ChemFOnt: Showing chemical card for Ascorbic acid (CFc000000031)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:19 UTC

Chemfont ID

CFc000000031

Molecule Identification

Common Name

Ascorbic acid

Definition

Ascorbic acid is found naturally in citrus fruits and many vegetables and is an essential nutrient in human diets. It is necessary to maintain connective tissue and bone. The biologically active form of ascorbic acid is vitamin C. Vitamin C is a water soluble vitamin. Primates (including humans) and a few other species in all divisions of the animal kingdom, notably the guinea pig, have lost the ability to synthesize ascorbic acid and must obtain it in their food. Vitamin C functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant (PubChem). Ascorbic acid is an electron donor for enzymes involved in collagen hydroxylation, biosynthesis of carnitine and norepinephrine, tyrosine metabolism, and amidation of peptide hormones. Ascrobic acid (vitamin C) deficiency causes scurvy. The amount of vitamin C necessary to prevent scurvy may not be adequate to maintain optimal health. The ability of vitamin C to donate electrons also makes it a potent water-soluble antioxidant that readily scavenges free radicals such as molecular oxygen, superoxide, hydroxyl radical, and hypochlorous acid. In this setting, several mechanisms could account for a link between vitamin C and heart disease. One is the relation between LDL oxidation and vitamins C and E. Vitamin C in vitro can recycle vitamin E, which can donate electrons to prevent LDL oxidation in vitro. As the lipid-phase vitamin E is oxidized, it can be regenerated by aqueous vitamin C. Other possibilities are that vitamin C could decrease cholesterol by mechanisms not well characterized, or could improve vasodilatation and vascular reactivity, perhaps by decreasing the interactions of nitric oxide with oxidants (PMID: 10799361 ). Moreover, ascorbic acid is found to be associated with hyperoxalemia, which is an inborn error of metabolism. Ascorbic acid is also a microbial metabolite produced by Ketogulonicigenium (PMID: 15785002 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Acide ascorbique	ChEBI
Acido ascorbico	ChEBI
Acidum ascorbicum	ChEBI
Acidum ascorbinicum	ChEBI
Ascoltin	ChEBI
Ascorbicap	ChEBI
Ascorbinsaeure	ChEBI
e 300	ChEBI
e-300	ChEBI
e300	ChEBI
L-(+)-Ascorbic acid	ChEBI
L-Ascorbate	ChEBI
Vitamin C	ChEBI
Monodehydroascorbate radical	Kegg
Ascorbate radical	Kegg
Semidehydroascorbic acid	Kegg
ASCOR	Kegg
L-(+)-Ascorbate	Generator
L-Ascorbic acid	Generator
Monodehydroascorbic acid radical	Generator
Ascorbic acid radical	Generator
Semidehydroascorbate	Generator
Ascorbate	Generator
(+)-Ascorbate	HMDB
(+)-Ascorbic acid	HMDB
(+)-Sodium L-ascorbate	HMDB
3-keto-L-Gulofuranolactone	HMDB
3-oxo-L-Gulofuranolactone	HMDB
Adenex	HMDB
