Bisabolene

Last updated
Bisabolenes
Bisabolene-alpha.svg
α-Bisabolene
Bisabolene-beta.svg
β-Bisabolene
Bisabolene-gamma.svg
γ-Bisabolene
Names
IUPAC names
(α): (E)-1-Methyl-4-(6-methylhepta-2,5-dien-2-yl)cyclohex-1-ene
(β): (S)-1-Methyl-4-(6-methylhepta-1,5-dien-2-yl)cyclohex-1-ene
(γ): (Z)-1-Methyl-4-(6-methylhept-5-en-2-ylidene)cyclohex-1-ene
Identifiers
3D model (JSmol)
α: 2414203
β: 2044625
γ: 2501191
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • α:InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6-8,15H,5,9-11H2,1-4H3/b14-7-
  • β:InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,15H,4-5,7,9-11H2,1-3H3/t15-/m1/s1
  • γ:InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8H,5,7,9-11H2,1-4H3/b15-14+
  • α:CC1=CCC(/C(C)=C/C/C=C(C)/C)CC1
  • β:CC1=CC[C@@H](C(CC/C=C(C)/C)=C)CC1
  • γ:CC(CC/1)=CCC1=C(C)/CC/C=C(C)/C
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).

Bisabolenes are a group of closely related natural chemical compounds which are classified as sesquiterpenes. Bisabolenes are produced from farnesyl pyrophosphate (FPP) [1] 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 [2] and fruit flies. [3] Bisabolenes are produced by several fungi, though their biological role in that group of organisms remains unclear. [4]

Contents

Three isomers are known, α-, β-, and γ-bisabolene, [5] [6] which differ by the positions of the double bonds.

Uses

Bisabolenes are intermediates in the biosynthesis of many other natural chemical compounds, [7] including hernandulcin, a natural sweetener. β-Bisabolene has a balsamic odor [8] and is approved in Europe as a food additive.

Bisabolene has been identified as a biologically producible precursor to a diesel fuel alternative and/or cold weather additive bisabolane. [9]

See also

Related Research Articles

<span class="mw-page-title-main">Carotene</span> Class of compounds

The term carotene (also carotin, from the Latin carota, "carrot") is used for many related unsaturated hydrocarbon substances having the formula C40Hx, which are synthesized by plants but in general cannot be made by animals (with the exception of some aphids and spider mites which acquired the synthesizing genes from fungi). Carotenes are photosynthetic pigments important for photosynthesis. Carotenes contain no oxygen atoms. They absorb ultraviolet, violet, and blue light and scatter orange or red light, and (in low concentrations) yellow light.

<span class="mw-page-title-main">Terpene</span> Class of oily organic compounds found in plants

Terpenes are a class of natural products consisting of compounds with the formula (C5H8)n for n ≥ 2. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. Terpenes are further classified by the number of carbons: monoterpenes (C10), sesquiterpenes (C15), diterpenes (C20), as examples. The terpene alpha-pinene is a major component of the common solvent, turpentine.

<span class="mw-page-title-main">Carotenoid</span> Class of chemical compounds; yellow, orange or red plant pigments

Carotenoids are yellow, orange, and red organic pigments that are produced by plants and algae, as well as several bacteria, archaea, and fungi. Carotenoids give the characteristic color to pumpkins, carrots, parsnips, corn, tomatoes, canaries, flamingos, salmon, lobster, shrimp, and daffodils. Over 1,100 identified carotenoids can be further categorized into two classes – xanthophylls and carotenes.

<span class="mw-page-title-main">Pyrethrin</span> Class of organic chemical compounds with insecticidal properties

The pyrethrins are a class of organic compounds normally derived from Chrysanthemum cinerariifolium that have potent insecticidal activity by targeting the nervous systems of insects. Pyrethrin naturally occurs in chrysanthemum flowers and is often considered an organic insecticide when it is not combined with piperonyl butoxide or other synthetic adjuvants. Their insecticidal and insect-repellent properties have been known and used for thousands of years.

<span class="mw-page-title-main">Astaxanthin</span> Chemical compound

Astaxanthin is a keto-carotenoid within a group of chemical compounds known as terpenes. Astaxanthin is a metabolite of zeaxanthin and canthaxanthin, containing both hydroxyl and ketone functional groups. It is a lipid-soluble pigment with red coloring properties, which result from the extended chain of conjugated double bonds at the center of the compound.

