2020 Savory E-book

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SAVORY
-R
 eaction Systems

-C
 ooking with Alliums
Sponsored by:

-A
 ncient Chemistry,
Modern World
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Editor’s Note
EDEN STUART
Associate Managing Editor
estuart@allured.com
2020 SAVORY E-BOOK
CONTENTS
4 Editor’s Note
by Eden Stuart
5 Savory Flavors: Reaction Systems
by Claus O. Schmidt, Gerhard E. Krammer,
Berthold Weber, Detlef Stöckigt, Klaus
Herbrand, Frank Ott, Günter Kindel, Stefan
Brennecke, Ian L. Gatfield and Heinz-
Jürgen Bertram, Symrise GmbH & Co. KG
14 Flavor Bites: 2,4,6-Trimethyl-
dihydro-4H-1,3,5-dithiazine
by John Wright
19 Cooking With Alliums
by Shane McDonald, Meghan Peltz and
David Bolliet, Kalsec
30 Flavor Bites: trans-2-Octenal
by John Wright
33 Flavor Bites: sec-Butylamine
by John Wright
36 Reaction Flavor Solutions – Ancient
Chemistry for the Modern World
by Luke Grocholl, Ph.D.
4 Editor’s Note 2020 Savory Flavors Ebook | www.berjeinc.com www.PerfumerFlavorist.com
Welcome to the Savory E-Book
T
hough I may personally be in possession of a sweet tooth, there’s
no denying that savory flavors are a force to be reckoned with:
a report from MarketsandMarkets estimated the global savory
ingredients market to be valued at $7.2 billion in 2020, projected to
reach $9.3 billion by 2025 growing at a CAGR of 5.2%a.
One of the fastest-growing segments that calls for savory flavoring is
plant-based meats, which drew in sales of more than $800 million in 2019b.
Though not always the case, consumers often desire these products to
provide them meat-like taste and textures, without the environmental or
health ramifications—consider it the best of both worlds.
Snacking, a popular category for savory (including applications such as
potato chips, pretzels and popcorn), saw a remarkable uptick as COVID-19
drastically increased the amount of time individuals spent at home—and, by
extension, close to their pantries. During the week of March 15, 2020, snack
sales grew 40% year over yearc.
The growing pet food market is also a savory driver. As Amy Marks-
McGee noted in “Forward Thinking: Top Dawg,” appearing in the November
2019 issue of Perfumer & Flavorist, millennial consumers’ desire for healthy
options for their “fur babies” has helped drive the 70% jump in fresh pet food
sold in grocery and pet stores between 2015 and 2018. Flavors for fur friends
often include poultry, fish and beef.
All of these applications create unique challenges, ones we hope to help
formulators address with this e-book, sponsored by Berjé and featuring
articles by Perfumer & Flavorist’s expert authors. We hope you enjoy.
Best,
D. Eden Stuart
a https://www.marketsandmarkets.com/Market-Reports/savory-ingredients-market-193325783.html
b https://www.statista.com/statistics/771457/plant-based-food-sales/
c https://www.statista.com/statistics/1115318/coronavirus-core-snacking-sales-growth-us/
 Savory Flavors Vol. 30 • March/April 2005

Reaction Systems
Identification and formation of thiazolidines
and thiazolines in fried chicken liver

by Claus O. Schmidt, Gerhard E. Krammer,

Berthold Weber, Detlef Stöckigt, Klaus Herbrand,
Frank Ott, Günter Kindel, Stefan Brennecke,
Ian L. Gatfield and Heinz-Jürgen Bertram,
Symrise GmbH & Co. KG

D
At a Glance uring frying of meat, many different
Chicken liver was fried under typical frying conditions chemical reactions take place.1 Meat is a
in the kitchen. After thermal treatment, the flavor was source of fat, proteins and carbohydrates.
extracted by solvent assisted flavor extraction (SAFE) and During thermal treatment, fatty acids,
the extract was analyzed by GC/MS and GC-olfactometry amino acids, sugars and other
(GC/O). Several compounds were isolated by preparative degradation products are formed which are able to
gas-chromatography. Structure elucidation by NMR and undergo further reactions. Well-known reactions
IR-techniques identified among others thiazolidine, 2-methyl- include the Maillard reaction between reducing sugars
thiazolidine, 2-ethylthiazolidine, 2-pentyl-thiazolidine, and amino acids and the Strecker degradation
2-isobutylthiazolidine, 2-(1-methyl-propyl)-thiazolidine, of amino acids.2
2-isopropyl-thiazolidine, and 2-propionyl-2- thiazoline. In the past, to elucidate the complex Maillard
These compounds are known to be formed in model Maillard reaction different model systems were analyzed with
reaction systems. Some of those compounds were now selected amino acids and carbohydrates in the pres-
detected for the first time in a natural food product. In order ence or absence of fat.3 Those model systems give
to verify the identity of the compounds, the abovementioned an insight in the formation of so-called processed
compounds were synthesized and their spectroscopic and flavors.4 Processed flavors contain a huge variety
chromatographic data were compared with the isolated of volatile organic compounds which yield char-
substances. The formation of above-mentioned compounds acteristic flavor types, like roasted, fried, caramel
can be explained by the degradation of cysteine to cysteamine or popcorn. However, the transferability of model
and subsequent other Maillard reactions under thermal systems for real food systems has to be verified.
treatment in the presence of a fat matrix and reducing sugars. Therefore, systems like fried meat products represent

Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2020 Allured Business Media.
5
Reaction Systems

T-1. Volatile organic compounds of the chicken liver extract

No. Compound RI on DB-1 RI on DB-WAX Flavor description

1 acetic acid ethyl ester – 877 rum, estery, sweet
2 2-butanone – 914 chocolate, rum, chemical
3 butanal – 870 chocolate, green
4 2-methylbutanal 634 922 cocoa, chocolate, fruity
5 3-methylbutanal – 924 chocolate, tomato
6 2-pentanone 645 998 sweet, lemon, fruity
7 2,3-pentadienone 655 1051 buttery, cream, fatty
8 hexanal 782 1094 leaf-like, green, aldehyde
9 2-methylpropanol 615 1081 whisky, rum, sweet
10 2-pentanol 685 1108 banana, fermented, rum
11 butanol 1146 fermented, candy sugar
12 1-penten-3-ol 674 1161 garlic, fatty (oily), onion
13 2-heptanone 873 1192 roquefort, cheesy, mushroom-like
14 pyridine 734 1201 fish, chemical
15 heptanal 883 1194 aldehyde, greasy
16 3-methyl-2-butenal 753 1208 cocoa, chemical, chocolate
17 2-methylbutanol 720 1205 fusel, fermented
18 3-methylbutanol 726 1201 fruity, fermented, overripe
19 2-oxo-propanol – 1299 sweet, juicy, cream, fruity
20 2-methyl-2-thiazoline 852 1314 green, herbal, tropical fruit
21 2,5-dimethylpyrazine 892 1336 nut, peanut
22 2,6-dimethylpyrazine 891 1339 nut (hazelnut), peanut, cocoa
23 hexanol 852 1358 green, apple, cherry
24 nonanal 1085 1396 aldehydic, peely
25 trimethylpyrazine 981 1415 roasted note, cocoa, candy sugar
26 2-methyl-thiazolidine 900 1435 fatty (oily), sweet
27 2E-octenal 1038 1434 aldehyde, cucumber, chicken
28 acetic acid – 1437 sour, fruity, fresh
29 1-octen-3-ol 966 1444 mushroom, earthy, green
30 heptanol 949 1450 fatty, coconut, waxy
31 thiazolidine 878 1490 bloody, fish, cocoa
32 2-acetylfuran 887 1502 sweet, astringent, vanilla
33 2,3-diethyl-5-methylpyrazine 1135 1497 cocoa, chocolate, pyrazine
34 benzaldehyde 934 1524 kernel, almond, marzipan
35 2-ethyl thiazolidine 997 1524 chemical
36 2-methyl thioethanol 814 1530 potato, vegetable
37 propionic acid – 1538 fruity, blueberry
38 2-isopropyl-thiazolidine 1064 1563 cocoa, chocolate, onion
39 isobutyric acid 743 1545 fruity, butter, sweet
40 butyric acid 748 1627 cheesy, sour, butter
41 2-acetyl-thiazol 988 1651 musty, roasted note
42 2-isobutyl-thiazolidine 1147 1648 sweet, cocoa, chocolate
43 2-hydroxymethylfuran 858 1648 mushroom, phenolic, tomato
44 2-(1-methyl-propyl)-thiazoline 1162 1659 peanut, cocoa, chocolate
45 3-methylbutyric acid 806 1686 isovaleric acid, blueberry
46 2-methylbutyric acid 826 1666 fruity, strawberry, apple
47 3-methylthiopropanol 950 1715 potato, vegetable, green
48 2-acetyl-2-thiazoline 1068 1759 pandan, crust
49 2E,3Z-decadienal 1271 1770 aldehyde, chicken, fatty
50 2-propionyl-2-thiazoline 1170 1838 roasty, sweet
51 2-pentyl-thiazolidine 1304 1838 nut (hazelnut), fatty (oily)
52 hexanoic acid 956 1844 lamb/mutton, overripe, animalic
53 2-ethyl-hexanoic acid 1112 1948 watery, juicy, cheesy
54 2-acetyl-pyrrole 1029 1959 chocolate, butter
55 2-formyl-pyrrole 983 2013 metallic, juicy, fruity

