Caryophyllene, or (−)-β-caryophyllene, is a natural bicyclic sesquiterpene that is a constituent of some essential oils, especially clove oil and the oil from the stems and flowers of Syzygium aromaticum. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer. Caryophyllene is notable for having a cyclobutane ring, a rarity in nature. IUPAC nomenclature is a systematic way of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... See also Avogadros number Atomic mass unit Dalton (unit) External links Learning by Simulations Calculation of Molecular Formulas from Molecular Masses Categories: Chemistry stubs | Mass | Chemical properties ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Density (symbol: Ï - Greek: rho) is a measure of mass per unit of volume. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... Allah is who made all of this. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII alpha-numeric strings. ... Terpenes are a class of hydrocarbons, produced by many plants, particularly conifers. ... An essential oil is a concentrated, hydrophobic liquid containing volatile aromatic compounds extracted from plants. ... Humulene, or α-humulene or α-caryophyllene, is a naturally occurring monocyclic sesquiterpene. ... Cyclobutane, C4H8, is a four carbon alkane in which all the carbon atoms are arranged cyclically, hence cyclobutane. ...
Caryophyllene is one of the chemical compounds that contributes to the spiciness of black pepper. Binomial name Piper nigrum L. Black pepper (Piper nigrum) is a flowering vine in the family Piperaceae, cultivated for its fruit, which is usually dried and used as a spice and seasoning. ...
The first total synthesis of caryophyllene in 1964 by E.J. Corey was considered one of the classic demonstrations of the possiblities of synthetic organic chemistry at the time. Elias James Corey (born July 12, 1928) is an American organic chemist. ...
Caryophyllene, a constituent of many essential oils, include clove oil, has a trans alkene contained in a 9-membered ring.
One interesting property is that it has 4 diastereoisomers possible, originating from a total of three disymmetric centres present in the molecule.
This phenomenon, also known as atropisomerism, is a feature of a number of natural products, and arises from a combination of angle strain in a medium sized ring caused by the rotation, together with trans-annular steric effects.
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