(6Z)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide

• ChemBase ID: 163603
• Molecular Formular: C18H27NO3
• Molecular Mass: 305.41188
• Monoisotopic Mass: 305.19909373
• SMILES: c1(c(ccc(c1)CNC(=O)CCCC/C=C\C(C)C)O)OC
• Canonical SMILES: COc1cc(CNC(=O)CCCC/C=C\C(C)C)ccc1O
• InChI: InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6-
• InChIKey: YKPUWZUDDOIDPM-VURMDHGXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6Z)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
• IUPAC Traditional name: zucapsaicin
• Synonyms: (6Z)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide; (Z)-8-Methyl-N-vanillyl-6-nonenamide; (Z)-Capsaicin; Civamide; Zucapsaicin; cis-Capsaicin; (Z)-N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide

Database IDs

• CAS Number: 25775-90-0
• MDL Number: MFCD00209942
• PubChem SID: 162257738
• PubChem CID: 1548942

CALCULATED PROPERTIES

• Acid pKa: 9.928692
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.7496533
• LogD (pH = 7.4): 3.7483943
• Log P: 3.7496696
• Molar Refractivity: 90.3174 cm^3
• Polarizability: 34.670914 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - C175690

Capsaicin analogue (C175680). It is used as a tool in neurobiological research. Prototype vanilloid receptor agonist. Topical analgesic.

REFERENCES

• Artursson., et al.: J. Pharma. Sci., 73, 1507 (1984)
• Fu., et al.: Pharma. Res., 2000, 17, 100 (1984)