Erythorbic acid

Erythorbic acid
Names
	IUPAC name D-erythro-Hex-2-enono-1,4-lactone
	Systematic IUPAC name (5R)-5-[(1R)-1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one
	Other names D-Araboascorbic acid, Erythorbate, Isoascorbic acid, D-isoascorbic acid
Identifiers
CAS Number	89-65-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:51438 ;
ChemSpider	16736142 ;
ECHA InfoCard	100.001.753
E number	E315 (antioxidants, ...)
PubChem CID	6981;
UNII	311332OII1 ;
CompTox Dashboard (EPA)	DTXSID6026537 ;
	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 Key: CIWBSHSKHKDKBQ-DUZGATOHSA-N ; 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	176.124 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 (fire diamond)	1 1 0
Related compounds
Other cations	Calcium erythorbate, sodium erythorbate, potassium erythorbate
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Erythorbic acid (isoascorbic acid, D-araboascorbic acid) is a stereoisomer (C5 epimer) 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.

Names


IUPAC name D-erythro-Hex-2-enono-1,4-lactone
Systematic IUPAC name (5R)-5-[(1R)-1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one
Other names D-Araboascorbic acid, Erythorbate, Isoascorbic acid, D-isoascorbic acid
Identifiers
CAS Number	89-65-6^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:51438^Y
ChemSpider	16736142^Y
ECHA InfoCard	100.001.753
E number	E315 (antioxidants, ...)
PubChem CID	6981
UNII	311332OII1^Y
CompTox Dashboard (EPA)	DTXSID6026537
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	176.124 g·mol⁻¹
Density	0.704 g/cm³
Melting point	164 to 172 °C (327 to 342 °F; 437 to 445 K) (decomposes)
Acidity (pK_a)	2.1
Hazards
NFPA 704 (fire diamond)	1 1 0
Related compounds
Other cations	Calcium erythorbate, sodium erythorbate, potassium erythorbate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references