Norcapsaicin

Base Information

• Chemical Name: Norcapsaicin
• CAS No.: 61229-08-1
• Deprecated CAS: 912457-67-1
• Molecular Formula: C17H25NO3
• Molecular Weight: 291.39
• DSSTox Substance ID: DTXSID901317984
• Nikkaji Number: J482.640J,J2.167.423K
• Wikidata: Q76386886
• Metabolomics Workbench ID: 47306
• Mol file: 61229-08-1.mol

Synonyms:norcapsaicin;61229-08-1;(E)-N-(4-Hydroxy-3-methoxybenzyl)-7-methyloct-5-enamide;(E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-7-methyloct-5-enamide;SCHEMBL8163896;CHEBI:174089;7-Methyl-N-vanillyl-5-octenamide;DTXSID901317984;N-(3-Methoxy-4-hydroxybenzyl)-7-methyl-5-octenamide;N-[(4-Hydroxy-3-methoxyphenyl)methyl]-7-methyl-5-octenamide, 9CI;(5E)-N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-7-METHYLOCT-5-ENAMIDE;5-Octenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-7-methyl-, (E)-

Chemical Property of Norcapsaicin

Chemical Property:

• Vapor Pressure: 2.94E-10mmHg at 25°C
• Boiling Point: 490.8°Cat760mmHg
• Flash Point: 250.6°C
• PSA: 58.56000
• Density: 1.053g/cm³
• LogP: 3.79040
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 291.18344366
• Heavy Atom Count: 21
• Complexity: 328

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C=CCCCC(=O)NCC1=CC(=C(C=C1)O)OC
• Isomeric SMILES: CC(C)/C=C/CCCC(=O)NCC1=CC(=C(C=C1)O)OC

Technology Process of Norcapsaicin

There total 11 articles about Norcapsaicin 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:

(E)-7-Methyloct-5-enoic acid (61229-06-9) → norcapsaicin (61229-08-1)

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 4-formylbutanoate (6026-86-4) → norcapsaicin (61229-08-1)

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

Reference yield:

methyl 5-hydroxypentanoate (14273-92-8) → norcapsaicin (61229-08-1)

Guidance literature:

Multi-step reaction with 6 steps

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

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

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

With methanol; potassium hydroxide; thionyl chloride; sodium amalgam; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/jo00240a024

upstream raw materials:

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

(E)-7-Methyloct-5-enoic acid

Methanesulfonic acid (E)-6-methyl-hept-4-enyl ester

(E)-7-methyl-5-octenenitrile

Downstream raw materials:

Nordihydrocapsaicin