Piperitone is a natural

monoterpene Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen funct ...

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...

which is a component of some

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. Both

stereoisomer In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...

s, the D-form and the L-form, are known. The D-form has a

peppermint Peppermint (''Mentha'' × ''piperita'') is a hybrid species of mint, a cross between watermint and spearmint. Indigenous to Europe and the Middle East, the plant is now widely spread and cultivated in many regions of the world.Euro+Med Plantbas ...

-like aroma and has been isolated from the oils of plants from the genera ''

Cymbopogon ''Cymbopogon'', also known as lemongrass, barbed wire grass, silky heads, Cochin grass, Malabar grass, oily heads, citronella grass or fever grass, is a genus of Asian, African, Australian, and tropical island plants in the grass family. Some ...

'', ''

Andropogon ''Andropogon'' ( common names: beard grass, bluestem grass, broomsedge) is a widespread genus of plants in the grass family, native to much of Asia, Africa, and the Americas, as well as southern Europe and various oceanic islands. Over 100 spec ...

'', and ''

Mentha ''Mentha'' (also known as mint, from Greek , Linear B ''mi-ta'') is a genus of plants in the family Lamiaceae (mint family). The exact distinction between species is unclear; it is estimated that 13 to 24 species exist. Hybridization occurs n ...

''. The L-form has been isolated from

Sitka spruce ''Picea sitchensis'', the Sitka spruce, is a large, coniferous, evergreen tree growing to almost tall, with a trunk diameter at breast height that can exceed 5 m (16 ft). It is by far the largest species of spruce and the fifth-larg ...

. Piperitone is used as the principal raw material for the production of synthetic

menthol Menthol is an organic compound, more specifically a monoterpenoid, made synthetically or obtained from the oils of corn mint, peppermint, or other mints. It is a waxy, clear or white crystalline substance, which is solid at room temperature and ...

and

thymol Thymol (also known as 2-isopropyl-5-methylphenol, IPMP), , is a natural monoterpenoid phenol derivative of ''p''-Cymene, isomeric with carvacrol, found in oil of thyme, and extracted from ''Thymus vulgaris'' (common thyme), ajwain, and vario ...

. The primary source of D/L-piperitone is from ''

Eucalyptus dives ''Eucalyptus dives'', commonly known as the broad-leaved peppermint or blue peppermint, is a species of tree that is endemic to south-eastern Australia. It has rough, finely fibrous bark on the trunk and larger branches, smooth bark above, lance- ...

'', produced mainly in

South Africa South Africa, officially the Republic of South Africa (RSA), is the southernmost country in Africa. It is bounded to the south by of coastline that stretch along the South Atlantic and Indian Oceans; to the north by the neighbouring countri ...

.Boland, D.J., Brophy, J.J., and A.P.N. House, ''Eucalyptus Leaf Oils'', 1991, {{ISBN, 0-909605-69-6

References

Ketones Monoterpenes Cyclohexenes