Allercorb	HMDB
Antiscorbic vitamin	HMDB
Antiscorbutic vitamin	HMDB
arco-Cee	HMDB
Ascor-b.i.d.	HMDB
Ascorb	HMDB
Ascorbajen	HMDB
Ascorbicab	HMDB
Ascorbicin	HMDB
Ascorbin	HMDB
Ascorbutina	HMDB
Ascorin	HMDB
Ascorteal	HMDB
Ascorvit	HMDB
C-Level	HMDB
C-Long	HMDB
C-Quin	HMDB
C-Span	HMDB
C-Vimin	HMDB
Cantan	HMDB
Cantaxin	HMDB
Catavin C	HMDB
Ce lent	HMDB
Ce-mi-lin	HMDB
Ce-vi-sol	HMDB
Cebicure	HMDB
Cebid	HMDB
Cebion	HMDB
Cebione	HMDB
Cecon	HMDB
Cee-caps TD	HMDB
Cee-vite	HMDB
Cegiolan	HMDB
Ceglion	HMDB
Ceklin	HMDB
Celaskon	HMDB
Celin	HMDB
Cell C	HMDB
Cemagyl	HMDB
Cemill	HMDB
Cenetone	HMDB
Cenolate	HMDB
Cereon	HMDB
Cergona	HMDB
Cescorbat	HMDB
Cetamid	HMDB
Cetane	HMDB
Cetane-caps TC	HMDB
Cetane-caps TD	HMDB
Cetebe	HMDB
Cetemican	HMDB
Cevalin	HMDB
Cevatine	HMDB
Cevex	HMDB
Cevi-bid	HMDB
Cevimin	HMDB
Cevital	HMDB
Cevitamate	HMDB
Cevitamic acid	HMDB
Cevitamin	HMDB
Cevitan	HMDB
Cevitex	HMDB
Cewin	HMDB
Chewcee	HMDB
Ciamin	HMDB
Cipca	HMDB
Citriscorb	HMDB
Citrovit	HMDB
Colascor	HMDB
Concemin	HMDB
Davitamon C	HMDB
Dora-C-500	HMDB
Duoscorb	HMDB
Ferrous ascorbate	HMDB, MeSH
gamma-Lactone L-threo-hex-2-enonate	HMDB
gamma-Lactone L-threo-hex-2-enonic acid	HMDB
HiCee	HMDB
Hybrin	HMDB, MeSH
ido-C	HMDB
Juvamine	HMDB
Kangbingfeng	HMDB
Kyselina askorbova	HMDB
L(+)-Ascorbate	HMDB
L(+)-Ascorbic acid	HMDB
L-3-Ketothreohexuronic acid lactone	HMDB
L-Lyxoascorbate	HMDB
L-Lyxoascorbic acid	HMDB
L-threo-Ascorbic acid	HMDB
L-Xyloascorbate	HMDB
L-Xyloascorbic acid	HMDB
Laroscorbine	HMDB
Lemascorb	HMDB
Liqui-cee	HMDB
Meri-c	HMDB
Natrascorb	HMDB
Natrascorb injectable	HMDB
Planavit C	HMDB
Proscorbin	HMDB
Redoxon	HMDB
Ribena	HMDB
Ronotec 100	HMDB
Rontex 100	HMDB
Roscorbic	HMDB
Rovimix C	HMDB
Scorbacid	HMDB
Scorbu C	HMDB
Scorbu-C	HMDB
Secorbate	HMDB
Sodascorbate	HMDB
Suncoat VC 40	HMDB
Testascorbic	HMDB
VASC	HMDB
Vicelat	HMDB
Vicin	HMDB
Vicomin C	HMDB
Viforcit	HMDB
Viscorin	HMDB
Viscorin 100m	HMDB
Vitace	HMDB
Vitacee	HMDB
Vitacimin	HMDB
Vitacin	HMDB
Vitamisin	HMDB
Vitascorbol	HMDB
Xitix	HMDB
L Ascorbic acid	MeSH, HMDB
Acid, ascorbic	MeSH, HMDB
Ascorbate, ferrous	MeSH, HMDB
Ascorbate, sodium	MeSH, HMDB
Magnesium ascorbate	MeSH, HMDB
Magnesium ascorbicum	MeSH, HMDB
Magnesium di-L-ascorbate	MeSH, HMDB
Di-L-ascorbate, magnesium	MeSH, HMDB
Ascorbic acid, monosodium salt	MeSH, HMDB
Magnesium di L ascorbate	MeSH, HMDB
Magnorbin	MeSH, HMDB
Sodium ascorbate	MeSH, HMDB
Acid, L-ascorbic	MeSH, HMDB
Ascorbate, magnesium	MeSH, HMDB
ASCORBIC ACID	ChEBI

Chemical Formula

C₆H₈O₆

Average Molecular Weight

176.1241

Monoisotopic Molecular Weight

176.032087988

IUPAC Name

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

Traditional Name

vitamin C

CAS Registry Number

50-81-7

SMILES

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

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

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.

