Ο 35 ppm/water » 61
17 ppm/oil *
F 25 ppm/beer 60
O: Sweet, "fried", resembling | F,S 17

fried potatoes, but not as
typical odor as the 2,5-isomer
O: Nutty, roasted Ο 200 ppb/water 46
F: Chocolate 35
O: Ether-like with corn note 70
Ο 54 ppm/water \ 61
8 ppm/oil '
Ο 9 ppm/water 64
F 3 ppm/beer 60
F: Roasted hazelnuts F,S 35
Ο 20 ppb/water F,S 62
270 ppb/oil
Ο 6 ppb/water F,S 62
O: Raw potato F,S 68

O: Nutty, roasted 52
O: Butterscotch, nutty 65
O: Pleasant earthy, nutty 69
Ο 130 ppb/water 62
F 2 ppm/beer 60
O: Nutty, roasted Ο 50 ppb/oil F,S 46

O: Grassy 70
Ο 100 ppb/water \ 62
320 ppb/oil '
F 1 ppm/beer 60
O: Buttery, baked, potatolike F 69
Ο: Burnt, butterscotch Ο <0.1 ppm/water F 65

PYRAZINES (cont.)
NAME / (SYNONYM) R
R
l 2 R
3 R
4
2-Isobutyl-3-methylpyrazine i-C,H 9 CH 3
(3-Isobutyl-2-methylpyrazine)
2,3,5-Trimethylpyrazine CH 3 CH 3 CH 3
2,3-Dimethyl-5-ethylpyrazine CH 3 CH 3 C H 2 5
(5,6-Dimethyl-2-ethylpyrazine)
2,5-Dimethyl-3-ethylpyrazine CH CH
3 C
2 5 H 3
2,6-Dimethyl-3-ethylpyrazine CH CH
3 C
2 5 H 3
2,3-Diethyl-5-methylpyrazine C H 2 5 C H 2 5 CH 3
2,6-Diethyl-5-methylpyrazine C H 2 5 CH 3 C H 2 5
2,3-Dimethyl-5-butylpyrazine CH 5 CH 3
2,3-Dimethyl-5-pentylpyrazine CH 3 CH 3 n-C H 5 n
2,3-Dimethyl-5-isopentylpyrazine CH 3 CH 3 i-C H 5 n
2,3-Dimethyl-5-(l-methylbutyl)-
pyrazine CH 3 CH 3 n-C H CH(CH )-
3 ? 3

F: Roasted hazelnuts Ο 400 ppb/water F,S 35

O: Green (bell pepper like), Ο 130 ppb/water 64
dry and sweet notes
Ο 35 ppb/water 62

O: Baked potato or roasted peanuts 23
F: Roasted hazelnuts Ο 1800 ppb/water 35
O: Very similar to 2,3-dimethyl-
pyrazine, but slightly heavier 58

O: Grassy 70
Ο 400 ppb/water 59
Ο 9 ppm/water > 61
27 ppm/oil f
F 1 ppm/beer 60
F: Chocolate, sweet F,S 53

O: Nutty, roasted 0 1 ppb/water 46
O: Roasted Ο 5 ppb/water F,S 66

O: Nutty, roasted 46
F: Lard 35
O: Earthy, baked potato-like 69
Ο 43 ppm/water ι 61
24 ppm/oil '
ο 0.4 ppb/water ι 62
24 ppb/oil /
F 25 ppb/beer 60

F: Walnut, steak 34
O: Nutty, roasted Ο 1 ppb/water 46
ο 15 ppm/water ι 61
24 ppm/oil '
F 5 ppb/beer 60
O: Grassy F 70
O: Sweet, earthy F 69
O: Sweet, smoked, caramel-like S 71
O: Caramel-like, coffee, sweet S 71
O: Honey-like, sweet S 71

PYRAZINES (cont.)
NAME / (SYNONYM) R
R
l 2 R
3 R
4
2,3-Dimethyl-5-(2-methylbutyl)-
pyrazine CH 3 CH 3
C H CH(CH )CH -
2 5 3 2
2,3-Dimethyl-5-(l,2-dimethylpropyl)-
pyrazine CH 3 CH 3
(CH ) CHCH(CH )-
3 2 3
2,3-Dimethyl-5-(2,2-dimethylpropyl)-
pyrazine CH 3 CH 3 (CH ) CCH - 3 3 2
(2,3-Dimethyl-5-neopentylpyrazine)
2,3-Dimethyl-5-(l-ethylpropyl)- CH 3 CH 3 (C H ) CH-
2 5 2
pyrazine
2,3-Dimethyl-5-(l,5-dimethyl- CH 3
CH 3
-4-hexenyl)pyrazine
R ( C H ) C :=CHCH C H C H ( C H ) -
3 2 2 2 3
3
2,3-Dimethyl-5-(3,7-dimethyl- CH 3 CH 3
-6-heptenyl)pyrazine
R
CH(CH ):=CHCH C H C H ( C H ) C H C H -
3 2 2 3 2 2
3
2,3,5,6-Tetramethylpyrazine CH 3 CH 3
CH 3 CH 3
3,6-Diethyl-2,5-dimethylpyrazine CH^ C
2
H
5 C H
3 C
2 5 H
(2,5-Diethyl-3,6-dimethylpyrazine)
2-Isobutyl-3,5,6-trimethylpyrazine i-C^H^ CH 3 CH 3 CH 3
2-(2-MethylbutyI)-3,5,6-trimethyl-
pyrazine C H CH(CH )CH lCH
2 5 3 2 3 CH 3 CH 3
2-Acetylpyrazine COCH-^
2-Acetyl-3-methylpyrazine COCH 3 CH 3
2-Acetyl-5-methylpyrazine COCH, CH,
6-Acetyl-2-methylpyrazine CH, COCH,

(2-Acetyl-6-methylpyrazine)
2-Acetyl-3-ethylpyrazine COCH 3 C H 2 5

O: Sweet, smoked, caramel-like S 71
Ο Sweet, caramel-like S 71
Ο: Brown sugar-like, roasted S 71

Ο: Honey-like, sweet S 71
Ο: Roasted nut S 71
Ο: Roasted nut 5 7 1
O: Fermented soybeans F,S 4

F: Lard 55
O: Similar to trimethylpyrazine but Ο 1000 ppb/water 58
without the odor intensity
Ο 10 ppm/water ι 61
38 ppm/oil '
F > 100 ppm/beer 60
F 100 ppm/beer F,S 60
O: Roasted nut, sweet S 71
Ο: Sweet, roasted F,S 71
F: Popcorn-like F,S 72
O: Popcorn, nutty 52
F: Chocolate, popcorn 55
O: Breadcrust-like, nutty, no green 64
notes, reminiscent of acetamide
Ο 62 ppb/water 55
F: Cereal, roast grain F,S 53
O: Nutty, vegetable Ο 4 ppb/water 46
F: Popcorn-like S 72
Ο: Popcorn F,S 52
F: Popcorn-like 72
F: Potatoes F,S 35
F: Reminiscent of slightly roasted 7
potatoes C o n t i n u e d on n e x t page

PYRAZINES (cont.)
NAME / (SYNONYM) R
l R
2 R
3 R
4
2-Methoxypyrazine OCH 3
2-Ethoxypyrazine OC H 2 5
2-Butoxypyrazine OC H -n 4 9
2 - (Methoxy met hy l)py raz i ne CH OCH 2 3

2-Methoxy-3-methylpyrazine OCH 3 CH 3
(3-Methoxy-2-methylpyrazine)
2-Methoxy-5-methylpyrazine OCH, CH,

(5-Methoxy-2-methylpyrazine)
2-Ethyl-3-methoxypyrazine C H 2 5 OCH 3
(3-Ethyl-2-methoxypyrazine)
2-Ethyl-5-methoxypyrazine C H 2 5 OCH 3
(5-Ethyl-2-methoxypyrazine)
2- Propyl-3-methoxypyrazine n-C H 3 y OCH 3
(3-Propyl-2-methoxypyrazine)
3- Isopropyl-2-methoxypyrazine OCH 3 i-C H 3 ?
(2-Isopropyl-3-methoxypyrazine)
2-Isopropyl-5-methoxypyrazine i-C-jH^ OCH 3
(5-Isopropyl-2-methoxypyrazine)
2-Butyl-3-methoxypyrazine n-C^H^ OCH 3
2-Isobutyl-3-methoxypyrazine i-C^H^ OCH

(3-Isobutyl-2-methoxypyrazine)

O: Sweet, nutty S 52
Ο: Not very characteristic Ο 700 ppb/water 63
O: Sweet, nutty S 52
Ο: Green, vegetable S 52
F: Nutty, earthy S 73
Ο: Ethereal character 58
Ο 150 ppb/water 59
O: Reminiscent of hazelnut, almond F,S 23

and peanut
O: Roasted peanuts, nutty, earthy 4
O: in concentration vegetably; in
dilution popcorn/potato 58
Ο 4 ppb/water 63
Ο 3 ppb/water 59
F: Hazelnuts, almonds, peanuts S 35

Ο: Green vegetably character 58
Ο 15 ppb/water 59
O: Raw potato, earthy, bell pepper F,S 4

F: Earthy, bell pepper 73
Ο 0.4 ppb/water 63
O: Bread-like/mousy F,S 66
F: Bell pepper S 73
Ο: Very similar to bell pepper Ο 0.006 ppb/water 63
F: Bell pepper, earthy F,S 73

O: Potato-like 7
O: Earthy, bell pepper, raw potato 4

O: Strong galbanum note 58
Ο 10 ppb/water 59
O: Strong galbanum note S 58

Ο 10 ppb/water -59
F: Bell pepper S 73
Ο: Strongly green (bell pepper-like) Ο 0.016 ppb/water F,S 64

O: (Green) bell pepper Ο 0.002 ppb/water 24
Ο 10 ppb/water 59

PYRAZINES (cont.)
NAME / (SYNONYM) R x R 2 R 3 R^
2-Isobutyl-5-methoxypyrazine i-C^H^ OCH^
2-Isobutyl-6-methoxypyrazine i-C H 4 9 OCH 3
3 - sec.Buty 1 - 2 - metho xy pyraz ine OCH 3 s-C H 4 g
(2-sec.Butyl-3-methoxypyrazine,
2-Methoxy-3-(l-methylpropyl)-
pyrazine)
2-Methoxy-3-(l-methylbutyl)pyrazine OCH 3 CH(CH )C H -n 3 3 ?
2-Isopentyl-3-methoxypyrazine i-C H 5 1 1 OCH 3
2-Hexyl-3-methoxypyrazine
-~ 6 13
C H 0 C H
3
(3-Hexyl-2-methoxypyrazine)
2-Methoxy-3-(2-methyloctyl)pyrazine OCH 3 CH CH(CH )C H 2 3 6 1 3
2-Methoxy-3-isononylpyrazine OCH 3 i-C H 9 1 9
2-Methoxy-3-acetylpyrazine OCH 3 COCH 3
2-Methoxy-3,5-dimethylpyrazine OCH 3 CH 3 CH 3
2-Methoxy-3,6-dimethylpyrazine OCH 3 CH 3 CH 3
2-Methoxy-3-isopropyl-5-methyl-
pyrazine OCH 3
i
" 3 7
C H C H
3
2-Methoxy-3-isopropyl-6-methyl- OCH 3 i-C H 3 ? CH 3
pyrazine
2-Methoxy-3-(DC-hydroxyisopropyl)- OCH 3 C(OH)(CH ) 3 2 CH 3
-5-methylpyrazine
2-Methoxy-3-(cC-hydroxyisopropyl)- OCH 3 C(OH)(CH ) 3 2 CH 3
-6-methylpyrazine

