N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide

• ChemBase ID: 128648
• Molecular Formular: C17H27NO3
• Molecular Mass: 293.40118
• Monoisotopic Mass: 293.19909373
• SMILES: CCCCCCCCC(=O)NCc1cc(c(cc1)O)OC
• Canonical SMILES: CCCCCCCCC(=O)NCc1ccc(c(c1)OC)O
• InChI: InChI=1S/C17H27NO3/c1-3-4-5-6-7-8-9-17(20)18-13-14-10-11-15(19)16(12-14)21-2/h10-12,19H,3-9,13H2,1-2H3,(H,18,20)
• InChIKey: RGOVYLWUIBMPGK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide
• IUPAC Traditional name: nonivamide
• Synonyms: N-[(4-Hydroxy-3-methoxyphenyl)methyl]nonanamide; 8-Nordihydrocapsaicin; AH 23491X; N-(4-Hydroxy-3-methoxybenzyl)nonamide; N-Vanillylnonamide; NSC 172795; Nonanoylvanillyl Amide; Nonivamide; Nonylic Acid Vanillylamide; Nonylic Vanillylamide; Vanillyl n-Nonylamide; Vanillyl Pelargonic Amide; N-Vanillylnonanamide; Pseudocapsaicin; vanillyl-N-nonylamidn; nonylic acid vanillyl amidn; pelargonic acid vanillylamide (PAVAn; pelargonyl vanillyl amide; Nonivamide; Capsaicin synthetic; N-(4-Hydroxy-3-methoxybenzyl)nonanamide; N-Vanillylpelargonamide; Nonanoic acid vanillylamide; Nonylvanylamide; N-Vanillylnonanamide; Pelargonic acid vanillylamide; 壬酸香草酰胺

Database IDs

• CAS Number: 2444-46-4
• EC Number: 219-484-1; 219-46-4
• MDL Number: MFCD00017286
• Beilstein Number: 2144300
• PubChem SID: 24892401; 24278775; 24886983; 162222955
• PubChem CID: 2998
• KEGG ID: D08282
• Wikipedia Title: Nonivamide

CALCULATED PROPERTIES

• Acid pKa: 9.928692
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.8245556
• LogD (pH = 7.4): 3.8232968
• Log P: 3.824572
• Molar Refractivity: 84.6522 cm^3
• Polarizability: 33.069572 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: insoluble in water; methanol: soluble100 mg/mL, clear to slightly hazy, colorless to deep brown-yellow; soluble in methanol
• Apperance: powder; white to off-white powder
• Melting Point: 54°C; 55-61 °C
• Flash Point: 190 °C; 190 °C (closed cup); 374 °F
• Auto Ignition Point: 330 °C
• Density: 1.10 g/cm^3
• Odor: pungent

Safety Information

• European Hazard Symbols: Irritant (Xi)
• UN Number: 2811
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 36/37/38-43
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• LD50: 511 mg/kg (rat, oral)
• GHS Hazard statements: H315-H317-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: rat ... Trpv1(83810), Trpv4(66026)

Product Information

• Purity: ≥97%; ≥97.0% (HPLC)
• Grade: purum
• Empirical Formula (Hill Notation): C17H27NO3

DETAILS

Sigma Aldrich - V9130

Other Notes
Synthetic analogue of capsaicin with similar bioactivity.

Toronto Research Chemicals - V097635

N-Vanillylnonanamide is a synthetic analogue of Capsaicin (175680) with similar bioactivity.

REFERENCES

• Turgut, C., et al.: Environ. Sci. Pollut. Res., 11, 7 (2003)
• Xu, Q., et al.: Environ. Toxicol., 20, 467 (2003)