Vitamin : Pyridoxine, Pyridoxal and Pyridoxamine
Department of Chemistry, Institute of Technology, Warsaw-
V I T A M I N B , also known as pyridoxine, or adermin,
6
is a derivative of pyridine and in that respect is
similar to nicotinic acid and nicotinamide, which
also belong to the complex mixture originally called
vitamin .
According to our present knowledge, vitamin is
a group of three substances : an alcohol, pyridoxine,
an aldehyde, pyridoxal and an amine, pyridoxamine.
A l l three are derivatives of /-hydroxypyridinc, and
thus there is a profound similarity between the
vitamin group and nicotinic acid and its
0
derivatives : in a l l of them the /^-position in the
pyridine ring is substituted by a group strongly
influencing the character of the moleculethe
phenolic group in vitamin and the carboxylic
group in nicotinic acid.
The principal component of vitamin B ,
pyridoxine, has the structure a-lnethyl-3-hydrOxy-
4.5-di(hydroxymethyl) pyridine, / .
This was elucidated in 1939 by
CH.OH
experiments described below,
HO \ CH.OH
but the first mention of the
relationship
CH,
41 /)'-hydroxypyridinc and vitamin
was given by R . R . WILLIAMS
i n 1921 i.e. long before vita
min B was isolated.
E
few years later J . GOLDBEROER and R . D .
A
LiLLiE- found certain types of dermatitis in rats fed
on diet free from vitamin , (lactoflavin). T h e
dermatitis was produced by an unknown factor
present in vitamin , since the rats d i d not recover
2
on administration of pure vitamin .
T h e n S. J . isolated a new crystalline
3
substance from rice bran. H e found the cmpyrical
formula of the hydrochloride of this product to be
C Hj,0,N.HCl.
e It was certainly pyridoxine,
although Ohdakc d i d not recognize the vitamin
character of the substance.
T h e name ' vitamin ' appeared i n 1934,
bestowed by P. G Y O R G Y who isolated this substance
1
from yeast, rice bran and liver. H e found it to bc
an antipellagra factor, which can accompany
vitamin in yeast, liver and other ' vitamin '
2
sources. T h e same author, together with T . W .
BlRCH , found vitamin B to bc a nitrogen base
5
0
which forms a hydrochloride.
T. U R B A S K I , D.Sc.
6-10
In a series of p a p e r s published in 1938
improved methods of isolating vitamin 6were
described. Further experiments showed that
vitamin B, is present in animal or vegetable tissue
in the form of a complex with proteins or carbo
hydrates which is subject to cleavage by the action
6
of enzymes or heat. The richest sources of vitamin 6
are yeast and rice bran. Various seeds including
corn also contain a considerable quantity, while
lesser amounts occur in molasses and liver. M i l k ,
egg yolk, spinach and green vegetables are poor
sources of vitamin .
CHEMICAL PROPERTIES AND STRUCTURE
OF P Y R I D O X I N E
The free base pyridoxine has the empirical formula
C H 0 N . It is a white crystalline substance with
8 u 3
C
m. pt i6oC. It is soluble i n water and most
organic solvents, and forms several salts e.g. the
hydrochloride (m. pt 204~26 with decomposition).
11
R . K U H N and his co-workers determined its
structure in an extremely skilful way within a very
short time. T h e main facts which led to their
conclusions were :
between
/ The substance contains three hydroxyl groups,
1
but only one of them can be methylated with
diazomethane ; thus the substance has one phenolic
and two alcoholic groups.
s I f pyridoxine methylated with diazomethane
was subjected to heating with lead tetracetate, no
oxidation occurred. This indicates that the alcoholic
groups are not attached to the neighbouring carbon
atoms since lead tetracetate is a reagent which
oxidizes oc-glycols.
3 Pyridoxine methylated with diazomethane can
be oxidized with cold potassium permanganate.
One of the alcoholic groups is oxidized to a carboxylic
group which readily forms a lactone with the second
alcoholic group. As only y'- and sometimes (5-lactones
can be formed in this way, the alcoholic groups can
only occupy the 1.4 or 1.5 positions.
0
4 The ultraviolet absorption spectrum shows a
great similarity between pyridoxine and /}-hydroxy-
pyridine. Both pyridoxine and /5-hydroxypyridine
give a cherry red colour with ferric chloride, which
indicates the phenolic character of their hydroxyl
groups : a- and y-hydroxypyridine are not phenolic
in character and do not become coloured with ferric
chloride.
Research 2 -11 . URBASKI: Vitamin : Pyridoxine, Pyridoxal and Pyridoxamine
6

