Record Information
Version1.0
Creation date2010-04-08 22:04:53 UTC
Update date2015-10-09 22:27:31 UTC
Primary IDFDB001224
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Ascorbic acid
DescriptionOccurs widely in animals and plants. Good sources are citrus fruits and hip berries. Isol. from ox adrenal cortex, lemons and paprika. Prod. industrially on a large scale from glucose. Vitamin (antiscorbutic), antioxidant, nutrient, preservative consistency enhancer. Used to reduce discoloration, mainly browning caused by polyphenol oxidase, in fruit and vegetable products. Used to enhance colour formn. and to reduced the formn. of nitrosamines in meat products. Used synergistically with Sulfur dioxide HVF10-P in wine and beer as a perservative. Assists formn. of the gluten network in bread making, thus enhancing bread volume
CAS Number50-81-7
Structure
Thumb
Synonyms
SynonymSource
(+)-Ascorbatebiospider
(+)-Ascorbic acidbiospider
3-Keto-L-gulofuranolactonebiospider
3-Oxo-L-gulofuranolactonebiospider
Adenexbiospider
Allercorbbiospider
Antiscorbic vitaminbiospider
Antiscorbutic vitaminbiospider
Ascoltinbiospider
Ascorbicapdb_source
Ascorbicinbiospider
Ascorinbiospider
Ascortealbiospider
Ascorvitbiospider
Cantanbiospider
Cantaxinbiospider
Catavin Cbiospider
Cebicurebiospider
Cebionbiospider
Cebionedb_source
Ceconbiospider
Cegiolanbiospider
Ceglionbiospider
Ceklinbiospider
Celaskondb_source
Celinbiospider
Cell Cbiospider
Cemagylbiospider
Cenetonebiospider
Cereonbiospider
Cergonabiospider
Cescorbatbiospider
Cetamidbiospider
Cetane-Caps TCbiospider
Cetebebiospider
Cetemicanbiospider
Cevalindb_source
Cevatinebiospider
Ceviminbiospider
Cevitaldb_source
Cevitamatebiospider
Cevitamic acidbiospider
Cevitaminbiospider
Cevitanbiospider
Cevitexbiospider
Cewinbiospider
Ciaminbiospider
Cipcabiospider
Citrovitdb_source
Colascorbiospider
Conceminbiospider
E300db_source
gamma-lactone L-threo-Hex-2-enonatebiospider
gamma-lactone L-threo-Hex-2-enonic acidbiospider
Hiceebiospider
Hybrinbiospider
Juvaminebiospider
L-(+)-ascorbatebiospider
L-(+)-ascorbic acidbiospider
L-Ascorbatebiospider
L-Ascorbic acid (8CI,9CI)biospider
L-threo-ascorbic acidbiospider
Laroscorbinebiospider
Lemascorbbiospider
Proscorbinbiospider
Redoxonbiospider
Testascorbicbiospider
Vicelatbiospider
Vicinbiospider
Viforcitbiospider
Viscorinbiospider
Vitacebiospider
Vitaceebiospider
Vitacimindb_source
Vitacinbiospider
Vitamin Cdb_source
Vitamisinbiospider
Vitascorboldb_source
Xitixbiospider
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H8O6
IUPAC name(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one
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 KeyInChIKey=CIWBSHSKHKDKBQ-JLAZNSOCSA-N
Isomeric SMILES[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO
Average Molecular Weight176
Monoisotopic Molecular Weight176
Classification
DescriptionThis compound 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 40.92%; H 4.58%; O 54.50%DFC
Melting PointMp 190-192°DFC
Boiling PointNot Available
Experimental Water Solubility400 mg/mL at 40 oCMERCK INDEX (1996)
Experimental logP-1.85AVDEEF,A (1997)
Experimental pKapKa2 11.34 (25°, 0.1M KNO3)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]18D +49 (MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-e99089fd55560fb70cfeView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0912000000-baa8cffda0478e1bc197View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9400000000-8ff8f48bfa2dd4fd3cf5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9400000000-c1dc72c6cbc49fbf3454View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9400000000-b207f4024993c5a74769View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0911000000-9af0c08e85e0c51a25c4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0560-9700000000-ab53eee999ee7fee672dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0kkj-9357500000-5c2c439f726b729dd50dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kdi-2900000000-f05a720e6e6361c97e5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bvl-5900000000-6ca3f37a74403d8495c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-5625440c512f60760fdfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0o90-2900000000-b7c897849334927f5bf5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bvi-4900000000-1f1fa10e7e06a79c028aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fu-9300000000-b98375c0cd3a54b61ef7View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC00072
Pubchem Compound ID644104
Pubchem Substance IDNot Available
ChEBI ID29073
Phenol-Explorer IDNot Available
DrugBank IDDB00126
HMDB IDHMDB00044
CRC / DFC (Dictionary of Food Compounds) IDBWR05-S:BWR07-U
EAFUS ID258
Dr. Duke IDASCORBATE|ASCORBIC-ACID|HEXURONIC-ACID
BIGG IDNot Available
KNApSAcK IDC00001179
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1006281
SuperScent IDNot Available
Wikipedia IDAscorbic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
acidulant64047 Any substance which is added to food to preserve or enhance its flavour and/or appearance.DUKE
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
