5233-99-8

Basic information

• Product Name: Epoxyfarnesol
• Synonyms: Epoxyfarnesol;(E,E)-(±)-10,11-Epoxyfarnesol;trans,trans-(±)-Epoxyfarnesol;(2E,6E)-10,11-Epoxy-3,7,11-trimethyl-2,6-dodecadien-1-ol
• CAS NO: 5233-99-8
• Molecular Formula: C₁₅H₂₆O₂
• Molecular Weight: 236.34986
• Mol File: 5233-99-8.mol
• Article Data: 19

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Epoxyfarnesol(CAS DataBase Reference)
• NIST Chemistry Reference: Epoxyfarnesol(5233-99-8)
• EPA Substance Registry System: Epoxyfarnesol(5233-99-8)

Safety Data

• Hazardous Substances Data: 5233-99-8(Hazardous Substances Data)

Upstream product

• 4602-84-0 farnesol 
• 29548-30-9 farnesyl acetate 
• 54795-59-4 (2E,6E)-10-bromo-11-hydroxy-3,7,11-trimethyldodeca-2,6-dien-1-yl acetate 
• 112383-67-2 3-[1-(tert-Butyl-dimethyl-silanyloxy)-1-cyclopropyl-ethylperoxycarbonyl]-propionic acid (2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyl ester 
• 112383-68-3 2-[1-(tert-Butyl-dimethyl-silanyloxy)-1-cyclopropyl-ethylperoxycarbonyl]-benzoic acid (2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyl ester 
• 34203-17-3 (2E,6E)-11-hydroxy-10-mesyloxy-3,7,11-trimethyl-2,6-dodecadienyl acetate 
• 158897-41-7 10,11-Epoxy-3,7,11-trimethyl-2(E),6(E)-dodecadienyl tert-butyldimethylsilyl ether 
• 4128-17-0 (2E,6E)-farnesyl acetate 
• 130648-11-2 Acetic acid (2E,6E)-(R)-11-hydroxy-10-methanesulfonyloxy-3,7,11-trimethyl-dodeca-2,6-dienyl ester 
• 106-28-5 Farnesol 
• 130790-62-4 (R,2E,6E)-10,11-dihydroxy-3,7,11-trimethyldodeca-2,6-dienyl acetate 
• 61890-77-5 (2E,6E)-1-(tert-butyldimethylsilyloxy)-3,7,1,1-trimethyldodeca-2,6,10-triene 
• 158897-40-6 10-Bromo-11-hydroxy-3,7,11-trimethyl-2(E),6(E)-dodecadienyl tert-butyldimethylsilyl ether 
• 81657-94-5 (2E,6E)-10-oxo-11-hydroxy 3,7,11-trimethyl-2,6-dodecadienyl acetate 

Downstream Products

• 82527-82-0 (2E,6E)-10,11-epoxyfarnesyl diazoacetate 
• 50502-44-8 10,11-epoxyfarnesyl acetate 
• 917612-07-8 (4E,8E)-4,8-dimethyl-11-p-tolylundeca-4,8-dien-1-ol 
• 917612-09-0 (4E,8E)-4,8-dimethyl-11-m-tolylundeca-4,8-dien-1-ol 
• 917612-26-1 (5E,9E)-5,9-dimethyl-12-m-tolyldodeca-5,9-dienenitrile 
• 917612-24-9 (5E,9E)-5,9-dimethyl-12-p-tolyldodeca-5,9-dienenitrile 
• 917612-36-3 (6E,10E)-6,10-dimethyl-13-p-tolyltrideca-6,10-dien-2-one 
• 917612-37-4 (6E,10E)-6,10-dimethyl-13-m-tolyltrideca-6,10-dien-2-one 
• 917611-87-1 (2E,6E)-10-(tert-butyldiphenylsilyloxy)-3,7-dimethyldeca-2,6-dien-1-ol 
• 917611-93-9 (2E,6E)-10-(tert-butyldiphenylsilyloxy)-3,7-dimethyldeca-2,6-dienyl diethyl phosphate 

Relevant articles and documents

Organocatalytic epoxidation and allylic oxidation of alkenes by molecular oxygen

Pyrrole-proline diketopiperazine (DKP) acts as an efficient mediator for the reduction of dioxygen by Hantzsch ester under mild conditions to allow the aerobic metal-free epoxidation of electron-rich alkenes. Mechanistic crossovers are underlined, explaining the dual role of Hantzsch ester as a reductant/promoter of the DKP catalyst and a simultaneous competitor for the epoxidation of alkenes when HFIP is used as a solvent. Expansion of this protocol to the synthesis of allylic alcohols was achieved by adding a catalytic amount of selenium dioxide as an additive, revealing a superior method to the classical application of t-BuOOH as a selenium dioxide oxidant.

Relay Cross Metathesis for the Iterative Construction of Terpenoids and Synthesis of a Diterpene-Benzoate Macrolide of Biogenetic Relevance to the Bromophycolides

We report a relay cross metathesis (ReXM) reaction for the construction of terpenoids in an iterative protocol. The protocol features the cross metathesis of a relay-actuated Δ6,7-functionalized C10-monoterpenoid alcohol with C10-monoterpenoid citral to form a C15-sesquiterpene. Subsequent functional group manipulation allows for the method to be repeated in an iterative fashion. The method is used for the synthesis of a diterpene-benzoate macrolide of biogenetic relevance to the bromophycolide family of natural products.

Biomimetic cyclization of epoxide precursors of indole mono-, sesquiand diterpene alkaloids by lewis acids

Cyclization of the synthesized epoxide precursors of indole mono-, sesqui- and diterpene alkaloids was performed to elucidate the mechanism for biomimetic cationic cyclization to polycyclic structures. 3-(6,7- Epoxygeranyl)indole (11), 3-(10,11-epoxyfarne