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

• ChemBase ID: 160833
• Molecular Formular: C6H8O6
• Molecular Mass: 176.12412
• Monoisotopic Mass: 176.03208798
• SMILES: C1(=C(O)C(=O)O[C@@H]1C(CO)O)O
• Canonical SMILES: OCC([C@H]1OC(=O)C(=C1O)O)O
• InChI: InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2?,5-/m1/s1
• InChIKey: CIWBSHSKHKDKBQ-DOAHDZERSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-5-(1,2-dihydroxyethyl)-3,4-dihydroxy-2,5-dihydrofuran-2-one
• IUPAC Traditional name: (5R)-5-(1,2-dihydroxyethyl)-3,4-dihydroxy-5H-furan-2-one
• Synonyms: (+)-Ascorbic Acid; 100M; L-threo-Ascorbic Acid; 3-Oxo-L-gulofuranolactone; 3-keto-L-Gulofuranolactone; Adenex; Allercorb; Ascorbajen; Cantan; Cantaxin; Vitacimin; Vitacin; Vitamin C; Davitamon C; Laroscorbine; Vitamisin; Vitascorbol; L-Ascorbic Acid

Database IDs

• CAS Number: 50-81-7
• PubChem SID: 162254968
• PubChem CID: 54676536

CALCULATED PROPERTIES

• Acid pKa: 4.3599176
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -3.082243
• LogD (pH = 7.4): -4.8322015
• Log P: -1.9135588
• Molar Refractivity: 37.0321 cm^3
• Polarizability: 14.376429 Å^3
• Polar Surface Area: 107.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White Solid
• Melting Point: 189-191°C (dec.)

Safety Information

• Storage Condition: Refrigerator

Product Information

• Classification: Genuine Natural Compounds

DETAILS

Toronto Research Chemicals - A786990

Physiological antioxidant. Coenzyme for a number of hydroxylation reactions; required for collagen synthesis. Widely distributed in plants and animals. Inadequate intake results in deficiency syndromes such as scurvy. Used as antimicrobial and antioxidant

REFERENCES

• Al-Meshal, I.A., et al.: Anal. Profiles Drug Subs., 11, 45 (1982)
• Levine, M., et al.: N. Engl. J. Med., 314, 892 (1982)
• Prust, C., et al.: Nature Biotech., 23, 195 (1982)