5 If pyridoxine methylated with diazomethane 8 K u h n and his co-workers synthesized a dibasic

is oxidized with hot potassium permanganate in
alkaline medium a tribasic acid is formed which
gives a brown colour with ferrous sulphate. This
colour reaction is characteristic of pyridinic acids,
which contain a carboxylic group in a-position. O n
heating the acid looses a molecule of water and a
molecule of carbon dioxide, forming the anhydride
of a dibasic acid. T h e acid produced from this
anhydride does not give the colour reaction with
ferrous sulphate.
These facts, together with the analytical data,
brought K u h n to the following conclusions :
acid Ilia. It proved to be identical with the acid
formed from the methyl ether of pyridoxine, so
formula lb was therefore rejected.
Independently the structure of pyridoxine was
also established by a team of workers i n the U . S . A .
1
Thus the acid Ilia was obtained - by oxidizing the
methyl ether of pyridoxine IV. This acid was
13
subsequently synthesized by a different method.
Both syntheses of the acid Ilia were important i n
providing a basis for the preparation of pyridoxine,
which both groups of investigators achieved shortly
afterwards.

a the three carboxyl groups are formed by the

oxidation o f two primary alcoholic a n d one SYNTHESIS OF PYRIDOXINE

methyl group ; R . K u h n and his co-workers synthesized pyridoxine 14

by starting from the acid Ilia and transforming th'

b the carboxyl group, which is eliminated as C 0 2
carboxyl groups according to the scheme :
on heating, occupies the a-position ;
- C O O H - * - C O N H . -+ - C N - * - C H . N H , - * - C H . O H .
the two remaining carboxyl groups are attached
to the neighbouring carbons. O n this basis Thus the acid Ilia gave the methyl ether of
K u h n gives the structure of the anhydride / / pyridoxine IV :
and three possible structures of pyridoxine, COOH CH.OH
la, lb and Ic :
CH.O COOH , ^ C K O H
CH I
3

CH I I
CH..OH
/
HO, / N
\CH,OH CHJOJ^NCO ix N
(IV)
CHJ (Ilia)
NT 4
N X
which was demcthylated to give the hydrobromidc :
(la) ( CH.Br CH OH2

CH.OH CH 3
HBr Ho/^CH.Br H, /^
(IV)
(66%) C H , N .+!
HO, CH.OH ,/\. CH 1
+1

t JcH OH /
l'
N 2
H H
(lb)
(Ic) (V)
6 K u h n and co-workers synthesized the anhydride A n identical synthesis was also described by A .
which possesses the structure / / . It proved to be ICHIBA and K . M i e n i . 1 5

identical with that obtained from the methyl ether

The method of synthesizing pyridoxine developed
of pyridoxine.
by S . . HARRIS and K . F O L K E R S gave the best 10

7 Careful oxidation of the methyl ether of.
pyridoxine with barium permanganate led to a
dibasic acid with an untouched methyl group. This
acid does not give any colour with ferrous sulphate.
It has therefore two possible structures, Ilia and 111b :
practical results from the viewpoints of yield a n d
cost o f production. T h e y started from ethoxy-
acetylacetonc VI and cyanacetamide VII which
with piperidine in alcoholic solution underwent ring
closure and formed a pyridine derivative VIII :

