Valencene

Base Information

• Chemical Name: Valencene
• CAS No.: 4630-07-3
• Deprecated CAS: 20479-02-1
• Molecular Formula: C₁₅H₂₆
• Molecular Weight: 206.371
• European Community (EC) Number: 225-047-6
• UNII: 96H21P91IG
• DSSTox Substance ID: DTXSID8047052
• Nikkaji Number: J12.786H
• Wikipedia: Valencene
• Wikidata: Q289496
• Metabolomics Workbench ID: 61782
• ChEMBL ID: CHEMBL3186909
• Mol file: 4630-07-3.mol

Synonyms:valencene

Chemical Property of Valencene

Chemical Property:

• Vapor Pressure: 0.0113mmHg at 25°C
• Refractive Index: n20/D 1.504(lit.)
• Boiling Point: 270.5°Cat760mmHg
• Flash Point: 106°C
• PSA: 0.00000
• Density: 0.89g/cm³
• LogP: 4.72520
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 297

Purity/Quality:

98%,99%, ^*data from raw suppliers

Valencene(>85%) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC=C2C1(CC(CC2)C(=C)C)C
• Isomeric SMILES: C[C@@H]1CCC=C2[C@]1(C[C@@H](CC2)C(=C)C)C
• Description: (+)-Valencene is a sesquiterpene that has been found in C. sativa and is an aromatic component of orange essence oil. (+)-Valencene (50 μM) induces heme oxgenase-1 (HO-1) expression in macrophages and inhibits the expression of inducible nitric oxide synthase (iNOS), the production of nitric oxide (NO), and the release of high-mobility group box-1 (HMGB1) in RAW 264.7 cells stimulated with LPS. It also increases the survival rate in a mouse model of sepsis induced by cecal ligation and puncture. (+)-Valencene has been used in the synthesis of nootkatone .
• Uses: Valencene is a sesquiterpene and an essential oil component found in a variety of plants, and has been shown to have functional antioxidant, antiradical and antimicrobial properties. (+)-Valencene can be used as a precursor to prepare: (+)-Nootkatone (a sesquiterpene) by dark singlet oxygenation. Benzoyloxyvalencene by reacting with tert-butyl peroxy benzoate via Kharasch?Sosnovsky allylic oxidation method. (+)-Lineariifolianone, a natural product.

Technology Process of Valencene

There total 9 articles about Valencene 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: 0.7%

β-gurjunene (17334-55-3) → valencene (10219-75-7,22343-24-4,24741-64-8,68773-84-2,4630-07-3) + (+)-nootkatone (4674-50-4)

Guidance literature:

With culture medium of Mucor species; Czapek-pepton medium; at 30 ℃; for 168h;

DOI:10.1248/cpb.54.861

Reference yield:

farnesyl pyrophosphate (372-97-4,13058-04-3,25744-33-6,27248-37-9,27248-38-0,40716-68-5) → valencene (10219-75-7,22343-24-4,24741-64-8,68773-84-2,4630-07-3)

Guidance literature:

With valencene synthase from Citrus sinensis; In aq. buffer; at 25 ℃; for 12h; pH=7.5; Enzymatic reaction;

DOI:10.1021/acschembio.5b00539

Reference yield:

11-hydroxy-4α,5α,7β-eremophil-1(10)-ene (20489-45-6,800385-99-3) → valencene (10219-75-7,22343-24-4,24741-64-8,68773-84-2,4630-07-3)

Guidance literature:

With sodium acetate; acetic anhydride;

DOI:10.1248/cpb.16.832

upstream raw materials:

valencene

11-hydroxy-4α,5α,7β-eremophil-1(10)-ene

β-gurjunene

farnesyl pyrophosphate

Downstream raw materials:

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2β-ol

(+)-nootkatone

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol

9α-hydroxy-2-oxo-4α,5α,7β-eremophila-1(10),11-diene

Refernces

• 1、 Espinal-Viguri, Maialen,Neale, Samuel E.,Coles, Nathan T.,MacGregor, Stuart A.,Webster, Ruth L.. "Room Temperature Iron-Catalyzed Transfer Hydrogenation and Regioselective Deuteration of Carbon-Carbon Double Bonds". supporting information. p. 572 - 582. Retrieved 2019/01/08.
• 2、 Furusawa, Mai,Hashimoto, Toshihiro,Noma, Yoshiaki,Asakawa, Yoshinori. "Biotransformation of aristolane- and 2,3-secoaromadendrane-type sesquiterpenoids having a 1,1-dimethylcyclopropane ring by Chlorella fusca var. vacuolata, Mucor species, and Aspergillus niger". . p. 861 - 868. Retrieved 2007/10/03.