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an interesting counterpart in order to study the
formation of certain potent aroma compounds, e.g.
thiazolines and thiazolidines. The aim of the follow-
ing study was to identify thiazoline and thiazolidines
in a natural product and postulate their mechanism
of formation. Moreover, this study was conducted in
order to verify our data from previous model studies
for culinary food systems.5
Results and Discussion
The results of the GC/MS analysis are summarized
in T-1. Sensorial evaluation of the compounds was
achieved by GC/O analysis. Most of the identified com-
pounds contribute to a typical savory flavor.
The flavor extract is dominated by degrada-
tion products of proteins, carbohydrates and fats.
Maillard reaction products especially yield a variety
of nitrogen- and sulfur-containing compounds.6
Earlier research on Maillard reaction model
systems indicated that thiazolidines can be formed
by reaction between different Strecker degradation
products and/or fatty acid degradation products.5
After isolation by preparative gas chromatography,
we identified several thiazolines and thiazolidines
that have so far never been found in a food product,
i.e. in a natural product. Most likely, the thiazolidines
were formed from the precursor cysteamine, which
undergoes a reaction with degradation products
F-2. Formation of 2-isopropyl-thiazolidine (I), 2-isobutyl-thiazolidine (II) and 2-(1-methyl-propyl)-thiazolidine
(III) after thermal treatment
from fatty acids or amino acids.7 F-1 explains the
formation of cysteamine from the amino acid cyste-
ine via decarboxylation.
Alternatively, the formation of cysteamine can be
explained by degradation of coenzyme A.8 However,
the concentration of coenzyme A in chicken liver
compared to the concentration of cysteine is rela-
tively low. Therefore, it can be assumed, that most
cysteamine is formed from cysteine as a precursor.
Amino acids can form aldehydes via Strecker
degradation under thermal treatment in the pres-
ence of reducing sugars. These aldehydes can react
with cysteamine in order to form thiazolidines.9 F-2
explains the formation of 2-isopropyl-thiazolidine
(I), 2-isobutyl-thiazolidine (II) and 2-(1-methyl-
propyl)-thiazolidine (III) in fried chicken liver from
cyteamine and Strecker degration products as
precursors.
F-1. Formation of cysteamine in fried chicken liver
7
Reaction Systems

F-3. Formation of 2-pentyl-thiazolidine (IV) F-4. Formation of 2-ethyl-thiazolidine (V)

During the frying process of chicken liver, oxida-

tion of unsaturated fatty acids also occurs. The
F-5. Formation of 2-propionyl-thiazoline (VI)
products of this oxidation process are aldehydes,
which can react with cysteamine to form thiazoli-
dines like 2-pentylthiazolidine (IV) (see F-3).
Propanal is a common degradation product either
from fatty acids or from carbohydrates, and it can
react with cysteamine to form 2-ethyl-thiazolidine
(V) (see F-4). The degradation of carbohydrates
during frying will result in oxidation, dehydration
and decarboxylation processes.10 The fragments of
the carbohydrates can undergo further reactions
leading to α-carbonyl-aldehydes. 2-Propionyl-
2-thiazolidine can be formed by a reaction of
cysteamine with different carbohydrate degradation
products. Afterwards, oxidation yields 2-propionyl-
2-thiazoline (VI) as shown in F-5.9
Obviously, the formation of 2-acetyl-2-thiazoline
might be easier, because cysteamine can react with
2-oxo-propanal, which is directly derived from
fructose (see F-6).9
This formation pathway is in accordance with our
findings, because 2-acetyl-2-thiazoline is obtained in
higher concentration than 2-propionyl-2-thiazoline.
Aroma relevant amounts of 2-acetyl-2-thiazoline
in wine and from cysteine/methylglyoxal solution
were reported by de Revel et al.11 F-6. Formation of 2-acetyl-thiazoline

Conclusions
The results indicate that during frying of chicken
liver a variety of compounds are formed that contrib-
ute to the overall roasty flavor of fried liver. Different
classes of molecules are formed during the heating
process and several reaction types can be observed,
such as dehydration, decarboxylation, aldol conden-
sation, oxidation, Strecker degradation and Maillard
reaction. Mostly acids, ketones, aldehydes, alcohols,
pyridines, thiazolidines, thiazolines, furans and
pyrrols were identified.
In order to evaluate the most important con-
tributors for the typical roast flavor, the extract was
analyzed by trained flavorists using GC-olfactometry.

8 2020 Savory Flavors Ebook | www.berjeinc.com www.PerfumerFlavorist.com

The chemical structure of most compounds was
identified by comparing their mass spectra with
MS libraries. Those compounds that could not
be identified were isolated via preparative gas
chromatography followed by structure elucida-
tion using NMR and IR. Proposed structures
were verified by synthesizing the compounds and
comparing their spectroscopic and chromato-
graphic data.
The identified compounds are already known
as products from Maillard reaction model
systems. The relevance of those model systems
can now be established, because the proposed
reaction products have been identified in fried
chicken liver. 5 The reaction mechanism for the
formation of thiazolidines involves a condensa-
tion reaction of cysteamine with aldehydes. The
reaction mechanism for thiazolines also starts
with cysteamine and aldehydes as precursors, but
an additional oxidation yields the thiazoline.
In our work, we identified one thiazoline and
five thiazolidines for the first time in a natural
food product. While 2-ethyl-thiazolidine only
has a chemical flavor, 2-isopropyl-thiazolidine,
2-isobutyl-thiazolidine, 2-(1-methyl-propyl)-
thiazolidine, 2-pentyl-thiazolidine and
2-propionyl-2-thiazoline yield a more nut-like and
F-7. Synthesis of thiazolidines
cocoa-like flavor, which cover a broad range of senso-
rial profiles.
Experimental Procedures
Samples: Raw chicken liver was purchased at a
local market in Holzminden, Germany. Some 500 g
of the liver were fried for 2 min in a Teflon pan with
a thin layer of Palmin fat. Afterwards, the fried liver
was ground in a “Grindomix” and extracted with 1
L diethylether/pentane 1:1 for 24 hr. The extraction
was repeated with 500 mL diethylether/pentane
1:1 for 4 hr. The volatile compounds of combined
organic extracts were separated from the fat by a
solvent assisted flavor extraction (SAFE) for 2 hr at
approximately 10-5mbar. The organic solvent was
removed by distillation at 45°C. The concentrated
extract was used for further analysis.
GC/MS: Finnigan MAT8200 MS coupled with
a Carlo Erba 5360 Mega Series GC, using a 60 m
DB-WAX column (0.25 μm, 0.32 mm).
NMR: Varian Unity Inova (400 Mhz) or Varian
Gemini 2000 (200 MHz).
Synthesis: All thiazolidines were prepared by
reaction of cysteamine hydrochloride with corre-
sponding aldehydes as described before 12 (see F-7).
2-Propionyl-thiazoline was synthesized via acylcya-
nide as shown in F-8.13,14
9
Reaction Systems

F-8. Synthesis of thiazolidines

Spectroscopic Data C-2). 13C-NMR, δ (ppm of relevant carbon): 20.5, 20.8

2-isopropyl-thiazolidine (I): 1H-NMR (CDCl3,
200 MHz), δ in ppm [multiplicity, coupling constant
(Hz), intensity; hydrogen atom at relevant carbon]:
1.05, 1.09 (2 d, J = 6.7, 6.7, 6H, C-2‘, C-3‘), 1.90 (dqq,
J = 6.7, 6.7, 7.5, 1H, C-1‘), 2.70-3.06 (m, 3H, C-4,
C-5), 3.48-3.64 (m, 1H, C-4), 4.29 (d, J = 7.5, 1H,
(2 CH3, C-2‘, C-3‘), 34.0 (CH, C-1‘), 34.8 (CH2, C-5),
52.5 (CH2, C-4), 79.0 (CH, C-2). MS (70 eV): 131 (7.1
percent, MM); 90 (4.7); 88 (100); 84 (5.8); 70 (9.9); 61
(11.3); 55 (8.5); 44 (8.7); 41 (5.8); 28 (8.5).
2-isobutyl-thiazolidine (II): 1H-NMR (CDCl3, 200
MHz), δ in ppm [multiplicity, coupling constant (Hz),

Processed flavors contain a huge variety of volatile organic compounds which yield characteristic flavor types, like roasted, fried, caramel or popcorn.

10 2020 Savory Flavors Ebook | www.berjeinc.com www.PerfumerFlavorist.com

intensity; hydrogen atom at relevant carbon]: 0.94,
0.96 (2 d, J = 6.4, 6.3, 6H, C-3‘, C-4‘), 1.52-1.90 (m,
3H, C-1‘, C-2‘), 2.76-3.08 (m, 3H, C-4, C-5), 3.46-
3.64 (m, 1H, C-4), 4.52 (dd, J = 5.8, 7.7, 1H, C-2).
13C-NMR, δ (ppm of relevant carbon): 22.3, 23.0
(CH2, C-4), 170.4 (Cq, C-2), 196.2 (Cq, C-1‘). MS (70
eV): 143 (41.7 percent, MM); 115 (43.4); 88 (6.6);
87 (17.4); 60 (29.7); 59 (17.1); 57 (100); 45 (8.5); 29
(52.1); 27 (20.5).