COOH CH.OC.H;
COOH CH.OCHj
I
CH ,0: COOH , I COOH CO

CH! J
I
4
CH, CH., + CH CN 2
piperidive CN
N N yield 8,".
CH., =0
(Ilia) (Hlb) CH, -co c=o NH
/
Consequently the structure Ic for pyridoxine should NH,
be rejected. (VI) (VII) (VIII)
508
. U R B A S K I : Vitamin : Pyridoxine, Pyridoxal and Pyridoxamine Research 2 -11

CH.,OC,H 5 .-, COOCH 3

J COOCH 3

NO.,, v H
>. N H ,
(PT
CN HO/NCOOCH, HOf^NcoocH,
(VIII) C N

yield 32%
CHJ
5
N )= "'1 )=o CH CH. N
NH NH
I
(IX) (A') CH C,H 2 5

[XVII) (XVIII)
Substance VIII was nitrated to IX and then reduced T h e product XVIII can be converted into pyridoxine
by platinum black to the amine X. Substance X, in the conventional way by stepwise transformation of
which is an a-pyridone derivative, can be transformed - C O O C H into - C H j O H . This synthesis suggested
3

by phosphorus pcntachloridc and phosphorus oxy- the possible functioning of a-alanine as a natural
chloridc into an oc-chloropyridinc derivative, because precursor of pyridoxine and it is interesting to note
a-pyridone reacts tautomerically as a-hydroxy- that E . E . S N E L L found alanine capable of replacing
1 9

pyridine : vitamin for the growth of Lactobacillus casei and

6

Streptococcus faecalis R.

{ J=o <
' V ' O H
PYRIDOXAL AND PYRIDOXAMINE
NH N
(PSEUDOPYRIDOXINE)
a-pyridone a-hydroxypyridine It was found in 1938-39 that vitamin is a growth-

promoting agent for yeast and bacteria. A biological

Thus product X can be transformed into A ' / : method for the assay of pyridoxine was then

, 2 5 CH OC H,2 2 CH OH 2 ..
PCI. + POCI, N H j / N c N H,(p -Pd) t NH/NCH.NH,, HCI NH/^CHjNHjCI HOMO HO^^CH.OH
yieldi6-5% CH,I N N JCI yUUjn-5% C H , I N K
yield (sy)>
7 CHJ 4 | 4 J yield 45-4,'oCV\

(XI) (XII) (XIII) (la)

This was reduced by hydrogen on platinum and 20

developed . Experiments on the growth of bacteria
palladium with the simultaneous removal of chlorine, on a medium containing pyridoxine led to some
giving the amine XII. Hydrolysis with hydrochloric important conclusions. E . E . SNELL, . M . GUIRARD
acid at i 7 5 - i 8 o C yielded the aminoalcohol XIII and R . J . W I L L I A M S 21
found that Strep lactis R
which on diazotization finally gave pyridoxine. A n would grow on such a medium many times faster
almost identical method was adopted by Merck A . G . than could be accounted for on the basis of actual
in Germany for the commercial synthesis of pyridoxine content. T h e explanation is that
17
pyridoxine . pyridoxine was converted into a more highly active
metabolite prior to utilization by the bacterial
Recently A . C O H E N 18
proposed a new method organism. This hypothetical metabolite was called
of preparing pyridoxine by starting from a-alanine pseudopyridoxine.
derivatives : N-benzyl-a-alaninc ester XIV and
In his later experiments E . E . S N E L L found that 2 2

a-hydroxymethylenesuccinic ester XV were cyclized

media containing pyridoxine could be activated by
to a 3-kcto-i .2.3.4-tetrahydropyridine derivative
simple heating in an autoclave. H e advanced a
XVI :
suggestion that pseudopyridoxine was formed by
the interaction of pyridoxine and aminoacids present
.., 3 COOCH 3
in the mixtures. H e developed his experiments 23

