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Chemistry of ascorbic acid information


l-Ascorbic acid
Names
IUPAC name
(5R)-[(1S)-1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one
Other names
Vitamin C
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 checkY
PubChem CID
  • 5785
UNII
  • PQ6CK8PD0R checkY
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 (pKa) 4.10 (first), 11.6 (second)
Pharmacology
ATC code
A11GA01 (WHO) G01AD03 (WHO), S01XA15 (WHO)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Lethal dose or concentration (LD, LC):
LD50 (median dose)
11.9 g/kg (oral, rat)[1]
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 checkY☒N ?)
Infobox references

Ascorbic acid is an organic compound with formula C
6
H
8
O
6
, 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 can be made via chemical synthesis, but has no significant biological role.

  1. ^ Safety (MSDS) data for ascorbic acid. University of Oxford

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Uric acid

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Pyrogallol

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