O: Strong green bell pepper note S 58

Ο 10 ppb/water 59
F: Coffee 35
F: Bell pepper S 73
F: Bell pepper S 73
F: Bell pepper S 73
F: Bell pepper S 73
F: Bell pepper S 73
Ο: Very similar to bell pepper Ο 0.001 ppb/water 63
F: Earthy, bell pepper S 73
F: Bell pepper S 73
Ο: Weak breadcrust-like, green and S 64

nutty notes
O: Bready/mousy Ο 4 ppb/water F,S 46
F: Medicinal, earthy S 73
Ο: Strongly green (green bean-like), Ο 0.05 ppb/water S 64

floral and ethereal undertone, no
nutty notes
O: Strongly green (green bean-like), Ο 0.045 ppb/water S 64

no nutty or floral notes
O: Weak, green (bell pepper-like), F,S 64

earthy undertone, chimney soot
O: Weak, green (bell pepper-like), S 64

earthy undertone, chimney soot,
nutty note

PYRAZINES (cont.)
NAME / (SYNONYM) R
1
2-Isobutyl-3-methoxy-5-methylpyrazine i-C^H^ OCH^ CH^
2-Isobutyl-3-methoxy-6-methylpyrazine i-C^H^ OCH^
2-Methoxy-3,6-diisobutylpyrazine OCH, -C H 4 9
i-C,H 9
2-Methoxy-3-acetyl-5-methyl- OCH COCH CH

3 3 3
pyrazine
2-Methoxy-3-acetyl-6-methyl- OCH 3 COCH 3
pyrazine
5-Isobutyl-2-methoxy-3-methyl- OCH 3 CH 3
i-C H4 9
pyrazine
5-(2-Methylbutyl)-2-methoxy- OCH 3 CH 3 CH CH(CH )C H

2 3 2 5
-3-methylpyrazine
5-Isopentyl-2-methoxy- OCH 3 CH 3 -C H 5 1 1
-3-methylpyrazine
5-(2-Methy Ipent yl)- 2 - methoxy - OCH 3 CH 3 CH CH(CH )C H

2 3 3 y
-3-methylpyrazine
2-Ethoxy-5-isobutyl-3-methyl- OC H 2 5 CH 3
i-C,H 9
pyrazine
5-Isobutyl-2-isopropoxy-3-methyl- OC H -i3 7 CH 3 i-C^H 9
pyrazine
5-Isobutyl-3-methyl-2-phenoxy- OC H 6 5 CH 3 i-C H4 9
pyrazine
5-Isobutyl-3-methyl-2-(methylthio)- SCH 3 CH 3
i-C H4 9
pyrazine
5-(2-Methylpentyl)-3-methyl- SCH 3 CH 3 CH CH(CH )C H

2 3 3 7
-2-(methylthio)pyrazine
5-Isobutyl-3-methyl-2-(phenylthio)- SC^H^ CH 3 i-C H4 9
pyrazine
2-Isobutyl-3-methoxy-5,6-dimethyl- '~ ^
l c
OCH 3 CH 3 CH 3
pyrazine
2,5-Dimethoxy-3,6-dimethylpyrazine OCH 3 CH 3 OCH 3 CH ?

O: Similar to bell pepper but with Ο 0.3 ppb/water 56

some minty notes
O: Minty camphoraceous in character Ο 2.6 ppb/water 56

with slight bell pepper undertone
F: Earthy, low bell pepper S 73
O: Weak, breadcrust-like, green F,S 64

musky note, chimney soot
O: Weakly green, unpleasant, no 64

nutty notes, chimney soot
O: Licorice-woody Ο 0.7 ppm/water 75
O: Licorice-woody, slightly green Ο 1 ppm/water 75
O: Licorice-woody, walnut-like Ο 1 ppm/water 75
O: Burdock, bell pepper Ο 0.5 ppm/water 75
O: Burdock-like brownish, Ο 0.2 ppm/water 75

slightly bell pepper,
galbanum green
O: Licorice-woody, Ο 1 ppm/water 75
walnut-like
O: Bell pepper, cacao bean Ο 1 ppm/water 75
O: Licorice-woody, walnut-like Ο 0.8 ppm/water 75
O: Burdock-like, slightly earthy Ο 1 ppm/water 75
O: Nutty, macadamia-like Ο 0.7 ppm/water 75
O: Minty-camphoraceous Ο 315 ppb/water 56
O: Green (bell pepper-like), nutty Ο 180 ppb/water S 64

notes, floral and ethereal undertone

PYRAZINES (cont.)
NAME / (SYNONYM) R 2 R
3
2,5-Dimethoxy-3,6-diisopropyl- OCH 3 i-C H 3 7 OCH 3 i-C H.

3
pyrazine
2,5-Dimethoxy-3-isopropyl- OCH 3 i-C H 3 7 OCH 3 CH 3
-6-methylpyrazine
2.5- Dimethoxy-3-acetyl- OCH 3 COCH 3 OCH 3 CH 3
-6-methylpyrazine
2.6- Dimethoxy-3-isopropyl- OCH 3 i-C H 3 7 CH 3 OCH 3
- 5- methy lpy razine
2-Ethoxy-3-methylpyrazine OC H 2 5 CH 3
2-Ethoxy-6-methy lpy razine OC H 2 5 CH 3
(6-Ethoxy-2-methylpyrazine)
2-Ethoxy-3-ethylpyrazine OC H 2 5 C H 2 5
2-Ethoxy-3-isobutylpyrazine OC H 2 5 i-C H 4 9
2-Butoxy-3-methylpyrazine CH
°C H 4 9
3
2-Butoxy-3-propylpyrazine OC H 4 9
n-C H 3 7
2-Methylamino-3-methylpyrazine NHCH 3 CH 3
N(CH ) C H
2-Dimethylamino-3-methylpyrazine 3 2 3
N(CH ) CH
2-Dimethylamino-6-methy lpy razine 3 2 3
2-Dimethylamino-3-isobutylpyrazine N(CH ) 3 2 i-C^
2-Dimethylamino-6-isobutylpyrazine N(CH,) ? i-C H4 9
2-(Methy lthiomethyl)py razine CH SCH

2 3
2-Methylthio-3-methylpyrazine SCH 3 CH 3
(2-Methyl-3-methylthiopyrazine)
5-Methylthio-2-methylpyrazine CH 3 SCH 3


notes, weakly sweet

notes
O: Unpleasant, weakly green, S 64

earthy notes, chimney soot
O: Nutty, green (bell pepper-like) Ο 70 ppb/water F,S 64

woody bynote
F: Earthy, nutty S 73
F: Hazelnuts, almonds, peanuts 35
F: Pineapple S 35
Ο: Raw potato 0 11 ppb/water S 56
F: Earthy, bell pepper S 73
F: Floral, medicinal S 73
F: Medicinal, earthy S 73
Ο: Weak, reminds of roasted peanuts, S 64

green and cocoa notes
O: Like 2-methylamino-3-methyl- Ο 180 ppb/water S 64

pyrazine but more green and
peanut-like, less cocoa notes
O: Reminds of unburnt coffee, Ο 1200 ppb/water S 64

peanut-like and sweet notes, no
cocoa notes
O: Strong cocoa note, reminds of Ο 1600 ppb/water S 64

fusel oil, green and burnt undertone
O: Weakly green, cocoa note, no Ο 5000 ppb/water S 64

peanut note
O: Weak sulfide note Ο 20 ppb/water S 58
F: Nutty, cracker S 73
Ο: Cooked meat, vegetable 58
Ο 1 ppb/water 59
O: Meaty, vegetably Ο 4 ppb/water S 58

PYRAZINES (cont.)
NAME / (SYNONYM) R
l R
2 R
3 R
4
2-Methylthio-3-isobutylpyrazine SCH 3 i-C H4 9
2-Methylthio-6-isobutylpyrazine SCH^ i-C H 4 9
2-(Furfurylthiomethyl)pyrazine CH -S-furfuryl
2
2-Methyl-3-(furfurylthio)pyrazine CH, S-furfuryl
2-Methyl-5-(furfurylthio)pyrazine CH, S-furfuryl
5-Methylcyclopenta [b jpyrazine
w
Co
CH 3
6,7-Dihydro-5H-cyclopenta [ b] pyrazine
2-Methyl-6,7-dihydro-5H-cyclopenta-
[ î>] pyrazine
5-Methyl-6,7-dihydro-5H-cyclopenta-
[ b] pyrazine
3,5-Dimethyl-6,7-dihydro-5H-cyclo-
penta [ b ] pyrazine 3
CH,
5,7-Dihydro-5,7-dimethylfuro[ 3,4-b- υπ,
pyrazine
CΝ Oι
CH 3
5,7-Dihydrothieno [ 3,4-b ] pyrazine
Co
F: Bell pepper S 73
Ο: Weakly green, roasted peanuts, Ο 0.33 ppb/water 64
cheese-like (Camembert) note
F: Bell pepper S 73
Ο: Powerful coffee, cooked meat Ο 1 ppb/water S 58

note, also strong chocolate
character
F: Roasted coffee-like S 23
Ο: Powerful coffee, cooked meat note Ο <1 ppb/water 58
F: Roasted, coffee-like S 23
Ο: Powerful coffee, cooked meat note Ο <1 ppb/water 58
O: Grilled meat F 66
F: Green, phenolic F,S 53
O: Earthy, baked, potato-like F,S 69

F: Chocolaty 53
O: Earthy, baked, potato-like F,S 69

F: Peanut 53
O: Earthy, baked, potato-like F 69
Ο: Roasted aroma character S 76
F: Roasted nut S 76

PYRAZINES (cont.)
NAME / (SYNONYM)
CH 3>
2-Methyl-5,7-dihydrothieno [3,4-b ] -
pyrazine
5-Methyl-3,4,5,7-tetrahydro-2H-
cyclopenta[b] pyrazine CD
4a,5,6,7,8,8a-Hexahydroquinoxaline CO
3
5,7-Dimethyl-l,2,3,4,7,8-hexahydro-
quinoxaline CO'
H CH 3
2,3-Dimethyl-4a,5,6,7,8,8a-hexahydro- I I I
quinoxaline ^^S^N'^^^
ÇH 3
5,7,7-Trimethyl-2,3,4,6,7,8-hexahydro- I JX H
3
quinoxaline ^^^^ ΟΗ Χ
3
2,3,5,6,7,8,9,10,11,12-Decahydrocyclodeca[b}-
pyrazine
CH 3
l,5(or 7)-Dimethyl-l,2,3,5,6,7-hexahydrodicyclo-
penta[b,e] pyrazine oCX>
\ ^ ^ •
CH 3
N

O: Roasted nut-like S 76
Ο: Bready, nut-like S 77
Ο: Intense popcorn S 77
Ο: Earthy, baked, potato-like F 69
Ο: Cedar wood, tobacco, buttery S 77
Ο: Sweet, tobacco-like fragrance note S 77
F: Nut-like, fatty S 77
Ο: Roasted bean-like M 78

THIOPHENES
NAME / (SYNONYM) R ± R 2 R 3 R^
Thiophene
2-Methylthiophene CH 3
3-Methylthiophene CH-j
C H
2-Ethylthiophene 2 5
2.4- Dimethylthiophene CH 3 CH 3
2.5- Dimethylthiophene CH 3 CH 3
3,4-Dimethylthiophene CH 3 CH 3
2-Thienyl alcohol OH
(2-Hydroxythiophene)
2-Acetylthiophene COCH 3
(Methyl 2-thienyl ketone)
2-Acetyl-3-methylthiophene COCH 3 CH 3
(Methyl 3-methyl-2-thienyl ketone)

2-Acetyl-5-methylthiophene COCH 3 CH
(Methyl 5-methyl-2-thienyl ketone)
2-Thiophenecarbaldehyde CHO
(2-Formylthiophene)

