(E,Z)-farnesol

Base Information

• Chemical Name: (E,Z)-farnesol
• CAS No.: 3879-60-5
• Molecular Formula: C15H26O
• Molecular Weight: 222.371
• Hs Code.: 2905290000
• European Community (EC) Number: 225-004-1
• NSC Number: 60597
• UNII: 413TVZ4919
• DSSTox Substance ID: DTXSID501034821
• Wikipedia: Farnesol
• Wikidata: Q27116653
• Metabolomics Workbench ID: 28201
• ChEMBL ID: CHEMBL488357
• Mol file: 3879-60-5.mol

Synonyms:Farnesol

Chemical Property of (E,Z)-farnesol

Chemical Property:

• Boiling Point: 283.4 °C at 760 mmHg
• Flash Point: 112.5 °C
• PSA: 20.23000
• Density: 0.875 g/cm³
• LogP: 4.39790
• Storage Temp.: ?20°C
• 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

2-trans,6-cis-Farnesol ≥95.0% (GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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

Technology Process of (E,Z)-farnesol

There total 10 articles about (E,Z)-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: 74.0%

ethyl (2Z,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienoate (20085-73-8) → (2Z,6Z)-farnesol (16106-95-9) + 2E,6Z-farnesol (3879-60-5)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃;

DOI:10.1021/ol990714i

Reference yield: 40.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (Z)-nerylacetone (3879-26-3) + Methyltriphenylphosphonium bromide (1779-49-3) → (2Z,6Z)-farnesol (16106-95-9) + 2E,6Z-farnesol (3879-60-5)

Guidance literature:

(Z)-nerylacetone; Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.75h;

With sec.-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

formaldehyd; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ol0513239

Reference yield:

farnesal (19317-11-4) → (2Z,6Z)-farnesol (16106-95-9) + 2E,6Z-farnesol (3879-60-5) + (2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol (3790-71-4) + Farnesol (106-28-5)

Guidance literature:

With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; formic acid triethylamine complex; N-tosylethylenediamine; In ethyl acetate; at 20 ℃; for 20h; Reagent/catalyst; Temperature; Solvent; Overall yield = 98 %; Inert atmosphere;

upstream raw materials:

1-phenylsulfonyl-2-methyl-4-hydroxy-but-2-ene

chlorure de geranylmagnesium

p-nitrobenzoate de trimethyl-3,7,11 dodecatriene-1,6 Z, 10-yl

formaldehyd

Downstream raw materials:

(3R,7R)-hexahydrofarnesol

(1S,2R)-5,5-dimethyl-2-(6-methylhepta-1,5-dien-2-yl)cyclohexanol

2,3,4,4a,5,6-hexahydro-1,4a-dimethyl-7-(1-methylethyl)-naphthalene

(+/-)-cedrene

Refernces

• 1、 -. "Method for Converting Farnesol to Nerolidol in the Presence of Alpha-Bisabolol". Paragraph 0118 - 0122; 0125 - 0137. . Retrieved 2013/11/06.
• 2、 Shao, Ying,Eummer, Jeffrey T.,Gibbs, Richard A.. "Stereospecific synthesis and biological evaluation of farnesyl diphosphate isomers". . p. 627 - 630. Retrieved 2008/03/11.