(-)-alpha-Curcumene

Base Information

• Chemical Name: (-)-alpha-Curcumene
• CAS No.: 4176-17-4
• Molecular Formula: C₁₅H₂₂
• Molecular Weight: 202.34
• DSSTox Substance ID: DTXSID50194584
• Nikkaji Number: J37.672H
• Wikidata: Q27108606
• Metabolomics Workbench ID: 53525
• ChEMBL ID: CHEMBL469717
• Mol file: 4176-17-4.mol

Synonyms:(R)-isomer of alpha-curcumene;(S)-isomer of alpha-curcumene;1-(1,5-dimethyl-4-hexenyl)-4-methylbenzene;2-methyl-6-p-tolyl-2-heptene;alpha-curcumene;ar-curcumene

Chemical Property of (-)-alpha-Curcumene

Chemical Property:

• Vapor Pressure: 0.00814mmHg at 25°C
• Boiling Point: 276.3°C at 760 mmHg
• Flash Point: 117.2°C
• PSA: 0.00000
• Density: 0.873g/cm³
• LogP: 4.84490
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 202.172150702
• Heavy Atom Count: 15
• Complexity: 190

Purity/Quality:

≥99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C(C)CCC=C(C)C
• Isomeric SMILES: CC1=CC=C(C=C1)[C@H](C)CCC=C(C)C
• Uses: (R)-(-)-Curcumene is found in essential oils, also used in the biopreservation of groundnut oil.

Technology Process of (-)-alpha-Curcumene

There total 136 articles about (-)-alpha-Curcumene 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: 97.0%

C15H19F3O3S + methylmagnesium bromide (75-16-1) → (S)-curcumene (3649-81-8,4176-17-4,644-30-4,4176-06-1)

Guidance literature:

With iron(III)-acetylacetonate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; at 0 ℃; for 0.25h;

DOI:10.1021/ja1034842

Reference yield: 89.0%

(S)-5-methyl-2-(6-methylhept-5-en-2-yl)benzoic acid (1580457-76-6) → (S)-curcumene (3649-81-8,4176-17-4,644-30-4,4176-06-1)

Guidance literature:

With quinoline; copper; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1039/c4ob00018h

Reference yield: 79.0%

(-)-(R)-4-(p-tolyl)pentanal (122091-57-0) + isopropyltriphenylphosphonium iodide (24470-78-8) → (R)-(-)-α-curcumene (4176-17-4,644-30-4,3649-81-8,4176-06-1)

Guidance literature:

isopropyltriphenylphosphonium iodide; With n-butyllithium; In tetrahydrofuran; hexane; at -15 ℃; for 0.583333h; Inert atmosphere;

(-)-(R)-4-(p-tolyl)pentanal; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tetasy.2015.11.009

upstream raw materials:

(-)-β-curcumene

2-(3-Methyl-but-2-enyl)-2-((S)-1-p-tolyl-ethyl)-[1,3]dithiane

diethoxyphosphoryl-acetic acid ethyl ester

isopropyltriphenylphosphonium iodide

Downstream raw materials:

(+)-(7S,9S)-dihydro-ar-turmerol

(+)-(7S,9R)-dihydro-ar-turmerol

(+)-(S)-dihydro-ar-curcumene

(S,E)-ethyl 6-p-tolyhept-2-enoate

Refernces

• 1、 Krajangsri, Suppachai,Wu, Haibo,Liu, Jianguo,Rabten, Wangchuk,Singh, Thishana,Andersson, Pher G.. "Tandem Peterson olefination and chemoselective asymmetric hydrogenation of β-hydroxy silanes". . p. 3649 - 3653. Retrieved 2019/03/28.
• 2、 Spielmann, Kim,De Figueiredo, Renata Marcia,Campagne, Jean-Marc. "Stereospecific Hydrogenolysis of Lactones: Application to the Total Syntheses of (R)-ar-Himachalene and (R)-Curcumene". . p. 4737 - 4743. Retrieved 2017/05/12.