Farnesylacetone

Base Information

• Chemical Name: Farnesylacetone
• CAS No.: 1117-52-8
• Molecular Formula: C18H30O
• Molecular Weight: 262.436
• Hs Code.: 29141900
• European Community (EC) Number: 212-097-9,214-246-3
• UNII: 3S0G4N267H
• DSSTox Substance ID: DTXSID5061087,DTXSID50883648
• Nikkaji Number: J60.733I,J24.208J
• Wikidata: Q27135719
• Metabolomics Workbench ID: 65007
• ChEMBL ID: CHEMBL486207
• Mol file: 1117-52-8.mol

Synonyms:farnesylacetone;farnesylacetone, (E,E)-isomer

Chemical Property of Farnesylacetone

Chemical Property:

• Vapor Pressure: 9.39E-06mmHg at 25°C
• Refractive Index: n20/D 1.481
• Boiling Point: 372.773 °C at 760 mmHg
• Flash Point: 140.43 °C
• PSA: 17.07000
• Density: 0.866 g/cm³
• LogP: 5.77480
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Sparingly), Ethyl Acetate (Slightly), Methanol (Sparingly)
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 9
• Exact Mass: 262.229665576
• Heavy Atom Count: 19
• Complexity: 352

Purity/Quality:

98% ^*data from raw suppliers

E,E-Farnesylacetone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=CCCC(=O)C)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/CCC(=O)C)/C)/C)C
• Uses: E,E-Farnesylacetone, is a natural organic compound which is present in many essential oils. It has been shown that, Farnesylacetone inhibits electron transport in isolated rat liver mitochondria.

Technology Process of Farnesylacetone

There total 58 articles about Farnesylacetone 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%

methyl (4E,8E)-2-acetyl-5,9,13-trimethyltetradeca-4,8,12-trienoate → 6,10,14-trimethyl-5,9,13-pentadecatriene-2-on (1117-52-8)

Guidance literature:

With sodium hydroxide; at 90 ℃; for 2h; Large scale;

Reference yield: 96.0%

(4E,8E)-ethyl 2-acetyl-5,9,13-trimethyltetradeca-4,8,12-trienoate (51921-98-3) → 6,10,14-trimethyl-5,9,13-pentadecatriene-2-on (1117-52-8)

Guidance literature:

With sodium hydroxide; at 100 ℃; for 5h; Temperature; Large scale;

Reference yield: 85.0%

trans geranyl acetone (3796-70-1) + [3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-magnesium chloride (62026-31-7) → 6,10,14-trimethyl-5,9,13-pentadecatriene-2-on (1117-52-8)

Guidance literature:

In tert-butyl methyl ether; at 0 ℃; for 6h; Inert atmosphere;

upstream raw materials:

trans geranyl acetone

sodium acetylide

methyl magnesium iodide

1-cyano-4,8,12-trimethyl-3E,7E,11-tridecatriene

Downstream raw materials:

(6E,10E)-geranyllinalool

(E,E,E)-geranylgeranylacetone

2E,6E,10E-geranylgeranyl bromide

(11E)-(4,8,12,16-tetramethylheptadeca-3,7,11,15-tetraenyl)benzene

Refernces

• 1、 Domingo, Victoriano,Dieguez, Horacio R.,Morales, Carmen P.,Arteaga, Jesus F.,Qulezdelmoral, Jose F.,Barrero, Alejandro F.. "Expedient access to A-ring -α Dioxygenated terpenoids: The first synthesis of (13E)- ent -labda-8(17),13-diene-3β,15,18-triol". . p. 67 - 72. Retrieved 2010.
• 2、 Odinokov et al.. "". . p. 657. Retrieved 1977.
• 3、 -. "Synthesis method and method for synthesizing plant alcohol, isoplant alcohol and geranyl geraniol by using intermediate farnesylacetone (by machine translation)". Paragraph 0061; 0072; 0082-0083. . Retrieved 2020/07/21.
• 4、 -. "Method for synthesizing ketone compounds by continuous cyclic catalytic reaction". Paragraph 0018. . Retrieved 2017/03/21.