R
3\ S**2
«1
Ο of GC eluates: Sickly, pungent F,M 19

F 8 ppb/water
F 300 ppb/skim milk 32
F 4 ppb/protein-
hydrolysate
solution 2%
Ο of GC eluates: Green, sweet F,M,S 19

Ο at GC exhaust: Onion-like, 31
gasoline-like, paraffinic
O: Heated onion or sulfury 79
O: Fatty, winey F,M 28
O: Styrene-like F,M 28
O: Fried onion F,M 28
O: Fried onions Ο 1.3 ppb/water F,M 80

O: Greenish 28
F: Fresh onion F,M 34

O: Fried onions Ο 1.3 ppb/water 80
O: Burnt F,M 28
O: Mustard-like F,M 28
Ο in syrup: 1 g/100 ml: Onion-like; ι 6
Ο in coffee: Malty, roasted
F 0.08 ppb/water 32
F 1 ppm/skim milk
F 0.3 ppb/protein-
hydrolysate
solution 2%
F: Mustard F,M 34
O: Nutty 28
F,M 28
O: Sweet, flowery
F,M 81
O: Nutty 6
O: Reminiscent of benzaldehyde 33
O: Spicy meat 28
O: Coconut-like 82
O: Sharp, sweet-nutty, somewhat
roasted grain-like F 200 ppb/water
F 8 ppm/skim milk 32
F 600 ppb/protein-
hydrolysate
solution 2%

THIOPHENES (cont.)
NAME / (SYNONYM) R 4
R
l 2 R
3 R
5-Methyl-2-thiophenecarbaldehyde CHO CH 3
(5-Methyl-2-formylthiophene)
3 - Methyl - 2 - thiophenecar baldehy de CHO CH 3
(3- Methyl - 2- f or mylthiophene)
l-(2-Thienyl)-l-propanone COC H 2 5
(2-Propionylthiophene)
l-(2- or 3-Thienyl)-propane-l,2-dione COCOCH 3
2-Methylthiophene-3-thiol CH 3 SH
2-Methylthiophene-4-thiol CH 3
SH
2,3-
DIHYDROTHIOPHENES
(4,5)
2-Methyl-2,3(or 2,5)-dihydrothiophene CH 3
2-Methyl-4,5-dihydrothiophene CH 3
2-Methyl-2,3-dihydrothiophene-3-thiol CH 3 SH
2- Methyl-2,3-dihydrothiophene-4-thiol CH 3 SH
3- Mercapto-2-methyl-2,3-dihydro- CH 3 SH OH
thiophen-4-ol
2-Methyl-4,5-dihydrothiophene- CH, SH
-3-thiol
2-Methyl-4,5-dihydrothiophene- CH, SH
-4-thiol
2-Methyltetrahydrothiophene- CH, SH
-3-thiol
2-Methyltetrahydrothiophene- CH, SH
-4-thiol

O: Cherry-like F,M 6
F: Cherry, bitter almond 34
F 1 ppb/water 1
O: Reminiscent of saffron F,M 6
Ο in syrup 1 g/100 ml: Creamy, F,M 6

caramel-like
Imparts a parline-like and woody note F,M 6

to coffee
O: Woody 28
Ο at GC exhaust: Roasted meat S 31
Ο at GC exhaust: Rubbery S 31
R 3 N ,R 2 R
3y ' 2
R
IJ \ TETRAHYDROTHIOPHENES
Ο at GC exhaust: Cabbage-like S 31
O: Heated onion or sulfury M 79
Ο at GC exhaust: Sweet, roasted meat S 31
Ο at GC exhaust: Rubbery, meaty S 31
Ο at GC exhaust: Meaty, savory, phenolic S 31
Ο at GC exhaust: Meaty S 31
Ο at GC exhaust: Roasted meat S 31
Ο at GC exhaust: Cis-form, meaty; S 31

trans-form, meaty, savory
Ο at GC exhaust: Meat-like S 31

3_(2H-)-THIOPHENONES
3 R
4
4-Hydroxy-5-methyl-3(2H)-thiophenone =o OH CH 3
4 - Mer capto - 5 - methyl - 3(2H)- =o SH CH 3
-thiophenone
4,5-Dihydro-3(2H)-thiophenone =o
2-Methyl-4,5-dihydro-3(2H)- CH 3 =0
-thiophenone
3,4-Dimethyl-2,5-dioxo-
-2,5-dihydrothiophene

4,5-DIHYDRO-3(2H)-THIOPHENONES
Ο at GC exhaust: Popcorn-like S 31
Ο at GC exhaust: Nutty S 31
F: Garlic F,M 7
F: Green, burnt, coffee F,M,S 7

Ο at GC exhaust: Acetylenic 31
O: Onion, a little H S
2 F 83

AROMATIC SULFUR COMPOUNDS
NAME / (SYNONYM)
oC-Toluenethiol
(Benzyl mercaptan, Phenylmethanethiol)
Benzyl methyl sulfide
2-Naphthalenethiol
(2-Naphthyl mercaptan)

Ο "Leek-like" (a more exact de F,S 17

scription than the older still
common "onion-like"). Has the
sharpness of leek odor,
yet not lachrymatory
O: Repulsive, garlic-like 23
F: Reminiscent of the natural land- F 1 ppb/milk 84
cress off-flavor
F 10 ppb/milk \ F,M 84
F 100 ppb/butter oil '
O: Disagreeable, mercaptan-like F,S 23

CYCLIC NON-AROMATIC SULFUR COMPOUNDS
NAME / (SYNONYM)
Ethylene sulfide
(Thiirane)
V
ΓΛ
1,2-Dithiacyclopentene \ y$
(3H-l,2-Dithiole) S
Ρ**
3-Methyl-l,2-dithiolane
Ο
CH,
/ 3
3,5-Dimethyl-l,2-dithiolane CH^X
3 S
-s
1,3-Dithiolane
^ ^ ^CH
2-Methyl-l,3-dithiolane ^S' 3
4-Methyl-l,3-dithiolane
CH,
b S
2,4-Dimethyl-l,3-dithiolane
s—S
1,2,4-Trithiolane
3,5-Dimethyl-l,2,4-trithiolane CH^g/'C^
S - S
3-Ethyl-5-methyl-l,2,4-trithiolane C H
3 ^ S ^ C
2 5 H
S—S
3,5-Diethyl-l,2,4-trithiolane ^'s^S ^ 5

O: Cooked cabbage 6
Ο of GC eluates: Sickly, cooked 19
cabbage, pungent
O: Pleasant smell like cooked 85

asparagus
T: Oniony metallic with cooked Τ 2 ppb 86

beef or braised and vegetable
nuances
Cooked onion, cooked vegetable Τ 10 ppb 86

nutty note
Sweet, sulfury character, in high Τ 2 ppb F,S 86

levels: reminiscent of degrading
onions
F: Onion and garlic roasted or 20 ppb/water F,S 34

boiled
T: Onion, root-vegetable-like Τ 50 ppb 86
T: Onion-like with slight metallic Τ 20 ppb 86

background notes
O: Roast beef M 78
O: Sulfurous 28
Ο: Characteristic of boiled beef F,M,S 87

O: Onion-like 88
F 10 ppb/water 1
O: Garlicky F,S 88
O: Garlicky F,S 88

CYCLIC NON-AROMATIC SULFUR COMPOUNDS (cont.)
NAME / (SYNONYM)
3,5-Di-(2-methylpropyl)-l,2,4-trithiolane ^
(CH ) CH CH
3 2 2 2
/
\ /^CH CH (CH )
S 2 2 3 2
1,2-Dithiane
Q S
S
3-Methyl-l,2-dithiane
S r 8
3,5-Dimethyl-l,2-dithiane
S
"S
2,6-Dimethyldithiin
(2,6-Dimethyl-4H-dithiin) CH ^s 3
/ c H
3
1,3-Dithiane
Q
C^CH 3
CH 3
Q
2,4-Dimethyl-l,3-dithiane
α S' Ν * 3
ÇH,
2,4,6-Trimethyl-l,3-dithiane
1,4-Dithiane
Ô
F at 1 ppm: Roasted, crisp bacon-like, 86

pork rind-like
Garlic character with slight Τ 2 ppb M,S 86

metallic nuance
F: Onion and garlic, 2 ppb/water 34

roasted or boiled
F: Onion and garlic, 10 ppb/water 34

roasted or boiled
O: Fuel gas-like F,S 88
F: Onion and garlic, roasted 2 ppb/water F,S 34

or boiled
T: Onion, garlic-like with a Τ 50 ppb 86
metallic by-note
Onion-like character with Τ 20 ppb 86

metallic notes
Onion, garlic and tomato Τ 50 ppb 86

like character
Allium-onion like character Τ 5 ppb 86

with slight metallic notes
Root-vegetable-like Τ 10 ppb 86
character
Onion-like or garlic-like character Τ 50 ppb F,S 86

CYCLIC NON-AROMATIC SULFUR COMPOUNDS (cont.)
NAME / (SYNONYM)
1,3,5-Trithiane
(s-Trithiane)
Ç H 3
S^S
2,4,6-Trimethyl-l,3,5-trithiane |^ J
(2,4,6-Trimethyl-s-trithiane) CH^^s^C^
C H
2 S
2,4,6-Triethyl-l,3,5-trithiane I J
C H;S^C H
2 2 5
6-Methyl-2,3-dihydrothieno [ 2,3-c ] furan

(Kahweofuran)

O: Sulfurous F,M 78
F 0.04 ppb/water 32
F 60 ppb/skim milk
F 0.08 ppb/protein-
hydrolysate
solution 2%
F dissolved in water: Dusty, earthy, F,M 89

nutty
F dissolved in water: Green, allium M 89

(onion, garden cress)
Ο in pure state: Violent, sulfury, but F,S

in high dilution develops a pleasant
roasted and smoky note

OXAZOLES
NAME / (SYNONYM) R± R 2 R ?
2-Acetyloxazole COCH 3
4-Butyloxazole n-c 4
H
9
5-Butyloxazole n-C H 4 9
4-Heptyloxazole n-C H 7 1 5
2,4-Dimethyloxazole CH 3 CH 3
4,5-Dimethyloxazole CH 3 CH 3
4,5-Diethyloxazole C H 2 5 C H 2 5
4-Methyl-5-propyloxazole CH 3 n-C H 3 ?
4-Methyl-5-butyloxazole CH 3 D-C H 4 9
4-Methyl-5-hexyloxazole CH,
2" 6 13
C H
4-Ethyl-5-propyloxazole C H 2 5 n-C H 3 7
4-Ethyl-5-butyloxazole C H 2 5 D-C H 4 9
4-Ethyl-5-pentyloxazole C H 2 5 n-C H 5 n
4-Propyl-5-methyloxazole n-C H 3 7 CH 3
4-Propyl-5-ethyloxazole n-C H 3 ? C H 2 5
4-Butyl-5-methyloxazole 0-C H 4 9 CH 3
4-Butyl-5-propyloxazole n-C H 4 9
C H 3 7
4-Pentyl-5-methyloxazole n-C H 5 u
CH 3
4- Hexy 1 - 5 - methy loxazole n-C H 6 1 3 CH 3
2,4-Diethyl-5-propyloxazole CH 3 CH 3 n-C H 3 ?
2,4,5-Trimethyloxazole CH 3 CH 3 CH 3

O: Nutty, popcorn-like F 90
O: Vegetable-like, green S 91
O: Green, sweet, vegetable F 90
O: Vegetable-like S 91
O: Nutty, sweet M 37
O: Green, sweet, vegetable F 90
O: Green, vegetable-like S 91
O: Green, weak bell pepper-like S 91
O: Celery-like, green S 91
O: Bell pepper-like S 91
O: Nutty, sweet, green F 90
F: Like boiled beef F,S 6