(2 CH3, C-3‘, C-4‘), 27.3 (CH, C-2‘), 35.0 (CH2, C-5),

45.7 (CH2, C-1‘), 52.5 (CH2, C-4), 79.0 (CH, C-2).
MS (70 eV): 145 (15.5 percent, MM); 130 (8.1);
98 (8.9); 88 (100); 70 (7.7); 56 (20.3); 44 (11.8); 43
(9.9); 42 (10.0); 41 (9.7).
2-(1-methyl-propyl)-thiazolidine (III) (mixture
of two diastereomers): 1H-NMR (CDCl3, 200
MHz), δ in ppm [multiplicity, coupling constant
(Hz), intensity; hydrogen atom at relevant carbon]:
0.94 (t, J =7.4, 3H, C-3‘), 1.01/1.08 (d, J = 6.8/6.8,
1H, C-4‘), 1.15-1.88 (m, 3H, C-1‘, C-2‘), 2.66- 3.04
(m, 3H, C-4, C-5), 3.52-3.65 (m, 1H, C-4), 4.34/4.41
(d, J = 7.4/6.8, 1H, C-2). 13C-NMR, δ (ppm of rel-
evant carbon): 11.3/11.4 (CH3, C-3‘), 16.4/16.6 (CH3,
C- 4‘), 27.7/28.0 (CH2, C-2‘), 34.5/34.7 (CH2, C-5),
39.9/40.4 (CH, C-1‘), 52.5/52.5 (CH2, C-5), 77.8/77.8
(CH, C-2). MS (70 eV): 145 (5.9 percent, MM); 90
(5.0); 88 (100); 84 (4.0); 70 (9.4); 61 (9.2); 44 (6.8);
42 (4.8); 41 (8.5); 30 (4.6).
2-pentyl-thiazolidine (IV): 1H-NMR (CDCl3, 200
MHz), δ in ppm [multiplicity, coupling constant
(Hz), intensity; hydrogen atom at relevant carbon]:
0.89 (t, J = 7.0, 3H, C-5‘), 1.20-1.58 (m, 6H, C-2‘,
C-3‘, C-4‘), 1.60-2.04 (m, 2H, C-1‘), 2.77-3.04 (m,
3H, C-4, C-5), 3.42-3.60 (m, 1H, C-4), 4.46 (dd, J
= 7.1, 5.7, 1H, C-2). 13C-NMR, δ (ppm of relevant
carbon): 14.0 (CH3, C-5‘), 22.5 (CH2, C-4‘), 27.7
(CH2, C-2‘), 31.7 (CH2, C-3‘), 35.0 (CH2, C-5), 36.7
(CH2, C-1‘), 52.2 (CH2, C-4), 73.5 (CH, C-2). MS (70
eV): 159 (10.9 percent, MM); 116 (7.3); 112 (17.1);
Acknowledgements
The authors thank M. Liebig for the sample
preparation.
Address correspondence to Claus O. Schmidt, Symrise GmbH & Co.
KG, Mühlenfeldstr. 1, D-37603 Holzminden, Germany; claus.oliver.
schmidt@symrise.com.
References
1. P. Werkhoff, J. Brüning, M. Güntert, J. Kaulen, G. Krammer
and H. Sommer, Adv. Food Sci., 19-27 (1996).
2. W. Baltes, Lebensmittelchemie. 5th Ed. (2000).
3. M. Güntert, J. Brüning, R. Emberger, M. Köpsel, W. Kuhn, T.
Thielmann and P. Werkhoff, J. Agric. Food Chem., 2027-2041
(1990).
4. K. Umano, Y. Hagi, K. Nakahara, A. Shyoji and T. Shibamoto,
J. Agric. Food Chem., 2212-2218 (1995).
5. G.E. Krammer, P. Werkhoff, I. Gatfield, C.O. Schmidt, H.
Sommer, J.P. Ley, M. Roloff, P. Bialas and H-J. Bertram,
Proceedings of the 10th Weurman Flavor Research Symposium
(2002).
6. T. Hofmann and P. Schieberle, J. Agric. Food Chem., 898-906
(1997).
7. W. Engel and P. Schieberle, J. Agric. Food Chem., 5394-5399
(2002).
8. D. Voet and J.G. Voet, Biochemistry (1992).
9. W. Engel, PhD Thesis (1999).

88 (100); 70 (8.2); 61 (8.1); 56 (21.7); 44 (8.1); 41
(8.3); 30 (7.3).
2-ethyl-thiazolidine (V): 1H-NMR (CDCl3, 200
MHz), δ in ppm [multiplicity, coupling constant
(Hz), intensity; hydrogen atom at relevant carbon]:
1.06 (t, J = 7.4, 3H, C-2‘), 1.72, 1.95 (2 m, 2H, C-1‘),
2.77-3.06 (m, 3H, C-4, C-5), 3.42-3.60 (m, 1H, C-4),
4.43 (dd, J = 7.3, 5.5, 1H, C-2). 13C-NMR, δ (ppm of
relevant carbon): 12.2 (CH3, C-2‘), 29.6 (CH2, C-1‘),
10. T. Hofmann and P. Schieberle, Z. Lebensm. Unters. Forsch. A,
229-236 (1998).
11. G. de Revel, S. Marchand and A. Bertrand, ACS Symposium
Series (871), 353-364 (2004).
12. A. Yashura and T. Shibamoto, Agric. Biol. Chem., 2273-2274
(1989).
13. S. Kirchmeyer, A. Mertens, M. Arvanaghi and G.A. Olah,
Synthesis, 498-499 (1983).

35.0 (CH2, C-5), 52.2 (CH2, C-4), 73.5 (CH, C-2). 14. T. Doornbos and H.G. Peer, Recueil, 711 (1972).
MS (70 eV): 117 (26.4 percent, MM); 88 (100); 71
(13.9); 70 (28.6); 61 (13.6); 58 (11.2); 56 (18.3); 44
(9.8); 41 (12.3); 28 (13.7).
2-propionyl-2-thiazoline (VI): 1H-NMR
(CDCl3, 200 MHz), δ in ppm [multiplicity, coupling
constant (Hz), intensity; hydrogen atom at relevant
carbon]: 1.14 (t, J = 7.3, 3H, C-3‘), 2.95 (q, J = 7.3,
2H, C-2‘), 3.33 (t, J = 8.8, 2H, C-5), 4.52 (t, J = 8.8,
2H, C-4). 13C-NMR, δ (ppm of relevant carbon):
7.6 (CH3, C-3‘), 32.1, 32.5 (2 CH2, C-2‘, C-5), 66.1

11
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Anise Cinnamon Marjoram Sage
Basil Cloves Onion Tarragon
Bay Leaves Cumin Oregano Thyme
Cardamon Dill Parsley
Cayenne Fennel Pepper
Chilies Garlic Rosemary

TEA INGREDIENTS
Anise Dandelion Linden Sarsparilla
Calendula Ginger Orange Peel Spearmint
Cardamon Hibiscus Peppermint Stevia
Chamomile Lemon Grass Rooibos Senna
Chicory Lemon Peel Rosebuds & Petals Valerian
Cinnamon Lemon Verbena Rosehips Yerba Matte
Cloves Licorice Safflower
 Vol. 37 • November 2012

Flavor Bites: 2,4,6-Trimethyl-

dihydro-4H-1,3,5-dithiazine
Application in meat, fish and seafood, and
other savory flavors

BY JOHN WRIGHT
johnwrightflavorist@gmail.com

I n the wide cornucopia of different profiles a flavorist will work

on in a lifetime, there is no question that heated flavors in
general, and meat flavors specifically, are the most complex and
challenging. Good, realistic, meaty notes are not exactly abundant, and,
unfortunately, most of the best meaty notes have quite a high degree of
profile specificity—an ingredient that will work well in chicken may
prove to be of limited use in roast beef and vice versa.
2,4,6-Trimethyldihydro-4H-1,3,5-dithiazine (FEMA# 4018, CAS# 638-
17-5; F-1), sometimes called thialdine, is one of the few exceptions to this
rule. It is generated naturally by the combination of acetaldehyde, hydro-
gen sulfide and ammonia formed in the degradation of sulfur-containing
amino acids. Hence it is found in nature in a very wide variety of cooked
foods, ranging from beef and pork to shrimp and squid, although in
some analyses it may actually be an artifact formed during the extraction
process. Perhaps the most obvious profile affinity for this chemical is roast

Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2020 Allured Business Media.

14 2020 Savory Flavors Ebook | www.berjeinc.com www.PerfumerFlavorist.com

beef, but it also fits very well into the meaty aspect
of a wide spectrum of flavor profiles. It can variously
be described as meaty, roasted, cooked and eggy, and
forms a central component of many “heated” flavor
profiles.
Several other interesting dithiazines are used
in flavors. 2,4,6-Triisobutyl-5,6-dihydro-4H-1,3,5-
dithiazine (FEMA# 4017, CAS# 74595-94-1) is the
most important. It is extremely characteristic of
fried bacon, and so while it is capable of being
used in a wide range of different profiles it can
only play a minor role because of its specificity.
Thus, it is nowhere near as generally useful as
2,4,6-trimethyldihydro-4H-1,3,5-dithiazine.
2-Ethyl-4,6-dimethyl-5,6-dihydro-4H-1,3,5-
dithiazine (FEMA# 4667; a mixture of the
2-ethyl-4,6-dimethyl and the 4-ethyl-2,6-dimethyl
derivatives) is similar in character and range of use
to 2,4,6-trimethyldihydro-4H-1,3,5-dithiazine, but
possibly slightly more orientated to seafood uses.
2-Isopropyl-4,6-dimethyl-5,6-dihydro-4H-1,3,5-
dithiazine (FEMA# 3782; also covers a mixture of the
2-isopropyl-4,6-dimethyl and 4-isopropyl 2,6-dimethyl
derivatives) is in the same general odor group but is
slightly more useful in cocoa flavors. 2-Isobutyl-4,6-
dimethyl -5,6-dihydro-4H-1,3,5-dithiazine (FEMA#
3781, another mixture of the 2-isobutyl-4,6-dimethyl
and 4-isobutyl-2,6-dimethyl derivatives) is distinctly
more nutty in character and is more directly appli-
cable to hazelnut, peanut and, to a lesser extent, cocoa
flavors.
The dose rates given throughout this article are the
levels suggested for use in flavors that are intended to
be dosed at 0.05% in a simple bouillon or ready-to-
drink beverage.
Meat Flavors
Roast beef: 2,4,6-Trimethyldihydro-4H-1,3,5-
dithiazine can form the foundation of a good roast
beef flavor. Levels of use can vary dramatically,
depending on the effect desired, from around
100 ppm, for a subtle effect, up to as high as 2,000
ppm, for a heavily roasted meaty character, fabulously
reminiscent of the pan scrapings from roasting beef.
Boiled beef: Although this ingredient fits well into
roasted meat flavors, it is almost equally at home
when the profile is boiled rather than roasted. The
range of levels of use is a little lower but also quite
varied, ranging from 100–1,000 ppm.
Burgers: Flavors in burgers are a distinctly special
case and can vary in composition depending on the
specific processing conditions. Levels of 2,4,6-trimeth-
yldihydro-4H-1,3,5-dithiazine in the region of 200
ppm in flavors can cover, to a degree, the unpleasant
“warmed-over” character in pre-cooked burgers.
Ham: After roast beef, ham flavors are the most
F-1. 2,4,6-Trimethyldihydro-4H-1,3,5-dithiazine
obviously important area of use for this chemical. It
adds depth and realism to a profile that can be overly
reliant on smoke notes. Levels of use vary, but can
also be as high as 2,000 ppm.
Pork: In a similar way 2,4,6-trimethyldi-
hydro-4H-1,3,5-dithiazine is highly effective in all
styles of pork flavors, including cured pork and pork
sausages, but the levels are typically lower, in the
region of 500 ppm.
Roast chicken: The aroma of roast chicken has
an almost coffeelike aspect and this ingredient has
no similarity whatever to that profile. Nevertheless
it is highly useful and adds meaty character and
realistic depth to roast chicken flavors at levels of use
in the region of 100 ppm in white meat flavors and
up to 500 ppm in dark meat chicken flavors.
Boiled chicken: Long-boiled chicken is an
important profile in Asia and 2,4,6-trimethyldi-
hydro-4H-1,3,5-dithiazine can play an important part
in recreating that effect. Levels of use can be higher
than typically used in roast chicken flavors and can
easily range above 500 ppm.
Lamb: In lamb flavors, 500 ppm of this chemical
is also an effective level, giving meaty and roasted
characters and de-emphasizing the fatty notes.
Bacon: This ingredient is not as central to the
character of bacon flavors as it is in other types
of meat but it can, nevertheless, add authen-
ticity and welcome complexity at around 50
ppm, especially when used in conjunction with
2,4,6-triisobutyl-5,6-dihydro-4H-1,3,5-dithiazine.
Fish and Seafood Flavors
Prawn, scampi, lobster and shrimp:
2,4,6-Trimethyl-dihydro-4H-1,3,5-dithiazine is superb
in all these flavors, realistically adding the strong
meaty note that underlies the seafood character.
Levels of use can range up to 500 ppm or 1,000 ppm
in flavors.
Squid and calamari: These profiles contain a sig-
nificant meaty note and so 500 ppm of this chemical
in a flavor is a good starting point.
15
Flavor Bites

