Chemistry of
ascorbic acid
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 well in water to give mildly
acidic solutions. It is a mild reducing agent.
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 (https://commonchemistry.cas.org/detai
l?cas_rn=50-81-7)
3D model (JSmol) Interactive image (https://chemapps.stolaf.edu/j
mol/jmol.php?model=OC%3D1C%28OC%28%3D
O%29C%3D1O%29%5BC%40%40H%5D%28O%2
9CO)
Interactive image (https://chemapps.stolaf.edu/j
mol/jmol.php?model=C%28%5BC%40%40H%5D%
28%5BC%40%40H%5D1C%28%3DC%28C%28%3D
O%29O1%29O%29O%29O%29O)
ChEBI CHEBI:29073 (https://www.ebi.ac.uk/chebi/searc
hId.do?chebiId=29073)
ChEMBL ChEMBL196 (https://www.ebi.ac.uk/chembldb/in
dex.php/compound/inspect/ChEMBL196)
ChemSpider 10189562 (https://www.chemspider.com/Chemic
al-Structure.10189562.html)
EC Number 200-066-2
E number E300 (antioxidants, ...)
IUPHAR/BPS 4781 (http://www.guidetopharmacology.org/GRA
C/LigandDisplayForward?tab=summary&ligandId
=4781)
KEGG D00018 (https://www.kegg.jp/entry/D00018)
PubChem CID 5785 (https://pubchem.ncbi.nlm.nih.gov/compou
nd/5785)
UNII PQ6CK8PD0R (https://fdasis.nlm.nih.gov/srs/srs
direct.jsp?regno=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 (https://www.whocc.no/atc_ddd_
index/?code=A11GA01) ) G01AD03 (WHO (http
s://www.whocc.no/atc_ddd_index/?code=G01A
D03) ), S01XA15 (WHO (https://www.whocc.no/
atc_ddd_index/?code=S01XA15) )
Hazards
NFPA 704 (fire diamond)
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 (http://hazard.com/msds/mf/baker/bak
er/files/a7608.htm)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F],
100 kPa).
verify (https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477350783&page2=
Chemistry+of+ascorbic+acid) (what is ?)
Infobox references
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.
History
Chemical properties
Uses
Synthesis
See also
Notes and references
Further reading
External links
Retrieved from
"https://en.wikipedia.org/w/index.php?
title=Chemistry_of_ascorbic_acid&oldid=10958762
27"
Last edited 3 months ago by Citation bot
