Zingiberene

Base Information

• Chemical Name: Zingiberene
• CAS No.: 495-60-3
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.356
• European Community (EC) Number: 207-804-2
• UNII: 8XOC63EI5F
• DSSTox Substance ID: DTXSID00197808
• Nikkaji Number: J17.884E
• Wikipedia: Zingiberene
• Wikidata: Q4117486
• Metabolomics Workbench ID: 28237
• Mol file: 495-60-3.mol

Synonyms:zingiberene

Chemical Property of Zingiberene

Chemical Property:

• Vapor Pressure: 0.0112mmHg at 25°C
• Boiling Point: 270.7°Cat760mmHg
• Flash Point: 107.5°C
• PSA: 0.00000
• Density: 0.854g/cm³
• LogP: 4.89130
• Storage Temp.: Amber Vial, -86°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Hexane (Slightly), Methanol (Slightly)
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 274

Purity/Quality:

99%, ^*data from raw suppliers

α-Zingiberene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC(C=C1)C(C)CCC=C(C)C
• Isomeric SMILES: CC1=CC[C@@H](C=C1)[C@@H](C)CCC=C(C)C
• Uses: α-Zingiberene is a sesquiterpine found in leaf glandular trichomes that is currently being evaluated for its cytotoxicity towards human tumour cell lines.

Technology Process of Zingiberene

There total 7 articles about Zingiberene 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: 36.0%

(3S,6R,7S)-1,10-bisaboladien-3-ol (87680-39-5) → β-sesquiphellandrene (19888-22-3,20307-83-9,20489-36-5,26882-41-7,27461-50-3,32182-04-0,73744-93-1,109278-27-5) + (-)-zingiberene (38738-45-3,107175-68-8,495-60-3)

Guidance literature:

With pyridine; trichlorophosphate; at 0 - 25 ℃;

DOI:10.1021/np5003753

Reference yield: 35.0%

(1R,4R)-1-methyl-4-[(S)-6-methylhept-5-en-2-yl]cyclohex-2-enol (87680-38-4) → β-sesquiphellandrene (19888-22-3,20307-83-9,20489-36-5,26882-41-7,27461-50-3,32182-04-0,73744-93-1,109278-27-5) + (-)-zingiberene (38738-45-3,107175-68-8,495-60-3)

Guidance literature:

With pyridine; trichlorophosphate; at 0 - 25 ℃;

DOI:10.1021/np5003753

Reference yield:

4-[(1S)-1,5-dimethylhex-4-enyl]cyclohex-2-en-1-one (343239-55-4) → β-sesquiphellandrene (19888-22-3,20307-83-9,20489-36-5,26882-41-7,27461-50-3,32182-04-0,73744-93-1,109278-27-5) + (-)-zingiberene (38738-45-3,107175-68-8,495-60-3)

Guidance literature:

Multi-step reaction with 2 steps

1: chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / tetrahydrofuran; n-heptane / 24 h / -5 - 2 °C / Inert atmosphere

2: pyridine; trichlorophosphate / 0 - 25 °C

With pyridine; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; trichlorophosphate; In tetrahydrofuran; n-heptane;

DOI:10.1021/np5003753

upstream raw materials:

methylmagnesium bromide

C₂₃H₂₉N₃O₂

C₂₃H₂₉N₃O₂

4-[(1S)-1,5-dimethylhex-4-enyl]cyclohex-2-en-1-one

Downstream raw materials:

C₃₁H₃₈O₄

C₃₁H₃₈O₄

C₃₁H₃₈O₄

(S)-curcumene

Refernces

• 1、 -. "COMPOSITIONS AND METHODS TO ATTRACT THE BROWN MARMORATED STINK BUG (BMSB), HALYOMORPHA HALYS". Paragraph 0091. . Retrieved 2013/07/05.
• 2、 -. "PLANT VOLATILES BASED ON R-CURCUMENE". Page/Page column 38; 40. . Retrieved 2010/09/18.