Erythrulosis

Structural formula
Fischer projection , open-chain representation
General
Surname	Erythrulosis
other names	1,3,4-trihydroxybutan-2-one
Molecular formula	C 4 H 8 O 4
Brief description	light yellow, viscous liquid
External identifiers / databases
CAS number 40031-31-0 (unspec.) EC number 609-775-5 ECHA InfoCard 100.129.795 PubChem 162406 Wikidata Q65557091
properties
Molar mass	120.10 g mol −1
Physical state	liquid
density	1.39 g cm −3
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Erythrulose is a monosaccharide from the group of tetroses .

Isomerism

Erythrulose exists in two stereoisomeric forms. The D -form is the only natural ketotetrose. The IUPAC name of the D form is ( R ) -1,3,4-trihydroxybutan-2-one. L -Erythrulose is of little importance.

Isomers of erythrulose
Surname	D -Erythrulose	L -Erythrulose
other names	( R ) -1,3,4-trihydroxybutan-2-one	( S ) -1,3,4-trihydroxybutan-2-one
Structural formula
CAS number	496-55-9	533-50-6
	40031-31-0 (unspec.)
EC number	-	610-990-1
	609-775-5 (unspec.)
ECHA info card	-	100.125.646
	100.129.795 (unspec.)
PubChem	5460177	5460032
	162406 (unspec.)
Wikidata	Q417337	Q27103403
	Q65557091 (unspec.)

use

Erythrulose is a component of some self-tanners . In combination with dihydroxyacetone (DHA) it creates a brown color on the skin. The staining occurs through the Maillard reaction of the keto group with free amino groups of the amino acids of the uppermost dead horny layer ( stratum corneum ) of the epidermis . In the process, brown colored pigments, so-called melanoids, are formed . The tanning effect of erythrulose without DHA develops after about two days and, according to the manufacturer, should last longer. According to the current state of knowledge, the reaction and the reaction products are completely harmless.

Manufacturing

Erythrulose is produced microbiologically through an aerobic fermentation process with the help of the bacterium Gluconobacter .

literature

• Erythrulose ( Memento of March 26, 2007 in the Internet Archive ) (English; PDF; 108 kB)

Web links

Commons : Erythrulose  - Collection of Images, Videos and Audio Files

• Natural tan from erythrulose

Individual evidence

1. ↑ ^{a b c d} data sheet Erythrulose, Pharmaceutical Secondary Standard; Certified Reference Material at Sigma-Aldrich , accessed December 26, 2019 ( PDF ).