I 0= ., further and heated pyridoxine a with ammonia i n

3-- \ + 2 an autoclave b with manganese dioxide.
NH \ CH.
.., I In both instances he obtained products much
H,C,H, HOH CHX H t 5
more active than pyridoxine. In the experiments a
(XIV) (XV) (XVI) they were 140 times more active than pyridoxine,
and in b 50 times. H e therefore suggested that
T h e product was dehydrogenated to XVII and after animation and partial oxidation are possible reactions
hydrogenolysis of the N-benzyl group the substance which can transform pyridoxine into pseudo
XVIII was obtained. pyridoxine. Pseudopyridoxine is therefore a mixture
509
 Research 2 - 1 1 . U R B A S K I : V i t a m i n 6 : Pyridoxine, Pyridoxal and Pyridoxamine

of two substances, the product of oxidation, which The product possessed the properties of pyridoxamine,
Snell called pyridoxal, and the product of amination, as determined from its action o n the growth o f
which he called pyridoxamine. T h e following Lact casei and Strep lactis R .
reaction scheme represents this transformation :
Harris, H e y l and Folkers also prepared pyridoxal
[O] NH :i [H] XXVaXi transformed it into pyridoxamine, providing
R.CH OH 2 R . C H O <lt R . C H NH 5t R.CH.NH., evidence that the same 4-hydroxymcthyl group was
Ptridoxine Pyridoxal Pyridoxamine transformed into an aldehyde and methylamino
group respectively. Pyridoxal was prepared by a
Snell's metabolic experiments with rats and human careful oxidation of pyridoxine in an alkaline medium :
beings also led to the conclusion that pyridoxine is
partially converted by animal organisms into CH,OH CHO
pseudopyridoxinc. HO/NCH.OH HO CH..OH
NH..OH
KMnO,
CH.NH, Independently R . K U H N found !1

CH ~^CH,
:L
N
that patients cured with pyridoxine
/.. (XXV)
excreted i n their urine a new
CH
N '
substance much more potent than CH.NH.
CH = NOH
pyridoxine, which possesses the
(XIX) / >,
structure XIX. HO/NCH.,OH [H]
CH I I
No details were given of how he arrived at this J TN
N
conclusion. (XXVI)
(XIX)
The structures of pyridoxal and pyridoxamine T h e aldehyde XXV was transformed into the oxime
were established by S. A . HARRIS, D . H E Y L a n d and this was catalytically reduced to pyridoxamine.
K . FOLKERS by 25
synthesizing these two products
and their isomers. T h e y started from substance XX, F i n a l confirmation of the struc
..
the methyl ether of the alcohol Xlla. homologous ture of pyridoxal was obtained
HO ,CHO
with substance XII, the ethyl when the same authors synthesized
H,OH
ether of the same alcohol. CH, the isomeric aldehyde XXVII,
NH /\cH,NH..
4
2
Diazotization of XX gave the N
which does not possess the growth
C H
product XXI. O n action of {XXVII) promoting activity of pyridoxal.
:i4 N J thionyl chloride the alcoholic
Further, E . E. S N E L L found that all three members
2 0

[Xlla) group was replaced by chlorine of the vitamin group occur i n natural tissues. I n
0

XXII which was then substituted by the amino group various papers E . E . SNELL and his co-worker 27

XXIII ; finally the ether group was hydrolyscd with showed that the three compounds pyridoxine,
hydrochloric acid at i 7 0 - i 8 o C and product XXIV pyridoxal and pyridoxamine each behave very
was obtained. There was no doubt about the differently towards different organisms.
structure of this compound, which on bio-assay
proved to be non-identical with pyridoxamine and Thus they found pyridoxal has 5,000-8,000 times
did not possess its activity. and pyridoxamine 6,000-9,000 times the activity of

CH,OCH ; 1 ., CH OCH
2 : l
.., ..
NH 2 CH..NH, /^- HO ..1 HO 'NcH-.NH, H O ^ C H . N H ,
SOCI (+ 21)
CH
\|| J
CH,
N'
CHJ V N {170-180")
CH

