Beta-Elemene

Base Information

• Chemical Name: Beta-Elemene
• CAS No.: 33880-83-0
• Deprecated CAS: 11033-44-6,20296-36-0,154028-29-2
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.356
• European Community (EC) Number: 251-713-0,610-676-4
• UNII: 2QG8CX6LXD
• DSSTox Substance ID: DTXSID40865690,DTXSID60881211
• Nikkaji Number: J14.848B
• Wikipedia: Elemene
• Wikidata: Q27132237
• NCI Thesaurus Code: C103177
• Metabolomics Workbench ID: 62460
• ChEMBL ID: CHEMBL448502
• Mol file: 33880-83-0.mol

Synonyms:beta-elemene

Chemical Property of Beta-Elemene

Chemical Property:

• Vapor Pressure: 0.031mmHg at 25°C
• Refractive Index: 1.501
• Boiling Point: 252.144 °C at 760 mmHg
• Flash Point: 98.341 °C
• PSA: 0.00000
• Density: 0.862 g/cm³
• LogP: 4.74720
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 284

Purity/Quality:

99% ^*data from raw suppliers

β-Elemene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CCC(C(C1)C(=C)C)(C)C=C
• Isomeric SMILES: CC(=C)[C@@H]1CC[C@@]([C@@H](C1)C(=C)C)(C)C=C
• Recent ClinicalTrials: Elemene Plus Stupp Protocol Versus Stupp Protocol Alone for Newly-diagnosed Glioblastoma
• Uses: β-Elemene is an active constituent of Delonix regia and an anti-inflammatory agent. β-Elemene is a useful compound for investigating the toll-like receptor 4 signaling pathway and the inhibition of TNF-?a, IL-?1b, IL-?6 and IL-?12 expressions.

Technology Process of Beta-Elemene

There total 51 articles about Beta-Elemene 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: 95.0%

2-((1R,2R,3R,6R)-2,6-Diisopropenyl-3-methyl-3-vinyl-cyclohexyloxy)-1,3-dimethyl-[1,3,2]diazaphospholidine 2-oxide → β-elemene (515-13-9,33880-83-0,68036-14-6,100762-52-5,110823-68-2,13833-25-5)

Guidance literature:

With tert-Amyl alcohol; ammonia; lithium; In tetrahydrofuran; at -33 ℃; for 10h;

Reference yield: 89.0%

methyl-triphenylphosphonium iodide (2065-66-9) + (1RS,2SR,4RS)-4-acetyl-2-isopropenyl-1-methylcyclohexane-1-carbaldehyde → (+/-)-β-elemene (515-13-9,13833-25-5,33880-83-0,68036-14-6,100762-52-5,110823-68-2)

Guidance literature:

methyl-triphenylphosphonium iodide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 0.666667h;

(1RS,2SR,4RS)-4-acetyl-2-isopropenyl-1-methylcyclohexane-1-carbaldehyde; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1016/S0040-4020(00)01130-3

Reference yield: 82.0%

(1R*,2S*,4R*)-1-methyl-2,4-di(prop-1-en-2-yl)cyclohexanecarbaldehyde + Methyltriphenylphosphonium bromide (1779-49-3) → (+/-)-β-elemene (515-13-9,13833-25-5,33880-83-0,68036-14-6,100762-52-5,110823-68-2)

Guidance literature:

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; at 20 ℃; for 0.333333h; Inert atmosphere; Cooling;

(1R*,2S*,4R*)-1-methyl-2,4-di(prop-1-en-2-yl)cyclohexanecarbaldehyde; In tetrahydrofuran; for 0.5h; Inert atmosphere; Cooling;

DOI:10.1002/ejoc.201800800

upstream raw materials:

(2E,8Ξ)-5-isopropenyl-2,8-dimethyl-deca-2,8-diene-1,10-diol

ethyl (5R*,E)-2-methyl-8-oxo-5-(prop-1-en-2-yl)non-2-enoate

ethyl 2-methyl-5-isopropenyl-8,8-ethylenedioxy-trans-2-nonenoate

ethyl 2,8-dimethyl-5-isopropenyl-undeca-trans-2-(trans/cis)-8-diene-1,10-dioate

Downstream raw materials:

1,3-di-isopropyl-4-methylbenzene

Refernces

• 1、 Hackl, Thomas,K?nig, Wilfried A.,Muhle, Hermann. "Isogermacrene A, a proposed intermediate in sesquiterpene biosynthesis". . p. 2261 - 2275. Retrieved 2007/10/03.
• 2、 Corey,Roberts, Bryan E.,Dixon, Brian R.. "Enantioselective total synthesis of β-elemene and fuscol based on enantiocontrolled Ireland-Claisen rearrangement". . p. 193 - 196. Retrieved 2007/10/02.