F: Nutty, sweet, green F 5 ppb 92
American Chemical Continued on next page
Society Library
1155 16th St. N. W.
Washington,
In The Maillard 0. C.
Reaction in Foods and 20031
Nutrition; Waller, G., et al.;
OXAZOLINES
NAME / (SYNONYM) R
l R
2 R
3
2-Ethyl-5-methyl-2-oxazoline C H 2 5 CH 3
5 - Methyl - 2 - propyl - 2 - oxazoline n-C H 3 ? CH 3
5-Methyl-2-pentyl-2-oxazoline n-C H 5 n
CH 3
2-Methyl-3-oxazoline CH 3
2,4-Dimethyl-3-oxazoline CH 3 CH 3
2,4,5-Trimethyl-3-oxazoline CH 3 CH 3 CH 3
2,4-Dimethyl-5-ethyl-3-oxazoline CH 3 CH 3 C H 2 5
2,5-Dimethyl-4-ethyl-3-oxazoline CH 3 C H 2 5 CH 3
2,4,5-Triethyl-3-oxazoline C H 2 5 C H 2 5
C H 2 5
4,5-Diethyl-2-isopropyl-3-oxazoline i-C H C H
3 7 2 5 C
2 5 H
4,5-Dipropyl-2-isopropyl-3-oxazoline i - C H 3 7 n- C H3 7 n-C H 3 ?
2-s-Butyl-4,5-diethyl-3-oxazoline C H 2 5 C H 2 5
2-Isopropyl-4,5,5-trimethyl-3- i-C H 3 7 CH 3 2xCH 3
-oxazoline
2-Isobutyl-4,5,5-trimethyl-3- i-C H 4 9 CH 3 2xCH 3
-oxazoline
2-t-Butyl-4,5,5-trimethyl-3- t-C H 4 9 CH 3 2xCH 3
-oxazoline
BENZOXAZOLES
2-Methylbenzoxazole

Η
η—N R
^ = N
O: Melon, fruity 35
F: Fresh mint 35
F: Mild, fruity 35
O: Nutty, sweet F 90
F: Nutty, vegetable, not roasted F 1.0 ppm/water F,S 92
90
O: Nutty, sweet
F: Woody, musty, green F 1.0 ppm/water F,S 92

O: Characteristic boiled beef 87
F: Nutty, sweet, green, woody F 0.5 ppm/water F,S 92
F: Nutty, sweet F 1.0 ppm/water F,S 92
0 : Very reminiscent of fresh carrots S 7
O: Green 93
O: Cocoa 7
O: Banana S 35
O: Cool, banana-like 93
O: Cocoa s 93
Rum-like note s 7
O: Cool, menthol-like, unroasted cocoa 93
O: Earthy (fungal) with a butter-like s 7
green leaf-like note
O: Earthy, diacetyl 93
O: Fresh mint and, depending on the 35
concentration, fresh banana or buttery
O: Cool, mint-like 93
O: Very sweet, of rather gassy-pungent F,S 17

character when undiluted, becoming
floral-sweet, heavy, when diluted

THIAZOLES
NAME / (SYNONYM) R 2 R 3
Thiazole
2-Methylthiazole CH,
4-Methylthiazole CH,
2-Ethylthiazole C H
2 5
2-Propylthiazole n-C H 3 7
2-Isopropylthiazole i-C H3 7
2-Butylthiazole n-C H 4 9
2-Isobutylthiazole i-C H4 9
2-Acetylthiazole COCH
(Methyl 2-thiazolyl ketone)
4- Acetylthiazole COCH 3
(Methyl 4-thiazolyl ketone)
2-Methoxy thiazole OCH 3
5- Methoxy thiazole OCH 3
2-Ethoxythiazole

R
%—Ν
F in beer: Sulfury, grainy, C S 2 Τ 23 ppm/beer F,M 25

O: Pyridine-like 23
O: Nutty, meaty 22
F: Green, vegetable F,M,S 52
O: Green, nutty F,M 23
F: Green, nutty F,M,S 52

F: Green, herby, nutty M,S 52
F: Green, vegetable S 52
F: Raw, green, herby S 52
F in water: Spoiled wine-like, slightly F,S 94

horseradish Ο 2 ppb/water
F in canned tomato juice or tomato
paste: More intense, fresh
tomato-like
O: Strong green, resembling that of 7
tomato leaf
Ο 3.5 ppb/water 95
F 3 ppb/water 1
F: Nutty, cereal, popcorn F,M,S 52

O: Cereal bready 46
O: Taco, grassy 70
O: Popcorn-like, strong, nutty- 82
roasted character
F 10 ppb/water 1
F: Nutty, cereal M,S 52

O: Hazelnut, earthy |
F: Nutty, steak with bitter aftertaste, 35
baked bread, meat
O: Cracker-like Ο 170 ppb/water 55
F: Sweet, roasted, phenolic M,S 52

F: Oatmeal, bread and caramel 35
F: Roasted, meaty, onion M,S 52

F: Braised vegetables, roast meat,
fresh onions 35
F: Phenolic, burnt, nutty M,S 52

F: Roasted peanuts, roast meat 35

THIAZOLES (cont.)
NAME / (SYNONYM) R 2 R 3
5-Ethoxythiazole OC H 2 5
2-Butoxythiazole OC^H^-n
2.4- Dimethylthiazole CH 3 CH 3
4.5- Dimethylthiazole CH 3 CH 3
2.4- Diethylthiazole C
2 5
H C
2 5 H
2.5- Diethylthiazole C
2 5
H C
2 5 H
4,5-Diethylthiazole C H 2 5 C H 2 5
2.4- Dipropylthiazole D'^-jH^ D'^-jH^
4.5- Dibutylthiazole D- 4 9 Π-°4 9

C H Η
5-Ethyl-4-methylthiazole CH 3 C H 2 5
2-Acetyl-4-methylthiazole COCH 3 CH 3
(Methyl 4-methyl-2-thiazolyl ketone)
5-Acetyl-4-methylthiazole CH^ COCH.

(Methyl 4-methyl-5-thiazolyl ketone)
4-Ethyl-5-propylthiazole n-CjH.
C
2 5 H
4-Ethyl-5-butylthiazole C H 2 5 n-C H, 4
4-Butyl-5-methylthiazole n- CH
" 4 9 C H 3
4-Butyl-5-ethylthiazole n-- C H 4 9 C H 2 5
4-Butyl-5-propylthiazole n- n-CjH.
" 4 9 C H
2-Methyl-5-methoxy thiazole CH 3 OCH 3

F: Cooked onion M,S 52

F: Cooked vegetables (sharp 35
resembling nuts)
F: Green vegetable S 52
O: Skunky-oily Ο 18 ppb/water 55
F,M
O: Meat, cocoa Ο 0.1 ppb/water 34, 35
F: Roasted, nutty, green 52

F,M,S 35
F: Braised meat, hazelnut Ο 0.5 ppm
O: Meaty, boiled poultry
Ο 470 ppb/water 96
O: Ethereal, musty, earthy Ο 6.5 ppb/water F 55
O: Slightly skunky and green peppery Ο 0.09 ppb/water F 55
Ο 5.1 ppb/water S 96
O: Sweet, fruity, minty Ο 26 ppb/water 55
Ο 0.19 ppb/water S 96
F: Nutty, green, earthy F,M,S 52

O: Green vegetables, unroasted
hazelnuts Ο 0.02 ppm 35
F: Very sharp, dry and earthy parsley]

F,M 7
F: Anthranilic, burnt F 300 ppb/water 1
F: Roasted, nutty, sulfury M,S 52

O: Peanut, earthy
F: Roasted nuts, sulfury, bitter Ο 0.05 ppm 35
metallic and earthy
O: Bell pepper O 0.06 ppb/water S 96
F: Cabbagy, sulfury, vegetable S 52

THIAZOLES (cont.)
3
4-Isobutyl-5-methoxy thiazole i-C H4 9 OCH 3
4-Isobutyl-5-ethoxy thiazole i-C H4 9 OC H 2 5
2,4,5-Trimethylthiazole CH 3 CH 3 CH 3
2,4-Dimethyl-5-ethylthiazole CH 3 CH 3 C H 2 5
4-Acetyl-2,5-dimethylthiazole CH 3 COCH 3 CH 3
5-Acetyl-2,4-dirnethylthiazole CH 3 CH 3 COCH 3
2,4-Dimethyl-5-vinylthiazole CH 3 CH 3 CH=CH 2
2,5-Dimethyl-4-butylthiazole CH 3 0-C H4 9
CH 3
2,5-Diethyl-4-methylthiazole C H 2 5 CH 3 C H 2 5
2-Isopropyi-4,5-dimethylthiazole i-C H 3 ? CH 3 CH 3
2-Propyl-4,5-diethylthiazole B- 3
C H C H
7
C
2 5 H 2 5
4-Isobutyl-5-methoxy-2- CH 3 i-C H4 9 OCH 3
-methylthiazole
4-Isobutyl-5-ethoxy-2-methyl- CH 3 i-C H4 9 OC H 2 5
thiazole
2-Butyl-4-isobutyl-5- i-C H4 9 OCH 3
-methoxy thiazole

F: Green pepper M,S 52

O: Vegetable soup (minestrone)
F: Pepper, onion, celery and green 35
vegetables (peas and haricot beans)
F: Cucumber, green potato M,S 52

35
F: Cucumber, green pepper, onions Ο 0.02 ppm
F,M,S 52
F: Cocoa, nutty
O: Cocoa, hazelnut, dark chocolate, 1 34, 35
green vegetables (haricot beans) j Ο 0.05 ppm/water
F: Nutty, roasted, meaty 52
O: Hazelnut, steak, meat, liver,
green vegetables, "Buccu" leaf Ο 0.02 ppm F,M,S 35
and black currant
F: Nuts, meat, steak Ο 0.002 ppm 34
F: Roasted, meaty, sulfury S 52
F: Roasted, nutty, meaty M,S 52

O: Sulfury as in meat
F: Boiled beef, chicken and turkey 35
O: Strong, characteristic, nut-like F 7
O: Sweet, earthy F 69
F: Green, nutty S 52
O: Pleasant, nutty F 90
O: Pleasant, nutty F 90
F: Green, vegetable 52
O: Onion and pepper
M,S 34, 35
F: Pepper, vegetables (green)
F: Green, vegetable, onion 52

F: Vegetables, sharp and green 35
M,S
O: Vegetable soup with touch of
barley, potato, green pepper Ο 0.0002 ppm 35
and onion
M

THIAZOLINES (DIHYDROTHIAZOLES)
NAME / (SYNONYM) R ± R2 R^
2-Acetyl-2-thiazoline COCH^
2,4-Dimethyl-3-thiazoline CH^ CH^
2,4,5-Trimethyl-3-thiazoline CH^ CH 3 CH 3
2-Propyl-3-thiazoline D- 3 7C H
2-(2-Methylpropyl)-4,5- C H C H (CH,)
? ? CH, CH,
-dimethyl-3-thiazoline *
2-(l-Methylpropyl)-4,5-dimethyl-CH(CH,)C H, 7 CH, CH,

-3-thiazoline * > 1
* y
2-Propyl-2,4,5-trimethyl- n-C,H 7 CH, CH,

-3-thiazoline CH 3

R
£—Ν
' -s
3
O: Cracker-like Ο 1.3 ppb/water 55

O: Freshly baked bread crust 22
F 3 ppb/water 1
F: Nutty, roasted, vegetable F 0.02 ppm F,M,S 92
F: Meaty, nutty, onion-like F 0.5 ppm F,M,S 92

