Homodihydrocapsaicin

Base Information

• Chemical Name: Homodihydrocapsaicin
• CAS No.: 20279-06-5
• Molecular Formula: C19H31NO3
• Molecular Weight: 321.46
• Hs Code.: 2924299090
• UNII: QE35S0T20Z
• DSSTox Substance ID: DTXSID30174127
• Nikkaji Number: J246.485C
• Wikipedia: Homodihydrocapsaicin
• Wikidata: Q5891091
• Metabolomics Workbench ID: 47309
• Mol file: 20279-06-5.mol

Synonyms:homodihydrocapsaicin;Homodihydrocapsaicin I;20279-06-5;n-(4-hydroxy-3-methoxybenzyl)-9-methyldecanamide;UNII-QE35S0T20Z;N-[(4-hydroxy-3-methoxyphenyl)methyl]-9-methyldecanamide;QE35S0T20Z;Decanamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-9-methyl-;DECANAMIDE, 9-METHYL-N-VANILLYL-;Decanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-9-methyl-;SCHEMBL1870592;N-(vanillyl)-9-methyldecanamide;DTXSID30174127;AKDLSISGGARWFP-UHFFFAOYSA-N;CHEBI:174344;HY-N5082;MS-24760;CS-0032400;FT-0775520;E80599;Q5891091;N-((4-Hydroxy-3-methoxyphenyl)methyl)-9-methyl-Decanamide;N-[(4-Hydroxy-3-methoxyphenyl)methyl]-9-methyldecanamide, 9CI

Chemical Property of Homodihydrocapsaicin

Chemical Property:

• Vapor Pressure: 6.08E-11mmHg at 25°C
• Boiling Point: 508°Cat760mmHg
• Flash Point: 261°C
• PSA: 62.05000
• Density: 1.017g/cm³
• LogP: 5.24400
• XLogP3: 5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 11
• Exact Mass: 321.23039385
• Heavy Atom Count: 23
• Complexity: 320

Purity/Quality:

≥98% ^*data from raw suppliers

DihydroHomocapsaicinI ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
• Uses: Dihydro Homocapsaicin I?is a related compound of Homocapsaicin?I (H589900), which is commonly found in herbs and?spices such as chilli peppers. Homocapsaicin?I is a?capsaicinoid and?an irritant.

Technology Process of Homodihydrocapsaicin

There total 18 articles about Homodihydrocapsaicin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

→ 9-methyl-N-vanillyl-7-decenamide (20279-06-5)

Guidance literature:

With indium(III) chloride; oxygen; ferric nitrate; at 30 ℃; for 0.5h; Schlenk technique;

Reference yield:

oxocan-2-one (539-87-7) → 9-methyl-N-vanillyl-7-decenamide (20279-06-5)

Guidance literature:

Multi-step reaction with 7 steps

1: conc. H₂SO₄ / Heating

2: pyridinium chlorochromate (PCC), sodium acetate / CH₂Cl₂ / 1.5 h / Ambient temperature

3: 1.) t-BuOK / 1.) DMF, RT, 5 min, 2.) a) RT, 20 h, b) 90 deg C, 1 h

4: aq. KOH / ethanol / 1 h / Heating

5: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min

6: diethyl ether / 72 h / Ambient temperature

7: H₂ / 10percent Pd/C / ethanol / 4 h / 760 Torr

With potassium hydroxide; thionyl chloride; sulfuric acid; potassium tert-butylate; hydrogen; sodium acetate; pyridinium chlorochromate; palladium on activated charcoal; In diethyl ether; ethanol; dichloromethane;

DOI:10.1021/jo00240a024

Reference yield:

(Z)-N-(4-hydroxy-3-methoxybenzyl)-9-methyldec-7-enamide (75652-50-5) → 9-methyl-N-vanillyl-7-decenamide (20279-06-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 4h; under 760 Torr;

DOI:10.1021/jo00240a024

upstream raw materials:

Vanillylamin

9-Methyldecanoyl chloride

(Z)-N-(4-hydroxy-3-methoxybenzyl)-9-methyldec-7-enamide

trans-9-methyl-N-vanillyl-7-decenamide

Refernces

• 1、 Kaga, Harumi,Miura, Masakatsu,Orito, Kazuhiko. "A Short Route to Dihydrocapsaicinoids". . p. 864 - 866. Retrieved 2007/10/02.