Methyl farnesoate

Base Information

• Chemical Name: Methyl farnesoate
• CAS No.: 10485-70-8
• Molecular Formula: C16H26 O2
• Molecular Weight: 250.381
• ChEMBL ID: CHEMBL171329
• DSSTox Substance ID: DTXSID80893654
• Metabolomics Workbench ID: 124240
• Nikkaji Number: J140.346J,J140.347H,J38.779G
• Wikidata: Q27149580
• Mol file: 10485-70-8.mol

Synonyms:methyl farnesoate;methyl farnesoate dihydrochloride;methyl farnesoate, (E,E)-isomer;methyl farnesoate, (E,Z)-isomer

Chemical Property of Methyl farnesoate

Chemical Property:

• Vapor Pressure: 0.000115mmHg at 25°C
• Boiling Point: 336°Cat760mmHg
• Flash Point: 161.7°C
• PSA: 26.30000
• Density: 0.905g/cm³
• LogP: 4.57860
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 8
• Exact Mass: 250.193280068
• Heavy Atom Count: 18
• Complexity: 342

Purity/Quality:

98%,99%, ^*data from raw suppliers

(E,E)-METHYL FARNESOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=CC(=O)OC)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/C(=O)OC)/C)/C)C
• Biological functions: MF has multiple physiological functions, including the regulation of metabolism, molting, reproduction, behavior, and morphogenesis in crustaceans.It stimulates general protein synthesis and ecdysteroid secretion by the Y-organ, and influences the molting cycle.MF plays a key role in the regulation of crustacean reproduction; it enhances egg production in females, and affects the reproductive morphology and behavior in males.The expression of the vitellogenin (Vg) gene is induced by MF in the hepatopancreas, although FA is more potent than MF for this activity.MF has either a stimulatory or an inhibitory role in metamorphosis, depending on the species and developmental stages.MF functions as a sex determinant and induces the production of male offspring in daphnids and other cladoceran species,and is also involved in predator-induced polyphenisms in Daphnia.

Technology Process of Methyl farnesoate

There total 8 articles about 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: 75.0%

methanol (67-56-1) + farnesal (19317-11-4) → methyl 3,7,11-trimethyldodeca-2,6,10-trienoate (10485-70-8)

Guidance literature:

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

DOI:10.1002/ejoc.200390189

Reference yield: 59.0%

pseudo-ionone (689-67-8) + trimethyl phosphonoacetate (5927-18-4) → methyl 3,7,11-trimethyldodeca-2,6,10-trienoate (10485-70-8)

Guidance literature:

With sodium methylate; In methanol; for 20h; Ambient temperature;

Reference yield:

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

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / PDC / CH₂Cl₂ / 24 h / 0 - 25 °C

2: 75 percent / KCN; MnO₂; acetic acid / 24 h / 20 °C

With potassium cyanide; manganese(IV) oxide; dipyridinium dichromate; acetic acid; In dichloromethane;

DOI:10.1002/ejoc.200390189

upstream raw materials:

pseudo-ionone

trimethyl phosphonoacetate

methanol

farnesal

Downstream raw materials:

farnesol

methyl farnesate 10,11-bromohydrin

(SS,RR)-monocyclofarnesal N-methylnitrone

(SR,RS)-monocyclofarnesal N-methylnitrone

Refernces

• 1、 Peter et al.. "". . p. 844,854. Retrieved 1977.
• 2、 Biernacki, Wladyslaw. "A FACILE SYNTHESIS OF METHYL (+/-)-10,11-EPOXY-3,7,11-TRIMETHYLDODECA-2,6-DIENOATE, THE INSECT JUVENILE HORMONE III". . p. 777 - 780. Retrieved 2007/10/02.