ChemicalBook > Product Catalog > Flavors and fragrances > Synthetic fragrances > Hydrocarbon spices > TERPENE HYDROCARBONS > BETA-CARYOPHYLLENE
BETA-CARYOPHYLLENE Chemical Properties
- Melting point:<25℃
- alpha D -8 to -9° (chloroform)
- Boiling point:262-264 °C(lit.)
- Density 0.902 g/mL at 20 °C(lit.)
- FEMA 2252 | BETA-CARYOPHYLLENE
- refractive index n
- Flash point:205 °F
- storage temp. 2-8°C
- form neat
- Specific Gravity0.90
- optical activity[α]23/D 7.5°, neat
- JECFA Number1324
- Merck 14,1875
- BRN 2044564
- CAS DataBase Reference87-44-5(CAS DataBase Reference)
- EPA Substance Registry SystemBicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- (87-44-5)
BETA-CARYOPHYLLENE Usage And Synthesis
- Chemical PropertiesClear colorless liquid
- Chemical Propertiesβ-Caryophyllene has a woody-spicy, dry, clove-like aroma.
- OccurrenceThree isomers (α-, β-, and γ-caryophyllene) are found in nature. The β-isomer is the most frequently encountered and most abundant. This sesquiterpene hydrocarbon occurs naturally in approximately 60 essential oils, mainly in that of cloves, from which it was originally isolated. The chemical structure has been thoroughly studied; other studies have been conducted on the isolation and the dipolar moment, as well as on its oxide. Reported found in lime peel oil, lemon, grapefruit, guava fruit, raspberry, black currant, carrot, celery seed, cinnamon bark, anise, nutmeg, cumin seed, ginger, pepper, peppermint oil, mace, laurel and caraway herb.
- Usesβ-Caryophyllene is notable for having a cyclobutane ring, a rarity in nature. β-Caryophyllene is one of the chemical compounds that contributes to the spiciness of black pepper. β-Caryophyllene was shown to selectively bind to the cannabinoid receptor type-2 (CB2) and to exert significant cannabimimetic antiinflammatory effects in mice.
- PreparationIsolated from oil of clove stems and separated from eugenol by treating the oil with 7% sodium carbonate solution, extracting with ether, repeating the carbonate treatment on the concentrated extracts, and finally steam distilling.
- DefinitionChEBI: A beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of <greek beta-caryophyllene, occurring in many essential oils, particularly oil of cloves.
- Aroma threshold valuesDetection at 64 to 90 ppb
- Taste threshold valuesTaste characteristics at 50 ppm: spicy, pepper-like, woody, camphoraceous with a citrus background.
- Synthesis Reference(s)Journal of the American Chemical Society, 86, p. 485, 1964 DOI: 10.1021/ja01057a040
- General DescriptionPale yellow oily liquid with an odor midway between odor of cloves and turpentine.
- Air & Water ReactionsInsoluble in water.
- Reactivity ProfileThe unsaturated aliphatic hydrocarbons, such as BETA-CARYOPHYLLENE, are generally much more reactive than the alkanes. Strong oxidizers may react vigorously with them. Reducing agents can react exothermically to release gaseous hydrogen. In the presence of various catalysts (such as acids) or initiators, compounds in this class can undergo very exothermic addition polymerization reactions.
- Fire HazardBETA-CARYOPHYLLENE is combustible.
- Safety ProfileA skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.
- CarcinogenicityCaryophyllene showed significant activity as an inducer of the detoxifying enzyme glutathione S-transferase in the mouse liver and small intestine. The ability of natural anticarcinogens to induce detoxifying enzymes has been found to correlate with their activity in the inhibition of chemical carcinogenesis (253a).
BETA-CARYOPHYLLENE Preparation Products And Raw materials
- Terpineol Ethanol NOOTKATONE(SG) DIHYDRO CUMINYL ALCOHOL Clove oil gamma-caryophyllene CARYOPHYLLENE ALCOHOL ACETATE,CARYOPHYLLENE ACETATE,ACETYL CARYOPHYLLENE Caryophyllene 4,5-epoxide EPSILON-CARYOPHYLLENE OXIDISEDBETA-CARYOPHYLLENE CARYOPHYLLENE OXIDE(RG) caryophyllene cyclase Caryophyllene monoepoxide P-CARYOPHYLLENE CARYOPHYLLENE ALCOHOL,beta-caryophyllene alcohol,beta-caryophyllene alcohol CARYOPHYLLENE,CARYOPHYLLENE:1,4,8-CYCLOUNDECATRIENE,2,6,6,9-TETRAMETHYL-, (E,E,E)-,,α-Caryophyllene, trans,trans,trans-2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene,ALPHA-CARYOPHYLLENE,A-CARYOPHYLLENE (-)-CARYOPHYLLENE OXIDE 95%,CARYOPHYLLENE OXIDE TECH. 90%,CARYOPHYLLENE OXIDE 95+%,(-)-beta-Caryophyllene epoxide,beta-Caryophyllene oxide,(-)-CARYOPHYLLENE OXIDE,CARYOPHYLLENE OXIDE,(-)-beta-Caryophyllene epoxide,4,12,12-trimethyl-9-methylene-5-oxatricyclo[8.2.0.]dodecane (caryophyllene oxide),beta-Caryophyllene oxide,Caryophyllene epoxide,Caryophyllene oxyde Terpenes and Terpenoids, turpentine-oil, caryophyllene fraction
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