Ascorbic Acid

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Ascorbic Acid are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Ascorbic Acid?

The molecule Ascorbic Acid presents a molecular formula of C20H26N2O2 and its IUPAC name is (2R)-2-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2H-furan-5-one.

Ascorbic acid is a molecule that has many purposes in the human body. It is most commonly known as a vitamin, and it is essential for human health. Ascorbic acid is also known as L-ascorbic acid, and its chemical formula is C6H8O6..

Ascorbic acid belongs in many foods, including citrus fruits, tomatoes, potatoes, and leafy green vegetables. It can be found as a supplement..

The human body needs ascorbic acid for several reasons. It is necessary for the formation of collagen, which is a protein that helps to form tissues and bones. Ascorbic acid is also needed for the absorption of iron..

Ascorbic acid has many other functions in the human body, including acting as an antioxidant. Antioxidants help to protect cells from damage. Ascorbic acid may also help to protect the body from some types of cancer..

Ascorbic acid is generally considered to be safe. However, taking large doses of ascorbic acid can cause side effects, such as diarrhea, nausea, and stomach cramps..

3D structure

Cartesian coordinates

Geometry of Ascorbic Acid in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Ascorbic Acid CJDRUOGAGYHKKD-HLIPEDHHSA-N chemical compound 2D structure molecule svg
Ascorbic Acid

 

