Showing Compound L-Ascorbic acid (FDB001224)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:53 UTC

Update date

2020-09-17 15:38:13 UTC

Primary ID

FDB001224

Secondary Accession Numbers

FDB030957

Chemical Information

FooDB Name

L-Ascorbic acid

Description

Ascorbic acid, also known as acide ascorbique or L-ascorbate, belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. Ascorbic acid is a drug which is used to treat vitamin c deficiency, scurvy, delayed wound and bone healing, urine acidification, and in general as an antioxidant. it has also been suggested to be an effective antiviral agent. Ascorbic acid is 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 humans, ascorbic acid is involved in the metabolic disorder called tyrosinemia, transient, of the newborn. Ascorbic acid is a very mild and grassy tasting compound. Outside of the human body, Ascorbic acid is found, on average, in the highest concentration within a few different foods, such as acerola, pepper (c. frutescens), and orange bell peppers and in a lower concentration in yogurts, yardlong beans, and peanuts. Ascorbic acid has also been detected, but not quantified in, several different foods, such as deerberries, cetacea (dolphin, porpoise, whale), acorns, lemon balms, and gelatins. This could make ascorbic acid a potential biomarker for the consumption of these foods. The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.

CAS Number

50-81-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(+)-Ascorbate	biospider
(+)-Ascorbic acid	biospider
3-Keto-L-gulofuranolactone	biospider
3-Oxo-L-gulofuranolactone	biospider
Adenex	biospider
Allercorb	biospider
Antiscorbic vitamin	biospider
Antiscorbutic vitamin	biospider
Ascoltin	biospider
Ascorbicap	db_source
Ascorbicin	biospider
Ascorin	biospider
Ascorteal	biospider
Ascorvit	biospider
Cantan	biospider
Cantaxin	biospider
Catavin C	biospider
Cebicure	biospider
Cebion	biospider
Cebione	db_source
Cecon	biospider
Cegiolan	biospider
Ceglion	biospider
Ceklin	biospider
Celaskon	db_source
Celin	biospider
Cell C	biospider
Cemagyl	biospider
Cenetone	biospider
Cereon	biospider
Cergona	biospider
Cescorbat	biospider
Cetamid	biospider
Cetane-Caps TC	biospider
Cetebe	biospider
Cetemican	biospider
Cevalin	db_source
Cevatine	biospider
Cevimin	biospider
Cevital	db_source
Cevitamate	biospider
Cevitamic acid	biospider
Cevitamin	biospider
Cevitan	biospider
Cevitex	biospider
Cewin	biospider
Ciamin	biospider
Cipca	biospider
Citrovit	db_source
Colascor	biospider
Concemin	biospider
E300	db_source
gamma-lactone L-threo-Hex-2-enonate	biospider
gamma-lactone L-threo-Hex-2-enonic acid	biospider
Hicee	biospider
Hybrin	biospider
Juvamine	biospider
L-(+)-ascorbate	biospider
L-(+)-ascorbic acid	biospider
L-Ascorbate	biospider
L-Ascorbic acid (8CI,9CI)	biospider
L-threo-ascorbic acid	biospider
Laroscorbine	biospider
Lemascorb	biospider
Proscorbin	biospider
Redoxon	biospider
Testascorbic	biospider
Vicelat	biospider
Vicin	biospider
Viforcit	biospider
Viscorin	biospider
Vitace	biospider
Vitacee	biospider
Vitacimin	db_source
Vitacin	biospider
Vitamin C	db_source
Vitamisin	biospider
Vitascorbol	db_source
Xitix	biospider

Predicted Properties

Not Available

Chemical Formula

C6H8O6

IUPAC name

InChI Identifier

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

InChI Key

CIWBSHSKHKDKBQ-JLAZNSOCSA-N

Isomeric SMILES

[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO

Average Molecular Weight

176.1241

Monoisotopic Molecular Weight

176.032087988

Classification

Not classified

Ontology

Physiological effect

Health effect:

Health condition:

Infections and infestations:

Meningitis

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Animal

Microbe:

Ketogulonicigenium:

