103475-43-0

Basic information

• Product Name: caryophyllene-1β,10α-epoxide
• Synonyms: caryophyllene-1β,10α-epoxide
• CAS NO: 103475-43-0
• Molecular Weight: 220.355
• Mol File: 103475-43-0.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: caryophyllene-1β,10α-epoxide(CAS DataBase Reference)
• NIST Chemistry Reference: caryophyllene-1β,10α-epoxide(103475-43-0)
• EPA Substance Registry System: caryophyllene-1β,10α-epoxide(103475-43-0)

Safety Data

• Hazardous Substances Data: 103475-43-0(Hazardous Substances Data)

Upstream product

• 87-44-5 β-caryophyllene 
• 61824-50-8 (Z)-(1R,9S)-4,11,11-Trimethyl-8-methylene-bicyclo[7.2.0]undec-3-en-5-one 
• 87-44-5 β-caryophyllene 
• 3691-12-1 (1S,4S,7R)-7-Isopropenyl-1,4-dimethyl-1,2,3,4,5,6,7,8-octahydro-azulene 
• 64-19-7 acetic acid 

Downstream Products

• 130756-35-3 clovanemagnolol 
• 133056-11-8 caryolanemagnolol 
• 1213270-03-1 C₂₁H₂₉BrO₂ 
• 1213270-07-5 C₄₀H₅₃NO₅ 
• 1213270-05-3 C₂₆H₃₅BrO₃ 
• 1213270-04-2 C₂₃H₃₀Br₂O₃ 
• 1213270-13-3 C₂₃H₃₁BrO₃ 
• 92174-64-6 Acetic acid (1S,5S,6S,9R)-6,10,10-trimethyl-2-methylene-bicyclo[7.2.0]undec-5-yl ester 
• 99881-55-7 1R,5R,9S-5-acetoxy-11,11-dimethyl-4,8-bismethylenebicyclo<7.2.0>undecane 
• 2649-64-1 clovanediol 
• 155485-76-0 (β,9β)-caryolane-1,9-diol 
• 92760-17-3 (1R,5S,8R,9R)-4,4,8-trimethylbicyclo<6.3.1.0^1,5>dodeca-2-en-9-ol 
• 88514-10-7 ((1S,8R)-4,10,10-Trimethyl-7-methylene-bicyclo[6.2.0]dec-4-yl)-methanol 
• 19431-76-6 caryophyllenol-I 

Relevant articles and documents

Thermoconversion of caryophyllene- to farnesene-type sesquiterpenes. Short access to the enantiomers of (6RS,7RS)- and (6RS,7SR)-6,7-epoxy-6,7-dihydro-β-farnesenes

Flash-vacuum thermolysis of the four diastereoisomeric 5,6-epoxy-5,6-dihydro-caryophyllenes 1-4 at 500-550°/0.1-0.7 Torr leads to the hitherto unreported enantiomers of (6RS,7RS)- and (6RS,7SR)-6,7-epoxy-6,7-dihydro-β-farnesenes ((±)-5 and (±)-6, resp.). In particular, (+)-5 is formed in 45% yield (ca. 90% ee) and is, thus, an attractive chiral building block for natural-product synthesis.

Chromium(III) terephthalate metal organic framework (MIL-101): Hf-free synthesis, structure, polyoxometalate composites, and catalytic properties

Hybrid materials of the metal-organic framework (MOF), chromium(III) terephthalate (MIL-101), and phosphotungstic acid (PTA) were synthesized in aqueous media in the absence of hydrofluoric acid. XRD analysis of the MIL101/PTA composites indicates the presence of ordered PTA assemblies residing in both the large cages and small pores of MIL-101, which suggests the formation of previously undocumented structures. The MIL101/PTA structure enables a PTA payload 1.5-2 times higher than previously achieved. The catalytic performance of the MIL101/PTA composites was assessed in the Baeyer condensation of benzaldehyde and 2-naphthol, in the three-component condensation of benzaldehyde, 2-naphthol, and acetamide, and in the epoxidation of caryophyllene by hydrogen peroxide. The catalytic efficiency was demonstrated by the high (over 80-90%) conversion of the reactants under microwave-assisted heating. In four consecutive reaction cycles, the catalyst recovery was in excess of 75%, whereas the product yields were maintained above 92%. The simplicity of preparation, exceptional stability, and reactivity of the novel composites indicate potential in utilization of these catalytic matrices in a multitude of catalytic reactions and engineering processes.

Stereochemistry of 14-hydroxy-β-caryophyllene and related compounds

The isomerization of β-caryophyllene (3), under treatment with SeO2, is described. Chemical correlations, between 3 and 14-hydroxy-β-caryophyllene (6) from Juniperus oxycedrus, are established. High resolution 1H NMR spectra and analysis by molecular mechanics of 3, 6 and 14-acetoxy-β-caryophyllene (7) indicate the existence of two conformational isomers, βα and ββ, in each compound. At 25°C, the βα conformer predominates in 3 and 7 but the ββ conformer predominates in 6. The higher percentage of 6ββ possibly derives from an intramolecular hydrogen bond. The treatment of 3, 6 and 7 with m-CPBA generates, in each case, two diastereomeric 4,5-epoxi-derivatives. The epoxides obtained from 6 have been isolated and analysed separately.

An ultrathin amino-acid based copper(II) coordination polymer nanosheet for efficient epoxidation of β-caryophyllene

Natural amino acids are important building blocks for the construction of intriguing coordination polymers (CPs) because of their abundance, inexpensiveness and environmental benignness. Herein, two copper(II) CPs, namely, 2D CuIle-e nanosheet (e: ethanol) and 1D CuIle-m nanoshuttle (m: methanol), were fabricated from L-isoleucine (Ile) and well characterized with single-crystal x-ray diffraction, XPS spectra, TEM and AFM, etc. More importantly, two novel and stable catalytic nanosystems, i.e. CuIle-e/acetone/TBHP (tert-butyl hydroperoxide) and CuIle-e/THF/O2/TBHP, were thus conveniently built by using ultrathin 2D CuIle-e nanosheet (~ 2.3 nm) in suitable aprotic solvents. Under mild conditions, complete conversion of β-caryophyllene and good yields (86.1% or 87.2%) for β-caryophyllene epoxide were gained via CuIle-e/acetone/TBHP or CuIle-e/THF/O2 (1 atm)/TBHP (10.0 mol%), respectively. Notably, ultrathin CuIle-e nanosheet showed fairly satisfactory stability, which may open a unique window for the facile fabrication of new amino-acid based CP nanosystems with outstanding catalytic performances in actual applications.