White fish: Low levels of this ingredient are Non-savory Flavors

appropriate in this delicate and challenging profile
type, especially if the character is fried; 100 ppm can
be quite effective.
Other Savory Flavors
Egg: Although 2,4,6-trimethyldihydro-4H-1,3,5-
dithiazine is notably meaty, it also has a distinct
eggy profile and fits well into all cooked egg flavors.
Levels of use vary but can easily top 2,000 ppm in a
flavor.
French fries: The best french fries have a hint of
meaty character. Levels of use of this chemical can
vary widely, especially since this application can
require a great deal of heat stability; 500 ppm is a
good starting point.
Black and white truffles: These flavors can
often appear extremely simple and lack realism.
2,4,6-Trimethyldihydro-4H-1,3,5-dithiazine supplies
an attractive level of added complexity at around
500 ppm in truffle flavors.
Fried onions: The use of this ingredient in fried
and boiled onion flavors is relatively obvious, given
the meaty nature of their profiles; 500 ppm is a
typical use level.
Green onions: Much less obviously, it also works
well in raw onion style flavors, including chive and
spring onion, at around 200 ppm.
Hazelnut: Such an obviously meaty ingredient
would seem to have little place outside the realm of
savory flavors, but 2,4,6-trimethyldihydro-4H-1,3,5-
dithiazine works surprisingly well in nut flavors,
especially hazelnut; 400 ppm is a reasonable starting
level.
Chocolate and cocoa: There is something dis-
tinctly eggy about the profile of good quality cocoa
and this chemical can be used at widely varying
levels in chocolate flavors depending on the effect
that is desired. Very dark chocolate or cocoa flavors
can easily accommodate 400 ppm, but milder, milk
chocolate styles can be improved by the addition of
just 20 ppm.
Peanut and peanut butter: After hazelnut,
peanut is the next best application in the nut area,
but the levels are rather lower, in the region of 100
ppm in flavors.
Condensed milk: Only subtle additions are
needed in condensed and other heated milk flavors,
but even 50 ppm of 2,4,6-trimethyldihydro-4H-1,3,5-
dithiazine can round out the other dominant sulfur
notes and contribute to a more authentic cooked
character.

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 FROM SWEET
TO SAVORY, WE Part of Berjé’s proficiency in the flavor industry comes
not only from stocking many ingredients, but also being
SUPPLY A FULL able to offer different varieties of those ingredients. The
SPECTRUM OF differences between Argentine, Californian, and Italian
Lemon Oil can be subtle, but they serve as a major point
READILY of distinction when used in a well-constructed flavor.
AVAILABLE This diversity of selection extends to the mint, spice, and
herb categories and to all oils that have different regional,
FLAVOR biological, or industrial grades.
INGREDIENTS.

Berjé goes to considerable lengths not

only to find flavor grade material but
also to test, analyze, and document
their flavor grade status. Quality
and safety are obsessions and our
ingredients come with an SQF
FOOD SAFETY CODE FOR
MANUFACTURING, edition
8.1 certification.

BERJÉ INC. - CERTIFIED TO SQF FOOD SAFETY CODE FOR

MANUFACTURING, EDITION 8.1 – CERTIFICATE #7751.
71 YEARS
3
GENERATIONS
1
AMBITION

Berjé has strived for excellence as a supplier and producer of Essential Oils, and Aromatic
Chemicals since our early days in New York City. In those six decades Berjé has built an
inventory of over 3000 ingredients that covers the esoteric to the everyday. Rigorous QC
standards, comprehensive traceability programs, and our recent SQF certification have
established Berjé as a top tier distributor.

With that foundation Berjé is breaking new ground on improving the industry’s
standard of service. Coupled with Berjé Trakia, a Bulgarian rose and lavender production
facility, our global network of partners gives us the reach to sell in over sixty countries
on six continents. As we further our commitment to promoting environmentally stable
solutions, Berjé guarantees the quality of the past and the best practices of a sustainable
business future.
Cooking With Alliums
Maillard reactions with different forms of onion and garlic extracts.

by Shane McDonald, Meghan Peltz and David Bolliet, Kalsec

Vol. 38 • April 2013

F
lavor chemists often use Maillard available in three forms: essential oil, powder
reaction technology to make and juice. This paper examines how the three
savory flavors. Realistic meat types of extracts perform in some model Maillard
and processed flavors can be flavor reactions.
made using this technology by
simulating the ingredients and Materials and Methods
conditions of authentic cooking. Onion and garlic oils were standardized product
Typically, this reaction requires codes provided by Kalsec. Onion, garlic and yeast
an amino acid source, such as a extract powders were obtained from commercial
defined amino acid or a protein sources. The onion and garlic juices were also from
hydrozylate, and reducing sugar. In commercial sources and contained salt as preserva-
meat flavors, sulfur from cysteine is often employed. tive for the high moisture products.
In the reactions in this paper, cysteine is supple-
mented with the sulfur-containing extracts of onion Reactions
(Allium cepa) and garlic (Allium sativum), common The reactions were formulated by the flavor
ingredients in savory cooking. These extracts are chemist, and the reaction performed in a Parr

Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2020 Allured Business Media.

19
Cooking With Alliums

T-1. Beef-type flavor reaction with onion extract reactor (Moline, IL). Formulae of
the reactions with percent by weight
1C 1J 1P 1O ingredients are shown in T-1, T-2 and
Ingredient Control With Juice With With Oil
T-3. Attempts were made to keep the
(%) (%) Powder (%) (%)
moisture and sodium levels equivalent
L-Arginine 1.00 1.00 1.00 1.00 between reactions of the same flavor
L-Cysteine 1.00 1.00 1.00 1.00 profile using the different extracts
while maintaining approximately equal
L-Methionine 0.10 0.10 0.10 0.10
sensory intensity. A control for each
L-Glutamic acid 4.00 4.00 4.00 4.00 flavor profile with no allium extract
was also made to aid in the analytical
L-Rhamnose 1.00 1.00 1.00 1.00
analysis. After the reactions, the prod-
D-Xylose 2.00 2.00 2.00 2.00 ucts were submitted for analytical and
Water 12.66 0.00 12.45 12.66 sensory analyses.
Salt 1.02 0.00 1.01 1.02 Beef reaction with onion extract: The
formulae for the beef-type flavor reaction
Glycerine 73.21 71.90 68.44 73.22 are depicted in T-1
T-1. Cysteine provides
Canola oil 0.99 0.99 0.99 0.99 sulfur for most meat-type reactions, with
Lactic acid 88% 3.00 3.00 3.00 3.00 some methionine added as well. Arginine
is used in many beef-type flavors, and glu-
Onion oil 0.00 0.00 0.00 0.01 tamic acid.1 Rhamnose creates furaneol,
Onion powder 0.00 0.00 5.00 0.00 a key contributor to beef flavor.2 Xylose
Onion juice 0.00 15.00 0.00 0.00 is a highly reactive pentose. The strat-
egy is to form complicated heterocyclic
compounds, such as the characterizing
Totals 100.00 100.00 100.00 100.00 2-methyl-3-furanthiol. Lactic acid adjusts
the pH of the reaction and also is found
in meat. Glycerine is a polar carrier and
also controls the water activity. The three
onion extracts were added to be approxi-
T-2. Chicken-type flavor reaction with garlic extract
mately the same onion strength in the
2C 2J 2P 2O final product. Water and salt contents
Ingredient Control With Juice With With Oil were manipulated to be similar between
(%) (%) Powder (%) (%) the four reactions. The canola oil was
L-Arginine 1.00 1.00 1.00 1.00 added as a diluent in order to accurately
weigh the onion oil. The reactions (300 g
L-Cysteine 3.00 3.00 3.00 3.00 each batch) were reacted for 150 min at
L-Methionine 0.10 0.10 0.10 0.10 105ºC in a closed vessel.
Chicken reaction with garlic
L-Glutamic acid 3.00 3.00 3.00 3.00
extract: The chicken reactions with
L-Rhamnose 0.25 0.25 0.25 0.25 garlic extracts are depicted in T-2
T-2. The
D-Fructose 3.00 3.00 3.00 3.00 strategy for these reactions is to make
simpler sulfur compounds. Therefore,
Ascorbic acid 1.00 1.00 1.00 1.00
the reaction time is shortened and a less
Water 9.00 0.00 8.73 9.00 reactive hexose (fructose) is used as a
Salt 1.48 0.00 1.47 1.48 reducing sugar. Chicken is more sulfury
Glycerine 74.17 69.75 70.33 74.15 than beef, so more cysteine was added.1
Arginine was removed. Ascorbic acid
Safflower oil 2.00 2.00 2.00 2.00 and cystiene react to form a chickenlike
Lactic acid 88% 3.00 3.00 3.00 3.00 flavor.3 Chicken fat is highly unsaturated
Garlic oil 0.00 0.00 0.00 0.02 and provides much of the characteristic
flavor of chicken. Since this is a veg-
Garlic powder 0.00 0.00 4.11 0.00
etarian reaction, safflower was added
Garlic juice 0.00 15.00 0.00 0.00 instead. Reaction conditions were 105ºC
Totals 100.00 100.00 100.00 100.00 for 90 minutes. The flavor was too acidic
after reacting, so the pH was adjusted to

