N-{[4-hydroxy-3-(2H3)methoxyphenyl]methyl}-8-methylnon-6-enamide

• ChemBase ID: 163602
• Molecular Formular: C18H27NO3
• Molecular Mass: 305.41188
• Monoisotopic Mass: 305.19909373
• SMILES: c1(c(ccc(c1)CNC(=O)CCCCC=CC(C)C)O)OC
• Canonical SMILES: COc1cc(CNC(=O)CCCCC=CC(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)
• InChIKey: YKPUWZUDDOIDPM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{[4-hydroxy-3-(^2H₃)methoxyphenyl]methyl}-8-methylnon-6-enamide; (6E)-N-{[4-hydroxy-3-(^2H₃)methoxyphenyl]methyl}-8-methylnon-6-enamide; (6Z)-N-{[4-hydroxy-3-(^2H₃)methoxyphenyl]methyl}-8-methylnon-6-enamide
• IUPAC Traditional name: N-{[4-hydroxy-3-(^2H₃)methoxyphenyl]methyl}-8-methylnon-6-enamide; (6E)-N-{[4-hydroxy-3-(^2H₃)methoxyphenyl]methyl}-8-methylnon-6-enamide; (6Z)-N-{[4-hydroxy-3-(^2H₃)methoxyphenyl]methyl}-8-methylnon-6-enamide
• Synonyms: N-[(4-Hydroxy-3-(methoxy-d3)phenyl)methyl]-8-methyl-6-nonenamide; (E/Z)-8-Methyl-N-vanillyl-6-nonenamide-d3; Capsaicin-d3(E/Z-Mixture); (6E)-N-[(4-hydroxy-3-(methoxy-d3)phenyl)methyl]-8-methyl-6-nonenamide; (E)-8-Methyl-N-vanillyl-6-nonenamide-d3; Capsaicin-d3; (E)-N-(4-Hydroxy-3-(methoxy-d3)benzyl)-8-methylnon-6-enamide; ALGRX 4975-d3; Adlea-d3; Axsain-d3; Capsaicine-d3; Capsin P 50-d3; Capzasin-HP-d3; Dolenon-d3; E-Capsaicin-d3; Mioton-d3; N-(4-Oxy-3-(methoxy-d3)benzyl)-8-methyl-6-nonenamide; NGX 4010-d3; NSC 56353-d3; Ovocap-d3; Ratden PE 40-d3; Togarashi Orenji-d3; Zostrix-d3; trans-8-Methyl-N-vanillyl-6-nonenamide-d3; trans-Capsaicin-d3; (6Z)-N-[(4-Hydroxy-3-(methoxy-d3)phenyl)methyl]-8-methyl-6-nonenamide; (Z)-8-Methyl-N-vanillyl-6-nonenamide-d3; (Z)-Capsaicin-d3; Civamide-d3; Zucapsaicin-d3; cis-Capsaicin-d3

Database IDs

• PubChem SID: 162257737
• PubChem CID: 57369257

CALCULATED PROPERTIES

• Acid pKa: 9.928692
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.749653
• LogD (pH = 7.4): 3.7483943
• Log P: 3.7496696
• Molar Refractivity: 90.3174 cm^3
• Polarizability: 34.67193 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Alcohol; Benzene; Chloroform; Ether
• Apperance: Off-White Solid
• Melting Point: 61-63°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C175692

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

Toronto Research Chemicals - C175687

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

Toronto Research Chemicals - C175682

A representative lot is a 5:1 E:Z mixture.Labelled Capsaicin (C175680). Has been isolated from paprika and cayenne. It is used as a tool in neurobiological research. Prototype vanilloid receptor agonist. Topical analgesic.Note this is a powerful irritant.

REFERENCES

• Artursson., et al.: J. Pharma. Sci., 73, 1507 (1984)
• Fu., et al.: Pharma. Res., 2000, 17, 100 (1984)
• Artursson., et al.: J. Pharma. Sci., 73, 1507 (1984)
• Fu., et al.: Pharma. Res., 17, 100 (1984)
• Molnar, et al.: Arzneim.-Forsch., 15, 718 (1965)
• Monsereenusorn,Y., et al.: Crit. Rev. Toxicol., 10, 321 (1965)