(-)-gamma-Cadinene

Base Information

• Chemical Name: (-)-gamma-Cadinene
• CAS No.: 1460-97-5
• Deprecated CAS: 28080-00-4
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.356
• UNII: 2GHT32E0JU
• DSSTox Substance ID: DTXSID301017689
• Nikkaji Number: J14.359F
• Wikidata: Q27132466
• Metabolomics Workbench ID: 62671
• Mol file: 1460-97-5.mol

Synonyms:gamma-cadinene;gamma-cadinene, (+)-gamma(1)-isomer;gamma-cadinene, (+)-isomer;gamma-cadinene, (-)-isomer

Chemical Property of (-)-gamma-Cadinene

Chemical Property:

• Vapor Pressure: 0.0103mmHg at 25°C
• Boiling Point: 272.1°Cat760mmHg
• Flash Point: 106.8°C
• PSA: 0.00000
• Density: 0.89g/cm³
• LogP: 4.58110
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 282

Purity/Quality:

95% ^*data from raw suppliers

(-)-γ-Cadinene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2C(CC1)C(=C)CCC2C(C)C
• Isomeric SMILES: CC1=C[C@H]2[C@H](CC1)C(=C)CC[C@@H]2C(C)C
• Uses: (-)-γ-Cadinene is a sesquiterpene and can be isolated from A. terreus. It is an antioxidant agent.

Technology Process of (-)-gamma-Cadinene

There total 12 articles about (-)-gamma-Cadinene 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:

(1S)-<1-2H>farnesyl diphosphate (115826-59-0) → γ-cadinene (1460-97-5)

Guidance literature:

With (?)-γ-cadinene synthase from Chitinophaga pinensis; In glycerol; at 28 ℃; for 3h; pH=8.2; Enzymatic reaction;

DOI:10.1002/anie.201608042

Reference yield:

(+)-α-cadinol (481-34-5,5937-11-1,19435-97-3,19912-62-0,39864-11-4,43060-37-3,58560-29-5,58580-31-7,65700-78-9,71300-63-5,81967-90-0,95342-27-1,106035-59-0,133645-25-7) → (-)-γ-cadinene (483-74-9,1460-97-5,6980-46-7,10208-81-8,24268-39-1,28080-00-4,30021-74-0,38357-83-4,39029-41-9,41610-66-6,68000-46-4)

Guidance literature:

With trichlorophosphate; In pyridine; benzene; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)86837-X

Reference yield:

vetidiol (113888-82-7) → (-)-γ-cadinene (483-74-9,1460-97-5,6980-46-7,10208-81-8,24268-39-1,28080-00-4,30021-74-0,38357-83-4,39029-41-9,41610-66-6,68000-46-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 125 mg / PBA / CHCl₃ / 24 h / 0 °C

2: pyridine

3: LAH / 20 h / Heating

4: POCl₃ / pyridine; benzene / 2 h / Ambient temperature

With lithium aluminium tetrahydride; trichlorophosphate; In pyridine; chloroform; benzene;

DOI:10.1016/S0040-4020(01)86837-X

upstream raw materials:

Kadin-4, 10(15)-dien-3α-ol

Khusol-tosylat

[1-²H]farnesal

(S)-<1-2H>(E,E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol

Refernces

• 1、 Burkhardt, Immo,Kreuzenbeck, Nina B.,Beemelmanns, Christine,Dickschat, Jeroen S.. "Mechanistic characterization of three sesquiterpene synthases from the termite-associated fungus: Termitomyces". . p. 3348 - 3355. Retrieved 2019.
• 2、 Rao,A.A. et al.. "-". . p. 233 - 239. Retrieved 1963.