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Encyclopedia > Terpene
Many terpenes are derived from conifer resins, here a pine.
Many terpenes are derived from conifer resins, here a pine.

Terpenes are a large and varied class of hydrocarbons, produced primarily by a wide variety of plants, particularly conifers, though also by some insects such as swallowtail butterflies, which emit terpenes from their osmeterium. They are the major components of resin, and of turpentine produced from resin. The name "terpene" is derived from the word "turpentine". Image File history File links Download high-resolution version (530x820, 82 KB) La bildo estas kopiita de wikipedia:fr. ... Image File history File links Download high-resolution version (530x820, 82 KB) La bildo estas kopiita de wikipedia:fr. ... For other uses, see Pine (disambiguation). ... In chemistry, a hydrocarbon is a cleaning solution consisting only of carbon (C) and hydrogen (H). ... Orders & Families Cordaitales † Pinales   Pinaceae - Pine family   Araucariaceae - Araucaria family   Podocarpaceae - Yellow-wood family   Sciadopityaceae - Umbrella-pine family   Cupressaceae - Cypress family   Cephalotaxaceae - Plum-yew family   Taxaceae - Yew family Vojnovskyales † Voltziales † The conifers, division Pinophyta, are one of 13 or 14 division level taxa within the Kingdom Plantae. ... This article does not cite any references or sources. ... For the band, see Turpentine (band). ... For the band, see Turpentine (band). ...


When terpenes are modified chemically, such as by oxidation or rearrangement of the carbon skeleton, the resulting compounds are generally referred to as terpenoids. Some authors will use the term terpene to include all terpenoids. Chemical structure of the terpenoid isopentenyl pyrophosphate. ...


Terpenes and terpenoids are the primary constituents of the essential oils of many types of plants and flowers. Essential oils are used widely as natural flavor additives for food, as fragrances in perfumery, and in traditional and alternative medicines such as aromatherapy. Synthetic variations and derivatives of natural terpenes and terpenoids also greatly expand the variety of aromas used in perfumery and flavors used in food additives. Vitamin A is an example of a terpene. An essential oil is a concentrated, hydrophobic liquid containing volatile aromatic compounds from plants. ... It has been suggested that Aromatherapy Candles be merged into this article or section. ... Vitamin A is an essential human nutrient. ...

Contents

Structure and biosynthesis

Isoprene

Terpenes are derived biosynthetically from units of isoprene, which has the molecular formula C5H8. The basic molecular formulas of terpenes are multiples of that, (C5H8)n where n is the number of linked isoprene units. This is called the isoprene rule or the C5 rule. The isoprene units may be linked together "head to tail" to form linear chains or they may be arranged to form rings. One can consider the isoprene unit as one of nature's preferred building blocks. Image File history File links Created on March 21, 2005 by User:Jag123 using ChemDraw Ultra 8. ... Image File history File links Created on March 21, 2005 by User:Jag123 using ChemDraw Ultra 8. ... Isoprene is a common synonym for the chemical compound 2-methyl-1,3-butadiene. ...


Isoprene itself does not undergo the building process, but rather activated forms, isopentenyl pyrophosphate (IPP or also isopentenyl diphosphate) and dimethylallyl pyrophosphate (DMAPP or also dimethylallyl diphosphate), are the components in the biosynthetic pathway. IPP is formed from acetyl-CoA via the intermediacy of mevalonic acid in the HMG-CoA reductase pathway. An alternative, totally unrelated biosynthesis pathway of IPP is known in some bacterial groups and the plastids of plants, the so-called MEP(2-Methyl-D-erythritol-4-phosphate)-pathway, which is initiated from C5-sugars. In both pathways, IPP is isomerized to DMAPP by the enzyme isopentenyl pyrophosphate isomerase. Chemical structure of isopentenyl pyrophosphate. ... Structure of dimethyallyl pyrophosphate Dimethylallyl pyrophosphate (or -diphosphate) (DMAPP) is an intermediate product of both mevalonic acid (MVA) pathway and DOXP/MEP pathway. ... Categories: Biochemistry stubs | Thiols ... Mevalonic acid is a key organic compound in biochemistry. ... The HMG-CoA reductase pathway, also known as MVA pathway or mevalonate-dependent (MAD) route, is an important cellular metabolic pathway present in virtually all organisms. ...

Dimethylallyl pyrophosphate
Isopentenyl pyrophosphate

As chains of isoprene units are built up, the resulting terpenes are classified sequentially by size as hemiterpenes, monoterpenes, sesquiterpenes, diterpenes, sesterterpenes, triterpenes, and tetraterpenes. Image File history File links DMAPP.png Summary Chemical structure of dimethylallyl diphosphate created with ChemDraw. ... Image File history File links DMAPP.png Summary Chemical structure of dimethylallyl diphosphate created with ChemDraw. ... Image File history File links IPP.png Summary Chemical structure of isopentenyl diphosphate created with ChemDraw. ... Image File history File links IPP.png Summary Chemical structure of isopentenyl diphosphate created with ChemDraw. ...


