Nov. 24,1923 
Studies on Rancidity 
339 
This would seem to indicate that the hydrogen peroxid reacts with the 
double bond of acrolein to form a compound that still contains the alde¬ 
hyde group. Many such reactions might be imagined, the products vary¬ 
ing somewhat with the quantities of the respective substances that are 
involved. Thus, for the formation of acrolein moloxid, two molecules of 
hydrogen peroxid would be required for one of acrolein; whereas for the 
formation of glyceric aldehyde, methyl glyoxal, oxyacrolein, malonic 
dialdehyde, or epihydrin aldehyde, one molecule of hydrogen peroxid 
would suffice; and for the formation of mesoxaldialdehyde three would 
be needed. Without considering for the present a large number of more 
complicated reaction products that might conceivably be formed, these 
substances were examined as to their behavior in the Kreis test, so far as 
practicable or desirable. 
H 
1 
H 
1 
1 
H-C 
+■§>■ 
H—C—O 
■° - h44 
h — <i=o 
+ 2 i> 
H—C=0 
Acrolein 
Acrolein peroxid 
H 
H 
H 
1 
„4 
H—O 
H— k —O—H 
H—C—OH 
1 
n 
+.| -> 
1 or 
C^O 
H—C 
h— d:=o 
H—O 
H—C—O—H 
1 
H—C—OH 
H—C=0 
i 
Glyceric 
aldehyde 
Dihydroxy- 
acetuae 
H 
<4 
H- 
h4 
H—C =0 
=0 ' 
H 
H—C—H 
I or H* 
c=o 
:-i= H ' 
H—C =0 
4- 
: 4 =, 
H or H- 
O H 
H—C—OH 
L=o 
H- 
=0 
Methyl 
glyoxal 
Malcmie 
dialddhyde 
Oxacrolein 
H 
or po +H/) 
H— i=o 
Epihydtih 
aldehyde 
H 
h— i 
hJ 
£>°=° 
+ g>°=° 
H>=° 
H—C =0 
<Uo + 4 h 2 o 
H—i =0 
Mesoxal 
dialdehyde. 
Glyceric ai^dbhydk.—T he condensation reaction between glyceric 
aldehyde and phloroglucin has already been studied by Wohl and Neu- 
berg (45). According to these authors, the only product that is formed, 
with any degree of readiness at least, is a white, crystalline substance, 
insoluble in water and fairly easily formed in aqueous solutions of the 
reagents even when condensing agents are not employed. While the 
possible presence of glyceric aldehyde in rancid coconut oil has been 
60379—24 - 2 
