10,11-Epoxyfarnesol

Base Information

• Chemical Name: 10,11-Epoxyfarnesol
• CAS No.: 5233-99-8
• Molecular Formula: C15H26O2
• Molecular Weight: 238.36600
• DSSTox Substance ID: DTXSID60435713
• Nikkaji Number: J2.809.341A,J2.067.894A
• Mol file: 5233-99-8.mol

Synonyms:10,11-Epoxyfarnesol;5233-99-8;(2E,6E)-9-(3,3-dimethyloxiran-2-yl)-3,7-dimethylnona-2,6-dien-1-ol;SCHEMBL10048472;DTXSID60435713;AKOS015905485;(2E,6E)-3,7,11-Trimethyl-10,11-epoxy-2,6-dodecadiene-1-ol;(2E,6E)-9-(3,3-dimethyl-2-oxiranyl)-3,7-dimethyl-2,6-nonadien-1-ol

Chemical Property of 10,11-Epoxyfarnesol

Chemical Property:

• PSA: 32.76000
• LogP: 3.60910
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 238.193280068
• Heavy Atom Count: 17
• Complexity: 300

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCCC(=CCO)C)CCC1C(O1)(C)C
• Isomeric SMILES: C/C(=C\CC/C(=C/CO)/C)/CCC1C(O1)(C)C

Technology Process of 10,11-Epoxyfarnesol

There total 27 articles about 10,11-Epoxyfarnesol 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: 91.0%

tert-butyl(((2E,6E)-9-(3,3-dimethyloxiran-2-yl)-3,7-dimethylnona-2,6-dien-1-yl)oxy)diphenylsilane (151409-24-4) → 10,11-epoxyfarnesol (5233-99-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 3h;

DOI:10.1271/bbb.110511

Reference yield: 91.0%

10,11-Epoxy-3,7,11-trimethyl-2(E),6(E)-dodecadienyl tert-butyldimethylsilyl ether (158897-41-7) → 10,11-epoxyfarnesol (5233-99-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 10h; Ambient temperature;

DOI:10.1021/jo00098a048

Reference yield: 90.0%

(2E,6E)-11-hydroxy-10-mesyloxy-3,7,11-trimethyl-2,6-dodecadienyl acetate (34203-17-3,130648-11-2) → 10,11-epoxyfarnesol (5233-99-8)

Guidance literature:

With potassium carbonate; In methanol; for 2h; Ambient temperature;

DOI:10.1002/bscb.19860950913

upstream raw materials:

farnesol

farnesyl acetate

(2E,6E)-10-bromo-11-hydroxy-3,7,11-trimethyldodeca-2,6-dien-1-yl acetate

3-[1-(tert-Butyl-dimethyl-silanyloxy)-1-cyclopropyl-ethylperoxycarbonyl]-propionic acid (2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyl ester

Downstream raw materials:

(4E,8E)-4,8-dimethyl-11-p-tolylundeca-4,8-dien-1-ol

(4E,8E)-4,8-dimethyl-11-m-tolylundeca-4,8-dien-1-ol

(5E,9E)-5,9-dimethyl-12-m-tolyldodeca-5,9-dienenitrile

(5E,9E)-5,9-dimethyl-12-p-tolyldodeca-5,9-dienenitrile

Refernces

• 1、 Prestwich, Glenn D.,Singh, Ambarish K.,Carvalho, Joan F.,Koeppe, John K.,Kovalick, Gae E.,Chang, Ernest S.. "PHOTOAFFINITY LABELS FOR INSECT JUVENILE HORMONE BINDING PROTEINS SYNTHESIS AND EVALUATION IN VITRO". . p. 529 - 537. Retrieved 1984.
• 2、 Orfanidou, Maria,Petsi, Marina,Zografos, Alexandros L.. "Organocatalytic epoxidation and allylic oxidation of alkenes by molecular oxygen". supporting information. p. 9172 - 9178. Retrieved 2021/11/30.
• 3、 Lichtor, Phillip A.,Miller, Scott J.. "Combinatorial evolution of site- and enantioselective catalysts for polyene epoxidation". . p. 990 - 995. Retrieved 2013/02/25.