all-trans-Methyl farnesoate

Base Information

• Chemical Name: all-trans-Methyl farnesoate
• CAS No.: 3675-00-1
• Molecular Formula: C16H26O2
• Molecular Weight: 250.381
• Mol file: 3675-00-1.mol

Synonyms:all-trans methylfarnesoate;Farnesyl methyl ester;Methyl3,7,11-trimethyl-2,6,10-dodecatrienoate;Methyl farnesylate;E,E-farnesic acid methyl ester;2,6,10-Dodecatrienoicacid,3,7,11-trimethyl-,methyl ester;Methyl farnesate;Methyl farnesoate;

Chemical Property of all-trans-Methyl farnesoate

Chemical Property:

• PSA: 26.30000
• LogP: 4.57860

Purity/Quality:

99%, ^*data from raw suppliers

2-trans-FarnesicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-trans-Farnesic Acid Methyl Ester is an intermediate in synthesizing trans-trans-10,11-Epoxy Farnesenic Acid Methyl Ester (E589400), a metabolite (2E,6E)-Farnesenic Acid.

Technology Process of all-trans-Methyl farnesoate

There total 39 articles about all-trans-Methyl farnesoate 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%

methanol (67-56-1) + (2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienoic acid (462-11-3) → methyl (E,E)-farnesoate (3675-00-1)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 43h; Inert atmosphere;

DOI:10.1016/j.tetlet.2016.08.079

Reference yield: 77.0%

methyllithium (917-54-4) + (2Z,6E)-3-(Diethoxy-phosphoryloxy)-7,11-dimethyl-dodeca-2,6,10-trienoic acid methyl ester (71712-61-3) → methyl (E,E)-farnesoate (3675-00-1)

Guidance literature:

methyllithium; With copper(l) iodide; In diethyl ether; at 0 ℃; for 0.0833333h; Inert atmosphere;

(2Z,6E)-3-(Diethoxy-phosphoryloxy)-7,11-dimethyl-dodeca-2,6,10-trienoic acid methyl ester; In diethyl ether; at -78 - -30 ℃; for 2h; Inert atmosphere;

Reference yield: 75.0%

methanol (67-56-1) + Farnesal (502-67-0) → methyl (E,E)-farnesoate (3675-00-1)

Guidance literature:

With potassium cyanide; manganese(IV) oxide; acetic acid; at 20 ℃; for 24h;

DOI:10.1002/ejoc.200390189

upstream raw materials:

diazomethane

trans-geranyl bromide

3-Methylbutenoic acid

trans geranyl acetone

Downstream raw materials:

Methyl (E)-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)-2-pentenoate

(2E,6E,10E,14E)-3,7,11,15-tetramethyl-13-(phenylsulfonyl)[16,16,16-2H₃]hexadeca-2,6,10,14-tetraen-1-ol

(2E,6E,10E,14E)-3,7,11,15-tetramethyl-13-(phenylsulfonyl)[16,16,16-2H₃]hexadeca-2,6,10,14-tetraenoate

6,10,14-trimethyl-5,9,13-pentadecatriene-2-on

Refernces

• 1、 Tatarazako, Norihisa,Oda, Shigeto,Watanabe, Hajime,Morita, Masatoshi,Iguchi, Taisen. "Juvenile hormone agonists affect the occurrence of male Daphnia". . p. 827 - 833. Retrieved 2003.
• 2、 Vlad, P. F.,Ungar, N. D.,Tuen, Nguen Van. "Superacidic cyclization of higher terpenoid acids and their esters". . p. 2404 - 2411. Retrieved 1995.
• 3、 -. "UNIQUE HALOGEN-INDUCED CYCLIZATIONS, REAGENTS THEREFOR, AND COMPOUNDS PRODUCED THEREBY". Page/Page column 116. . Retrieved 2012/04/04.