N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnonanamide

• ChemBase ID: 105269
• Molecular Formular: C18H29NO3
• Molecular Mass: 307.42776
• Monoisotopic Mass: 307.21474379
• SMILES: COc1c(O)ccc(CNC(=O)CCCCCCC(C)C)c1
• Canonical SMILES: COc1cc(CNC(=O)CCCCCCC(C)C)ccc1O
• InChI: InChI=1S/C18H29NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h10-12,14,20H,4-9,13H2,1-3H3,(H,19,21)
• InChIKey: XJQPQKLURWNAAH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnonanamide
• IUPAC Traditional name: dihydrocapsaicin
• Synonyms: Dihydrocapsaicin; N-[(4-Hydroxy-3-methoxy-phenyl)methyl]- 8-methyl-nonanamide; Dihydrocapsaicie; 6,7-Dihydrocapsaicie; 8-Methyl-N-vanillylnonanamide; Vanillylamide of 8-methylnonanoic acie; DHe; CCRIS 1589; Dihydrocapsaicin; Dihydrocapsaicin; 8-METHYL-N-VANILLYLNONANAMIDE; N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methylnonanamide; 6,7-Dihydrocapsaicin; Dihydro Capsaicin; N-(4-羟基-3-甲氧基苄基)-8-甲基壬酰胺; 二氢辣椒素

Database IDs

• CAS Number: 19408-84-5
• MDL Number: MFCD00057794
• Beilstein Number: 2815150
• PubChem SID: 24278532; 162092525
• PubChem CID: 107982
• Chemspider ID: 97096
• Unique Ingredient Identifier: W9BV32M08A
• Wikipedia Title: Dihydrocapsaicin

CALCULATED PROPERTIES

• Acid pKa: 9.928692
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.1115746
• LogD (pH = 7.4): 4.110316
• Log P: 4.1115913
• Molar Refractivity: 89.2008 cm^3
• Polarizability: 34.911514 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; chloroform: soluble50 mg/mL, clear, colorless to faintly yellow; Ethyl Acetate; Methanol; Sparingly soluble in water
• Apperance: White to off-white solid; White to Off-White Solid
• Melting Point: 64 - 65°C; 66-68°C

Safety Information

• Storage Condition: 2-8°C; Refrigerator
• RTECS: RA5998000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811; 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Australian Hazchem: 2XE
• Risk Statements: 25-36/37/38; R:25; R25, R36/37/38
• Safety Statements: 26-45; S:28-36/37/39-45-53; S26, S36/37/39, S45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• NFPA704:
  

  1

  2

  0
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... TRPV1(7442)rat ... Trpv4(66026)

Product Information

• Purity: ~90%; ≥80% (HPLC)
• Biological Source: from Capsicum sp.
• Quality: natural
• Empirical Formula (Hill Notation): C18H29NO3
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 02159588

Purity: ~90%

Sigma Aldrich - M1022

Biochem/physiol Actions
VR1 vanilloid receptor agonist.
Linkage
Capsaicin analog.

Sigma Aldrich - 37274

Biochem/physiol Actions
VR1 vanilloid receptor agonist.
Linkage
Capsaicin analog.

Toronto Research Chemicals - D448750

Capsaicin (C175680) analog. A VR1 vaniloid receptor agonist.

REFERENCES

• Ralevic, V., et al.: Biochem. Pharmacol., 65, 143 (2003)
• Thompson, R., et al.: Anal. Bioanal. Chem., 381, 1432 (2003)
• Tuoya., et al.: Life Sci., 78, 1515 (2003)