20 2020 Savory Flavors Ebook | www.berjeinc.com www.PerfumerFlavorist.com

5.5–6.0 after the reaction to improve T-3. Vegetable broth flavor reaction with onion and garlic extracts
palatability.
Vegetable broth flavor reaction with 3C 3J 3P 3O
Ingredient Control With Juice With With Oil
onion and garlic extracts: The third
(%) (%) Powder (%) (%)
reaction, a vegetable broth reaction,
is considerably different, T-3. Canola Oleoresin carrot 5.00 5.00 5.00 5.00
oil is the carrier. After the reaction, Oleoresin celery 5.00 5.00 5.00 5.00
the oil is decanted from the aqueous
Canola oil 90.00 90.00 90.00 90.00
residue, and the oil filtered via
suction filtration through filter paper. D-Dextrose 2.50 2.50 2.50 2.50
The flavor is reminiscent of mirepoix,
Autolyzed yeast 2.50 2.50 2.50 2.50
mainly flavored by celery and carrot
oleoresins. The Maillard reactants Water 21.66 0.00 21.19 21.66
for the control sample were yeast Salt 2.50 0.00 2.48 2.50
extract and dextrose. The only sulfur Lactic acid 88% 3.00 3.00 3.00 3.00
sources are onion and garlic extracts.
Formulae were made to 100% oil and Onion oil 0.00 0.00 0.00 0.01
reacted at 121ºC for 60 min. Onion powder 0.00 0.00 5.00 0.00
Onion juice 0.00 15.00 0.00 0.00
Analytical
Reaction flavors were sampled by
Garlic oil 0.00 0.00 0.00 0.02
headspace solid phase microextrac- Garlic powder 0.00 0.00 4.11 0.00
tion (SPME), using a 50/30 mm DVB/ Garlic juice 0.00 15.00 0.00 0.00
Carboxen/PDMS SPME fiber (Supelco,
Garlic juice 0.00 15.00 0.00 0.00
Bellefonte, PA). Volatile analysis was
done by gas chromatography mass Totals (oils only) 100.00 100.00 100.00 100.00
spectrometry (GC/MS), using a Varian
3800 GC and Varian Saturn 2000 MS
(Palo Alto, CA). Samples were analyzed T-4. GC Temperature gradient
with no dilution or addition of any
solvent, with 0.1 min adsorption at Temperature (°C) Rate (°C/min) Hold time (min)
25ºC and 3 min desorption in the GC
injector set at 240°C. GC temperature 40 – 5
gradient is summarized in T-4
T-4. Helium 140 3 –
was used as carrier gas, at a constant
240 10 4
flow rate of 1 mL/min. A Supelco fused
silica SLB-5ms column (30 m x 0.25
mm ID; 0.25 mm film thickness) was
used for separation of the volatile spectrum methodology on a 0–15 universal scale evaluated the
compounds. MS detection range was beef reaction with onion sources, the chicken reaction with garlic
30–300 m/z, with a scan rate of 0.7 sources and the vegetable broth reaction with garlic and onion
sec/scan. Tentative peak identification sources over a series of panel sessions. Panelists evaluated the
was done using several inline libraries, blindly coded 2-ounce samples individually, discussed attributes
including NIST98, and Adams.4 as a group and rated attributes individually. Panelists were
allowed to cleanse their palates with distilled water or crackers, as
Sensory needed.
A basic savory base system consist- Statistics were run using Compusense software, sample P-values
ing of 3 g salt plus 0.5 g monosodium were calculated using analysis of variance (2-way). Typically, P £
glutamate (MSG) for every 1,000 g of 0.05 is considered statistically significant, while 0.05 <P £ 0.10 is
water was used to test the reaction considered borderline statistically significant.
flavors with differing forms of onion
and garlic extracts. Samples were Results and Discussion
prepared 1–2 hours before sensory F-1 and F-2 show descriptive sensory profiles of the beef flavor
evaluation and were served at room reactions with added onion essential oil, juice and powder. The
temperature. Descriptive panelists beef reaction formulated with onion oil was described as having
(n=12–15) trained using a modified significantly more fermented aroma (P < 0.05) and flavor (P = 0.02)

21
Cooking With Alliums

F-1. Sensory aroma profile of beef-type flavor reactions with added onion juice, onion powder or onion oil

Descriptive Aroma Profile of

Beef Flavor Reactions with Onion Sources
Overall Aroma
10
Off Notes/Chemical Aroma 8 Meaty/Brothy Aroma

4
Green/Celery/Vegetable Aroma Dirty/Earthy/Musty Aroma
2
0

Burnt Aroma Onion/Garlic Aroma

Brown Aroma Fermented Aroma Juice

Powder
Petroleum/Rubber Aroma
Oil

F-2. Sensory flavor profile of beef-type flavor reactions with added onion juice, onion powder or onion oil

Descriptive Flavor Profile of

Beef Flavor Reactions with Onion Sources
Overall Flavor
Aftertaste
10
Meaty/Brothy Flavor
8
Bitter Dirty/Earthy/Musty Flavor
6

Sour 4 Onion/Garlic Flavor

Salt 0 Fermented Flavor

Sweet Petroleum/Rubber Flavor

Pungency Brown Flavor

Juice
Off Notes/Chemical Flavor Burnt Flavor Powder
Green/Celery/Vegetable Flavor Oil

22 2020 Savory Flavors Ebook | www.berjeinc.com www.PerfumerFlavorist.com

F-3. Headspace SPME GC-MS chromatograms of beef reaction flavors with no onion added (1C), or with added
     onion juice (1J), onion powder (1P), or onion oil (1O)

5-methyl furfural
2-methyl furan

Furfural
1C
1

0
2-methyl furan

5-methyl furfural
2
Furfural

1J
Detection (MCounts)

5-methyl furfural
2-methyl furan

2
Furfural

1P
1

Dipropyl disulfide
Methyl propyl disulfide
2-methyl furan

5-methyl furfural

2
1O
Furfural

0
5 10 15 20 25 30
Time (minutes)

F-4. Sensory aroma profile of chicken-type flavor reactions with added garlic juice, garlic powder or garlic oil

Descriptive Aroma Profile of

Chicken Flavor Reactions with Garlic Sources
Overall Aroma
10
Off Notes/Chemical Aroma 8 Chicken/Brothy Aroma

6
4
Browned Aroma Fatty Aroma
2
0

Green/Herbal Aroma Garlic/Onion Aroma

Juice
Dirty/Earthy/Musty Aroma Fermented Aroma
Powder
Oil
Petroleum Aroma

23
Cooking With Alliums
characteristics. Panelists found the juice and powder
formulations to be similar in profile.
F-3 shows the GC/MS chromatograms of beef type
flavor reactions with onion extracts.
F-4 and F-5 depict descriptive sensory profiles
of the chicken flavor reactions with added garlic
essential oil, juice and powder. Panelists found
the three formulations to be similar in profile. The
reactions containing garlic oil were slightly higher in
fermented and green/herbal characteristics. Brown
aroma and flavor attributes were associated more
strongly in the powder reactions but not to a signifi-
cant degree.
GC/MS chromatograms of chicken reaction
flavors with garlic extracts are shown in F-6
F-6.
F-7 and F-8 show descriptive sensory profiles
of the vegetable broth flavor reactions with added
onion and garlic essential oil, juice and powder. The
onion and garlic oil, juice and powder inputs had a
greater impact on the sensory profile than the previ-
ous reactions. Onion and garlic powder expressed
the strongest with significantly more overall aroma
(P < 0.01), onion/garlic aroma (P < 0.01) and flavor
(P = 0.01) and browned aroma and flavor attributes.
Panelists found the reaction formulated with onion
and garlic juice to be weaker than the reaction
formulated with oil.
GC/MS chromatograms of vegetable reaction
flavors with garlic and onion extracts are presented
in F-9
F-9.
F-5. Sensory flavor profile of chicken-type flavor reactions with added garlic juice, garlic powder or garlic oil
Descriptive Flavor Profile of
Chicken Flavor Reactions with Garlic Sources
Overall Flavor
Aftertaste
10
Astringency 8 Fatty Flavor
6
Pungency
4
2
Bitter
0
Sour
Salt
Sweet
Off Notes/Chemical Flavor
24 2020 Savory Flavors Ebook | www.berjeinc.com www.PerfumerFlavorist.com
Discussion
In beef, onion oil was noticeable for greater
“fermented” onion flavor (F-1F-1 and F-2
F-2). It also has
somewhat less meaty and brothy notes compared to
the other extracts, as well as burnt and dirty notes.
Otherwise, differences were minor. Juice tended to
be similar to the powder. The powder, however, had
greater brown aroma and flavor, probably due to the
additional sugars and amino acids in the powder.
Analytical work performed on the beef reaction
F-3) showed that 2-methyl furan, furfural
flavors (F-3
and 5-methyl furfural were the predominantly
produced volatile compounds. Sample 1O was the
only onion-containing reaction flavor that had some
measurable levels of volatile compounds characteris-
tic of onion, specifically methyl propyl disulfide and
dipropyl disulfide.
F-4 and F-5
In the chicken (F-4 F-5), garlic oil had some-
what more petroleum and fermented aromas, and
less chicken aroma. The powder had more browned
aroma. The juice had the least fermented and petro-
leum aromas but the greatest dirty notes. It also had
the least fatty flavor.
By headspace SPME GC/MS, 2-acetylfuran was
the only peak that could be detected in all four
chicken reaction flavors. When garlic was added as
a reagent, we detected allyl mercaptan, allyl methyl
sulfide, diallyl sulfide and diallyl disulfide in the final
Chicken/Brothy Flavor
Garlic/Onion Flavor
Fermented Flavor
Petroleum Flavor
Dirty/Earthy/Musty Flavor
Juice
Green/Herbal Flavor
Powder
Browned Flavor Oil
F-6. Headspace SPME GC/MS chromatograms of chicken-type flavor reactions with no garlic added (2C),
or with added garlic juice (2J), garlic powder (2P), or garlic oil (2O)