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 )

Functional Ontology

Not Available

Adipose tissue (HMDB: HMDB0000044)

Epithelium

Epidermis (HMDB: HMDB0000044)

Eye Lens (HMDB: HMDB0000044)

Muscle tissue

Skeletal muscle (HMDB: HMDB0000044)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 15640471)
Breast milk (PMID: 24027187)
Cerebrospinal Fluid (CSF) (PMID: 1503069)
Cellular Cytoplasm (HMDB: HMDB0000044)
Amniotic Fluid (PMID: 16139832)
Saliva (PMID: 12097436)

Organ substructure

Adrenal cortex (HMDB: HMDB0000044)
Adrenal medulla (HMDB: HMDB0000044)

Organ

Cell

Hematocyte

Platelet (HMDB: HMDB0000044)

Excreta

Biofluid or Excreta

Urine (PMID: 2026685)

Cellular substructure

Cytoplasm (HMDB: HMDB0000044)
Extracellular (HMDB: HMDB0000044)

Source

Exogenous

Exogenous (HMDB: HMDB0000044)

Food

Beverage

Fermented beverage

Grape wine (FooDB: FOOD00612)

Vegetable

Cabbage

Broccoli (FooDB: FOOD00034)

Leaf vegetable

Lettuce (FooDB: FOOD00095)

Vegetables (HMDB: HMDB0000044)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Fruit

Fruits (HMDB: HMDB0000044)

Berry

Nanking cherry (FooDB: FOOD00885)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

The Oncogenic Action of Succinate (PathBank: SMP0002292)
Tyrosinemia, Transient, of the Newborn (PathBank: SMP0120779)
Aromatic L-Aminoacid Decarboxylase Deficiency (PathBank: SMP0120457)
Tyrosine Hydroxylase Deficiency (PathBank: SMP0120562)
Hawkinsinuria (PathBank: SMP0120711)
Tyrosinemia Type I (PathBank: SMP0120729)
Alkaptonuria (PathBank: SMP0120453)
Dopamine beta-Hydroxylase Deficiency (PathBank: SMP0120563)
Refsum Disease (PathBank: SMP0120749)
Monoamine Oxidase-A Deficiency (MAO-A) (PathBank: SMP0120817)
The Oncogenic Action of Fumarate (PathBank: SMP0002295)

Metabolic pathway

Oxidation of Branched-Chain Fatty Acids (PathBank: SMP0087255)
Phytanic Acid Peroxisomal Oxidation (PathBank: SMP0087312)
Tyrosine Metabolism (PathBank: SMP0087328)
Carnitine Synthesis (PathBank: SMP0087187)
Ascorbate Metabolism (PathBank: SMP0012446)
Catecholamine Biosynthesis (PathBank: SMP0063606)
Flavonoid Biosynthesis (PathBank: SMP0012021)
Flavone and Flavonol Biosynthesis (PathBank: SMP0012025)
Xanthophyll Cycle (PathBank: SMP0012035)
Gibberellin Biosynthesis I (Early C-3 Hydroxylation) (PathBank: SMP0012069)
Gibberellin Biosynthesis II (Early C-13 Hydroxylation) (PathBank: SMP0012070)
Gibberellin Biosynthesis III (Non C-3, Non C-13 Hydroxylation) (PathBank: SMP0012071)
Ascorbate Biosynthesis (PathBank: SMP0063817)

Drug action pathway

Disulfiram Action Pathway (PathBank: SMP0000429)

Role

Industrial application

Pharmaceutical industry

Biomarker

Meningitis (MarkerDB: MDB00000023)
Hyperoxalemia (MarkerDB: MDB00000023)

Physical Properties

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