Thujene

Last updated
Thujene
Alpha-thujene.png
Thujene3D.png
Names
IUPAC name
1-Isopropyl-4-methylbicyclo[3.1.0]hex-3-ene
Other names
α-Thujene
3-Thujene
Thujiene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.018.806 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
Properties
C10H16
Molar mass 136.238 g·mol−1
Boiling point 151 °C (304 °F; 424 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Thujene (or α-thujene) is a natural organic compound classified as a monoterpene. [1] It is found in the essential oils of a variety of plants, and contributes pungency to the flavor of some herbs such as Summer savory. [2]

The term thujene usually refers to α-thujene. A less common chemically related double-bond isomer is known as β-thujene (or 2-thujene). Another double-bond isomer is known as sabinene.

Chemical structure comparison
Alpha-thujene.png Beta-thujene.png Sabinene.png
α-Thujeneβ-ThujeneSabinene

See also

Related Research Articles

Alkene Chemical compound

In chemistry, an alkene is a hydrocarbon that contains a carbon–carbon double bond.

<i>Cis</i>–<i>trans</i> isomerism

Cistrans isomerism, also known as geometric isomerism or configurational isomerism, is a term used in organic chemistry. The prefixes "cis" and "trans" are from Latin: "this side of" and "the other side of", respectively. In the context of chemistry, cis indicates that the functional groups are on the same side of the carbon chain while trans conveys that functional groups are on opposing sides of the carbon chain. Cis-trans isomers are stereoisomers, that is, pairs of molecules which have the same formula but whose functional groups are rotated into a different orientation in three-dimensional space. It is not to be confused with EZ isomerism, which is an absolute stereochemical description. In general, stereoisomers contain double bonds that do not rotate, or they may contain ring structures, where the rotation of bonds is restricted or prevented. Cis and trans isomers occur both in organic molecules and in inorganic coordination complexes. Cis and trans descriptors are not used for cases of conformational isomerism where the two geometric forms easily interconvert, such as most open-chain single-bonded structures; instead, the terms "syn" and "anti" are used.

Peptide bond

A peptide bond is an amide type of covalent chemical bond linking two consecutive alpha-amino acids from C1 of one alpha-amino acid and N2 of another, along a peptide or protein chain.

Stereoisomerism

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 space. This contrasts with structural isomers, which share the same molecular formula, but the bond connections or their order differs. By definition, molecules that are stereoisomers of each other represent the same structural isomer.

<i>alpha</i>-Linolenic acid

α-Linolenic acid (ALA),, is an n−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils.

Maltose

Maltose, also known as maltobiose or malt sugar, is a disaccharide formed from two units of glucose joined with an α(1→4) bond. In the isomer isomaltose, the two glucose molecules are joined with an α(1→6) bond. Maltose is the two-unit member of the amylose homologous series, the key structural motif of starch. When alpha-amylase breaks down starch, it removes two glucose units at a time, producing maltose. An example of this reaction is found in germinating seeds, which is why it was named after malt. Unlike sucrose, it is a reducing sugar.

Sabinene

Sabinene is a natural bicyclic monoterpene with the molecular formula C10H16. It is isolated from the essential oils of a variety of plants including holm oak (Quercus ilex) and Norway spruce (Picea abies). It has a strained ring system with a cyclopentane ring fused to a cyclopropane ring.

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.

Ocimene

Ocimenes are a group of isomeric hydrocarbons. The ocimenes are monoterpenes found within a variety of plants and fruits. α-Ocimene and the two β-ocimenes differ in the position of the isolated double bond: it is terminal in the alpha isomer. α-Ocimene is cis-3,7-dimethyl-1,3,7-octatriene. β-Ocimene is trans-3,7-dimethyl-1,3,6-octatriene. β-Ocimene exists in two stereoisomeric forms, cis and trans, with respect to the central double bond. The ocimenes are often found naturally as mixtures of the various forms. The mixture, as well as the pure compounds, are oils with a pleasant odor. They are used in perfumery for their sweet herbal scent, and are believed to act as plant defense and have anti-fungal properties. Like the related acyclic terpene myrcene, ocimenes are unstable in air. Like other terpenes, the ocimenes are nearly insoluble in water, but soluble in common organic solvents.

Farnesene

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.

Cadinene

Cadinene is the trivial chemical name of a number of isomeric hydrocarbons that occur in a wide variety of essential oil-producing plants. The name is derived from that of the Cade juniper , the wood of which yields an oil from which cadinene isomers were first isolated.

Ramberg–Bäcklund reaction

The Ramberg–Bäcklund reaction is an organic reaction converting an α-halo sulfone into an alkene in presence of a base with extrusion of sulfur dioxide. The reaction is named after the two Swedish chemists Ludwig Ramberg and Birger Bäcklund. The carbanion formed by deprotonation gives an unstable episulfone that decomposes with elimination of sulfur dioxide. This elimination step is considered to be a concerted cycloelimination.

Terpineol

Terpineol is any of four isomeric monoterpenoids. Terpenoids are terpene that are modified by the addition of a functional group, in this case, an alcohol. Terpineols have been isolated from a variety of sources such as cardamom, cajuput oil, pine oil, and petitgrain oil. Four isomers exist: α-, β-, γ-terpineol, and terpinen-4-ol. β- and γ-terpineol differ only by the location of the double bond. Terpineol is usually a mixture of these isomers with α-terpineol as the major constituent.

Calendic acid is an unsaturated fatty acid, named for the pot marigold, from which it is obtained. It is chemically similar to the conjugated linoleic acids; laboratory work suggests it may have similar in vitro bioactivities.

Melengestrol

Melengestrol is a steroidal progestin of the 17α-hydroxyprogesterone group and an antineoplastic drug which was never marketed. An acylated derivative, melengestrol acetate, is used as a growth promoter in animals.

Isomer

In chemistry, isomers are molecules or polyatomic ions with identical molecular formulas — that is, same number of atoms of each element — but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers.

Noretynodrel

Noretynodrel, or norethynodrel, sold under the brand name Enovid among others, is a progestin medication which was previously used in birth control pills and in the treatment of gynecological disorders but is now no longer marketed. It was available both alone and in combination with an estrogen. The medication is taken by mouth.

Cedrene

Cedrene is a sesquiterpene found in the essential oil of cedar. The two isomers present in the oil are (−)-α-cedrene and (+)-β-cedrene, which differ in the position of a double bond.

1-Dodecene is an alkene with the formula C10H21CH=CH2, consisting of a chain of twelve carbon atoms ending with a double bond. While there are many isomers of dodecene depending on which carbon the double bond is placed, this isomer is of greater commercial importance. It is classified as an alpha-olefin. Alpha-olefins are distinguished by having a double bond at the primary or alpha (α) position. This location of a double bond enhances the reactivity of the compound and makes it useful for a number of applications, especially for the production of detergents.

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. L. Tschugaeff (1900). "Ueber das Thujen, ein neues bicyclisches Terpen". Berichte der deutschen chemischen Gesellschaft . 33 (3): 3118–3126. doi:10.1002/cber.19000330363.
  2. PDR for Herbal Medicines, Third Edition, Joerg Gruenwald (Editor), page 802. ISBN   1-56363-512-7