Neocembrene

Base Information

• Chemical Name: Neocembrene
• CAS No.: 31570-39-5
• Deprecated CAS: 11075-93-7,38748-84-4,41943-02-6
• Molecular Formula: C₂₀H₃₂
• Molecular Weight: 272.474
• UNII: 2WGK4P4230
• ChEMBL ID: CHEMBL518765
• Metabolomics Workbench ID: 28598
• Nikkaji Number: J18.005J
• Wikidata: Q5058639
• Wikipedia: Cembrene_A
• Mol file: 31570-39-5.mol

Synonyms:1,5,9-trimethyl-12-(1-methylethenyl)-1,5,9-cyclotetradecatriene;cembrene A

Chemical Property of Neocembrene

Chemical Property:

• Vapor Pressure: 2.48E-05mmHg at 25°C
• Refractive Index: nD30 1.5102
• Boiling Point: 369.7°Cat760mmHg
• Flash Point: 169°C
• PSA: 0.00000
• Density: 0.831g/cm³
• LogP: 6.76190
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 272.250401021
• Heavy Atom Count: 20
• Complexity: 404

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCCC(=CCC(CCC(=CCC1)C)C(=C)C)C
• Isomeric SMILES: C/C/1=C\CC/C(=C/C[C@@H](CC/C(=C/CC1)/C)C(=C)C)/C

Technology Process of Neocembrene

There total 31 articles about Neocembrene 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: 81.0%

(3R,6E,10E)-6,10-dimethyl-3-isopropenylpentadeca-6,10-dien-1-al (79859-58-8) → (–)-(R)-cembrene A (38748-84-4,57918-06-6,71213-92-8,72690-72-3,72690-73-4,72691-72-6,73246-00-1,105662-19-9,139492-81-2,31570-39-5)

Guidance literature:

With titanium tetrachloride; zinc; In 1,2-dimethoxyethane; for 3h; Ambient temperature;

DOI:10.1055/s-1996-4290

Reference yield: 68.0%

2-[(1R,3E,7E,11E)-4,8,12-trimethylcyclotetradeca-3,7,11-trien-1-yl]propan-2-ol (53915-41-6) → (–)-(R)-cembrene A (38748-84-4,57918-06-6,71213-92-8,72690-72-3,72690-73-4,72691-72-6,73246-00-1,105662-19-9,139492-81-2,31570-39-5)

Guidance literature:

DOI:10.1002/hlca.19900730721

Reference yield:

geranylgeranyl pyrophosphate (13100-78-2) → (–)-(R)-cembrene A (38748-84-4,57918-06-6,71213-92-8,72690-72-3,72690-73-4,72691-72-6,73246-00-1,105662-19-9,139492-81-2,31570-39-5) + (S,1E,5E,9E)-1,5,9-trimethyl-12-(prop-1-en-2-yl)cyclotetradeca-1,5,9-triene (72691-72-6)

Guidance literature:

With β-himachalene synthase elution fraction; In water; at 28 ℃; for 4h; Overall yield = 1.0 mg; Enzymatic reaction;

DOI:10.3762/bjoc.15.99

upstream raw materials:

2-[(1R,3E,7E,11E)-4,8,12-trimethylcyclotetradeca-3,7,11-trien-1-yl]propan-2-ol

((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (2E,6E,10E)-(1R,14S)-14-isopropenyl-3,7,11-trimethyl-cyclotetradeca-2,6,10-trienyl ester

(1R,3S,4S,7E,11E)-3,4-epoxycembra-7,11,15-triene

(3R,6E,10E)-6,10-dimethyl-3-isopropenylpentadeca-6,10-dien-1-al

Downstream raw materials:

2E,6E,10E-Cembratrien