2-Acetylfuran
4
2C
2

Diallyl disulfide
2-Acetylfuran
Diallyl sulfide
Allyl methyl sulfide
Allyl mercaptan

4
2J
2
Detection (MCounts)

0
Diallyl sulfide

2-Acetylfuran

Diallyl disulfide
Allyl mercaptan
Allyl methyl sulfide

4
2P
2

Diallyl disulfide
Allyl mercaptan

Diallyl sulfide
Allyl methyl sulfide

2-Acetylfuran

4
2O
2

0
5 10 15 20 25 30
Time (minutes)

F-7. Sensory aroma profile of vegetable broth flavor reactions with added garlic/onion juice, garlic/onion powder
or garlic/onion oil

Descriptive Aroma Profile of Vegetable Broth Reactions

with Garlic and Onion Sources
Overall Aroma
8

Brothy Aroma Vegetable Aroma

6

2
Chemical/Off Notes Aroma Browned Aroma

Herbal/Green Aroma Onion/Garlic Aroma

Juice
Powder
Fermented/Sulfur Aroma Dirty/Earthy/Musty Aroma
Oil

25
Cooking With Alliums

F-8. Sensory flavor profile of vegetable broth flavor reactions with added garlic/onion juice, garlic/onion powder
or garlic/onion oil

Descriptive Flavor Profile of Vegetable Broth Reactions

with Garlic and Onion Sources
Overall Flavor
Aftertaste
10
Vegetable Flavor
8
Metallic Browned Flavor
6
Pungency 4 Onion/Garlic Flavor

Bitter 0 Dirty/Earthy/Musty Flavor

Sour Fermented/Sulfur Flavor

Salt Herbal/Green Flavor Juice

Powder
Sweet Chemical/Off Notes Flavor Oil
Brothy Flavor

F-9. Headspace SPME GC/MS chromatograms of vegetable broth flavor reactions with no garlic/onion added
(3C), or with added garlic/onion juices (3J), garlic/onion powders (3P), or garlic/onion oils (3O)
Isovaleraldehyde

Limonene

1.5
Butanal

Furfural

1.0
3C
0.5
0.0
Isovaleraldehyde

1.5
Pentanal

Limonene
Butanal

Furfural

1.0 3J
Detection (MCounts)

0.5
0.0
Isovaleraldehyde

Diallyl sulfide
Pentanal
Butanal

Limonene

1.5
Furfural

1.0 3P
0.5
0.0
Dipropyl disulfide
Diallyl sulfide
Butanal

Diallyl disulfide
Limonene
Isovaleraldehyde

1.5
Pentanal

Furfural

1.0 3O
0.5

0.0
5 10 15 20 25 30
Time (minutes)

26 2020 Savory Flavors Ebook | www.berjeinc.com www.PerfumerFlavorist.com

products 2J, 2P, and 2O, with sample 2O containing
the highest levels of these compounds (F-6).
Vegetable broth and onion and garlic powders
had a much greater impact in the oil reactions
than the oils or juices (see F-7 and F-8
F-8). This was
especially evident in the brown and broth flavors,
possibly due to the additional Maillard reactants in
the powders. They also had less fermented sulfur
and chemical notes. The oils were second in onion
and garlic flavor impact but without the browning.
The juices failed to have a great impact.
Analytically, we detected furfural, three aldehydes
(butanal, isovaleraldehyde and pentanal) and limo-
nene in all four vegetable broth reaction flavors. While
sample 3J did not show much difference compared to
sample 3C, samples 3P and 3O did have low levels of
garlic and onion volatile sulfide compounds (F-9).
Conclusions
All of the allium extracts made noticeable contribu-
tions to the flavor of the reactions, but also had some
notable limitations. Onion and garlic oils are by far
the most concentrated means of imparting the flavor
into the reaction, followed by powders, then juices.
Using oils allows for more flexibility in formulating
reactions, but also contributes other flavor notes that
may limit their use. Powders are the best option if
brown notes are desirable. The resulting residues
need to be removed in oil-based reactions and need
to be hydrated in aqueous reactions. The juices were
dilute, but imparted the onion and garlic flavors
to the glycerine-base reactions without the brown
notes or the fermented/petroleum note. When using
juices in the reaction, the flavor chemist needs much
greater concentrations to be effective. Also, they are
obligated to design the reaction with considerable
amount of water, which affects the water activity of
the reaction. Juices also need to be preserved, via
freezing, or salt or acid addition. Flavor chemists
may want to employ mixtures of oils, juices and
powders for customized flavor profiles.
The economics of using the different forms of
allium extracts were not a focus of the study. After
the study was completed, calculations using com-
modity pricing available to the authors demonstrated
that the oils had the lowest cost in usage, followed by
powders and juices. However, commodity prices can
fluctuate widely, so flavor chemists need to factor in
their own current costs.
Acknowledgements
The authors would like to thank Robin Boyle and
the Kalsec Inc. sensory staff and panelists for pre-
paring and evaluating the products for this study.
Address correspondence to Kalsec Inc., 3713 W. Main St., Kalamazoo,
MI  49006; smcdonald@kalsec.com.
References
1. D Young, Practical Meat Flavor Creation. In: Successful
Flavors–from Formulation to QC to Applications and Beyond,
G Mosciano, ed, p 119, Allured Publishing, Carol Stream, IL
(2006)
2. M Wright, Creating Elegant Flavors. In: Flavor Creation–2nd edn,
J Wright, p 179, Allured Publishing, Carol Stream, IL (2011)
3. L Huber, S Kuramoto and F Smith, Process of Preparing a
Flavoring Substance and the Resulting Product. United States
Patent US3157516 (1964)
4. RP Adams, Identification of Essential Oil Components by Gas
Chromatography/Mass Spectrometry, 4th edn. Allured Publishing
(2007)
27
 Vol. 43 • January 2018

Flavor Bites: trans-2-Octenal

With a powerful fatty character paired with just a hint of a
fruity green apple note, this material works well in a variety
of savory, dairy, nut and fruit flavors, as well as tea.

BY JOHN WRIGHT
johnwrightflavorist@gmail.com t rans-2-Octenal (FEMA# 3215, CAS# 2548-87-0) has an extremely
powerful fatty character, but it also has a subtle hint of the fruity
green apple note that dominates the profile of the lower unsaturated
aldehydes, such as trans-2-hexenal. This interesting combination of odor
characteristics does not reduce its effectiveness in the wide range of flavors
that can make obvious use of an overtly fatty note, but it does make it very
effective in an unusually diverse range of less obvious flavors.

Note that the dose rates given throughout this article are the levels sug-
gested for use in flavors intended to be dosed at 0.05% in ready-to-drink
beverages or in a simple bouillon.

Savory Flavors
Bacon: The brightness and sheer power of this raw material make it
especially effective when set in competition with some of the bacon sulfur
notes, giving an attractive fatty character at around 200 ppm.

Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2020 Allured Business Media.

30 2020 Savory Flavors Ebook | www.berjeinc.com www.PerfumerFlavorist.com

 Beef, Roast: trans-2-Octenal can be used in all
types of beef flavors, including boiled beef, but it
is obviously most effective in roast beef profiles. A
good starting point is 150 ppm.
Bread: Bread flavors, in their many different
guises, are given more lift and authenticity by quite
high levels, around 200 ppm, of this material. It is
arguably most effective in pizza base flavors.
Chicken: The unsaturated aldehyde notes play a
vital role in all chicken flavors, and the best effect
is, in my opinion, achieved by using a combination
including about 100 ppm of trans-2-octenal.
Corn, Toasted: Corn chip and cornflake flavors
both make good use of the fatty note of this ingre-
dient. Ideal levels vary, depending on the profile
required, but 100 ppm is a good place to start.
Garlic and Onion, Fried: Neither garlic nor
onion flavors have much call for an intrusive fatty
note, but fried or toasted versions are certainly
helped by modest levels, around 20 ppm in both
instances, of trans-2-octenal.
Grill: At the other extreme, grill and barbeque
flavors require much higher levels of trans-2-octenal,
usually in conjunction with other unsaturated
aldehydes. Even a level as high as 300 ppm is not out
of place.
Ham: trans-2-Octenal, added at a level in the
region of 100 ppm, is particularly helpful in ham
flavors. It conveys something of the fatty character
from the meat itself and also makes the cooked
aspect of the flavor profile appear to be less “boiled.”
Mushroom, Cooked: Many chemicals could
potentially help to build the cooked character of
mushrooms, which has an intrinsic rawness, but
this ingredient stands out because it combines well
with 1-octen-3-ol and reduces the perception of raw
mushrooms. A level of 50 ppm is effective.
Potato: Cooked potato flavors cover a wide range
of different profiles and trans-2-octenal is decidedly
more in fried potato flavors than in mashed potato
flavors. Levels of use can run as high as 200 ppm.
Rice: The same comments are obviously equally
true for rice flavors, but, even in plain boiled rice
flavors, trans-2-octenal can be used to good effect at
a significant level, around 50 ppm.
Seafood: This ingredient is surprisingly useful in
white fish flavors at levels in the region of 100 ppm.
It also performs well at a similar level of use in all
types of seafood flavors, especially crab and lobster.
Tomato, Fresh: It might seem better to use trans-
2-octenal in cooked or dried tomato flavors, but, in
reality, it actually performs best in fresh flavors. A
good starting point is 100 ppm.
Nut Flavors
Hazelnut: trans-2-Octenal is a very useful addi-
tion to all categories of nut flavors, but it works
particularly well in hazelnut and praline flavors. A
level of 200 ppm is ideal in most profiles.
Peanut: The same comments are true of peanut
flavors, but the ideal level does vary depending on
the profile. Generally, the best level of addition is a
little lower for hazelnut flavors, nearer 100 ppm.
Walnut: Walnut flavors, just like hazelnut flavors,
can make good use of quite high levels of trans-
2-octenal, and 200 ppm is also the ideal level of
addition in this flavor category.
31
Flavor Bites
Dairy Flavors
Butter, Fresh: The role of trans-2-octenal in dairy
flavors in general is relatively subtle, but it plays
its most important part in this category in butter
flavors. A good starting level in fresh butter flavors is
50 ppm.
Cheese, Cheddar: The attractive fatty note of this
ingredient is also helpful in cheese flavors, particu-
larly cheddar cheese. The best level of addition is in
the region of 20 ppm.
Milk: A level of 10 ppm works equally well in
fresh milk flavors and in condensed milk flavors, just
adding a slight hint of a fatty note but significantly
increasing authenticity.
Fruit Flavors
Apricot: In fruit flavors we are always looking
at subtle additions of trans-2-octenal, just a hint of
a fatty note to add realism to the profile. In apricot
flavors, a good level of use is around 10 ppm.
Blueberry: trans-2-Octenal also works very well
in blueberry flavors and here the level, although still
subtle, can usefully be taken a little higher than for
apricot flavors, up to 20 ppm.
32 2020 Savory Flavors Ebook | www.berjeinc.com www.PerfumerFlavorist.com
Orange: In all the many different types of orange,
tangerine and mandarin flavors, 10 ppm of trans-
2-octenal adds notable authenticity, blending well
with higher molecular weight unsaturated aldehydes.
Peach: This ingredient works in peach flavors in a
very similar way to apricot flavors, and the ideal level
of addition is also similar, in the region of 10 ppm.
Plum: Plum flavors might seem simple, but they
can be surprisingly difficult to make with a really
authentic character. A tiny addition of trans-2-octe-
nal can have a surprisingly beneficial effect. A level
of 5 ppm is close to ideal.
Watermelon: In contrast, few watermelon flavors
make any real claim to authenticity and seem domi-
nated by tutti frutti notes. Nevertheless, 10 ppm of
this ingredient does provide a welcome contrast to
the harsh cucumber green notes.
Other Flavors
Tea: trans-2-Octenal is an important ingredient in
all styles of tea flavors. It is probably most at home
in black tea flavors, where the best level of use is
around 50 ppm. It also adds depth and realism to
green tea flavors, although at a slightly lower level,
nearer 30 ppm.
 Vol. 43 • March 2018