(XX) (XXI) (XXII) (XXIII i (XXIV)

Acting on substance XXI with ammonia at 140C pyridoxine as a growth factor for Strep lactis R . F o r
in methyl alcohol, they obtained the substance XIX other organisms, such as Lact casei, pyridoxal was
identical with pyridoxamine : also found to be highly active, but pyridoxine and
pyridoxamine almost inactive. O n the contrary,
CH,OCH ; 1 CH.NH, for Saccharomyces carlsbcrgensis all the compounds have
H/\CH,OH HO / X
jCH.OH approximately equal activities. It is assumed that
the variation i n activity is due to differences i n the
CH CH,
N ease with which the various organisms convert
(XXI) (XIX) pyridoxine into pyridoxamine and pyridoxal.
. U R B A S K I : Vitamin : Pyridoxine, Pyridoxal and Pyridoxamine Research 2 11

The original presence or formation of the members
of vitamin groups renders microbiological assay
for vitamin B invalid if the growth of unsuitable
g excretion of iron might be one of the factors causing
organisms is examined. For that reason it is
preferable to use organisms which respond equally to
all three members of the group e.g. Sacch carlsbergcnsis
and Neurosppra sitophila.
P H Y S I O L O G I C A L A C T I O N OF V I T A M I N B
pyridoxine deficient rats excreted in their urine a
complex of xanthurenic acid and iron. This
anaemia. O n the basis of this and some later work
the role of pyridoxine was established as a factor
producing metabolism of tryptophane and par
ticularly of kynurenine and xanthurenic acid. This
property of pyridoxine was later elucidated in the
course of work on the coenzyme action of phos-
6 phorylated pyridoxal quoted below. 40

None of the members of the vitamin B group E

The discovery that vitamin B is closely related to
g

produces a definite pharmacological action and this certain enzymes was the most important part of
is the main reason why the part played by this the research on its biological action. The first
vitamin was obscure. T h e earliest experiments observation was related to the role of vitamin 6

showed a connection between vitamin and certain 6

in the transformation of certain amino acids to
skin disorders, so typical for most group vitamins. amines i.e. of their decarboxylation by decarboxylase.
This was confirmed by later experiments. A special Thus W . D . B E L L A M Y and I. C . G U N S A L U S found 33

type of dermatitis, acrodinia, occurring on peripheral that addition of pyridoxine and nicotinic acid or
parts of the bodies of animals is due to lack of pyridoxal stimulated production of tyrosine decar
vitamin . It was also suggested that vitamin
6
boxylase. T h e n J . BADDILEY and E . F. G A L E 3 4

is an agent in the metabolism of unsaturated fatty and, almost simultaneously, W . W . UMBREIT and
2
acids ". Experiments with rats gave evidence of I. C . GUNSALUS discovered that phosphorylated
35

the importance of pyridoxine i n the process of
29
transformation of proteins into fats .
More recently a relation between the vitamin
deficiency and anaemia has been clearly shown by
several authors. S. L E P K O V S K Y found that anaemia
30
pyridoxal can act as co-decarboxylase. In addition,
others 30
prepared phosphorylated pyridoxal with
40 to 5 0 per cent coenzyme activity from pyridoxal
0
and phosphorus oxychloride. T h e exact position
of the phosphoric acid group i n this coenzyme is

not yet known.

produced by the lack of pyridoxine does not respond
to iron and copper, but prompt improvement A further discovery was the function of pyridoxine
follows administration of pyridoxine. M. M. derivatives as agents playing important parts i n
WINTROBF. et alii 31
showed that pigs fed on a diet biological transaminations. Previously E . E . S N E L L 3 7

supplemented with vitamins A and D and all known had suggested that the possible conversion of pyridoxal
vitamins except B develop a severe microcytic
E into pyridoxamine may be explained by a trans
anaemia frequently accompanied by epileptic con amination reaction. In a number of papers he
vulsions. Administration of pyridoxine produced showed that a relation existed between members of
rapid regeneration of blood. vitamin B group and the process of transamination.
E

T h e n H . C . LICHSTEIN, I. C . GUNSALUS and W . W .

