Thunbergene

Base Information

• Chemical Name: Thunbergene
• CAS No.: 1898-13-1
• Deprecated CAS: 27898-40-4,23267-49-4,17635-58-4
• Molecular Formula: C20H32
• Molecular Weight: 272.474
• Hs Code.: 2902199090
• DSSTox Substance ID: DTXSID80880701
• Metabolomics Workbench ID: 28599
• Mol file: 1898-13-1.mol

Synonyms:Thunbergene;Cembrene;(+)-Thunbergen;(+)-Cembrene;(1S,2E,7E,11E)-2,4(18),7,11-Cembratraene;Thumbelene;DTXSID80880701;(1E,3Z,6E,10E,14S)-3,7,11-Trimethyl-14-(1-methylethyl)-1,3,6,10-cyclotetradecatetraene;1898-13-1;41F9848B-1F92-4929-BD50-32C995663B66

Chemical Property of Thunbergene

Chemical Property:

• Vapor Pressure: 3.35E-05mmHg at 25°C
• Melting Point: 59-61 °C
• Refractive Index: 1.7290 (estimate)
• Boiling Point: 365.2°Cat760mmHg
• Flash Point: 166.8°C
• PSA: 0.00000
• Density: 0.831g/cm³
• LogP: 6.61780
• Storage Temp.: Freezer (-20°C)
• XLogP3: 6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 272.250401021
• Heavy Atom Count: 20
• Complexity: 402

Purity/Quality:

98%Min ^*data from raw suppliers

CEMBRENE 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCCC(=CCC=C(C=CC(CC1)C(C)C)C)C
• Isomeric SMILES: C/C/1=C\CC/C(=C/C/C=C(\C=C\[C@@H](CC1)C(C)C)/C)/C
• Uses: (+)-Cembrene (cas# 1898-13-1) is an essential oil. An antioxidant.

Technology Process of Thunbergene

There total 18 articles about Thunbergene 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: 60.0%

(R)-Cembrenen (132340-78-4) → cembrene (1898-13-1)

Guidance literature:

With Wilkinson's catalyst; hydrogen; In ethanol; benzene; for 1.33333h;

DOI:10.1002/hlca.19900730721

Reference yield:

Isocembrol (4R) (25269-17-4,53494-49-8,63568-83-2,63568-84-3,68421-38-5,78087-96-4,79897-32-8,80126-41-6,121702-09-8,121702-10-1,121702-11-2) → cembrene (1898-13-1) + (1S,2E,7E,11E)-2,4(18),7,11-cembratetraene (25269-16-3)

Guidance literature:

With trichlorophosphate; In pyridine; 1.) 0 deg C, 2.) room temperature, 24 h;

Reference yield:

(14R,all-E)-14,15-Epoxy-3,7,11,15-tetramethyl-1-(phenylthio)hexadeca-2,6,10-trien (63859-99-4) → cembrene (1898-13-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 44 percent / BuLi / hexane

2: 35 percent / Oxodiperoxymolybdaen(pyridin)hexamethylphosphoramid (MoOPH) / tetrahydrofuran / 38 h / Ambient temperature

3: 33 percent / Pyridin, SOCl₂ / 1) 0 deg C, 2 h, 2) r.t., 2 h

4: 60 percent / H₂, 3)3>Cl / ethanol; benzene / 1.33 h

With pyridine; Wilkinson's catalyst; n-butyllithium; thionyl chloride; MoO₅*pyridine*HMPA; hydrogen; In tetrahydrofuran; ethanol; hexane; benzene;

DOI:10.1002/hlca.19900730721

upstream raw materials:

Cembrol

Isocembrol (4R)

(R)-Cembrenen

(1S,2E, 4S,7E,11E)-2,7,11-cembratriene-4-ol

Downstream raw materials:

levulinic acid

1,7,11-trimethyl-4-(1-methylethyl)cyclotetradecane