Flavor Bites: sec-Butylamine

For flavorists, the amines category might be among
the least popular for flavor creation. Difficult to use and
pungent, these chemicals can be used in a variety of
savory, some fruit and even whiskey flavors.

I
n the rich and varied palette of flavor chemicals available
BY JOHN WRIGHT
to the adventurous flavorist, it would be hard to find a less
johnwrightflavorist@gmail.com
popular category than the amines. They are amazingly pungent
and difficult to use. Trimethylamine is far and away the most
popular, probably used more than all other amines combined,
but it is not necessarily always the best choice. The biggest challenge
posed by trimethylamine is its very high volatility. In many applications,
it boils off entirely and it is very difficult to judge the right level to add
to even the least challenging end products. Higher molecular weight
amines reduce this problem, but there is a trade-off. They lose some of
the bright fishy note and gain a distinctly unattractive musty nuance.
There are a dozen obvious alternatives to trimethylamine and it is worth
looking at each in turn.
Note that the dose rates given throughout this article are the levels
suggested for use in flavors intended to be dosed at 0.05% in ready-to-drink
beverages or in a simple bouillon.

Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2020 Allured Business Media.

33
Flavor Bites
Savory Flavors
Bacon: A moderate addition of fishy character to
fried bacon flavor can lift the profile, add realism and
welcome complexity. Levels vary depending, amongst
other things, on the level of smokiness, but 2 ppm is
a good place to start.
Beef, Roast: Here the addition can be a little
more robust. A level of 5 ppm of sec-Butylamine
gives roast beef flavors a pleasant hint of “bloody’
character.
Cheese, Blue: In blue cheese flavors the amine
note forms a perfect partnership with the methyl
ketone complex, giving added impact and defini-
tion. Higher levels, around 10 ppm, can be very
effective.
Cheese, Cheddar: sec-Butylamine works in all the
many styles of cheese flavors but it is most effec-
tive in blue cheese and Cheddar cheese styles. The
best level for Cheddar cheese flavors depends on the
profile and is higher in “sharper” profiles. A level of 2
ppm is a good indication for regular Cheddar flavors,
up to 5 ppm for sharp Cheddars.
Fish: White fish and oily fish flavors are the most
obvious and natural home for sec-Butylamine. A
reasonable starting point is 500 ppm.
34 2020 Savory Flavors Ebook | www.berjeinc.com www.PerfumerFlavorist.com
Mushroom, Dried: Dried mushrooms, especially
dried porcini mushrooms, have a quite significant
fishy element to their profile, and 100 ppm of sec-
Butylamine is typically needed to achieve realism in
these flavors.
Pork: Pork flavors vary considerably, but roast
pork flavors can derive some benefit from a modest
addition of this amine, around 2 ppm.
Potato: French fried and potato chip flavors gain
added realism from just 1 ppm of sec-Butylamine.
Rice: Cooked rice can be a subtle flavor category,
but it is enhanced by this amine at levels up to
5 ppm.
Seafood: Here this ingredient really comes into
its own. A good starting point is 300 ppm, but even
higher levels can be helpful in some flavor types,
especially scampi.
Soy Sauce: The ideal level of sec-Butylamine for
soy sauce flavors is quite difficult to determine and
depends on the other ingredients, especially the
pyrazines. Start at 1 ppm and work up slowly.
Tomato: Fishy tomato flavors do not really sound
so attractive, but this ingredient has a place even in
this category. A very modest addition, around half a
ppm, is all that is required.
ALTERNATIVES TO
TRIMETHYLAMINE
From this brief comparison, it is evident
that there are several viable alternatives to
trimethylamine, but my personal favorite is sec-
Butylamine. It works well in a wide range of flavors,
is relatively heat stable and does not have any
significant off-notes at higher levels.
n-Butylamine (FEMA# 3130, CAS# 109-73-9) A
good alternative, significantly more heat stable.
isobutylamine (FEMA# 4239, CAS# 78-81-9)
Probably a little better than n-butylamine.
sec-Butylamine (FEMA# 4240, CAS# 13952-
84-6) In my opinion the best alternative, more heat
stable and free from musty notes at high levels.
N,N-Dimethylphenethylamine (FEMA# 4248,
CAS# 19352-01-9) Performs very well in shellfish Other Flavors
flavors. Grape: Now, we are away from the savory cate-
gory, it gets quite hard to see the rationale for adding
Hexylamine (FEMA# 4243, CAS# 111-26-2) Heat
an amine note. This is especially true for fruit flavors,
stable but quite musty at higher levels. but a trace, around 0.1 ppm, of sec-Butylamine has a
2-Methybutylamine (FEMA# 4241, CAS# 96-15-1) surprisingly realistic effect in Concord grape flavors.
Quite effective in fish sauce flavors but musty at As a side benefit, it would make a flavor devilishly
high levels. difficult to match!
Kiwi: If grape flavor was hard to visualize then
3-Methylbutylamine (FEMA# 3219, CAS# 107- kiwi is even more a stretch of the imagination.
85-7) Also quite musty at higher levels. Nevertheless, 0.1 ppm of sec-Butylamine is equally
intriguing in this flavor category
2-Phenylethylamine (FEMA# 3220,
Malt: With malt flavors, we are on more solid
CAS#64-04-0) Interesting combination of fishy and
ground, and a moderate addition of 2 ppm of this
rose nuances, especially effective in cocoa and amine adds lift and realism.
some fruit flavors. Milk, Condensed: sec-Butylamine is obviously
isopropylamine (FEMA# 4238, CAS# 75-31-0) effective in cheese flavors, but it can also work in
Good character but not much of an improvement on other dairy flavors. Condensed milk is probably the
most obvious and 0.2 ppm is a good level to try.
trimethylamine in respect of volatility.
Rhubarb: Now we are back on more dangerous
Triethylamine (FEMA# 4246, CAS# 121-44-8) A ground, but 0.1 ppm of this amine is quite effective
good alternative to trimethylamine, more heat stable in lifting rhubarb flavors, especially those intended
and attractive at a range of concentrations. for yogurt.
Tangerine: sec-Butylamine is quite interesting in
Trimethylamine oxide (FEMA# 4245, all citrus flavors, but it is most effective in tangerine
CAS# 1184-78-7) A trimethylamine generator, solving and mandarin flavors. Only a trace, around 0.1 ppm,
in part the stability problem but still difficult to dose is required, but the effect is intriguing.
correctly. Whiskey: In the same way, it is quite interesting
to add this amine to any distilled spirit or even wine
Tripropylamine (FEMA# 4247, CAS# 102-69-2)
flavor, but it really comes into its own in whiskey
Only really useful in combination with other amines.
flavors. Half a ppm is a good level of addition.

35
 Reaction
Flavor Solutions –
ANCIENT
CHEMISTRY
FOR THE
MODERN
WORLD
As alternative proteins continue to drive
the green, clean food movement, reaction
flavors serve as a functional tool to provide
the savory flavors found in cooked meats
and vegetables.

BY LUKE GROCHOLL, Ph.D., MilliporeSigma

Vol. 43 • December 2018

Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2020 Allured Business Media.

