ASCORBIC ACID (CHEM004780)

Record Information
Version1.0
Creation Date2016-05-19 01:54:45 UTC
Update Date2026-05-14 16:24:07 UTC
Accession NumberCHEM004780
Identification
Common NameASCORBIC ACID
ClassSmall Molecule
Description
Ascorbic acid, also known as ascorbate, belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group. Ascorbic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Dopamine and ascorbic acid can be converted into norepinephrine and dehydroascorbic acid through the action of the enzyme dopamine beta-hydroxylase. In cattle, ascorbic acid is involved in the metabolic pathway called the tyrosine metabolism pathway.
Contaminant Sources
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Acide ascorbiqueChEBI
Acido ascorbicoChEBI
Acidum ascorbicumChEBI
Acidum ascorbinicumChEBI
AscoltinChEBI
AscorbicapChEBI
AscorbinsaeureChEBI
e 300ChEBI
e-300ChEBI
e300ChEBI
L-(+)-Ascorbic acidChEBI
L-AscorbateChEBI
Vitamin CChEBI
Monodehydroascorbate radicalKegg
Ascorbate radicalKegg
Semidehydroascorbic acidKegg
ASCORKegg
L-(+)-AscorbateGenerator
L-Ascorbic acidGenerator
Monodehydroascorbic acid radicalGenerator
Ascorbic acid radicalGenerator
SemidehydroascorbateGenerator
AscorbateGenerator
Ascorbic acid, monosodium saltMeSH
Ferrous ascorbateMeSH
L Ascorbic acidMeSH
Magnesium di L ascorbateMeSH
MagnorbinMeSH
Sodium ascorbateMeSH
Acid, L-ascorbicMeSH
Ascorbate, magnesiumMeSH
Acid, ascorbicMeSH
Ascorbate, ferrousMeSH
Ascorbate, sodiumMeSH
HybrinMeSH
Magnesium ascorbateMeSH
Magnesium ascorbicumMeSH
Magnesium di-L-ascorbateMeSH
Di-L-ascorbate, magnesiumMeSH
(+)-AscorbateHMDB
(+)-Ascorbic acidHMDB
(+)-Sodium L-ascorbateHMDB
3-keto-L-GulofuranolactoneHMDB
3-oxo-L-GulofuranolactoneHMDB
AdenexHMDB
AllercorbHMDB
Antiscorbic vitaminHMDB
Antiscorbutic vitaminHMDB
arco-CeeHMDB
Ascor-b.i.d.HMDB
AscorbHMDB
AscorbajenHMDB
AscorbicabHMDB
AscorbicinHMDB
AscorbinHMDB
AscorbutinaHMDB
AscorinHMDB
AscortealHMDB
AscorvitHMDB
C-LevelHMDB
C-LongHMDB
C-QuinHMDB
C-SpanHMDB
C-ViminHMDB
CantanHMDB
CantaxinHMDB
Catavin CHMDB
Ce lentHMDB
Ce-mi-linHMDB
Ce-vi-solHMDB
CebicureHMDB
CebidHMDB
CebionHMDB
CebioneHMDB
CeconHMDB
Cee-caps TDHMDB
Cee-viteHMDB
CegiolanHMDB
CeglionHMDB
CeklinHMDB
CelaskonHMDB
CelinHMDB
Cell CHMDB
CemagylHMDB
CemillHMDB
CenetoneHMDB
CenolateHMDB
CereonHMDB
CergonaHMDB
CescorbatHMDB
CetamidHMDB
CetaneHMDB
Cetane-caps TCHMDB
Cetane-caps TDHMDB
CetebeHMDB
CetemicanHMDB
CevalinHMDB
CevatineHMDB
CevexHMDB
Cevi-bidHMDB
CeviminHMDB
CevitalHMDB
CevitamateHMDB
Cevitamic acidHMDB
CevitaminHMDB
CevitanHMDB
CevitexHMDB
CewinHMDB
ChewceeHMDB
CiaminHMDB
CipcaHMDB
CitriscorbHMDB
CitrovitHMDB
ColascorHMDB
ConceminHMDB
Davitamon CHMDB
Dora-C-500HMDB
DuoscorbHMDB
gamma-Lactone L-threo-hex-2-enonateHMDB
gamma-Lactone L-threo-hex-2-enonic acidHMDB
HiCeeHMDB
ido-CHMDB
JuvamineHMDB
KangbingfengHMDB
Kyselina askorbovaHMDB
L(+)-AscorbateHMDB
L(+)-Ascorbic acidHMDB
L-3-Ketothreohexuronic acid lactoneHMDB
L-LyxoascorbateHMDB
L-Lyxoascorbic acidHMDB
L-threo-Ascorbic acidHMDB
L-XyloascorbateHMDB
L-Xyloascorbic acidHMDB
LaroscorbineHMDB
LemascorbHMDB
Liqui-ceeHMDB
Meri-cHMDB
NatrascorbHMDB
Natrascorb injectableHMDB
Planavit CHMDB
ProscorbinHMDB
RedoxonHMDB
RibenaHMDB
Ronotec 100HMDB
Rontex 100HMDB
RoscorbicHMDB
Rovimix CHMDB
ScorbacidHMDB
Scorbu CHMDB
Scorbu-CHMDB
SecorbateHMDB
SodascorbateHMDB
Suncoat VC 40HMDB
TestascorbicHMDB
VASCHMDB
VicelatHMDB
VicinHMDB
Vicomin CHMDB
ViforcitHMDB
ViscorinHMDB
Viscorin 100mHMDB
VitaceHMDB
VitaceeHMDB
VitaciminHMDB
VitacinHMDB
VitamisinHMDB
VitascorbolHMDB
XitixHMDB
