(E)-BETA-FARNESENE

Base Information

• Chemical Name: (E)-BETA-FARNESENE
• CAS No.: 18794-84-8
• Molecular Formula: C15H24
• Molecular Weight: 204.356
• Hs Code.: 2901299090
• Mol file: 18794-84-8.mol

Synonyms:1,6,10-Dodecatriene,7,11-dimethyl-3-methylene-, (E)- (8CI);(E)-7,11-Dimethyl-3-methylene-1,6,10-dodecatriene;(E)-b-Farnesene;trans-b-Farnesene;b-Farnesene;

Chemical Property of (E)-BETA-FARNESENE

Chemical Property:

• Appearance/Colour: colorless to light yellow liquid
• Vapor Pressure: 0.0101mmHg at 25°C
• Melting Point: < 25ºC
• Refractive Index: 1.487 (589.3 nm 18℃)
• Boiling Point: 272.5 °C at 760 mmHg
• Flash Point: 230ºF(110ºC)
• PSA: 0.00000
• Density: 0.807 g/cm³
• LogP: 5.20150
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly)
• Water Solubility.: 100μg/L at 20℃

Purity/Quality:

99.9% ^*data from raw suppliers

trans-β-Farnesene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 38

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: trans-β-Farnesene is a sesquiterpene natural product made my different plants to repel pest aphid species.

Technology Process of (E)-BETA-FARNESENE

There total 92 articles about (E)-BETA-FARNESENE 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: 86.0%

2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)oxy)tetrahydro-2H-pyran (79577-53-0,110990-63-1,120732-61-8,120732-65-2,67858-93-9) → (E)-β-farnesene (18794-84-8)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 60 ℃; for 16h;

DOI:10.1021/jo800355y

Reference yield: 85.0%

1-dimethylphenylsilyl-6,10-dimethyl-2-vinyl-1,5,9-undecatriene (87513-97-1) → (E)-β-farnesene (18794-84-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dimethyl sulfoxide; at 80 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)96677-3

Reference yield: 40.2%

(3RS)-nerolidyl diphosphate (40716-67-4) → (E)-β-farnesene (18794-84-8) + (E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol (40716-66-3) + 8α-hydroxy-presilphiperfolene

Guidance literature:

With recombinant presilphiperfolan-8β-ol synthase; at 30 ℃; for 5h; pH=7; aq. buffer;

upstream raw materials:

Farnesol

(E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol

β-caryophyllene

(E)-7,11-dimethyl-3-methylene-dodeca-6,10-diene-1,2-diol

Downstream raw materials:

2,6,10-trimethyldodecane

formaldehyd

succinic acid

acetone

Refernces

• 1、 Dzhemilev,U.M. et al.. "-". . . Retrieved 1979.
• 2、 Mandai, Tadakatsu,Kawada, Mikio,Otera, Junzo. "Highly Stereoselective Total Syntheses of β-Farnesene, β-Sinensal, and Dendrolasin Employing 2-(Hydroxymethyl)-4-(phenylthio)-1-butene as a Building Block". . p. 5183 - 5185. Retrieved 1983.
• 3、 Yarden, Gal,Shani, Arnon,Leal, Walter Soares. "(Z,E)-α-Farnesene - An electroantennogram-active component of Maladera Matrida volatiles". . p. 283 - 287. Retrieved 1996.
• 4、 Picaud, Sarah,Brodelius, Maria,Brodelius, Peter E.. "Expression, purification and characterization of recombinant (E)-β-farnesene synthase from Artemisia annua". . p. 961 - 967. Retrieved 2005.
• 5、 Huang,Williams,Roessner,Scott. "Sesquiterpenes produced by truncated taxadiene synthase". . p. 9701 - 9704. Retrieved 2000.
• 6、 -. "PROCESS FOR MAKING A CONJUGATED DIENE FROM AN ALLYL ALCOHOL". Page/Page column 36. . Retrieved 2022/01/05.
• 7、 Nestl, Bettina M.,Geinitz, Christopher,Popa, Stephanie,Rizek, Sari,Haselbeck, Robert J.,Stephen, Rosary,Noble, Michael A.,Fischer, Max-Philipp,Ralph, Erik C.,Hau, Hoi Ting,Man, Henry,Omar, Muhiadin,Turkenburg, Johan P,Van Dien, Stephen,Culler, Stephanie J.,Grogan, Gideon,Hauer, Bernhard. "Structural and functional insights into asymmetric enzymatic dehydration of alkenols". . p. 275 - 281. Retrieved 2017/02/23.