angiotensin receptor blocker61016 A hormone antagonist that blocks angiotensin receptors.DUKE
anti advanced glycation end products52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti aggregantDUKE
anti aging52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti Alzheimeran52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti arthritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti asthmatic49167 A drug used to treat asthma.DUKE
anti atherosclerotic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cataract52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cervicaldysplasic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti CFSDUKE
anti climactericDUKE
anti cold52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti Crohn's52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti CTSDUKE
anti decubiticDUKE
anti dementia52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti depressant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti diabetic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antidote50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
anti eczemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti edemicDUKE
anti encephalitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti endometrioticDUKE
anti fatigue52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti fibroticDUKE
anti gallstoneDUKE
anti gastriticDUKE
anti gingivitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti glaucomicDUKE
anti hangover52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hemorrhagic50248 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.DUKE
anti hepatitic62868 Any compound that is able to prevent damage to the liver.DUKE
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti hypertensive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti infertility52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti lepric33282 A substance that kills or slows the growth of bacteria.DUKE
anti lithicDUKE
anti Lyme33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti maculiticDUKE
anti measles22587 A substance that destroys or inhibits replication of viruses.DUKE
anti menopausal52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti migraine52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti mutagenicDUKE
anti neuramidase52425 An antiviral drug targeted at influenza viruses. Its mode of action consists of blocking the function of the viral neuraminidase protein (EC 3.2.1.18), thus preventing the virus from budding from the host cell.DUKE
anti nitrosicDUKE
anti obesity52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti orchiticDUKE
anti osteoarthritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti osteoporotic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti Parkinsonian48407 A drug used in the treatment of Parkinson's disease.DUKE
anti parotiticDUKE
anti periodontiticDUKE
anti pneumonic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti podriacDUKE
anti poliomyelitic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti pyretic35493 A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.DUKE
anti radicularDUKE
anti Raynaud's52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti retinoticDUKE
anti rheumatic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti rhinitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti scorbutic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti shingles22587 A substance that destroys or inhibits replication of viruses.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti stress52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti syndrome-X52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
apoptoticDUKE
asthma preventive49167 A drug used to treat asthma.DUKE
beta-adrenergic receptor blocker37962 Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.DUKE
beta-glucuronidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cardioprotective38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
cold preventiveDUKE
collagenicDUKE
detoxicant50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
fistula preventive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
hypocholesterolemicDUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
hypotensiveDUKE
immunomodulator50846 Biologically active substance whose activity affects or plays a role in the functioning of the immune system.DUKE
immunostimulant50847 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.DUKE
interferonogenicDUKE
lithogenicDUKE
mucolytic77034 A compound that alters the structure of mucus so as to decrease its viscosity and thereby facilitate its removal by ciliary action and expectoration. Compare with antitussives, which suppress the cough reflex, and expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
uricosuricDUKE
urinary acidulantDUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
vulnerary73336 A drug used in treating and healing of wounds.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
very mild
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
grassy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.