Cubebene

Last updated
Cubebenes
A-Cubebene.svg
α-Cubebene
B-Cubebene.svg
β-Cubebene
Names
IUPAC name
  • (α): (1R,5S,6R,7S,10R)-4,10-Dimethyl-7-propan-2-yltricyclo[4.4.0.01,5]dec-3-ene
  • (β): (1R,5S,6R,7S,10R)-10-Methyl-4-methylidene-7-propan-2-yltricyclo[4.4.0.01,5]decane
Identifiers
3D model (JSmol)
EC Number
  • 605-792-7
PubChem CID
UNII
Properties
C15H24
Molar mass 204.357 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Cubebenes are a pair of chemical compounds, classified as sesquiterpenes, first isolated from Piper cubeba berries, known as cubebs.

The volatile oil from the distillation of cubebs is a pale green or blue-yellow viscous liquid with a warm woody, slightly camphoraceous odor [1] consisting of cubebene which comes in two forms, α- and β-cubebene, both with the molecular formula C15H24. [2] They differ only in the position of a double bond which is endocyclic (part of the five-membered ring) in α-cubebene, but exocyclic in β-cubebene. [3]

Related Research Articles

Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.

The ionones are a series of closely related chemical substances that are part of a group of compounds known as rose ketones, which also includes damascones and damascenones. Ionones are aroma compounds found in a variety of essential oils, including rose oil. β-Ionone is a significant contributor to the aroma of roses, despite its relatively low concentration, and is an important fragrance chemical used in perfumery. The ionones are derived from the degradation of carotenoids.

Rose oil

Rose oil is the essential oil extracted from the petals of various types of rose. Rose ottos are extracted through steam distillation, while rose absolutes are obtained through solvent extraction, the absolute being used more commonly in perfumery. Even with their high price and the advent of organic synthesis, rose oils are still perhaps the most widely used essential oil in perfumery.

<i>Piper cubeba</i> species of plant

Piper cubeba, cubeb or tailed pepper is a plant in genus Piper, cultivated for its fruit and essential oil. It is mostly grown in Java and Sumatra, hence sometimes called Java pepper. The fruits are gathered before they are ripe, and carefully dried. Commercial cubeb consists of the dried berries, similar in appearance to black pepper, but with stalks attached – the "tails" in "tailed pepper". The dried pericarp is wrinkled, and its color ranges from grayish brown to black. The seed is hard, white and oily. The odor of cubeb is described as agreeable and aromatic and the taste as pungent, acrid, slightly bitter and persistent. It has been described as tasting like allspice, or like a cross between allspice and black pepper.

Caryophyllene chemical compound

Caryophyllene, more formally (−)-β-caryophyllene, is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of Cannabis sativa, rosemary, and hops. It is usually found as a mixture with isocaryophyllene and α-humulene, a ring-opened isomer. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature.

Humulene chemical compound

Humulene, also known as α-humulene or α-caryophyllene, is a naturally occurring monocyclic sesquiterpene (C15H24), containing an 11-membered ring and consisting of 3 isoprene units containing three nonconjugated C=C double bonds, two of them being triply substituted and one being doubly substituted. It was first found in the essential oils of Humulus lupulus (hops), from which it derives its name. Humulene is an isomer of β-caryophyllene, and the two are often found together as a mixture in many aromatic plants.

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 are endocyclic and in β-phellandrene, one of them is exocyclic. Both are insoluble in water, but miscible with ether.

Farnesene chemical compound

The term farnesene refers to a set of six closely related chemical compounds which all are sesquiterpenes. α-Farnesene and β-farnesene are isomers, differing by the location of one double bond. α-Farnesene is 3,7,11-trimethyl-1,3,6,10-dodecatetraene and β-farnesene is 7,11-dimethyl-3-methylene-1,6,10-dodecatriene. The alpha form can exist as four stereoisomers that differ about the geometry of two of its three internal double bonds. The beta isomer exists as two stereoisomers about the geometry of its central double bond.

Bisabolol chemical compound

Bisabolol, or more formally α-(−)-bisabolol or also known as levomenol, is a natural monocyclic sesquiterpene alcohol. It is a colorless viscous oil that is the primary constituent of the essential oil from German chamomile and Myoporum crassifolium. It is poorly soluble in water and glycerin, but soluble in ethanol. The enantiomer, α-(+)-bisabolol, is also found naturally but is rare. Synthetic bisabolol is usually a racemic mixture of the two, α-(±)-bisabolol.

Copaiba Resin and essential oil from South American Copaifera trees

Copaiba is a stimulant oleoresin obtained from the trunk of several pinnate-leaved South American leguminous trees. The thick, transparent exudate varies in color from light gold to dark brown, depending on the ratio of resin to essential oil. Copaiba is used in making varnishes and lacquers.

