trans,trans-Farnesol

Base Information

• Chemical Name: trans,trans-Farnesol
• CAS No.: 106-28-5
• Molecular Formula: C15H26O
• Molecular Weight: 222.371
• Hs Code.: 29052290
• European Community (EC) Number: 225-004-1,679-283-3
• UNII: X23PI60R17
• DSSTox Substance ID: DTXSID2040789
• Nikkaji Number: J5.049K,J505.873B,J672.101J,J8.753J
• Wikipedia: Farnesol
• Wikidata: Q420449
• NCI Thesaurus Code: C64169
• RXCUI: 1362903
• Metabolomics Workbench ID: 28196
• ChEMBL ID: CHEMBL25308
• Mol file: 106-28-5.mol

Synonyms:Farnesol

Chemical Property of trans,trans-Farnesol

Chemical Property:

• Vapor Pressure: 0.00037mmHg at 25°C
• Melting Point: 61-63 °C
• Refractive Index: n20/D 1.490(lit.)
• Boiling Point: 283.4 °C at 760 mmHg
• PKA: 14.42±0.10(Predicted)
• Flash Point: 112.5 °C
• PSA: 20.23000
• Density: 0.875 g/cm³
• LogP: 4.39790
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), DMSO (Slightly) Ethyl Acetate (Slightly), Methanol (Spar
• Water Solubility.: Miscible with alcohol. Immiscible with 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% ^*data from raw suppliers

(E,E)-Farnesol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43
• Safety Statements: S24/25:Avoid contact with skin and eyes.

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 is widely present in the flowers, leaves, stems and other parts of plants, especially in some Chinese herbal medicine plants and spice plants with a high content, such as Cinnamomum chinensis, Pinellia sinensis, loquat leaves, etc., which are well developed and utilized An important resource for prospects. Farnesol is one of the important active components of Chinese herbal medicine plants, and also one of the main fragrance components of some important essential oils of spice plants. Therefore, it has been widely used in medicine, pesticides, cosmetics and daily chemicals that require its biological activity.
• Uses: Farnesol is a natural organic compound which is present in many essential oils. trans,trans-Farnesol is an intermediate used in the biological synthesis of cholesterol from mevalonic acid. It is used in the perfume industry. Further, it is used in the preparation of terpenes such as squalenes, cembranoids and forskolin. It is also used in the synthesis of Cecropia juvenile hormone.

Technology Process of trans,trans-Farnesol

There total 74 articles about trans,trans-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: 97.0%

(2E,6E)-1-(tert-butyldimethylsilyloxy)-3,7,1,1-trimethyldodeca-2,6,10-triene (61890-77-5) → Farnesol (106-28-5)

Guidance literature:

With phosphomolybdic acid hydrate; silica gel; In tetrahydrofuran; at 20 ℃; for 0.25h;

DOI:10.1021/jo0502697

Reference yield: 95.0%

ethyl farnesoate (19954-66-6) → Farnesol (106-28-5)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1002/chem.201503118

Reference yield: 93.0%

trans,trans-farnesyl diphenylurethane (76386-25-9) → Farnesol (106-28-5)

Guidance literature:

With potassium hydroxide; In ethanol; water; for 6h; Heating;

DOI:10.1021/ja00394a032

upstream raw materials:

methyl (E,E)-farnesoate

formaldehyd

(E)-6,10-dimethyl-5,9-undecadien-1-yne

trimethylaluminum

Downstream raw materials:

(+/-)-drim-7-en-11-ol

1,3-dimethyl-2-(hydroxymethyl)-1-(4'-methoxy-4'-methylpentyl)cyclohex-3-ene

1-phenyl-5-<(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienylthio>-1H-tetrazole

((1R,4aS,6R,8aR)-2,5,5,8a-Tetramethyl-6-phenylselanyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-methanol

Refernces

• 1、 Ling, Yong,Wang, Zhiqiang,Zhu, Hongyan,Wang, Xuemin,Zhang, Wei,Wang, Xinyang,Chen, Li,Huang, Zhangjian,Zhang, Yihua. "Synthesis and biological evaluation of farnesylthiosalicylamides as potential anti-tumor agents". . p. 374 - 380. Retrieved 2014.
• 2、 Kobayashi,S. et al.. "-". . p. 1169 - 1172. Retrieved 1977.
• 3、 Grigor'eva,N.Ya. et al.. "-". . . Retrieved 1979.
• 4、 Wada,Kobata,Hayashi,Shibata. "Two chemotypes of Boletinus cavipes". . p. 1036 - 1039. Retrieved 1995.
• 5、 Ueda, Daijiro,Yamaga, Hiroaki,Murakami, Mizuki,Totsuka, Yusuke,Shinada, Tetsuro,Sato, Tsutomu. "Biosynthesis of sesterterpenes, head-to-tail triterpenes, and sesquarterpenes in Bacillus clausii: Identification of multifunctional enzymes and analysis of isoprenoid metabolites". . p. 1371 - 1377. Retrieved 2015.
• 6、 Pitzele et al.. "". . p. 1347,1348, 1350. Retrieved 1976.
• 7、 -. "METHOD FOR PRODUCING CARBOXYLIC ACID PRENYL AND PRENOL". Paragraph 0086-0099. . Retrieved 2019/12/31.
• 8、 Lee, J. Scott,Pan, Jian-Jung,Ramamoorthy, Gurusankar,Poulter, C. Dale. "Structure-Function Studies of Artemisia tridentata Farnesyl Diphosphate Synthase and Chrysanthemyl Diphosphate Synthase by Site-Directed Mutagenesis and Morphogenesis". supporting information. p. 14556 - 14567. Retrieved 2017/10/24.