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Record Information
Version1.0
Creation Date2016-09-30 22:18:54 UTC
Update Date2019-02-05 20:35:43 UTC
MCDB ID BMDB00044
Secondary Accession NumbersNone
Metabolite Identification
Common NameAscorbic acid
DescriptionAscorbic 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.
Structure
Thumb
Synonyms
ValueSource
AscorbateGenerator
Chemical FormulaC6H8O6
Average Molecular Weight176.1241
Monoisotopic Molecular Weight176.032087988
IUPAC Name(2S)-2-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxy-2,3-dihydrofuran-3-one
Traditional Name(2S)-2-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxy-2H-furan-3-one
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(CO)[C@]1([H])OC(O)=C(O)C1=O
InChI Identifier
InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8,10-11H,1H2/t2-,5+/m1/s1
InChI KeyTYQCGQRIZGCHNB-MVHIGOERSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentFuranones
Alternative Parents
Substituents
  • 3-furanone
  • Vinylogous acid
  • Vinylogous ester
  • 1,2-diol
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Oxacycle
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.9ALOGPS
logP-1.3ChemAxon
logS0.16ALOGPS
pKa (Strongest Acidic)0.72ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.26 m³·mol⁻¹ChemAxon
Polarizability14.98 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0005-9700000000-7a799a3b3b979d9598d0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052k-9000000000-450579c53a443c3cececJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052f-9000000000-06b81a073ca87770c390JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Concentrations
StatusValueReferenceDetails
Detected and Quantified22.71 +/- 1.42 uM details
Detected and Quantified34 +/- 1.7 uM details
Detected and Quantified153 uM
  • Int. Dairy Journa...
details
Detected and Quantified51 uM details
Detected and Quantified51 uM details
Detected and Quantified57 uM details
Detected and Quantified51 uM details
Detected and Quantified68 uM details
Detected and Quantified57 uM details
Detected and Quantified63 uM details
Detected and Quantified57 uM details
Detected and Quantified74 uM details
Detected and Quantified74 uM details
Detected and Quantified85 uM details
Detected and Quantified63 uM details
Detected and Quantified57 uM details
Detected and Quantified63 uM details
Detected and Quantified11 uM details
Detected and Quantified11 uM details
Detected and Quantified74 uM details
Detected and Quantified74 uM details
Detected and Quantified74 uM details
Detected and Quantified68 uM details
Detected and Quantified68 uM details
Detected and Quantified68 uM details
Detected and Quantified34.7 +/- 0.2 uM details
Detected and Quantified39 +/- 1 uM details
Detected and Quantified34.0 +/- 0.3 uM details
Detected and Quantified8.2 +/- 0.3 uM details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVitamin C
METLIN IDNot Available
PubChem Compound644104
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. [PubMed:1880195 ]
  2. Ingela Andersson, R. Öste (1994). Int. Dairy Journal 4 (1994) 161-172. International Dairy Journal.
  3. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
  4. USDA Food Composition Databases [Link]
  5. Fooddata+, The Technical University of Denmark (DTU) [Link]