F at 0.2-1 ppm: Fresh chopped
meat-like with light sour effect 97
Τ at 2 ppm: Chemical
Ο at 0.2 ppm: Green, vegetable 97

nutty and roasted
Τ at 0.2 ppm: Sweet, green, vege
table, roasted, cocoa powderlike
Ο at 2 ppm: Sweet, roasted meat 97

like, roasted nut-like, dark chocolate-
-like, baked goods-like and vegetable
green-like
Τ at 2 ppm: Sweet, roasted meat-like,
roasted nut-like, chocolate-like,
vegetable green-like, hydrolyzed
vegetable protein-like.
Having a hydrolyzed vegetable protein
aftertaste and astringent and choco
late-like notes
Ο at 2 ppm: Sweet, herbaceous, spicy, 97

chocolate-like, nutty, vegetable-
-like, hydrolyzed vegetable protein-
-like, roasted
F at 2 ppm: Herbaceous, vegetable,
green-like, nutty, roasted, chocolate-
-like, astringent
Ο at 1 ppm: Sweet, green bean-like, 97

cucumber-like, geranium-like and
spicy
F at 1 ppm: Cucumber-like, green bean-
-like, spicy, watermelon-like, black
pepper-like, astringent

BENZOTHIAZOLES
NAME / (SYNONYM) R^ R 2 R 3
Benzothiazole H
2-(Methylthio)benzothiazole SCH
1,3,5-DITHIAZINES
NAME / (SYNONYM)
ι J
2,4,6-Trimethyldihydro-l,3,5-dithiazine
C H 3 ^ N ^ N
C H 3
H
Ç 2 H 5
2-Ethyl-4,6-dimethyldihydro-l,3,5-dithiazine I J
C H ' ^ N C H 3
H
C H 3
ι ό
4-Ethyl-2,6-dimethyldihydro-l,3,5-dithiazine
C H

O: Quinoline-like, rubbery F 7
Ο: Similar to pyridine 34
O: Heated rubber-like, heavy and dirty 82
O: Imparts characteristic fatty Ο 5 ppb/water F 6, 7

and smoky odor to meat aroma
H 2
O: Roasted beef-like F,M,S 88

Typical note of heated meat 6
O: Cooked beef-like F,S 88
O: Onion-, cooked beef-like F,S 88

ALDEHYDES AND KETONES
NAME / (SYNONYM)
Ethanal CH CHO
3
(Acetaldehyde)
Butanal n-C H CHO

3 7
(Butyraldehyde)

O: Pungent ethereal-nauseating, in F,M,S 17

high dilution reminiscent of coffee
or wine
O: Characteristic pungent and penetrating 23
Ο of GC eluates: Pungent 19
O: Sour, greenhouse 98
Ο 100°C Caramel, sweet
180°C: Burnt sugar 18
O: Green, sweet Ο 0.21 ppm/air ι 50
(recognition) >
Ο 0.12 mg/m Zair 99
Ο 0.041 mg/m /air 3
55
Ο 0.005 mg/m /air 100
23,
141, 142
Ο 15 ppb/water 101
Ο 120 ppb/water 20
F: Green leaves, fruity F 25 ppb/beer 25
F 50 ppm/beer 103
O: Very diffusive, penetrating F,S 17

pungent-irritating
Only in extreme dilution
truly fruity, banana-like,
green-fresh odor
O: Characteristic pungent 23
Ο of GC eluates: Burnt, green, 19
nasty
Ο <0.013 mg/m /air3
104, 105
Ο 0.042 mg/m /air 55
23,
141, 142
Ο 9 ppb/water 106
F in beer: Melon, green leaves, F 1.0 ppm/beer 25
varnish
F 1.0 ppm/beer 103

ALDEHYDES AND KETONES (cont.)
NAME / (SYNONYM)
2-Methylpropanal (CH ) CHCHO

3 2
(Isobutyraldehyde)
2-Methylbutanal CH CH CH(CH )CHO

3 2 3
fcC- Met hy lbu ty raldehy de)
3-Methylbutanal (CH ) CHCH CHO

3 2 2
(Isovaleraldehyde)

O: Extremely diffusive, penetrating F,M,S 17

pungent and undiluted-unpleasant
sour, repulsive. In extreme dilution
almost pleasant, fruity banana-like,
"overripe-fruit-like"
Ο 100°C: Rye bread, fruity, aromatic; 18
180°C: Penetrating chocolate
t 19
98
O: Harsh, grain, baked poatoes

ο 0.14 mg/m /air 104

ο 0.015 mg/m /air 107
0 0.1 ppb/water ι 62
43 ppb/oil '
ο 0.01 ppm/water 20
ο 2.3 ppb/water 102
F in beer: Banans, melon, varnish, F 1 ppm/beer 25
green leaves, bitter
O: Powerful, choking when undiluted, F,M 17

but in extreme dilution tolerable
almost pleasant fruity-"fermented"
with a peculiar note resembling
that of roasted cocoa or coffee.
F: Sweet, slightly fruity-chocolate-like
when diluted to < 20 ppm. Pungent
at higher concentrations
Ο of GC eluates: Burnt, sickly 19
Ο 100°C: Musty, fruity aromatic; 18
180°C: Burnt cheese
1 ppb/water 102
140 ppb/oil 62
F in beer: Green grass, fruity, sour/ 1.25 ppm/beer 25
/medicinal
O: Very powerful, penetrating, acrid- 17

pungent, causes cough-reflexes un
less highly diluted. In extreme di
lution fruity, rather pleasant.
F: Peach-like, heavy fruity at ^10 ppm
Ο 100 C: Sweet, chocolate, toasted
bready;
Ο 180°C: Burnt cheese 18
Ο of GC eluates: Burnt, green, sickly 19
0.2 ppb/water 62
13 ppb/oil
7 ppb/water 20
2 ppb/water 102
0.17 ppm/water 44
F in beer: Unripe banana, apple, 0.6 ppm/beer 25
cherry, cheese

ALDEHYDES AND KETONES (cont.)
NAME / (SYNONYM)
2,3-Butanedione CH COCOCH
3 3
(Diacetyl, dimethylglyoxal)
2,3-Pentanedione CH COCOC H
3 2 5
(Acetylpropionyl)
4-Hydroxy-2,3,5-hexanetrione CH COCOCH(OH)COCH
3 3
(Acetylformoin)

DESCRIPTION THRESHOLD VALUE REM. REFE
O: Very powerful and diffusive, F,M,S 17

pungent, buttery, chlorine-
-quinone-like in high con
centration, oily-buttery in
extreme dilution
O: Quinonic, buttery, chlorine-like 18
F: Sharp
Ο of GC eluates: Buttery, sickly 19
Ο 0.0025 mg/m /air 108
Ο 0.0026 mg/m /air 109

23,
141, 142
Ο 6.5 ppb/water 20
F in beer: Diacetyl, butterscotch F 0.15 ppm/beer 25
O: Buttery, penetrating F 0.1 ppm/beer 98
O: Oily-buttery, pungent and some F,S 17

what "quinone-like", less sharp
and volatile than diacetyl. Weak
aqueous solutions practically
odorless
F aqueous solution: Sweet
Ο of GC eluates: Butter, sickly 19
O: Burnt, grain, malty, burnt butter 1 ppm/beer 98
F in beer: Diacetyl, fruity 0.9 ppm/beer 25
Τ 18 ppm/orange 26
juice

v' 3
R
CYCLOPENTANONES
ι
Ri
NAME / (SYNONYM) R £ R 3 R 4 R 5
2- Methylcyclopentan-l-one =0 CH^
3- Methylcyclopentan-l-one =0 CH^
2-Mercapto-3-methyl-2- =0 SH CH 3
-cyclopenten-l-one
5-Imino-2-methyl-l- OH CH 3 =NH
-cyclopenten-l-ol
5-Imino-4-methyl-l- OH CH 3 =NH
-cyclopenten-l-ol
2-Hydroxy-3-methyl-2- =0 OH CH 3
-cyclopenten-l-one
(Methylcyclopentenolone,
Cyclotene)
3-Ethyl-2-hydroxy-2- =0 OH
-cyclopenten-l-one
(Ethylcyclopentenolone)
3.4- Dimethyl-2-hydroxy-2- =0 OH CH 3 CH 3
-cyclopenten-l-one
3.5- Dimethyl-2-hydroxy-2- =0 OH CH 3 CH 3
-cyclopenten-l-one

CYCLOPENTENONES
1- R ,s '\Γ^ ΤR
Ri
2
- R
ft
5
»i
O: Roasted beef M 78
Ο: Roasted beef M 78
Ο: Seaweed-like M 78
Ο Cooked rice M 78
Ο: Rice cracker M 78
Ο: Fragrant, burnt, licorice 1 F,M,S 18

F: Sweet j
O: Strong caramel-like 42
O: Caramel, maple-like 30
Τ 5 ppm/orange 26
juice
F: Sweet, somewhat similar 23
to licorice
O: Strong caramel-like F,M,S 42

F: Caramel-like, exhibits flavor-
enhancing characteristics 23
O: Strong caramel-like F,M 42
O: Strong caramel-like F,M 42

NON-CYCLIC SULFUR COMPOUNDS
NAME / (SYNONYM)
Hydrogen sulfide HS?

Carbon disulfide CS.
Dimethyl sulfide CH,SCH

(Methyl sulfide, (Methylthio)methane)

O: Very unpleasant, chokingly repulsive F,M,S 17

often described as reminiscent of
"rotten eggs" or "decaying seaweed"
etc.
O: Eggy, suifidy Ο 4.7 ppb/air 50
(H S from Na S)
2 2
(recogn)
0.47 ppb/air
(hLS gasXrecpgn)
0.0001 mg/m /air 112
0.18 mg/m /air , 99
0.00021-0.0016 mg/m j
/air , '
113
0.012 mg/m /air , 114

0.0047-0.009 mg/rri Λ
/air ' 115
23,
141, 142
10 ppb/water 116
5 ppb/water 1
5 ppb/beer 98
O: Diffusive, chokingly repulsive F,S 17
ethereal-sulfuraceous
GC exhaust: Sweet, cabbage-like,
almost herbaceous, slightly green
O: Vegetable, sulf idy 0.21 ppm/ajr (recogn) 50
0.07 mg/m-j/air 117
0.05 mg/m /air, 118
0.08-0.5 mg/m /air 119
23,
141, 142
O: Extremely diffusive, repulsive, F,M,S 17
reminiscent of wild radish, sharp
green, cabbage-like. Only in high
dilution bearable and most accept
able, pleasant, vegetable-like
Ο of GC eluates: Sulfurous, sickly 19
O: Vegetable, sulfidy Ο 1 ppb/air (recogn) 50
ο 0.0094 mg/m /air. 99
ο 0.002-0.03 rag/m /air 113
ο 0.014 mg/m /air 120,
TP 121, 122
ο 0.003 mg/m /air 123
* 23,
141, 142
ο 10 ppb/water 124
ο 0.33 ppb/water 106
ο 1 ppb/water 20
F 12 ppb/water 125
F 0.03 ppb/water 32
F in beer: Cooked vegetable (corn, F 50 ppb/beer 25
onion), garlic, ^ S
F 60 ppb/beer 103
F 0.02 ppb/protein- 32
hydrolysate solution 2%
NON-CYCLIC SULFUR COMPOUNDS (cont.)
NAME / (SYNONYM)
Diethyl sulfide C H .SC H .

