(2Z,6E)-Farnesol

Base Information

• Chemical Name: (2Z,6E)-Farnesol
• CAS No.: 4602-84-0
• Molecular Formula: C15H26O
• Molecular Weight: 222.371
• Hs Code.: 29052200
• European Community (EC) Number: 225-004-1
• UNII: SQ4TI19PXT
• DSSTox Substance ID: DTXSID30274196
• Nikkaji Number: J133.568E
• Wikipedia: Farnesol
• Wikidata: Q27102070
• Metabolomics Workbench ID: 28208
• Mol file: 4602-84-0.mol

Synonyms:(Z,E)-Farnesol;(2Z,6E)-Farnesol;cis,trans-Farnesol;2-cis,6-trans-Farnesol;3790-71-4;(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol;(2-cis,6-trans)-farnesol;(Z,E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol;Farnesol, (2Z,6E)-;UNII-SQ4TI19PXT;SQ4TI19PXT;(2Z,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol;2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-, (Z,E)-;(2-cis,6-trans)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol;3,7,11-trimethyldodeca-2Z,6E,10-trien-1-ol;Farnesyl alcohol;NSC60597;(Z)-Farnesol;cis,trans-.alpha.-Farnesol;SCHEMBL806894;CIS-2-TRANS-6-FARNESOL;CHEBI:16774;DTXSID30274196;4602-84-0;LMPR0103010013;FEMA NO. 2478, (2Z,6E)-;2-cis,6-trans-Farnesol, >=95.0% (GC);C03220;EN300-7460532;3,7,11-trimethyl-dodeca-2cis,6trans,10-trien-1-ol;Q27102070;2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-, (2Z,6E)-;6,10-Dodecadien-1-ol, 3,7,11-trimethyl-, (E)-(.+.)-;N1S

Chemical Property of (2Z,6E)-Farnesol

Chemical Property:

• Appearance/Colour: colourless liquid with a floral odour
• Vapor Pressure: 0.00037mmHg at 25°C
• Melting Point: 25°C
• Refractive Index: n20/D 1.490(lit.)
• Boiling Point: 283.4 °C at 760 mmHg
• PKA: 14.69±0.10(Predicted)
• Flash Point: 112.5 °C
• PSA: 20.23000
• Density: 0.875 g/cm³
• LogP: 4.39790
• Storage Temp.: −20°C
• Sensitive.: Light Sensitive
• Water Solubility.: Not miscible or difficult to mix in water.
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 7
• Exact Mass: 222.198365449
• Heavy Atom Count: 16
• Complexity: 265

Purity/Quality:

99.9% ^*data from raw suppliers

Farnesol (mixture of isomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CC(=CCCC(=CCCC(=CCO)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C\CO)/C)/C)C
• Description: Farnesol has a characteristic flowery odor.
• Uses: It can be used to induce apoptosis in cell cultures. It is also used as an antimicrobial agent. It is used in perfumes and as a flavoring agent. farnesol is described as a substance of high biological potential, capable of acting in the skin as a true bioactivator. A biological precursor and fatty alcohol, farnesol is one component of vitamin K. It is said to help smooth wrinkles, normalize sebum secretion, and increase the skin’s elasticity, tissue tension, and moisture-binding capability. It is able to penetrate the epidermis. In humans, farnesol is found in the skin and is involved in sterol biosynthesis. It is also used for its deodorant, odor-masking, and skin-soothing properties. In clinical studies, farnesol has demonstrated anti-microbial activity, though it is unclear if this remains the case once incorporated into a cosmetic formulation. It is widely present in vegetables and found in many essential oils (for example, acacia, lilac, lily of the valley, rose, orange blossom, oak moss, and sandalwood).

Technology Process of (2Z,6E)-Farnesol

There total 26 articles about (2Z,6E)-Farnesol 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: 98.0%

1-chloro-3,7,11-trimethyldodeca-2,6,10-triene (6784-45-8) → farnesol (4602-84-0)

Guidance literature:

With N-chloro-succinimide; In dichloromethane; at 0 - 20 ℃; for 1.25h;

Reference yield: 85.0%

methyl 3,7,11-trimethyldodeca-2,6,10-trienoate (10485-70-8) → farnesol (4602-84-0)

Guidance literature:

With lithium aluminium tetrahydride;

DOI:10.1016/0040-4039(80)80126-2

Reference yield: 85.0%

ethyl 3,7,11-trimethyldodeca-2,6,10-trienoate (20723-88-0) → farnesol (4602-84-0)

Guidance literature:

With lithium aluminium tetrahydride;

DOI:10.1246/cl.1981.1159

upstream raw materials:

farnesal

(+/-)-nerolidol

acetic anhydride

methylammonium carbonate

Downstream raw materials:

farnesal

methyl (E,E)-farnesoate

Farnesylcarbamat

cis-α-farnesene

Refernces

• 1、 De Meireles, Augusto L.P.,Costa, Maíra Dos Santos,Da Silva Rocha, Kelly A.,Gusevskaya, Elena V.. "Heteropoly acid catalyzed cyclization of nerolidol and farnesol: Synthesis of α-bisabolol". . p. 271 - 275. Retrieved 2015/07/07.
• 2、 Nakano, Chiaki,Ootsuka, Takahiro,Takayama, Kazutoshi,Mitsui, Toshiaki,Sato, Tsutomu,Hoshino, Tsutomu. "Characterization of the Rv3378c gene product, a new diterpene synthasefor producing tuberculosinol and (13R, S)-isotuberculosinol (nosyberkol), from the mycobacterium tuberculosis H37Rv genome". body text. p. 75 - 81. Retrieved 2011/09/30.