It is known that kynurenine, an amino acid, and U M B R E I T found that pyridoxal phosphate functioned
33

xanthurenic acid, a quinoline derivative, can be as the coenzyme of the transaminase of certain acids.
excreted by animals suffering from nutritional
disorders. It has also been shown that both sub The process of transamination shown below was
stances are products of incomplete metabolism of suggested by F. SCHLENK and A . F I S C H E R . 39

tryptophane. S. LEPKOVSKY et alii - established the 3

Another function of pyridoxal phosphate was
exact dietary deficiency necessary to produce the found by W . W . UMBREIT, W . A . WOOD and I. C .
excretion of xanfhurenic acid. They found that GUNSALUS . T h e y proved it to be the coenzyme
40

CO + N H , R
I I I
COOH CH, C= N CHN C H N H . , -|- C H O
J 1 II I
HOOC CH., HOOC
HO| CH.OH HOOC CH
!
H<Y (CH.OH
protein
CH HO, CH..OH ? X
|CH,OH
1 V
N ' ru \protein
'^ N ^
fyndoxamine-protein pyridoxal-protein
complex
complex
Research 2 - 11 j. . B U R G O Y N E : Inflammability of Gases

for tryptophanase which catalyses the breakdown L C

HARRIS, S. A . and FOLKERS, K . J. Amer. chem. Soc. 61
of tryptophane to indole, pyruvic acid and ammonia. (>939) 1245. 07
1 7
B.I.O.S. Report Mo. 766, 159
The complex behaviour of the vitamin group 6
1 8
COHEN, A . Xlth intern. Congr. Chem. London, 1947
gives no clear indication of its use in therapy. They Abstr. 247/3
may be useful remedies against some types of
1 0
SNELL, E . E . J. biol. Chem. 158 (1945) 497
2 0
ATKIN, L . , SCHULTZ, A . S. and FREY, G . N . J. Amer,
anaemia and some skin disorders, including such chem. Soc. 61 (1939) 1931
symptoms of pellagra which arc not relieved by the and WILLIAMS, W . L . Ind. Eng. Chem.
usual treatment with vitamin , , and nicotinic 2
Anal. 15 (1943) 141
acid. It is certain that pyridoxine is an invaluable
2 1
SNELL, E . E . , GUIRARD, B. M . and WILLIAMS, R . J . J .
biol. Chem. 143 (1942) 519
remedy against certain nervous disorders accom 2 2
Proc. Soc. exper. biol. Med. 51 (1942) 356
panied by insomnia and irritability, and also against 2 3
J. Amer. chem. Soc. 66 (1944) 2082
2

vomiting in pregnancy. It is of value i n treating C.I.O.S. Report XXIV13

2 6
HARRIS, S. A . , H E Y L , D . and FOLKERS, K . J. Amer,
muscular dystrophy, paralysis agitans and chorea.
chem. Soc. 66 (1944) 2088
2 0
SNELL, E . E . - J. biol. Chem. 157 (1945) 491
2 7
e.g. and RANNEFELD, A . N . ibid 157(1945)475
REFERENCES 2 8
BIRCH, T . W . ibid 124 (1938) 775
1
WILLIAMS, R. R. Ind. Eng. Chem. 13 (1921) 1107 2 9
MCHENRY, E . W . and GAVIN, G . ibid 138(1941)471
2
GOLDBERGER, J . and LiLLiE, R. D . U.S. Publ. Health 3 0
LEPKOVSKY, S. ibid 149 (194) ' 9 5
Service 41 (1926) 1025
ibid 155 (1944) 299
3
OHDAKE, S. J . Bull. agr. chem. Soc. Japan 8 (1932) 111 3 1
WiNTROBE, M . M . , SAMTER, M . and Lisco, H . Bull.
4
GYRGY, P. Nature, Land. 133 (1934) 498 John, Hopkins Hosp. 64 (1939) 399
Biochem. J. 29 (1935) 7 4 . 7 > 77
1 6

