Erythorbic acid

Erythorbic acid

Names
IUPAC name (5R)-5-[(1R)-1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one
Other names D-Araboascorbic acid, Erythorbate, Isoascorbic acid, E315, (D-)Erythroascorbic acid
Identifiers
CAS Number	89-65-6 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:51438 Y
ChemSpider	16736142 Y
ECHA InfoCard	100.001.753
E number	E315 (antioxidants, ...)
PubChem CID	6981
UNII	311332OII1 Y
InChI InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5-/m1/s1 Y Key: CIWBSHSKHKDKBQ-DUZGATOHSA-N Y InChI=1/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5-/m1/s1 Key: CIWBSHSKHKDKBQ-DUZGATOHBV
SMILES OC=1[C@H](OC(=O)C=1O)[C@H](O)CO
Properties
Chemical formula	C6H8O6
Molar mass	176.12 g·mol−1
Density	0.704 g/cm3
Melting point	164 to 172 °C (327 to 342 °F; 437 to 445 K) (decomposes)
Acidity (pKa)	2.1
Hazards
NFPA 704	1 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Erythorbic acid (isoascorbic acid, D-araboascorbic acid, (D-)erythroascorbic acid) is a stereoisomer of ascorbic acid (vitamin C). It is synthesized by a reaction between methyl 2-keto-D-gluconate and sodium methoxide. It can also be synthesized from sucrose or by strains of Penicillium that have been selected for this feature. It is denoted by E number E315, and is widely used as an antioxidant in processed foods.

Clinical trials have been conducted to investigate aspects of the nutritional value of erythorbic acid. One such trial investigated the effects of erythorbic acid on vitamin C metabolism in young women; no effect on vitamin C uptake or clearance from the body was found. A later study found that erythorbic acid is a potent enhancer of nonheme-iron absorption.

Since the U.S. Food and Drug Administration banned the use of sulfites as a preservative in foods intended to be eaten fresh (such as salad bar ingredients), the use of erythorbic acid as a food preservative has increased.

It is also used as a preservative in cured meats and frozen vegetables.

It was first synthesized in 1933 by the German chemists Kurt Maurer and Bruno Schiedt.