ASCORBIC ACIDChEBI
Chemical FormulaC6H8O6
Average Molecular Mass176.124 g/mol
Monoisotopic Mass176.032 g/mol
CAS Registry Number50-81-7
IUPAC Name(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one
Traditional Namevitamin C
SMILES[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO
InChI IdentifierInChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1
InChI KeyCIWBSHSKHKDKBQ-JLAZNSOCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentButenolides
Alternative Parents
Substituents
  • 2-furanone
  • Vinylogous acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • 1,2-diol
  • Carboxylic acid ester
  • Enediol
  • Secondary alcohol
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Primary alcohol
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility245 g/LALOGPS
logP-1.6ALOGPS
logP-1.9ChemAxon
logS0.14ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.03 m³·mol⁻¹ChemAxon
Polarizability14.93 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00126
HMDB IDHMDB0014273
FooDB IDFDB001224
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDASCORBATE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAscorbic_Acid
Chemspider IDNot Available
ChEBI ID29073
PubChem Compound ID54670067
Kegg Compound IDC01041
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Bilic N: Assay for both ascorbic and dehydroascorbic acid in dairy foods by high-performance liquid chromatography using precolumn derivatization with methoxy- and ethoxy-1,2-phenylenediamine. J Chromatogr. 1991 May 10;543(2):367-74.
2. Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.
3. Weiss WP, Hogan JS, Smith KL: Changes in vitamin C concentrations in plasma and milk from dairy cows after an intramammary infusion of Escherichia coli. J Dairy Sci. 2004 Jan;87(1):32-7. doi: 10.3168/jds.S0022-0302(04)73138-0.
4. Int. Dairy Journal 4 (1994) 161-172
5. Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013
6. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)
7. USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/
8. Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=10799361
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=12180551
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=12569111
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=15917019
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=15925292
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=15949874
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=16425787
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=16522902
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=16611389
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=16725131
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=17253561
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=17623524
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=17636648
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=18813862
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=19273781
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=19580823
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=19692922
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=3015170
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=491997
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=5477017
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=7711198
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=8467348
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=8726814
33. https://www.ncbi.nlm.nih.gov/pubmed/?term=9506998