? l 7 l
((Ethylthio)ethane) Z 5 Z 5
Dibutyl sulfide n- /. g /. Q-!2

C H sc H
((Butylthio)butane) n y 4 y
Diallyl sulfide CH =CHCH SCH CH=CH

2 2 2 2
(3-(2-Propenylthio)propene)
Dimethyl disulfide CH SSCH 3 3
((Methyldithio)methane,
Methyl disulfide)
Diethyl disulfide C I-LSSC H,

? 7
((Ethyldithio)ethane) Δ
^ L 5
Dipropyl disulfide n-C^SSC^-n

((Propyldithio)propane)

Ο 0.010 mg/m Zair F,M 99

Ο 0.0045 mg/xn /air 117
Ο 0.31 mg/m /air 126
23,
141, 142
F in beer: Cooked vegetable (onion, F 1.2 ppb/beer 25
garlic), ^ S
F 3 ppb/beer 103
0.09 mg/m /air 99
F in beer: Rubber, rotten onion, 0.002 ppb/beer 25
sulfury
O: Powerful, penetrating garlic- F,S 17

radish-like of poor tenacity
Not a lachrymator, but produces
some irritation of eyes and mucous
membrane
F: Green and sharper than diallyl di
sulfide
Ο 0.00065 mg/m /air 99
O: Intensely onion-like, very dif F,M,S 17
fusive, nonlachrymatory
Ο of GC eluates: Sulfurous, sickly, 19
cooked cabbage
Ο 0.003-0.014 mg/m /air 113
23,
141, 142
Ο 12 ppb/water 129
F 30 ppb/water 1
F 21 ppb/water 130
F 0.06 ppb/water 32
F 3 ppb/beer 103
F 0.6 ppb/skim milk 32
hydrolysate solu
tion 2%
Ο 0.0003 mg/m /air
3
F,M 131
23,
141, 142
F 30 ppb/water 1
F in beer: Garlic, burnt rubber, H^S F 0.4 ppb/beer 25
O: Very penetrating and powerful, F,S 17
diffusive, of garlic/onion type
but with no lachrymatory effect.
Poor tenacity. In extreme di
lution more herbaceous-green
than truly sulfuraceous.
F: Cooked onions F 3.2 ppb/water 80

NAME (SYNONYM)
Diallyl disulfide CH =CHCH SSCH CH=CH

2 2 2 2
(3-(2-Propenyldithio)propene)
Methyl propyl disulfide CH SSC H -n

3 3 7
(1 -(Methy ldi thio)propane)

Methyl propenyl disulfide CH SSCH=CHCH

3 3
(1 - (Methy ldi thi o)propene)
Propyl propenyl disulfide fi-C H SSCH=CHCH

3 7 3
(l-(Propyldithio)propene)
Dimethyl trisulfide CH SSSCH

3 3
(Methyl trisulfide,
(Methyltrithio)methane)
Dipropyl trisulfide n-C H SSSC H -n

3 7 3 7
(1 -(Propyltr ithio)propane)
Methyl propyl trisulfide CH SSSC H -n

3 3 ?

O: Pungent, not truly reminiscent of F,S 17

garlic, but heavier, more sulfide-
-like, obnoxious
Taste - Only in extreme dilutions
resembling that of garlic
O: Characteristic garlic 23
Ο 0.0072 mg/m /air 99
O: Powerful penetrating sulfuraceous F,S 17

herbaceous of onion-type, but non-
lachrymatory and not very tenacious,
In extreme dilution sweet and more
pleasant "natural" odor

F: Almost identical to its odor
F: Cooked onions 23
O: Powerful, diffusive, penetrating, F,M,S 23

reminiscent of fresh onions
Ο of GC eluates: Sulfurous, burnt, 19
cooked cabbage
0.0073 mg/m /air (recogn) 132
0.01 ppb/water 129
F 3 ppb/water 1
O: Very powerful and diffusive, F,S 17

garlic-like, penetrating and
repulsive when undiluted, but in
extreme dilution rather pleasant,
sweet-herbaceous, distinctly
garlic-like
O: Onion 83
O: Very powerful and penetrating, F,S 17

warm-herbaceous-oily of onion-
-like character, particularly upon
dilution.
F in cone. Ο ppm: Sweet, onion-like
and warm-oily

NON-CYCLIC SULFUR COMPOUNDS
NAME / (SYNONYM)
Methanethiol CH SH
3
(Methyl mercaptan)
Ethanethiol C^SH
(Ethyl mercaptan)
1-Propanethiol n-C H SH3 7
(Propyl mercaptan)

O: Rotten cabbage, very diffusive F,M,S 17

and objectionable
Ο of GC eluates: Sickly, sulfurous, 19
cooked cabbage
O: Sulfidy, pungent Ο 2.1 ppb/air irecogn) 50
Ο 0.081mg/m /air 99
Ο 0.0005 mg/myair 133
Ο 0.0002 mg/ra /air 123
Ο 0.003 mg/m /air 134
23,
141, 142
F in beer: Putrefaction (of egg, F 2 ppb/water 25

cabbage), drains, estery
O: Earthy, sulfidy Ο 1.0 ppb/air (recogn) F,M 50

Ο 0.00^066-0.0076 mg/ 99
/m /air ,
Ο 0.0001 mg/m Xair 135
Ο 0.00065 mg/m /air 136
23,
141, 142
Ο 0.016 mg/m /air 134
F 0.008 ppb/water 32
F in beer: Putrefaction (of leek, F 1.7 ppb/beer 25
onion, garlic, egg)
F 0.01 ppm/beer 98
hydrolysate solu
tion 2%
O: Very powerful, penetrating and F,M,S 17

diffusive, cabbage-like, sulfur-
aceous, unpleasant unless extreme
ly diluted
F in cone. < 1 ppm: Sweet onion-
cabbage-like, not unpleasant
Ο 0.005 mg/m /air, 99
Ο 0.07-0.03 mgim /air 137
Ο 0.0016 mg/m /air 138
Ο 0.018 mg/m.j/air 134
* 23,
141, 142
F 0.06 ppb/water 32
F in beer: Putrefaction (of onion, F 0.15 ppb/beer 25
garlic, egg)
hydrolysate solu
tion 2%

276 MAILLARD RE ACTIONS
NON-CYCLIC SULFUR COMPOUNDS (cont)
NAME / (SYNONYM)
1-Butanethiol fi- 4 9
C H S H
(Butyl mercaptan)
2-Methyl-l-propanethiol i-C^h^SH
(Isobutyl mercaptan)
1-Hexanethiol n-C^H^-jSH
(Hexyl mercaptan)
3-Methyl-l-butanethiol CH CH(CH )CH CH SH

3 3 2 2
(Isopentyl mercaptan)
(CH ) C=CHCH SH
3-Methyl-2-butene-l-thiol 3 2 2
1-(Methy lthio)-l-ethanethiol CH CH(SHXSCH )

3 3
1-(Methy lthio)-l-propanethiol CH CH CH(SHXSCH )

3 2 3
1 -(Methy lthio)-1 -hexanethiol n- 5H CH(SHXSCH )

C
i:L 3
l-(Ethylthio)-l-ethanethiol CH CH(SHXSC H )
3 2 5

O: Powerful, diffusive, reminiscent of F,S 17

cabbage. Often described as skunk
like or just sulfuraceous. In extreme|
dilution intensely sweet and non
descript
Taste slightly bitter
Ο 0.0037 mg/m /air, 99
Ο 0.007-0.04 rag/m /air 137
Ο 0.003 mg/m /air
3 138
Ο 0.003 mg/m /air 139
23,
141, 142
Ο 6 ppb/water 51
F 0.004 ppb/water 32
garlic, egg)
0.8 ppb/skim milk 32
0.001 ppb/protein- 32
hydrolysate solu
tion 2%
0.000002-0.0002 mg/ F 135
/m /air ,
0.007 mg/m /air 134
23,
141, 142
garlic, egg)
O: Extremely powerful and diffusive F,S 17
Ο 0.00002 mg/m /air 139
23,
141, 142
O: Repulsive, characteristic mer- F,S 23
captan-like
Ο 0.0018 mg/m /air 99
Intense leek or onion-like- This M 7

compound is responsible for the
skunky odor of "sunstruck beer"
O: Strong, meaty, onion-like F,M 7

Ο in very aqueous solutions 1-5 ppb: \
Meaty rather than onion-like 1 140
F 5 ppb/water
1
F dissolved in water: Allium (onion), M
meaty 89
F dissolved in water: Allium (onion) M 89

black currant, rhubarb and green
bell pepper
F dissolved in water: Allium (onion, M 89

leek), black currant

NAME / (SYNONYM)
1 -(Propylthio)-1 - propanethiol C H CH(SHXSC H )

2 5 3 ?
Bis(l-mercaptoethyl) sulfide CH CH(SH)SCH(SH)CH

3 3
Bis(l-mercaptopropyl) sulfide C H CH(SH)SCH(SH)C H

2 5 2 5
Bis(l-mercaptoisobutyl) sulfide i-C H CH(SH)SCH(SH)i-C H

3 7 3 7
Bis(l-mercaptohexyl) sulfide n-C H CH(SH)SCH(SH)C H - η

5 11 5 11
3-(Methylthio)-l-propanol CH S(CH ) OH
3 2 3
(Methionol, methyl 3-
-hydroxypropyl sulfide)
3-Methylthio-l-hexanol CH (CH ) CH(SCH XCH ) OH

3 2 2 3 2 2
[Methylthio)propan
3-(Methylthio)propanal CH,SCH CH CHO 2 2
[Methional,
[Methional, 3-(Mel
3-(Methylthio)-
propionaldehyde]
3-(Methylthio)hexanal C H CH(SCH )CH CHO

3 7 3 2
1-Methy lthio-2-butanone C H COCH SCH

2 5 2 3

F dissolved in water: Allium (onion), M 89

black currant
F dissolved in water: Allium (onion, M 89

chives), meaty
F dissolved in water: Green, fruity, M 89

Allium (onion, garlic)

mushroom and soup

green, fatty
Ο and F: Powerful, sweet, soup- or meat- F,S 17

-like
O: In undiluted form displays a rather
repulsive odor with perceptible
notes of sulfuraceous character.
Extreme dilution causes a marked
improvement to agreeable and
pleasant, food-like note.
Green, fatty and sulfury note F 7
O: Powerful and diffusive onion-meat- F,M,S 17

-like, in dilution more pleasant, less
onion-like, reminiscent of bouillon
F 5 ppm: Pleasant, warm meat- or soup-
-like, at higher cone, with a slight
"bite" or pungency
Ο 100°C or 180 C; Potato 18
O: Cooked-cabbage ι F 0.05 ppm/water 130
F: "Sunlight" flavor J
F 10 ppb/water 1
Ο 0.2 ppb/water j 62
0.2 ppb/oil
F in beer: Mashed potato, warm, 250 ppb/beer 25
soup-like
F dissolved in water: Strongly green, M 89

privet
O: Reminiscent of mushroom, with a F,S 23

characteristic garlic undertone
O: Mushroom-like 31

NAME / (SYNONYM)
4-Mercapto-4-methyl-2-pentanone CH C(SH)(CH )CH COCH

3 3 2 3
Methyl 3-(methylthio)propionate ChLSCr-LChLCOOCH,

S-Methyl thiohexanoate CH SCO(CH ) CH

3 2 4 3
S-Methyl thioheptanoate CH SCO(CH ) CH

3 2 5 3

O: Unpleasant odor of cat urine F 7
Ο: Extremely powerful, diffusive F,M,S 17

penetrating sweet, sulfuraceous,
only in dilution becoming endur
able and fruity-sweet. Its onion
like character in high cone, changes
to "cooked"-fruity in minute cone.
F: Fruity-sweet, pineapple-like in cone.
< 5 ppm, most pleasant <1 ppm. The
flavor is clearly perceptible and
agreeable well below 0.1 ppm
Ο 0.3 ppb/water F 123
Ο 2 ppb/water F 123

