5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one

• ChemBase ID: 169628
• Molecular Formular: C17H26O4
• Molecular Mass: 294.38594
• Monoisotopic Mass: 294.18310931
• SMILES: c1c(c(cc(c1)CCC(=O)CC(CCCCC)O)OC)O
• Canonical SMILES: CCCCCC(CC(=O)CCc1ccc(c(c1)OC)O)O
• InChI: InChI=1S/C17H26O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-16(20)17(11-13)21-2/h8,10-11,14,18,20H,3-7,9,12H2,1-2H3
• InChIKey: NLDDIKRKFXEWBK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
• IUPAC Traditional name: gingerol
• Synonyms: (±)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone; (±)-[6]-Gingerol; rac-[6]-Gingerol

Database IDs

• CAS Number: 39886-76-5
• PubChem SID: 162263760
• PubChem CID: 3473

CALCULATED PROPERTIES

• Acid pKa: 9.945873
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.6165044
• LogD (pH = 7.4): 3.615294
• Log P: 3.61652
• Molar Refractivity: 83.1092 cm^3
• Polarizability: 32.557247 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - G387200

rac-[6]-Gingerol is the racemic mixture of [6]-Gingerol (the active constituent of fresh ginger) and its enantiomer. rac-[6]-Gingerol shows antihepatotoxic effects as well as suppression of spontaneous Ca2+ spikes and isometric contraction.

REFERENCES

• Hikino, H. et al.: J. Ethnopharmacol., 14, 31 (1985)
• Kimura, I. et al.: Jap. J. Pharmacol., 48, 257 (1985)