Types

Second or third instar caterpillar of Papilio glaucus emit terpenes from their osmeterium
Second or third instar caterpillar of Papilio glaucus emit terpenes from their osmeterium
  • Hemiterpenes consist of a single isoprene unit. Isoprene itself is considered the only hemiterpene, but oxygen-containing derivatives such as prenol and isovaleric acid are hemiterpenoids.
  • Monoterpenes consist of two isoprene units and have the molecular formula C10H16. Examples of monoterpenes are: geraniol, limonene and terpineol.
  • Sesquiterpenes consist of three isoprene units and have the molecular formula C15H24. Examples of sesquiterpenes are: farnesol. The sesqui- prefix means one and a half.
  • Diterpenes are composed for four isoprene units and have the molecular formula C20H32. They derive from geranylgeranyl pyrophosphate. Examples of diterpenes are cafestol, kahweol, cembrene and taxadiene (precursor of taxol). Diterpenes also form the basis for biologically important compounds such as retinol, retinal, and phytol.
  • Sesterterpenes, terpenes having 25 carbons and five isoprene units, are rare relative to the other sizes. The sester- prefix means half to three, i.e. two and a half.
  • Triterpenes consist of six isoprene units and have the molecular formula C30H48. The linear triterpene squalene, the major constituent of shark liver oil, is derived from the reductive coupling of two molecules of farnesyl pyrophosphate. Squalene is then processed biosynthetically to generate either lanosterol or cycloartenol, the structural precursors to all the steroids.
  • Tetraterpenes contain eight isoprene units and have the molecular formula C40H56. Biologically important tetraterpenes include the acyclic lycopene, the monocyclic gamma-carotene, and the bicyclic alpha- and beta-carotenes.
  • Polyterpenes consist of long chains of many isoprene units. Natural rubber consists of polyisoprene in which the double bonds are cis. Some plants produce a polyisoprene with trans double bonds, known as gutta-percha.

Image File history File links Download high-resolution version (894x669, 64 KB) Second-Third Papilio glaucus instar showing osmeterium File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Terpene Eastern tiger swallowtail Swallowtail butterfly Osmeterium ... Image File history File links Download high-resolution version (894x669, 64 KB) Second-Third Papilio glaucus instar showing osmeterium File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Terpene Eastern tiger swallowtail Swallowtail butterfly Osmeterium ... An instar is a developmental stage of arthropods, such as insects, between each molt. ... Binomial name Papilio glaucus Linnaeus, 1758 The Eastern Tiger Swallowtail, Papilio glaucus, is a large (12 cm wingspan) Swallowtail Butterfly. ... 3-Methyl-2-buten-1-ol is a natural alcohol. ... 3-Methylbutanoic acid, or more commonly isovaleric acid, is a natural fatty acid found in a wide variety of plants and essential oils. ... Monoterpenes consist of two isoprene units and have the molecular formula C10H16. ... Geraniol, also called rhodinol, is a monoterpenoid and an alcohol. ... Limonene is a hydrocarbon, classed as a terpene. ... Terpineol is a naturally occurring monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. ... Sesquiterpenes consist of three isoprene units and have the molecular formula C15H24. ... Farnesol is a natural organic compound which is a sesquiterpene alcohol found as a colorless liquid. ... Chemical structure of geranylgeranyl pyrophosphate. ... Cafestol is a diterpene molecule present in coffee. ... Cembrene, or sometimes neocembrene, is a natural monocyclic diterpene. ... Paclitaxel is a drug used in the treatment of cancer. ... Retinol, the animal form of vitamin A, is a yellow fat-soluble, antioxidant vitamin important in vision and bone growth. ... Retinal, technically called retinene1 or retinaldehyde, is a light-sensitive retinene molecule found in the photoreceptor cells of the retina. ... Phytol is a natural linear diterpene alcohol which is used in the preparation of vitamins E and K1. ... Squalene is a natural organic compound originally obtained for commercial purposes primarily from shark liver oil, though there are botanic sources as well, including amaranth seed, rice bran, wheat germ, and olives. ... Shark liver oil is obtained from sharks caught for food purposes only, living in cold, deep oceans. ... Lanosterol is a tetracyclic triterpenoid which is the compound from which all steroids are derived. ... Cycloartenol is a sterol precursor in photosynthetic organisms and plants. ... This article is about the chemical family of steroids. ... Lycopene is a bright red carotenoid pigment, a phytochemical found in tomatoes and other red fruits. ... Carotene is responsible for the orange colour of the carrots and many other fruits and vegetables. ... Carotene is a terpene, an orange photosynthetic pigment, important for photosynthesis. ... Carotene is a terpene, an orange photosynthetic pigment, important for photosynthesis. ... This does not cite any references or sources. ... Cis-2-butene Trans-2-butene In chemistry, geometric isomerism or cis-trans isomerism is a form of stereoisomerism and describes the orientation of functional groups within the molecule. ... Species About 100-120 species, including: Palaquium amboinense Palaquium barnesii Palaquium bataanense Palaquium beccarianum Palaquium borneense Palaquium burckii Palaquium clarkeanum Palaquium cochleariifolium Palaquium dasyphyllum Palaquium ellipticum Palaquium formosanum Palaquium galactoxylum Palaquium gutta Palaquium herveyi Palaquium hexandrum Palaquium hispidum Palaquium hornei Palaquium impressinervium Palaquium kinabaluense Palaquium lanceolatum Palaquium leiocarpum Palaquium lobbianum...

Agri-chemical use

Research into terpenes has found that many of them possess qualities that make them ideal active ingredients as part of natural agricultural pesticides.


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External links

Wikimedia Commons has media related to:
Gallery Terpenes
  • Institute of Chemistry - terpenes
  • Structures of alpha pinene and beta pinene

  Results from FactBites:
 
Definition of terpene - Merriam-Webster Online Dictionary (75 words)
Learn more about "terpene" and related topics at Britannica.com
Find more about "terpene" instantly with Live Search
See a map of "terpene" in the Visual Thesaurus
Terpene Violin Varnish and Propolis Soap--Used as a Ground for Violin Varnish (2588 words)
Terpene Violin Varnish and Propolis Soap--Used as a Ground for Violin Varnish
He is well known for innovative and sometimes controversial ideas such as terpene varnish, plate bending, and the glazing method of finishing.
The turpentine varnish is made by cooking the terpene resin with the linseed oil.
  More results at FactBites »

 
 

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