Literature Cited
1. Schutte, L. CRC Crit. Rev. Food Technol. 1974, 4, 457-505.
2. Nursten, H.E. Food Chem. 1980-81, 6, 263-277.
3. Vernin, G. Parfums, Cosmétiques, Arômes, 1980, (32, April-May),
77-89.
4. Maga, J.; Sizer, C. CRC Crit. Rev. Food Technol. 1973, 39-115.
5. Maga, J. J. Agric. Food Chem. 1981, 29, 691-694.
6. Ohloff, G; Flament, I. Heterocycles 2, 1978, 663-695.
7. Ohloff, G.; Flament, I. Fortschr. Chem Org. Naturst. 1978, 36,
231-283.
8. Shibamoto, T. J. Agric. Food Chem. 1980, 28, 237-243.
9. Suyama, K.; Adachi, S. J. Agric. Food Chem. 1980, 28, 546-549.
10. Maga, J.; Sizer, C. J. Agric. Food Chem. 1973, 21, 22-30.
11. Maga, J. CRC Crit. Rev. Food Sci. Nutr. 1982, 13, 1-48.
14. Maga, J. J. Agric. Food Chem. 1978, 26, 1049-1050.
15. Maga, J. CRC Crit. Rev. Food Sci. Nutr. 1981, 12. 295-307.
17. Arctander, S. "Perfume and Flavor Chemicals", Vol. I, II; published
by the author, Montclair, NJ, USA, 1969.
18. Hodge, J. "Chemistry and Physiology of Flavors"; Schultz, H.W.;
Day, E.A.; Libbey, L.M., Eds.; AVI Publishing Co., Westport, Conn.,
1967; pp. 465-491.
19. Persson, T.; von Sydow, E. J. Food Sci. 1973, 38, 377-385.
20. Mulders, J. Z. Lebensm. Unters.-Forsch. 1973, 151, 310-317.
21. Evans, C.D.; Moser, H.A.; List, G.R. J. Am. Oil Chem. Soc. 1971,
48, 495-498.
22. Baltes, W. Deut. Lebensm. Rundschau 1979, 75, 2-7.
23. "Fenaroli's Handbook of Flavor Ingredients", 2nd ed., Vol. I; Furia,
T.E.; Bellanca, N., Eds. CRC Press, Inc., Cleveland, Ohio, 1975.
24. Buttery, R.; Seifert, R.; Guadagni, D.; Ling, L. J. Agric. Food
Chem. 1969, 17, 1322-1327.
25. Meilgaard, M. Master Brew. Ass. Am. Techn. Quart. 1975, 12, (3),
151-168.
26. Shaw, P.; Tatum J.; Kew, T.; Wagner, C.Jr.; Berry, R. J. Agric.
Food Chem. 1970, 18, 343-345.
27. Brulé, G.; Dubois, P.; Obretenov, T. Ann. Technol. Agric. 1971, 20,
305-312.
28. Sakaguchi, M.; Shibamoto, T. J. Agric. Food Chem. 1978, 26,
1260-1262.
29. Baltes, W. Lebensmittelchem. gerichtl. Chem. 1980, 34, 39-47.
30. Shigematsu, H.; Shibata, S.; Kurata, T.; Kato, H.; Fujimaki, M. J.
Agric. Food Chem. 1975, 23, 233-237.
31. Ouweland, G.; Peer, H. J. Agric. Food Chem. 1975, 23, 501-505.
32. Golovnja, R.V.; Rothe, M. Nahrung 1980, 24, 141-154.
33. Rödel, W.; Kruse, H-P. Nahrung 1980, 24, 129-139.
34. Vernin, G. Ind. Aliment. Agric. 1980, 97, 433-449.

35. Vernin, G. Parfums, Cosmétiques, Arômes, 1979, (29, June-July),

77-87.
36. Mulders, Ε.; Kleipool, R.; ten Noever de Brauw, M.C. Chem. Ind.
(London) 1976, 613-614.
37. Shibamoto, T. J. Agric. Food Chem. 1977, 25, 206-208.
38. Manley, C.; Wittack, M.; Fagerson, I. J. Food Sci. 1980, 45, 1096,
1098.
39. Pittet, Α.; Rittersbacher, P.; Muralidhara, R. J. Agric. Food
Chem. 1970, 18, 929-933.
40. Nunomura, N.; Sasaki, M.; Yokotsuka, T. Agric. Biol. Chem. 1980,
44, 339-351.
41. Pyysalo, T. "Studies on the Volatile Compounds of Some Berries in
Genus Rubus, Especially Cloudberry (Rubus chamaemorus L.) and
Hybrids between Raspberry (Rubus ideaeus L.) and Artie bramble
(Rubus arcticus L.)". Materials and Processing Technology, Tech
nical Research Centre of Finland, Publication No. 14, Helsinki,

1976.
42. Shaw, P.; Tatum, J.; Berry, R. J. Agric. Food Chem. 1968, 16.
979-982.
43. Shimazaki, H.; Tsukamoto, S.; Saito, T.; Eguchi, S.; Komata, Y.
U.S. 4,013,800 (1977).
44. Keith, E.; Powers, J. J. Food Sci. 1968, 33, 213-218.
45. Lee, K.; Ho, C-T.; Giorlando, C.; Peterson, R.; Chang, S. J. Agric.
Food Chem. 1981, 29, 834-836.
46. Tressl, R. Monatsschr. Brau. 1979, 32, (5), 240-246, 248.
47. Ho, C-T.; Jin, Q.Z.; Lee, K.; Carlin, J. J. Agric. Food Chem. 1982,
30, 362-364.
48. Ho, C-T.; Jin, Q.Z.; Lee, K.; Carlin, J. Lebensm.-Wiss.u.-Technol.
1982, 15, 169-170.
49. Yoshikawa, K.; Libbey, L.M.; Cobb, W.Y.; Day, E.A. J. Food Sci.
1965, 30, 991-994.
50. Leonardos, G.; Kendall, D.; Barnard, N. J. Air Pollut. Control
Assoc. 1969, 19, 91-95.
51. Baker, R. J. Am. Water Works, Assoc. 1963, 55, 913-916.
52. Pittet, Α.; Hruza, D. J. Agric. Food Chem. 1974, 22, 264-269.
53. Polak's Frutal Works N.V., Douwe Egberts Koninklijke Tobaks-
fabrik - Koffiebranderijen - Theehandel. Brit. 1,248,380 (1971).
54. Buttery, R.; Ling, L.; Teranishi, R.; Mon, T. J. Agric. Food Chem.
1977, 25, 1227-1229.
55. Teranishi, R.; Buttery, R.; Guadagni, D. "Geruch- und Geschmack-
stoffe", Int. Symp.; Bad Pyrmont, 1974; Drawert, F., Ed.; Verlag
Hans Carl, Nürnberg, 1975; pp. 177-186.
56. Seifert, R.; Buttery, R.; Guadagni, D.; Black, D.; Harris, J. J.
Agric. Food Chem. 1972, 20, 135-137.
57. Hunter, I.; Walden, M.; Scherer, J.; Lundin, R. Cereal Chem. 1969,
46, 189-195.
58. Calabretta, P. Perfumer Flavorist 1978, 3, June/July, 33-42.
59. Calabretta, P. Cosmetics Perfumery 1975, 90, June, 74, 76, 79-80.
60. Collins, E. J. Agric. Food Chem. 1971, 19, 533-535.
61. Koehler, P.E.; Mason, M.E.; Odell, G.V. J. Food Sci. 1971, 36,
816-818.

62. Guadagni, D.; Buttery, R.; Turnbaugh, J. J. Sci. Food Agric. 1972,
23, 1435-1444.
63. Seifert, R.; Buttery, R.; Guadagni, D.; Black, D.; Harris, J. J.
Agric. Food Chem. 1970, 18, 246-249.
64. Takken, H.; van der Linde, L.; Boelens, M.; van Dort, J. J. Agric.
Food Chem. 1975, 23, 638-642.
65. Sizer, C.E.; Maga, J.A.; Lorenz, K. Lebensm.-Wiss.u. -Technol.
1975, 8, 267-269.
66. Tressl, R.; Renner, R.; Kossa, T.; Köppler, H. European Brewery
Convention, 16th Congress Proc. 1977, 693-707.
67. Deck, R.E.; Chang, S.S. Chem. Ind. (London) 1965, 1343-1344.
68. Fenaroli, G. Riv. Ital. E.P.P.O.S 1978, 60, 1-16.
69. Coleman, E.; Ho, C-T. J. Agric. Food Chem. 1980, 28, 66-68.
70. Boyko, Α.; Morgan, M.; Libbey, L. "Analysis of Food and Beverages;
Headspace Techniques," Charalambous, G. (Ed.), Academic Press:
New York, 1978; pp. 57-79.

71. Kitamura, K.; Shibamoto, T. J. Agric. Food Chem. 1981, 29,
188-192.
72. Roberts, D. (R.J. Reynolds Tobacco Company), U.S. 3,402,051
(1968).
73. Parliment, T.; Epstein, M. J. Agric. Food Chem. 1973, 21,
714-716.
74. Murray, K.; Shipton, J.; Whitfield, F. Chem. Ind. (London) 1970,
897-898.
75. Masuda, H.; Yoshida, M.; Shibamoto, T. J. Agric. Food Chem.
1981, 29, 944-949.
76. Evers, W.; Katz, I.; Wilson, R.; Thelmer, E. (International Flavors
and Fragrances, Inc.) U.S. 3,647,792 (1972).
77. Pittet, Α.; Muralidhara, M.; Thelmer, E. (International Flavors and
Fragrances, Inc.) U.S. 3,705,158 (1972).
78. Nishimura, O.; Mihara, S.; Shibamoto, T. J. Agric. Food Chem.
1980, 28, 39-43.
79. Arnold, R.; Libbey, L.; Lindsay, R. J. Agric. Food Chem. 1969, 17,
390-392.
80. Boelens, M.; de Valois, P.; Wobben, H.; van der Gen, A. J. Agric.
Food Chem. 1971, 19, 984-991.
81. Ho, C.; Coleman, E. J. Food Sci. 1980, 45, 1094-1095.
82. Peterson, R.; Izzo, H.J.; Jungermann, E.; Chang, S. J. Food Sci.
1975, 40, 948-954.
83. Tokarska, B.; Karwowska, K. Nahrung 1981, 25, 565-571.
84. Walker, N.; Gray, I. J. Agric. Food Chem. 1970, 18, 346-352.
85. Tressl, R.; Bahri, D.; Holzer, M.; Kossa, T. J. Agric. Food Chem.
1977, 25, 459-463.
86. Shu, C-K.; Mookherjee, B.; Vock, M. (International Flavors and
Fragrances, Inc.) U.S. 4,259,507 (1981).
87. Chang, S.S.; Hiriai, C.; Reddy, B.R.; Herz, K.O.; Kato, A. Chem.
Ind. (London) 1968, 1639-1641.
88. Kubota, K.; Kobayashi, Α.; Yamanishi, T. Agric. Biol. Chem. 1980,
44, 2677-2682.
89. Boelens, M.; van der Linde, L.; de Valois, P.; van Dort, H.; Takken,
H. J. Agric. Food Chem. 1974, 22, 1071-1076.

