Showing Compound L-Ascorbic acid (FDB001224)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:53 UTC

Update date

2024-11-29 22:26:18 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 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Synonym	Source
(+)-Ascorbate	HMDB
(+)-Ascorbic acid	HMDB
(+)-Sodium L-ascorbate	HMDB
3-keto-L-Gulofuranolactone	HMDB
3-Keto-L-gulofuranolactone	biospider
3-oxo-L-Gulofuranolactone	HMDB
3-Oxo-L-gulofuranolactone	biospider
Acid, ascorbic	MeSH
Acid, L-ascorbic	MeSH
Acide ascorbique	ChEBI

Showing 1 to 10 of 180 entries

Predicted Properties

Property	Value	Source
Water Solubility	245 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-1.9	ChemAxon
logS	0.14	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	37.03 m³·mol⁻¹	ChemAxon
Polarizability	14.93 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H8O6

IUPAC name

(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one

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

Description

Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

ascorbic acid (CHEBI:29073 )
Water-soluble vitamins (C00072 )

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

Physico-Chemical Properties - Experimental

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

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	L-Ascorbic acid, non-derivatized, GC-MS Spectrum	splash10-004i-4900000000-e99089fd55560fb70cfe	Spectrum
GC-MS	L-Ascorbic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0912000000-baa8cffda0478e1bc197	Spectrum
GC-MS	L-Ascorbic acid, non-derivatized, GC-MS Spectrum	splash10-00di-9400000000-8ff8f48bfa2dd4fd3cf5	Spectrum
GC-MS	L-Ascorbic acid, non-derivatized, GC-MS Spectrum	splash10-00di-9400000000-c1dc72c6cbc49fbf3454	Spectrum
GC-MS	L-Ascorbic acid, non-derivatized, GC-MS Spectrum	splash10-00di-9400000000-b207f4024993c5a74769	Spectrum
GC-MS	L-Ascorbic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0911000000-9af0c08e85e0c51a25c4	Spectrum
GC-MS	L-Ascorbic acid, non-derivatized, GC-MS Spectrum	splash10-004i-4900000000-e99089fd55560fb70cfe	Spectrum
GC-MS	L-Ascorbic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0912000000-baa8cffda0478e1bc197	Spectrum
GC-MS	L-Ascorbic acid, non-derivatized, GC-MS Spectrum	splash10-00di-9400000000-8ff8f48bfa2dd4fd3cf5	Spectrum
GC-MS	L-Ascorbic acid, non-derivatized, GC-MS Spectrum	splash10-00di-9400000000-c1dc72c6cbc49fbf3454	Spectrum
GC-MS	L-Ascorbic acid, non-derivatized, GC-MS Spectrum	splash10-00di-9400000000-b207f4024993c5a74769	Spectrum
GC-MS	L-Ascorbic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0911000000-9af0c08e85e0c51a25c4	Spectrum
Predicted GC-MS	L-Ascorbic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0560-9700000000-ab53eee999ee7fee672d	Spectrum
Predicted GC-MS	L-Ascorbic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0kkj-9357500000-5c2c439f726b729dd50d	Spectrum
Predicted GC-MS	L-Ascorbic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Ascorbic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Ascorbic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Ascorbic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Ascorbic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Ascorbic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Ascorbic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Ascorbic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Ascorbic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Ascorbic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Ascorbic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-0002-9300000000-d8c8254ad1dd4de2674c	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, positive	splash10-004i-1900000000-da5bc92501d37735007f	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-0006-0900000000-b653774b8718c29fe97a	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-9200000000-5d1ea04ef6404f5ecf7c	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative	splash10-000i-9000000000-0371d7191fa8a89176f3	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 6V, negative	splash10-004i-0900000000-76825c62319d5f4cbed9	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 10V, negative	splash10-016r-2900000000-700d5d6247efb36c48d7	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 13V, negative	splash10-014i-8900000000-4d76fc951d56a75a025e	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 16V, negative	splash10-05tr-9300000000-0967cf71e141f71c2e00	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 20V, negative	splash10-052r-9100000000-2bca6a943255612f1e7d	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-000i-9000000000-804b40cc657a43d298fb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-0a4i-9000000000-cad0cc415c906a783cfc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-0a4r-9000000000-f79a7dfc866621b3c926	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-004i-0900000000-707796161cd4fae98f67	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-004i-0900000000-035a78987127cc9f23f5	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-004i-0900000000-dac785ef05051971e946	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-00or-1900000000-a91dc1a29cb724a17811	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-016r-3900000000-78f1f46067d2459f17c7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-014i-6900000000-8044f242bb90f54a595a	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0kdi-2900000000-f05a720e6e6361c97e5f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bvl-5900000000-6ca3f37a74403d8495c9	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-5625440c512f60760fdf	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0o90-2900000000-b7c897849334927f5bf5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bvi-4900000000-1f1fa10e7e06a79c028a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-08fu-9300000000-b98375c0cd3a54b61ef7	2016-08-03	View Spectrum

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

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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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

Showing 1 to 10 of 105 entries

Enzymes

Not Available

Pathways

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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

Showing 1 to 2 of 2 entries

Files

MSDS

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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.