36 2020 Savory Flavors Ebook | www.berjeinc.com www.PerfumerFlavorist.com

C ooking is a distinctly human trait.
No other animal engages in this
behavior, yet considerable evidence
suggests humans have been cooking
and roasting food for as long as
there have been homo sapiens.1 We know some of
the same odors that make our mouths water at a
neighborhood barbeque could have been enjoyed
around a cooking fire 800,000 years ago. There’s
even evidence to suggest that humans and their
near relative have been roasting meat and root
vegetables for almost two million years. Using fire
to roast food not only brings out flavors, it helps
preserve the food for consumption later by killing
harmful microorganisms and reducing water
content. Cooking food is also thought to be one of
the key drivers in how humans evolved such big,
sophisticated brains.2 When heated sufficiently,
sugars, proteins and other components of meat and
vegetables undergo chemical reactions making them
easier to digest, thus delivering more calories for the
same meal than raw food itself would. Primatologists
estimate it would have taken primitive man over
nine hours of every day gathering and eating raw
plants and meat to provide enough energy to drive
a big, human brain. By cooking food, our ancestors
significantly reduced the time and energy needed
to gather enough food to power their big brains –
allowing for ever-expanding cranial size and brain
power as we evolved. The calories delivered by easily
digestible cooked meats and vegetables in a single
day provide more than enough energy for large
brains, allowing our ancestors to develop the big
brains of modern man.
Early cooks, like today’s modern chefs, prepared
healthy meals that satisfied the calories we required
to evolve in the creatures we are. Early barbequers
did not roast meat and vegetables to drive evolution,
however. Like today’s gourmet chefs and backyard
griller, it was surely taste that led to heating and
roasting foodstuffs. This almost magical transforma-
tion of raw ingredients or prepared dough to savory
sausages, soups or breads was poorly understood
for most our human history. It wasn’t until modern
chemistry that we really understood what happens in
a sauce pan or at the end of a skewer.
37
Reaction Flavor Solutions – Ancient Chemistry for the Modern World

Labeling Challenges of Natural Reaction Flavors

The demand for natural savory flavors can be met by
natural reaction flavors, but labeling reaction flavor blends
may not be as straight forward as the simple “natural
flavor” tag used for aroma chemicals.
The US FDA defines a natural flavor as “the essential
oil, oleoresin, essence or extractive, protein hydrolysate,
distillate, or any product of roasting, heating or
enzymolysis, which contains the flavoring constituents
derived from a spice, fruit or fruit juice, vegetable or
vegetable juice, edible yeast, herb, bark, bud, root, leaf
or similar plant material, meat, seafood, poultry, eggs,
dairy products, or fermentation products thereof, whose
significant function in food is flavoring rather than
nutritionalb.” Reaction flavor components (amino acids
and sugars) derived from natural sources therefore
can be labelled as natural flavors. In order to meet this
designation, however, it must be demonstrated that the
constituents are consumed during heating or cooking and
thus converted completely to flavor. In addition, the other
components of a reaction flavor (fats, salts, other proteins,
etc.) must be declared separately on the product label.
The USDA also weighs in on reaction flavor labeling.
In guidance documentation, the USDA suggests a reaction
flavor cannot be labelled as natural flavor since it “does
not come from a natural source, as such, but is carefully
formulated in specific proportions to ensure a product
mixture of desired flavor characteristicsc.” This guidance
seems to be in contradiction to FDA regulations, however,
the USDA does allow for ingredients in a reaction flavor
that are either consumed during heating or meet the
FDA definition of flavor to be listed as flavors. These
components can be declared natural flavors if they
meet the FDA natural definition. Proteins and sugars not
consumed when heating as well as fats, salts, processing
aids and other components of a reaction flavor must be
listed separately on a product label just as under FDA
requirements.
In the EU, declaration of natural flavor is more
complex than U.S. regulations. Although the EU has a clear
definition of natural flavorsd, reaction flavors, or “Thermal
Process Flavors” are defined separately in the EU code.
The EU defines a thermal process flavor as “a product
obtained after heat treatment from a mixture of ingredients
not necessarily having flavoring properties themselves, of
which at least one contains nitrogen (amino) and another
is a reducing sugar.” Additionally, the EU requires flavor
molecules to be listed on an approved list (called the Union
list or the community list), however, this list applies only
to flavoring substances (defined chemical substance with
flavoring properties).
Reaction flavors also greatly expand the possibilities for vegetarian and vegan
diets by providing the essential savory, even meaty taste we’ve evolved to love.
Because thermal process flavors are listed as a distinct
flavor category from natural flavors in the EU regulations,
they are declared as “flavors” or “flavorings” but not
“natural flavors” or “natural flavorings” on product labels
even if they are of natural origin. Natural-derived thermal
process flavor components can be declared as natural only
if they meet the natural flavor definition and are listed in
the EU Union List of Flavourings and Source Materials.
Terms such as “all natural” are important to the flavor
industry. Neither the United States nor the EU has clear
definitions of natural food or natural ingredients, but
both regulatory bodies do clearly define natural flavors.
Suppliers of raw materials for thermal process flavors,
therefore have a challenge. Customers request natural
declarations, however, natural origin products may not be
listed on the EU Union Lists. When vetting ingredients for
reaction flavor blends, then natural-sourced ingredients
are desired when the ingredients themselves are not
defined as flavors. Analytical verification by isotopic
analysis is also used to confirm natural origin ingredients.
With the strong emphasis on clean food labels,
and global concerns on food fraud, it is important to
understand requirements on label designations. Because
of the narrow definitions of natural flavors, natural
source raw materials may need to be listed separately
on consumer labels, even when the food itself can be
declared all natural.
b US FDA 21 CFR 101.1.22(a)(3))
c askfsis.custhelp.com
d EC No 1334/2008

38 2020 Savory Flavors Ebook | www.berjeinc.com www.PerfumerFlavorist.com

Culinary Chemistry
In the early 20th century French physician and
chemist Louis Camille Maillard hoped to syntheti-
cally produce proteins from simple molecules. He
described in detail the reaction between reduc-
ing sugars and amino acids which, when heated
together, form acrylamide that further reacts
yielding pyrazines, pyroles and related savory
flavors. Maillard also described how, under contin-
ued heating further cascade reactions resulted in
melanoidins: more complex chemicals that Maillard
correctly proposed as being the source of browning
colors in breads and roasted meats. Today these
reactions are often called nonenzymatic browning
reactions because the chemistry works by heat alone
without the need for catalysts or enzymes. It is for
this insight that heating amino-acids and reducing
sugars together, a process that takes place while
cooking, that the Maillard reaction gets its name.
Despite describing this non-enzymatic browning,
Maillard did not explore this culinary chemistry and
focused his research on protein metabolism.
Although other scientists would explore
Maillard’s reaction scheme it was not until the
Second World War that a concerted effort was taken
to understand the chemistry behind cooking. The
war demonstrated the national security need for a
modern, secure and stable food supply. Research
started by military need continued into peacetime
when, in 1953 the American chemist John Hodge
published a landmark paper on browning reac-
tions.3 This paper focused on the chemistry of
dehydrated food, but more importantly included
a review of Maillard and other chemists’ works on
amino-acid/sugar reactions to describe the whole
complex chemistry of roasting as a single orga-
nized, if complex, system. Hodge’s paper is now one
of the most cited in food science and the basis of all
reaction flavors.
A growing interest in
healthier foods and
greener and more ethical
food production is
driving the demand for
vegetarian alternatives
that provide all the flavor
of meaty foods.
The initial drive for Hodge, the USDA and the
military interests that supported this food science
was in preserving food to help with industrial-
izing and expanding the food supply chain. A very
important result, however, was the understanding
of the flavor chemistry associated with preserving
foods. Canned, precooked foods suffer from flavor
loss and require heating for palatability. Reaction
flavors based on Maillard browning as described
by Hodge provided an elegant solution. A flavor
mixture of amino acids and reducing sugars can
mimic the reactants in uncooked food. The flavor
mixture often includes fats, salts, glutamates, other
(non-reactive) proteins as well as processing aids
to give a fully rounded savory flavor. These reaction
flavor mixtures can release the complex Maillard
browning flavors under reheating conditions. In this
manner, the simple act of heating prepared foods
results in the rapid generation of complex roasting
and savory flavors in the short time it takes to heat
up a can of food. A full day of roasting and stewing
Keeping all
our Flavors
connected.
Stay safe, healthy
and well.
39
Reaction Flavor Solutions – Ancient Chemistry for the Modern World
was no longer necessary to deliver the full flavor
experience that was lost in prepared foods.
Maillard and Cultural Implications
Modern demand on flavorists goes far beyond
simply making precooked foods more palatable upon
heating. For the flavor industry, Maillard brown-
ing raw materials offer a significant opportunity. A
growing interest in healthier foods and greener and
more ethical food production is driving the demand
for vegetarian alternatives that provide all the flavor
of meaty foods. The vegetarian meat substitute
market, for example, is growing at a rate ~50% faster
than other process foodsa.
Vegetarian meat substitutes also feed into more
traditional markets. Halal dietary rules prohibit
the consumption of certain animals, like pork,
and prescribes that acceptable animals must be
slaughtered in a specific manner. Non-animal
derived alternatives provide Muslims with a robust
alternative where animal-source food ingredients
may come into question. Kosher dietary require-
ments have similar restrictions on acceptable meat
sources and preparation and add the additional
layer of prohibiting the mixing of meat and dairy.
Here, a wholly vegan product can meet kosher
requirements and with the help of savory reac-
tion flavors, deliver tastes not otherwise available.
Vegetarian reaction flavors also support Hindu and
Buddhist vegetarian cultures. Other cultural and
religious diets, such as Jainism, an Indian-origin
a www.marketsandmarkets.com/PressReleases/meat-substitutes.asp
40 2020 Savory Flavors Ebook | www.berjeinc.com www.PerfumerFlavorist.com
religion that practices a strict vegan diet, may
benefit from reaction flavors.
Because reaction flavors result in a complex
cascade of savory flavors, they provide flavor solu-
tions not available from other flavor blends. They
enhance and preserve the taste of meaty and savory
foods and add, develop and change while being
cooked. Reaction flavors also greatly expand the
possibilities for vegetarian and vegan diets by pro-
viding the essential savory, even meaty taste, we’ve
evolved to love.
We’ve come a long way from the first primitive
people who roasted meats and roots over an open
fire. That, until recently, little understood miracle
of chemistry likely played an important part of
our evolution and remains the delight of weekend
barbequers and gourmet chefs alike. Flavorists can
continue to embrace reaction flavors to provide
unique, new savory characters to prepared foods or
to add to the ever expanding feast of vegetarian meet
substitutes. The complex nature of reactions flavors
will continue to provide opportunities and challenges
for flavorists everywhere.
References
1. Evolutionary Adaptations to Dietary Changes, F. Luca, G.H.
Perry, and A. Di Rienzo, Annu Rev Nutr. 2010 Aug 21; 30:
291–314.
2. Raw Food Not Enough to Feed Big Brains, Gibbons, A.
Science, Oct. 22, 2012 ,
3. Chemistry of browning reactions in model systems, Hodge, J.,
Journal of Agricultural and Food Chemistry 1(15): 928-943