90. Lee, M-H.; Ho, C-T.; Chang, S. J. Agric. Food Chem. 1981, 29,
686-688.
91. Ho, C-T.; Tuorto, R. J. Agric. Food Chem. 1981, 29, 1306-1308.
92. Mussinan, C.J.; Wilson, R.A.; Katz, I.; Hruza, Α.; Vock, M.H. ACS
Symp. Series 1976, 26, 133-143.
93. Hetzel, D.S. (Pfizer Inc.) Ger. Offen. 2,120,577 (1971); Chem.
Abstr. 76 (1972), 72505.
94. Kazeniac, S.; Hall, R. J. Food Sci. 1970, 35, 519-530.
95. Buttery, R.; Seifert, R.; Guadagni, D.; Ling, L. J. Agric. Food
Chem. 1971, 19, 524-529.
96. Buttery, R.; Guadagni, D.; Lundin, R. J. Agric. Food Chem. 1976,
24, 1-3.
97. Vock, M.; Giacino, C.; Hruza, Α.; Withycombe, D.; Mookherjee, B.;
Mussinan, C. (International Flavors and Fragrances, Inc.) U.S.
4,243,688 (1981).
98. Palamand, S.R.; Hardwick, W.A. Master Brew. Ass. Am. Techn.
Quart. 1968, 6, 117-128.
99. Katz, S.H.; Talbert, E.J. U.S. Bureau of Mines, Technical Report
No. 480 (1930).
100. Hartung, L.D.; Hammond, E.G.; Miner, J.R. Livest. Waste Manage.
Pollut. Abatement, Proc. Int. Symp., 1971, 105-106.
101. "Flath, R.A.; Black, D.R.; Guadagni, D.G.; Me Fadden, W.H.;
Schultz, T.H. J. Agric. Food Chem. 1967, 15, 29-35.
102. Amoore, J.E.; Forrester, L.J.; Pelosi, P. Chem. Senses Flavor,
1976, 2, 17-25.
103. Harrison, G. J. Inst. Brew. 1970, 76, 486-495.
104. Hellman, T.M.; Small, F.H. Chem. Eng. Progr. 1973, 69, 75-77.
105. Hellman, T.M.; Small, F.H. J. Air Pollut. Contr. Assoc. 1974, 24,
979-982.
106. Guadagni, D.; Buttery, R.; Okano, S. J. Sci. Food Agric. 1963, 14,
761-765.
107. Amoore, J.E. Chem. Senses Flavor 1977, 2, 267-281.
108. van Anrooij, A. "Desodorisatie langs photochemischen weg",
Thesis, Utrecht, 1931.
109. Appel, L. Am. Perfum. Cosmet. 1969, 84, 45-50.
110. Sega, G.M.; Lewis, M.J.; Woskow, M.H. Proc. Am. Soc. Brew.
Chem. 1967, 156-164.
111. Stahl, W.H. "Compilation of Odor and Taste Threshold Values
Data". ASTM Data Series DS 48, 1973.
112. Henning, H. "Der Geruch", 2nd Ed. Barth, Leipzig, 1924.
113. Lindvall, T. Nord. Hyg. Tidskr. 1970, 51, Suppl. 2, 1-181.
114. Randebrock, E.M. "Gustation and Olfaction"; Ohloff, G.; Thomas,
A.F., Eds.; Academic Press: London/New York, 1971; pp. 111-125.
115. Adams, D.F.; Young, F.A.; Luhr, R.A. Tappi 1968, 51, 62A - 67A.
116. Pippen, E.L.; Mecchi, E.P. J. Food Sci. 1969, 34, 443-446.
117. Deadman, K.A.; Prigg, J.A. Research Communication GC 59, The
Gas Council, London, 1959.

118. Hildenskiold, R.S. Gig. Sanit. 1959, 24, (6), 3-8 (in Russ.).
119. Baikov, B.K. Gig. Sanit. 1963, 28, (3), 3-8 (in Russ.).
120. Laffort, P. "Theories of Odor and Odor Measurement; Tanyolac,
N.N., Ed; Robert College: Bebek, Istanbul, 1968; pp. 247-270.
121. Laffort, P. Olfactologica 1968, 1, 95-104.
122. Laffort, P.; Dravnieks, A. J. Theor. Biol. 1973, 38, 335-345.
123. Guadagni, D.; Buttery, R.; Harris, J. J. Sci. Food Agric. 1966, 17,
142-144.
124. de Grunt, F.E. National Institute for Water Supply. Voorburg,
Netherlands, 1975, (unpublished data).
125. Patton, S.; Forss, D.A.; Day, E.A. J. Dairy Sci. 1956, 39,
1469-1470.
126. Ifeadi, N.G. "Quantitative measurement and sensory evaluation of
dairy waste odor". Thesis, Ohio State Univ., Columbus, 1972.
127. Kauffmann, M. Z. Sinnesphysiol. 1907, 42, 271-280.
128. Amoore, J.E.; Venstrom, D. J. Food Sci. 1966, 31, 118-128.

129. Buttery, R.; Guadagni, D.; Ling, L.; Seifert, R.; Lipton, W. J.
Agric. Food Chem. 1976, 24, 829-832.
130. Patton, S. J. Dairy Sci. 1954, 37, 446-452.
131. Zwaardemaker, H. "Handbuch der physiologischen Metodik III;"
Vol. 1, Tigerstedt, R. Ed.; S. Hirzel, Leipzig, 1914, pp. 46-108.
132. Wilby, F.V. J. Air Pollut. Control Assoc. 1969, 19, 96-100.
133. Freudenberg, K.; Reichert, M. Tappi, 1955, 38, 165A-166A.
134. Blanchard, J. Gas (Rome) 1976, 26, 287-309.
135. Stuiver, M. "Biophysics of the sense of smell." Thesis, Groningen,
1958.
136. Endo, R.; Kohgo, T.; Oyaki, T. "10. Research on odor nuisance in
Hokkaido (part 2). Chemical analysis of odors." Proc. 8th Annual
Meeting Japan Society of Air Pollution, Symposium (1): Hazard
nuisance pollution problems due to odors (English translation for
APTIC by SCITRAN), 1967.
137. Blinova, A.E. Hyg. Sanit. USSR. 1965, 30, 18-22.
138. Kniebes, D.V.; Chisholm, J.A.; Stubbs, R.C. Gas (Rome) 1969, 19,
211-217.
139. Patte, F. "Le Codage Moléculaire de la Stimulation Olfactive
- Clarifications et mises au point." Thesis, Lyon, 1978.
140. Brinkman, H.; Copier, H.; de Leuw, J.M.; Sing, Boen Tjan. J.
Agric. Food Chem. 1972, 20, 177-181.
141. van Gemert, L.J.; Nettenbreijer, A.H., Eds. "Compilation of Odor
Threshold Values in Air and Water". National Institute for Water
Supply, Voorburg, Netherlands. Central Institute for Nutrition and
Food Research, TNO, Zeist, Netherlands, 1977.
142. van Gemert, L.J.; Belz, R.; van Straten, S.; Jetten, J. "Compilation
of Odor Threshold Values in Air." Supplement III. Report No. R.
6633. Central Institute for Nutrition and Food Research, TNO,
Zeist, Netherlands, 1980.
RECEIVED December 14, 1982


Sensory Properties of Volatile Maillard Reaction Products and Related Compounds

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12

Sensory Properties of Volatile Maillard Reaction

In r e c e n t d e c a d e s a l a r g e n u m b e r of papers and r e v i e w s about r e s e a r c h on

In The Maillard Reaction in Foods and Nutrition; Waller, G., et al.;

The t h r e s h o l d values g i v e n by d i f f e r e n t i n v e s t i g a t o r s vary c o n s i d e r -

The v o l a t i l e c o m p o u n d s f o r m e d by the M a i l l a r d r e a c t i o n are only one group

1) ' S i m p l e ' sugar d e h y d r a t i o n / f r a g m e n t a t i o n p r o d u c t s :

In The Maillard Reaction in Foods and Nutrition; Waller, G., et al.;

A m o n g the h e t e r o c y c l i c s t h e r e is one group w h i c h w i l l be t h o r o u g h l y

T h e r e are other c o m p o u n d s than h e t e r o c y c l i c s that also d e s e r v e a t t e n t i o n :

P y r a n o n e s , f u r a n o n e s , and r e l a t e d c o m p o u n d s (6, 7). Structurally

In The Maillard Reaction in Foods and Nutrition; Waller, G., et al.;

Pyrroles (5 - 8). About fifty members of this group have

P y r i d i n e s (6, 9). P y r i d i n e s have been found in c o f f e e , b a r l e y and

P y r a z i n e s (4, 6, 10, 11). The pyrazines constitute a very

Sulfur compounds S u l f u r - c o n t a i n i n g v o l a t i l e s c o n t r i b u t e to both

• O x a z o l e s and O x a z o l i n e s (14, 15)

In The Maillard Reaction in Foods and Nutrition; Waller, G., et al.;

N o t a t i o n , s y m b o l s and a b b r e v i a t i o n s used in the f o l l o w i n g t a b l e s :

S y n o n y m s are at t i m e s g i v e n , e s p e c i a l l y when a c c e p t e d t r i v i a l n a m e s exist

F s i g n i f i e s F l a v o r , i.e. odor and taste t o g e t h e r (the senses of s m e l l and

Ο s i g n i f i e s O d o r , i.e. a p r o p e r t y p e r c e i v e d through the sense o f s m e l l

L e a v i n g out one or both of these l e t t e r s s i g n i f i e s l a c k of such i n f o r m a t i o n ,

T h e s e values are usually e v a l u a t e d through the sense of s m e l l ; they are

Ο 0.05 p p b / w a t e r the odor threshold of an a r o m a c o m p o u n d

Τ 150 p p m / w a t e r the t a s t e threshold of a c o m p o u n d in b e e r

* F o r further values, see r e f e r e n c e s N o s . 23, 141, and 142.

M f o r M o d e l S y s t e m , i.e. the c o m p o u n d has been i d e n t i f i e d in a

S f o r S y n t h e t i c , i.e. the c o m p o u n d has been s y n t h e s i z e d .

In The Maillard Reaction in Foods and Nutrition; Waller, G., et al.;

2-Furfuryl methyl ether ChLOCH

In The Maillard Reaction in Foods and Nutrition; Waller, G., et al.;

O: Peculiar spice-smoky, F,M,S, 17

O: Powerful sweet, burnt; F,S 17

O: Mild, sweet, fruity-caramellic, F,S 17

In The Maillard Reaction in Foods and Nutrition; Waller, G., et al.;

2-Furfuryl methyl sulfide CH SCH 2 3

2-Furfuryl acetate CH OCOCH 2 3

2-Furfuryl propionate CH OCOC H 2 2 5

2-Ethyl furoate COOC H 2 5

(2-Furancarboxylic acid, ethyl ester)

(2-Furyl hydroxymethyl ketone)

In The Maillard Reaction in Foods and Nutrition; Waller, G., et al.;

DESCRIPTION THRESHOLD VALUE REM. REF

O: Burnt, buttery, vanilla-like F 6

Τ >200 ppm/ orange juice 26

In The Maillard Reaction in Foods and Nutrition; Waller, G., et al.;

2,5-Diformylfuran CHO CHO

2-(l,2-Dioxopropyl)-5-methylfuran COCOCH^ CH,

In The Maillard Reaction in Foods and Nutrition; Waller, G., et al.;

DESCRIPTION THRESHOLD VALUE REM. REF

O: Sweet-spicy, warm and slightly

F > 100 ppm/water M,S 27

Ο: Burnt, pungent, fruity

O: Caramel F 2 ppm/water M,S 27

O: Like roasted rye bread F 22

O: Nut-like, bitter almond-like F 22

Continued on next page

In The Maillard Reaction in Foods and Nutrition; Waller, G., et al.;

S-Methyl 2-thiofuroate COSCH 3

(2-Thiofuroic acid, methyl ester)

5-Methylthio-2-furaldehyde CHO SCH 3

S-2-Furfuryl thioacetate CH SCOCH 2 3

O: Penetrating amine-type remini F,S 17