Chemistry of ascorbic acid

l-Ascorbic acid
Names
	IUPAC name (5R)-[(1S)-1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one
	Other names Vitamin C; l-threo-Hex-2-enono-1,4-lactone;
Identifiers
CAS Number	50-81-7 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:29073 ;
ChEMBL	ChEMBL196 ;
ChemSpider	10189562 ;
EC Number	200-066-2;
E number	E300 (antioxidants, ...)
IUPHAR/BPS	4781;
KEGG	D00018 ;
PubChem CID	5785;
UNII	PQ6CK8PD0R ;
	InChI InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1 Key: CIWBSHSKHKDKBQ-JLAZNSOCSA-N ;
	SMILES OC=1C(OC(=O)C=1O)[C@@H](O)CO; C([C@@H]([C@@H]1C(=C(C(=O)O1)O)O)O)O;
Properties
Chemical formula	C6H8O6
Molar mass	176.124 g·mol−1
Appearance	White or light yellow solid
Density	1.65 g/cm3
Melting point	190 to 192 °C (374 to 378 °F; 463 to 465 K) decomposes
Solubility in water	330 g/L
Solubility	Insoluble in diethyl ether, chloroform, benzene, petroleum ether, oils, fats
Solubility in ethanol	20 g/L
Solubility in glycerol	10 g/L
Solubility in propylene glycol	50 g/L
Acidity (pKa)	4.10 (first), 11.6 (second)
Pharmacology
ATC code	A11GA01 (WHO) G01AD03 (WHO), S01XA15 (WHO)
Hazards
NFPA 704 (fire diamond)	1 1 0
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	11.9 g/kg (oral, rat)
Safety data sheet (SDS)	JT Baker
	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

Ascorbic acid is an organic compound with formula C₆H₈O₆, originally called hexuronic acid. It is a white solid, but impure samples can appear yellowish. It dissolves freely in water to give mildly acidic solutions. It is a mild reducing agent.

Ascorbic acid exists as two enantiomers (mirror-image isomers), commonly denoted "l" (for "levo") and "d" (for "dextro"). The l isomer is the one most often encountered: it occurs naturally in many foods, and is one form ("vitamer") of vitamin C, an essential nutrient for humans and many animals. Deficiency of vitamin C causes scurvy, formerly a major disease of sailors in long sea voyages. It is used as a food additive and a dietary supplement for its antioxidant properties. The "d" form (erythorbic acid) can be made by chemical synthesis, but has no significant biological role.

Names


IUPAC name (5R)-[(1S)-1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one
Other names Vitamin C l-threo-Hex-2-enono-1,4-lactone
Identifiers
CAS Number	50-81-7^N
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:29073^N
ChEMBL	ChEMBL196^N
ChemSpider	10189562^N
EC Number	200-066-2
E number	E300 (antioxidants, ...)
IUPHAR/BPS	4781
KEGG	D00018^Y
PubChem CID	5785
UNII	PQ6CK8PD0R^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+/m0/s1^N Key: CIWBSHSKHKDKBQ-JLAZNSOCSA-N^N
SMILES OC=1C(OC(=O)C=1O)[C@@H](O)CO C([C@@H]([C@@H]1C(=C(C(=O)O1)O)O)O)O
Properties
Chemical formula	C₆H₈O₆
Molar mass	176.124 g·mol⁻¹
Appearance	White or light yellow solid
Density	1.65 g/cm³
Melting point	190 to 192 °C (374 to 378 °F; 463 to 465 K) decomposes
Solubility in water	330 g/L
Solubility	Insoluble in diethyl ether, chloroform, benzene, petroleum ether, oils, fats
Solubility in ethanol	20 g/L
Solubility in glycerol	10 g/L
Solubility in propylene glycol	50 g/L
Acidity (pK_a)	4.10 (first), 11.6 (second)
Pharmacology
ATC code	A11GA01 (WHO) G01AD03 (WHO), S01XA15 (WHO)
Hazards
NFPA 704 (fire diamond)	1 1 0
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	11.9 g/kg (oral, rat)
Safety data sheet (SDS)	JT Baker
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references