Thujene

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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
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).
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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]

Organic compound chemical compound that contains carbon (except for a several compounds traditionally classified as inorganic compounds)

In chemistry, an organic compound is generally any chemical compound that contains carbon. Due to carbon's ability to catenate, millions of organic compounds are known. Study of the properties and synthesis of organic compounds is the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds, along with a handful of other exceptions, are not classified as organic compounds and are considered inorganic. No consensus exists among chemists on precisely which carbon-containing compounds are excluded, making the definition of an organic compound elusive.

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. Modified terpenes, such as those containing oxygen functionality or missing a methyl group, are called monoterpenoids. Monoterpenes and monoterpenoids are diverse. They have relevance to the pharmaceutical, cosmetic, agricultural, and food industries.

Essential oil Hydrophobic liquid containing volatile aroma compounds from plants

An essential oil is a concentrated hydrophobic liquid containing volatile chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetherolea, or simply as the oil of the plant from which they were extracted, such as oil of clove. An essential oil is "essential" in the sense that it contains the "essence of" the plant's fragrance—the characteristic fragrance of the plant from which it is derived. The term essential used here does not mean indispensable as with the terms essential amino acid or essential fatty acid which are so called since they are nutritionally required by a given living organism. In contrast to fatty oils, essential oils typically evaporate completely without leaving a stain or residue.

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.

In chemistry, isomers are ions or molecules with identical formulas but distinct structures. Isomers do not necessarily share similar properties. Two main forms of isomerism are structural isomerism and stereoisomerism.

Sabinene chemical compound

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.

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

See also

Related Research Articles

Alkene unsaturated chemical compound containing one carbon-to-carbon double bond

In organic chemistry, an alkene is an unsaturated hydrocarbon that contains at least one carbon–carbon double bond. The words alkene and olefin are often used interchangeably (see nomenclature section below). Acyclic alkenes, with only one double bond and no other functional groups, known as mono-enes, form a homologous series of hydrocarbons with the general formula CnH2n. Alkenes have two hydrogen atoms fewer than the corresponding alkane (with the same number of carbon atoms). The simplest alkene, ethylene (C2H4), with the International Union of Pure and Applied Chemistry (IUPAC) name ethene, is the organic compound produced on the largest scale industrially. Aromatic compounds are often drawn as cyclic alkenes, but their structure and properties are different and they are not considered to be alkenes.

<i>Cis</i>–<i>trans</i> isomerism term used in organic chemistry; 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

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, and only to be used with alkenes. 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 covalent chemical bond linking two consecutive amino acid monomers along a peptide or protein chain

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 isomeric molecules that have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in space

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.

Proline group of stereoisomers

Proline (symbol Pro or P) is a proteinogenic amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated NH2+ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO form under biological conditions), and a side chain pyrrolidine, classifying it as a nonpolar (at physiological pH), aliphatic amino acid. It is non-essential in humans, meaning the body can synthesize it from the non-essential amino acid L-glutamate. It is encoded by all the codons starting CC (CCU, CCC, CCA, and CCG).

Maltose chemical compound, sugar that exists in wheat

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 beta-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.

Tetrazene is a chemical compound with the molecular formula N4H4. In IUPAC nomenclature, derivatives of this compound are known collectively as tetrazenes. The most common of such derivatives is tetrazene explosive (commonly known simply as tetrazene), which is used for sensitization of priming compositions.

Open-chain compound compound with a linear structure, rather than a cyclic one

In chemistry, an open-chain compound or acyclic compound is a compound with a linear structure, rather than a cyclic one. An open-chain compound having no side chains is called a straight-chain compound. Many of the simple molecules of organic chemistry, such as the alkanes and alkenes, have both linear and ring isomers, that is, both acyclic and cyclic, with the latter often classified as aromatic. For those with 4 or more carbons, the linear forms can have straight-chain or branched-chain isomers. The lowercase prefix n- denotes the straight-chain isomer; for example, n-butane is straight-chain butane, whereas i-butane is isobutane. Cycloalkanes are isomers of alkenes, not of alkanes, because the ring's closure involves a C-C bond. Having no rings, all open-chain compounds are aliphatic.

Phellandrene is the name for 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 group of chemical compounds

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 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.

Cadinene family of chemical compounds

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.

Terpineol family of chemical compounds

Terpineol is a monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. There are four isomers, alpha-, beta-, gamma-terpineol, and terpinen-4-ol. beta- and gamma-terpineol differ only by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-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.

Hexachlorocyclohexane group of chemical compounds

Hexachlorocyclohexane (HCH) is any of several polyhalogenated organic compounds consisting of a six-carbon ring with one chlorine and one hydrogen attached to each carbon. There are many isomers for this structure, differing by the stereochemistry of the individual chlorine substituents on the cyclohexane. It is sometimes erroneously called "benzene hexachloride" (BHC). They have been used as models for analyzing the effects of different geometric positions of the large atoms with dipolar bonds on the stability of the cyclohexane conformation. Some isomers are pesticides.

Melengestrol chemical compound

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Noretynodrel chemical compound

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.

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.

Flumethrin insecticide

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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