<i>alpha</i>-Pinene chemical compound

α-Pinene is an organic compound of the terpene class, one of two isomers of pinene. It is an alkene and it contains a reactive four-membered ring. It is found in the oils of many species of many coniferous trees, notably the pine. It is also found in the essential oil of rosemary and Satureja myrtifolia. Both enantiomers are known in nature; (1S,5S)- or (−)-α-pinene is more common in European pines, whereas the (1R,5R)- or (+)-α-isomer is more common in North America. The racemic mixture is present in some oils such as eucalyptus oil and orange peel oil.

Cannabis flower essential oil essential oil of hemp

Cannabis flower essential oil, also known as hemp essential oil is an essential oil obtained by steam distillation from the flowers, panicles, stem, and upper leaves of the hemp plant. Hemp essential oil is distinct from hemp seed oil and hash oil: the former is a vegetable oil that is cold-pressed from the seeds of low-THC varieties of hemp, the latter is a THC-rich extract of dried female hemp flowers (marijuana) or resin (hashish).

<i>Ravensara aromatica</i> species of plant

Ravensara aromatica is a member of the laurel family, Lauraceae, and originates in Madagascar. The name ravensara is a latinization of the Malagasy word ravintsara. Other Malagasy names include havozo, hazomanitra and tavolomanitra. The leaves and twigs of R. aromatica have a mildly camphorous aroma similar to eucalyptus. The essential oil of R. aromatica is used as a fragrance material in the perfumery industry, and as an antiseptic, anti-viral, antibacterial, expectorant, anti-infective in natural and folk medicine.

α-Santalol chemical compound

α-Santalol is an organic compound that is classified as a sesquiterpene. It comprises about 55% of the oil of sandalwood, another less abundant component being β-santalol. As of 2002, about 60 tons of sandalwood oil are produced annually by steam distillation of the heartwood of Santalum album. It is a valued component for perfumes.

<i>Thymus pannonicus</i> species of plant

Thymus pannonicus, known by its common name Hungarian thyme or Eurasian thyme, is a perennial herbaceous plant, distributed in central and eastern Europe and Russia. It grows over open dry meadows, grasslands, and rocks.

Bisabolene group of chemical compounds

Bisabolenes are a group of closely related natural chemical compounds which are classified as sesquiterpenes. Bisabolenes are produced from farnesyl pyrophosphate (FPP) and are present in the essential oils of bisabol, and of a wide variety of other plants including cubeb, lemon, and oregano. Various derivates also function as pheromones in different insects, such as stink bugs and fruit flies. Bisabolenes are produced by several fungi, though their biological role in that group of organisms remains unclear.

<i>Eryngium planum</i> Species of flowering plant in the celery family Apiaceae

Eryngium planum, the blue eryngo or flat sea holly, is a species of flowering plant in the family Apiaceae, native to the area that includes central and southeastern Europe and central Asia. It is an herbaceous perennial thistle growing to 50 cm (20 in) with branched silvery-blue stems, and numerous small blue conical flowerheads surrounded by spiky bracts in summer.

Guaienes are a series of closely related natural chemical compounds that have been isolated from a variety of plant sources. The guaienes are sesquiterpenes with the molecular formula C15H24. α-Guaiene is the most common and was first isolated from guaiac wood oil from Bulnesia sarmientoi. The guaienes are used in the fragrance and flavoring industries to impart earthy, spicy aromas and tastes.

α-Vetivone chemical compound

α-Vetivone is an organic compound that is classified as a sesquiterpene. It is a major component of the oil of vetiver, which is used to prepare certain high value perfumes.

Bergamotenes are a group of isomeric chemical compounds with the molecular formula C15H24. The bergamotenes are found in a variety of plants, particularly in their essential oils.

References

  1. Lawless, Julia (1995), The Illustrated Encyclopedia of Essential Oils: The Complete Guide to the Use of Oils in Aromatherapy and Herbalism, Element Books, ISBN   978-1-85230-721-9
  2. Wikisource-logo.svg This article incorporates text from a publication now in the public domain : Chisholm, Hugh, ed. (1911). "Cubebs". Encyclopædia Britannica . 7 (11th ed.). Cambridge University Press. p. 607.
  3. Ohta, Yoshimoto; Sakai, Tsutomu; Hirose, Toshio (1966). "Sesquiterpene hydrocarbons from the oil of cubeb α-cubebene and β-cubebene". Tetrahedron Letters. 7 (51): 6365–6370. doi:10.1016/S0040-4039(00)70179-1.