Molecule descriptors

 
IUPAC name(2R)-2-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2H-furan-5-one
InChI codeInChI=1S/C20H26N2O2/c1-3-10-11-8-14-17-20(12-6-4-5-7-13(12)21(17)2)9-15(16(11)18(20)23)22(14)19(10)24/h4-7,10-11,14-19,23-24H,3,8-9H2,1-2H3/t10-,11-,14-,15-,16-,17-,18-,19+,20+/m0/s1
InChI KeyCJDRUOGAGYHKKD-HLIPEDHHSA-N
SMILESCC[C@H]1[C@@H]2C[C@H]3[C@@H]4N(C)c5ccccc5[C@]45C[C@@H]([C@H]2[C@@H]5O)N3[C@@H]1O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (+)-Ascorbic acid
  • (+)-ascorbate
  • (2R)-2-[(1S)-1,2-Dihydroxyethyl]-4,5-dihydroxy-furan-3-one
  • (2R)-2-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2H-furan-5-one
  • (2R)-2-[(1S)-1,2-dihydroxyethyl]-4,5-dihydroxy-2,3-dihydrofuran-3-one
  • (2R)-2-[(1S)-1,2-dihydroxyethyl]-4,5-dihydroxyfuran-3-one
  • (5R)-5-((1S)-1,2-DIHYDROXYETHYL)-3,4-DIHYDROXYFURAN-2(5H)-ONE
  • (5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one
  • (5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one
  • (5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one (non-preferred name)
  • (R)-5-((S)-1,2-dihydroxyethyl)-3,4-dihydroxyfuran-2(5H)-one
  • (r)-5-(1,2-dihydroxy-ethyl)-3,4-dihydroxy-5h-furan-2-one
  • .Ascorbinsaure
  • 2,3-DEHYDRO-L-THREO-HEXONO-1,4-LACTONE
  • 2-(1,2-Dihydroxyethyl)-4,5-dihydroxyfuran-3-one
  • 3,4-Dihydroxy-5beta-[(S)-1,2-dihydroxyethyl]furan-2(5H)-one
  • 3-Keto-L-gulofuranolactone
  • 3-Oxo-L-gulofuranolactone
  • 3-Oxo-L-gulofuranolactone (enol form)
  • 3eka
  • 4-((E)-2-[(2-HYDROXYETHYL)SULFANYL]DIAZENYL)BENZENECARBOXYLICACID
  • 47A605F0-4187-47A8-B0CE-F9E7DA1B0076
  • 50-81-7
  • 53262-66-1
  • 6730-29-6
  • A0537
  • A8158
  • AB00376923
  • AB00376923_04
  • AB00376923_05
  • Acide ascorbique
  • Acido ascorbico
  • Acidum ascorbicum
  • Acidum ascorbinicum
  • Adenex
  • Allercorb
  • Antiscorbic vitamin
  • Antiscorbutic factor
  • Antiscorbutic vitamin
  • Arco-cee
  • Ascoltin
  • Ascor
  • Ascor-B.I.D.
  • Ascorb
  • Ascorbajen
  • Ascorbic Acid
  • Ascorbic Acid (L-Ascorbic Acid; Vitamin C)
  • Ascorbic Acid DC97SF
  • Ascorbic Acid mixture with Vitamin B Complex
  • Ascorbic acid (JP17/USP/INN)
  • Ascorbic acid mixture with Vitamin B
  • Ascorbic acid, l-
  • Ascorbicab
  • Ascorbicap
  • Ascorbicin
  • Ascorbicum acidum
  • Ascorbin
  • Ascorbinsaeure
  • Ascorbutina
  • Ascorin
  • Ascorteal
  • Ascorvit
  • BCP27915
  • BP-12831
  • BPBio1_000363
  • BSPBio_000329
  • C 1000
  • C-Level
  • C-Long
  • C-Quin
  • C-Span
  • C-Vimin
  • C00072
  • CCG-207946
  • CCRIS 57
  • CE-VI-Sol
  • Cantan
  • Cantaxin
  • Caswell No. 061B
  • Catavin C
  • Ce lent
  • Ce-Mi-Lin
  • Cebicure
  • Cebid
  • Cebion
  • Cebione
  • Cecon
  • Cee-Caps TD
  • Cee-Vite
  • Cegiolan
  • Ceglion
  • Ceklin
  • Celaskon
  • Celin
  • Cell C
  • Cemagyl
  • Cemill
  • Cenetone
  • Cenolate
  • Cereon
  • Cergona
  • Cescorbat
  • Cetamid
  • Cetane-Caps TC
  • Cetane-Caps TD
  • Cetebe
  • Cetemican
  • Cevalin
  • Cevatine
  • Cevex
  • Cevi-Bid
  • Cevimin
  • Cevital
  • Cevitamate
  • Cevitamic acid
  • Cevitamin
  • Cevitan
  • Cevitex
  • Cewin
  • Ciamin
  • Cipca
  • Citriscorb
  • Citrovit
  • Colascor
  • Concemin
  • Cortalex
  • Chewcee
  • Chromagen
  • D00018
  • DB00126
  • DSSTox_CID_106
  • DSSTox_GSID_20106
  • DSSTox_RID_75370
  • Davitamon C
  • Dora-C-500
  • Duoscorb
  • E 300
  • E-300
  • E300
  • E80759
  • Ester C
  • Ester-C
  • FEMA No. 2109
  • Ferancee
  • Ferrous ascorbate
  • GTPL4532
  • GTPL4781
  • HMS2096A11
  • HMS2231N16
  • HMS3713A11
  • HSDB 818
  • HY-B0166
  • Hex-2-enonic acid gamma-lactone, L-threo-
  • Hicee
  • Hybrin
  • IDO-C
  • INS NO.300
  • INS-300
  • Iron(II) ascorbate
  • Iron-ascorbic acid complexes
  • Juvamine
  • Kangbingfeng
  • Kyselina askorbova
  • L(+)-Ascorbic acid
  • L(+)-ascorbate
  • L-(+)-Ascorbic Acid
  • L-(+)-ascorbate
  • L-3-Ketothreohexuronic acid lactone
  • L-Ascorbic acid, FCC, FG
  • L-Ascorbic acid, free radical form
  • L-Ascorbic acid, meets USP testing specifications
  • L-Ascorbic acid, mixt. with vitamin B
  • L-Ascorbic acid, plant cell culture tested
  • L-Ascorbic acid, powder, cell culture tested, gamma-irradiated
  • L-Ascorbic acid, tested according to Ph.Eur.
  • L-Lyxoascorbic acid
  • L-Threoascorbic acid
  • L-Xyloascorbic acid
  • L-ascorbate
  • L-lyxoascorbate
  • L-threo-Ascorbic acid
  • L-threo-Hex-2-enonic acid, gamma-lactone
  • L-threo-hex-2-enono-1,4-lactone
  • L-xyloascorbate
  • Laroscorbine
  • Lemascorb
  • Liqui-Cee
  • MFCD00064328
  • MLS002153776
  • Meri-C
  • NCGC00091517-01
  • NCGC00091517-02
  • NCGC00091517-03
  • NCGC00091517-06
  • NCGC00164357-01
  • NCGC00188972-01
  • NCGC00256504-01
  • NCGC00259676-01
  • NCI-C54808
  • NSC 218455
  • NSC 33832
  • NSC-218455
  • NSC-33832
  • Natrascorb
  • Natrascorb injectable
  • PQ6CK8PD0R
  • Parentrovite
  • Planavit C
  • Prestwick3_000325
  • Proscorbin
  • Q199678
  • Q27101942
  • Redoxon
  • Ribena
  • Ronotec 100
  • Rontex 100
  • Roscorbic
  • Rovimix C
  • SMR001233160
  • SW198791-2
  • Scorbacid
  • Scorbu C
  • Scorbu-C
  • Secorbate
  • Sodascorbate
  • Stuartinic
  • Suncoat VC 40
  • Testascorbic
  • Tolfrinic
  • Vasc
  • Vicelat
  • Vicomin C
  • Viforcit
  • Viscorin
  • Viscorin 100M
  • Vitace
  • Vitacee
  • Vitacimin
  • Vitacin
  • Vitamin B mixture with vitamin C
  • Vitamin C (Ascorbic acid)
  • Vitamin C,(S)
  • Vitamin c (as ascorbic acid)
  • Vitamisin
  • Vitascorbol
  • Xitix
  • Xyloascorbic acid, L-
  • [14C]-ascorbic acid
  • [14C]ascorbic acid
  • ascorbate
  • ascorbic acid
  • ascorbic acid (vit C)
  • bmse000182
  • component of Cortalex
  • component of E and C-Level
  • component of Endoglobin Forte
  • component of Ferancee
  • gamma-lactone L-threo-Hex-2-enonate
  • gamma-lactone L-threo-Hex-2-enonic acid
  • hex-1-enofuranos-3-ulose
  • l-ascorbic acid
  • s3114
  • vitamin C

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC100006770
  • ZINC100019304
  • UNII-PQ6CK8PD0R
  • AKOS016843589
  • DTXSID5020106
  • DTXSID50986567
  • CHEMBL40274
  • CHEBI:29073
  • Tox21_110315
  • Tox21_112104
  • Tox21_202127
  • Tox21_302958
  • Tox21_112104_1
  • EINECS 200-066-2
  • SCHEMBL785
  • SCHEMBL4430

Physico-Chemical properties

IUPAC name(2R)-2-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2H-furan-5-one
Molecular formulaC20H26N2O2
Molecular weight326.433
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity99.87
LogP1.6
Topological polar surface area46.9

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.