FOLLIS, R. H., MILLER, M . H., STEIN, H . J.,

5
BIRCH, T . W . and GYRGY, P. ibid 30 (1936) 304 ALEAYAGO, R., HUMPHREYS, S., SUKSTA, A . and CART-
6
KUHN, R. and WENDT, G . Ber. 71 (1938) 780, 1118 WRIGHT, G . E . ibid 72 (1943) i
7
LEPKOVSKY, S. Science 87(1938) 169
8
KERESZTESY, J . C . and STEVENS, J . R. Proc. Soc. exper.
CARTWRIGHT, G . E . , WINTROBE, M . M . and HUM
PHREYS, S. J. biol. Chem. 153 (1944) 171
biol. Med. 38(1938)64
* ICHIBA, . and MICHI, K . Inst. phys. chem. Res., Tokyo
3 2
LEPKOVSKY, S., ROBOZ, E . and HAAGEN-SMIT, A . J .
ibid 149 (194) "95
34 (1938) 623
1 0
GYORGY, P. J. Amer. chem. Soc. 60 (1938) 983
REID, D. F., LEPKOVSKY, S., BONNER, D. and TATUM, E. L .
" K U H N , R. and WENDT, G . Ber. 71 (1938) 780, ibid 155 (1944) 2
99
1118, 1534
3 3
BELLAMY, W . D . and GUNSALUS, I. C . J. Bad. 48
ibid 72 (1939) 305 (1944) 191
ANDERSAG, H., WESTPHAL, K . and WENDT, G . J . biol. Chem. 155 (1944) 357
ibid 72 (1939) 309
1 1
BADDILEY, J . and G A L E , E . F. Mature, Land. 155
WENDT,, G . and WESTPHAL, . ibid 72 (1945) 727
(> 939) 310 3 5
UMBREIT, W. W . and GUNSALUS, I. C . J. biol. Chem.
1 1
STILLER, E. J., KERESZTESY, J . C . and STEVENS, J . R. 159 (1945) 333
J. Amer. chem. Soc. 61 (1939) 1237 3 6
H E Y L , D., HARRIS, S. A . and FOLKERS, K . iwtli Meet.
1:1
HARRIS, S. A . , STILLER, E. J . and FOLKERS, K . ibid Gi Amer. chem. Soc. 1946 35
(1939) 1242 3 7
SNELL, E . E . J. biol. Chem. 154 (1944) 313
1 1
KUHN, R., WESTPHAL, ., WENDT, G . and WESTPHAL,. 3 8
LICHSTEIN, H . C , GUNSALUS, L C , UMBREIT, W. \ V .
.Xaturwiss. 27 (1939) 469 ibid 161 (1945) 311'
1 0
ICHIBA, A . and Mieni, K . Inst. phys. chem. Res., Tokyo 3 9
SCHI.ENK, F. and FISCHER, A . Arch. Biol. 12 (1947) 69
35 (1938) 73 411
UMBREIT, W . W . , WOOD, W . A . and GUNSALUS, I. C .
ibid 36 (1939) i , 173 J. biol. Chem. 165 (1946) 731
ibid "169 (1947) 631

Inflammability of Gases
J. H . B U R G O Y N E , D.Sc, F.R.I.C.

Imperial College of Science and Technology, London

LIMITS OF I N F L A M M A B I L I T Y A T limits. Thus, while a mixture containing the fuel gas

ATMOSPHERIC TEMPERATURE and oxygen i n stoichiometric proportions may be
I T has long been known that gases capable of flame expected to propagate flame mere readily than others
propagation in air can only be inflamed between because it has a m a x i m u m calorific value, dilution
certain limits of concentration. A moment's with either constituent may be expected to reduce
rcllection shows the theoretical necessity of such the calorific value such that eventually the tern-