Homocapsaicin

Base Information

• Chemical Name: Homocapsaicin
• CAS No.: 58493-48-4
• Molecular Formula: C19H29NO3
• Molecular Weight: 319.444
• UNII: S5KLC0JPH3
• DSSTox Substance ID: DTXSID50894012
• Nikkaji Number: J482.641H
• Wikipedia: Homocapsaicin
• Wikidata: Q76386883
• Metabolomics Workbench ID: 47308
• Mol file: 58493-48-4.mol

Synonyms:homocapsaicin;E-Homocapsaicin;58493-48-4;S5KLC0JPH3;UNII-S5KLC0JPH3;(E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-9-methyldec-7-enamide;N-VANILLYL-9-METHYLDEC-7-(E)-ENAMIDE;TRANS-N-VANILLYL-9-METHYLDEC-7-ENAMIDE;VANILLYLAMIDE OF 9-METHYLDEC-TRANS-7-ENOIC ACID;(3e)-n-(4-hydroxy-3-methoxybenzyl)-9-methyldec-7-enamide;7-Decenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-9-methyl-, (7E)-;7-DECENAMIDE, N-((4-HYDROXY-3-METHOXYPHENYL)METHYL)-9-METHYL-, (E)-;HOMOCAPSAICIN [DSC];SCHEMBL1878909;DTXSID50894012;9-methyl-N-vanillyl-7-decenamide;CHEBI:165229;JKIHLSTUOQHAFF-VQHVLOKHSA-N;trans-9-methyl-N-vanillyl-7-decenamide;HOMOCAPSAICIN (CONSTITUENT OF CAPSICUM);HOMOCAPSAICIN (CONSTITUENT OF CAPSICUM) [DSC];(e)-n-(4-hydroxy-3-methoxybenzyl)-9-methyldec-7-enamide;(7E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-9-methyldec-7-enamide;N-[(4-Hydroxy-3-methoxyphenyl)methyl]-9-methyl-7-decenamide, 9CI

Chemical Property of Homocapsaicin

Chemical Property:

• Vapor Pressure: 1.74E-11mmHg at 25°C
• Boiling Point: 521.3°C at 760 mmHg
• Flash Point: 269.1°C
• Density: 1.031g/cm³
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 319.21474379
• Heavy Atom Count: 23
• Complexity: 355

Purity/Quality:

90%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)C=CCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
• Isomeric SMILES: CC(C)/C=C/CCCCCC(=O)NCC1=CC(=C(C=C1)O)OC

Technology Process of Homocapsaicin

There total 18 articles about Homocapsaicin 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:

oxocan-2-one (539-87-7) → trans-9-methyl-N-vanillyl-7-decenamide (58493-48-4)

Guidance literature:

Multi-step reaction with 5 steps

1: DIBAL / toluene / 1 h / -78 °C

2: KOtBu / dimethylformamide / Ambient temperature

3: 79 percent / CrO₃ / acetone / 1) 0 deg C, 30 min, 2)r.t., 1.5 h

4: SOCl₂ / 2 h / Heating

5: diethyl ether / 1) r.t. 2 h, 2) reflux, 2 h

With chromium(VI) oxide; thionyl chloride; potassium tert-butylate; diisobutylaluminium hydride; In diethyl ether; N,N-dimethyl-formamide; acetone; toluene;

Reference yield:

(E)-9-Methyldec-7-enoic acid (61229-05-8) → trans-9-methyl-N-vanillyl-7-decenamide (58493-48-4)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / 2 h / Heating

2: diethyl ether / 2 h / Heating

With thionyl chloride; In diethyl ether;

DOI:10.1016/0040-4020(96)00414-0

Reference yield:

methyl 7-oxoheptanoate (35376-00-2) → trans-9-methyl-N-vanillyl-7-decenamide (58493-48-4)

Guidance literature:

Multi-step reaction with 5 steps

2: Na(Hg), MeOH / tetrahydrofuran / 8 h / -20 °C

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

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

5: diethyl ether / 72 h / Ambient temperature

With methanol; potassium hydroxide; thionyl chloride; sodium amalgam; In tetrahydrofuran; diethyl ether; ethanol;

DOI:10.1021/jo00240a024

upstream raw materials:

Vanillylamin

(E)-9-Methyldec-7-enoic acid chloride

(E)-1-hydroxy-6-methylhept-4-ene

(E)-9-Methyldec-7-enoic acid

Downstream raw materials:

9-methyl-N-vanillyl-7-decenamide

Refernces

• 1、 Kaga, Harumi,Goto, Kouhei,Fukuda, Takashi,Orito, Kazuhiko. "An Alternate Synthesis of the Capsaicinoids". . p. 946 - 948. Retrieved 2007/10/02.