50502-44-8

Basic information

• Product Name: 10,11-Epoxyfarnesylacetate
• Synonyms: 10,11-Epoxyfarnesylacetate
• CAS NO: 50502-44-8
• Molecular Formula: C₁₇H₂₈O₃
• Molecular Weight: 278.38654
• Mol File: 50502-44-8.mol
• Article Data: 19

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 10,11-Epoxyfarnesylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 10,11-Epoxyfarnesylacetate(50502-44-8)
• EPA Substance Registry System: 10,11-Epoxyfarnesylacetate(50502-44-8)

Safety Data

• Hazardous Substances Data: 50502-44-8(Hazardous Substances Data)

Usage

Chemical class

Epoxy compounds

Derivative

Farnesyl derivative

Source

Derived from farnesyl, a key component in the biosynthesis of sesquiterpenoids

Bioactive properties

Potential anti-inflammatory and anti-tumor effects

Potential applications

Pharmaceutical or therapeutic agent

Field of study

Cancer research

Complexity

Complex compound

Interest to researchers

Potential applications in medicine and drug development

Structure

Contains an epoxy group at the 10,11 position of the farnesyl backbone

Molecular weight

Approximately 238.37 g/mol (tentative, based on the molecular formula)

Appearance

Likely a colorless to pale yellow oil or solid (based on typical appearance of related compounds)

Solubility

Likely soluble in organic solvents such as ethanol, methanol, or acetone (based on typical solubility of related compounds)

Stability

May be sensitive to light, heat, and moisture (based on typical stability of related compounds)

Synthesis

Can be synthesized through various chemical reactions, such as the reaction of farnesol with an oxidizing agent to introduce the epoxy group (tentative, based on the information provided)

Upstream product

• 4128-17-0 (2E,6E)-farnesyl acetate 
• 5233-99-8 10,11-epoxyfarnesol 
• 108-24-7 acetic anhydride 
• 54795-59-4 (2E,6E)-10-bromo-11-hydroxy-3,7,11-trimethyldodeca-2,6-dien-1-yl acetate 
• 106-28-5 Farnesol 
• 130790-62-4 (R,2E,6E)-10,11-dihydroxy-3,7,11-trimethyldodeca-2,6-dienyl acetate 
• 130648-11-2 Acetic acid (2E,6E)-(R)-11-hydroxy-10-methanesulfonyloxy-3,7,11-trimethyl-dodeca-2,6-dienyl ester 
• 4602-84-0 farnesol 
• 76386-25-9 trans,trans-farnesyl diphenylurethane 
• 29548-30-9 farnesyl acetate 
• 34175-52-5 (10S,2E,6E)-1-acetoxy-10,11-dihydroxy-3,7,11-trimethyldodeca-2,6-dien-1-yl 

Downstream Products

• 120733-46-2 (2E,6E)-10-hydroxy-3,7,11-trimethyldodeca-2,6,11-trienyl acetate 
• 876725-77-8 tert-Butyl-[(4E,8E)-11-(3,3-dimethyl-oxiranyl)-5,9-dimethyl-2-methylene-undeca-4,8-dienyloxy]-diphenyl-silane 
• 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 

Relevant articles and documents

Total synthesis of (±)-terpestacin and (±)-11-epi-terpestacin

(Chemical Equation Presented) The total synthesis of racemic terpestacin and 11-epi-terpestacin using the allene ether Nazarov reaction as the key step is described. All stereochemistry is derived from the stereogenic carbon atom that is formed during the Nazarov reaction.

Exploiting the Potential of Meroterpenoid Cyclases to Expand the Chemical Space of Fungal Meroterpenoids

Fungal meroterpenoids are a diverse group of hybrid natural products with impressive structural complexity and high potential as drug candidates. In this work, we evaluate the promiscuity of the early structure diversity-generating step in fungal meroterpenoid biosynthetic pathways: the multibond-forming polyene cyclizations catalyzed by the yet poorly understood family of fungal meroterpenoid cyclases. In total, 12 unnatural meroterpenoids were accessed chemoenzymatically using synthetic substrates. Their complex structures were determined by 2D NMR studies as well as crystalline-sponge-based X-ray diffraction analyses. The results obtained revealed a high degree of enzyme promiscuity and experimental results which together with quantum chemical calculations provided a deeper insight into the catalytic activity of this new family of non-canonical, terpene cyclases. The knowledge obtained paves the way to design and engineer artificial pathways towards second generation meroterpenoids with valuable bioactivities based on combinatorial biosynthetic strategies.

Syntheses of deuterium labeled prenyldiphosphate and prenylcysteine analogues for in vivo mass spectrometric quantification

A Wittig reaction employing Li(CD3)2CP(C 6H5)3 was used to prepare d6- farnesol and d6-geranylgeraniol. Reductive amination of aniline-2,3,4,5,6-d5 was used to prepare