Paracymene
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''p''-Cymene is a naturally occurring aromatic organic compound. It is classified as an
alkylbenzene The alkylbenzenes are derivatives of benzene, in which one or more hydrogen atoms are replaced by alkyl groups of different sizes. They are a subset of the aromatic hydrocarbons. The simplest member is toluene, in which a hydrogen atom of the benze ...
related to a monoterpene. Its structure consists of a benzene ring ''para''-substituted with a methyl group and an isopropyl group. ''p''-Cymene is insoluble in water, but miscible with organic solvents.


Isomers and production

In addition to ''p''-cymene, two less common geometric isomers are ''o''-cymene, in which the alkyl groups are ''ortho''-substituted, and ''m''-cymene, in which they are ''meta''-substituted. ''p''-Cymene is the only natural isomer, as expected from the terpene rule. All three isomers form the group of cymenes. Cymene is also produced by alkylation of toluene with propylene.


Related compounds

It is a constituent of a number of
essential oil An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the o ...
s, most commonly the oil of
cumin Cumin ( or , or Article title
) (''Cuminum cyminum'') is a
thyme. Significant amounts are formed in sulfite pulping process from the wood terpenes. ''p''-Cymene is a common ligand for ruthenium. The parent compound is ''η''6-cymene)RuCl2sub>2. This
half-sandwich compound Half sandwich compounds, also known as piano stool complexes, are organometallic complexes that feature a cyclic polyhapto ligand bound to an MLn center, where L is a unidentate ligand. Thousands of such complexes are known. Well-known examples in ...
is prepared by the reaction of ruthenium trichloride with the terpene α-
phellandrene Phellandrenes are a pair of organic compounds that have a similar molecular structure and similar chemical properties. α-Phellandrene and β-phellandrene are cyclic monoterpenes and are double-bond isomers. In α-phellandrene, both double bonds ...
. The
osmium Osmium (from Greek grc, ὀσμή, osme, smell, label=none) is a chemical element with the symbol Os and atomic number 76. It is a hard, brittle, bluish-white transition metal in the platinum group that is found as a trace element in alloys, mos ...
complex is also known. Hydrogenation gives the saturated derivative ''p''-menthane.


References

{{Hydrocarbons Flavors Alkylbenzenes C4-Benzenes Monoterpenes Isopropyl compounds