Ketogulonicigenium vulgare

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 40.92%; H 4.58%; O 54.50%	DFC
Melting Point	Mp 190-192°	DFC
Boiling Point	Not Available
Experimental Water Solubility	400 mg/mL at 40 oC	MERCK INDEX (1996)
Experimental logP	-1.85	AVDEEF,A (1997)
Experimental pKa	pKa2 11.34 (25°, 0.1M KNO3)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]18D +49 (MeOH)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Not Available

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C00072

Pubchem Compound ID

644104

Pubchem Substance ID

Not Available

ChEBI ID

29073

Phenol-Explorer ID

Not Available

DrugBank ID

DB00126

HMDB ID

HMDB00044

CRC / DFC (Dictionary of Food Compounds) ID

BWR05-S:BWR07-U

EAFUS ID

258

Dr. Duke ID

ASCORBATE|ASCORBIC-ACID|HEXURONIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00001179

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1006281

SuperScent ID

Not Available

Wikipedia ID

Ascorbic acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
acidulant	64047	Any substance which is added to food to preserve or enhance its flavour and/or appearance.	DUKE
aldose reductase inhibitor	48550	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
analgesic	35480	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 blocker	61016	A hormone antagonist that blocks angiotensin receptors.	DUKE
anti advanced glycation end products	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti aggregant			DUKE
anti aging	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti allergic	50857	A drug used to treat allergic reactions.	DUKE
anti Alzheimeran	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti arthritic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti asthmatic	49167	A drug used to treat asthma.	DUKE
anti atherosclerotic	38070	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 bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti cataract	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti cervicaldysplasic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti CFS			DUKE
anti climacteric			DUKE
anti cold	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti Crohn's	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti CTS			DUKE
anti decubitic			DUKE
anti dementia	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti depressant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti diabetic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antidote	50247	Any protective agent counteracting or neutralizing the action of poisons.	DUKE
anti eczemic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti edemic			DUKE
anti encephalitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti endometriotic			DUKE
anti fatigue	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti fibrotic			DUKE
anti gallstone			DUKE
anti gastritic			DUKE
anti gingivitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti glaucomic			DUKE
anti hangover	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti hemorrhagic	50248	Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.	DUKE
anti hepatitic	62868	Any compound that is able to prevent damage to the liver.	DUKE
anti hepatotoxic	62868	Any compound that is able to prevent damage to the liver.	DUKE
anti herpetic	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti histaminic	37956	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 hypertensive	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti infertility	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti lepric	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti lithic			DUKE
anti Lyme	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti maculitic			DUKE
anti measles	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti menopausal	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti migraine	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti mutagenic			DUKE
anti neuramidase	52425	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 nitrosic			DUKE
anti obesity	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti orchitic			DUKE
anti osteoarthritic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti osteoporotic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antioxidant	22586	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 Parkinsonian	48407	A drug used in the treatment of Parkinson's disease.	DUKE
anti parotitic			DUKE
anti periodontitic			DUKE
anti pneumonic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti podriac			DUKE
anti poliomyelitic	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti pyretic	35493	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 radicular			DUKE
anti Raynaud's	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti retinotic			DUKE
anti rheumatic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti rhinitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti scorbutic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti shingles	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti stress	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti syndrome-X	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti ulcer	49201	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 viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
apoptotic			DUKE
asthma preventive	49167	A drug used to treat asthma.	DUKE
beta-adrenergic receptor blocker	37962	Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.	DUKE
beta-glucuronidase inhibitor	23924	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 antagonist	48706	Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cardioprotective	38070	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 preventive			DUKE
collagenic			DUKE
detoxicant	50247	Any protective agent counteracting or neutralizing the action of poisons.	DUKE
diuretic	35498	An agent that promotes the excretion of urine through its effects on kidney function.	DUKE
fistula preventive	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
hypocholesterolemic			DUKE
hypoglycemic	35526	A drug which lowers the blood glucose level.	DUKE
hypotensive			DUKE
immunomodulator	50846	Biologically active substance whose activity affects or plays a role in the functioning of the immune system.	DUKE
immunostimulant	50847	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
interferonogenic			DUKE
lithogenic			DUKE
mucolytic	77034	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
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
uricosuric			DUKE
urinary acidulant			DUKE
vasodilator	35620	A drug used to cause dilation of the blood vessels.	DUKE
vulnerary	73336	A drug used in treating and healing of wounds.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
very mild	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
grassy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not 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.