Polyketides are a class of natural products derived from a precursor molecule consisting of a chain of alternating ketone (or reduced forms of a ketone) and methylene groups: (-CO-CH2-). First studied in the early 20th century, discovery, biosynthesis, and application of polyketides has evolved. It is a large and diverse group of secondary metabolites caused by its complex biosynthesis which resembles that of fatty acid synthesis. Because of this diversity, polyketides can have various medicinal, agricultural, and industrial applications. Many polyketides are medicinal or exhibit acute toxicity. Biotechnology has enabled discovery of more naturally-occurring polyketides and evolution of new polyketides with novel or improved bioactivity.

<span class="mw-page-title-main">Farnesol</span> Chemical compound

Farnesol is a natural 15-carbon organic compound which is an acyclic sesquiterpene alcohol. Under standard conditions, it is a colorless liquid. It is hydrophobic, and thus insoluble in water, but miscible with oils.

<span class="mw-page-title-main">Farnesene</span> 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.

<span class="mw-page-title-main">Zingerone</span> Chemical compound

Zingerone, also called vanillylacetone, is a major flavor component of ginger, providing the sweet flavor of cooked ginger. Zingerone is a crystalline solid that is sparingly soluble in water and soluble in ether.

Mycolic acids are long fatty acids found in the cell walls of the Mycolata taxon, a group of bacteria that includes Mycobacterium tuberculosis, the causative agent of the disease tuberculosis. They form the major component of the cell wall of mycolata species. Despite their name, mycolic acids have no biological link to fungi; the name arises from the filamentous appearance their presence gives mycolata under high magnification. The presence of mycolic acids in the cell wall also gives mycolata a distinct gross morphological trait known as "cording". Mycolic acids were first isolated by Stodola et al. in 1938 from an extract of M. tuberculosis.

Polyketide synthases (PKSs) are a family of multi-domain enzymes or enzyme complexes that produce polyketides, a large class of secondary metabolites, in bacteria, fungi, plants, and a few animal lineages. The biosyntheses of polyketides share striking similarities with fatty acid biosynthesis.

<span class="mw-page-title-main">Hinokitiol</span> Chemical compound

Hinokitiol (β-thujaplicin) is a natural monoterpenoid found in the wood of trees in the family Cupressaceae. It is a tropolone derivative and one of the thujaplicins. Hinokitiol is used in oral and skin care products, and is a food additive used in Japan.

<span class="mw-page-title-main">Methyl eugenol</span> Chemical compound

Methyl eugenol (allylveratrol) is a natural chemical compound classified as a phenylpropene, a type of phenylpropanoid. It is the methyl ether of eugenol and is important to insect behavior and pollination. It is found in various essential oils.

<span class="mw-page-title-main">Chemical defense</span>

Chemical defense is a strategy employed by many organisms to avoid consumption by producing toxic or repellent metabolites or chemical warnings which incite defensive behavioral changes. The production of defensive chemicals occurs in plants, fungi, and bacteria, as well as invertebrate and vertebrate animals. The class of chemicals produced by organisms that are considered defensive may be considered in a strict sense to only apply to those aiding an organism in escaping herbivory or predation. However, the distinction between types of chemical interaction is subjective and defensive chemicals may also be considered to protect against reduced fitness by pests, parasites, and competitors. Repellent rather than toxic metabolites are allomones, a sub category signaling metabolites known as semiochemicals. Many chemicals used for defensive purposes are secondary metabolites derived from primary metabolites which serve a physiological purpose in the organism. Secondary metabolites produced by plants are consumed and sequestered by a variety of arthropods and, in turn, toxins found in some amphibians, snakes, and even birds can be traced back to arthropod prey. There are a variety of special cases for considering mammalian antipredatory adaptations as chemical defenses as well.

β-Farnesene synthase (EC 4.2.3.47, farnesene synthase, terpene synthase 10, terpene synthase 10-B73, TPS10) is an enzyme with systematic name (2E,6E)-farnesyl-diphosphate diphosphate-lyase ((E)-β-farnesene-forming). This enzyme catalyses the following chemical reaction

β-Phellandrene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase . This enzyme catalyses the following chemical reaction

(–)-β-Pinene synthase (EC 4.2.3.120, β-geraniolene synthase, (–)-(1S,5S)-pinene synthase, geranyldiphosphate diphosphate lyase (pinene forming)) is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (–)-β-pinene-forming]. This enzyme catalyses the following chemical reaction

(S)-β-macrocarpene synthase is an enzyme with systematic name (S)-β-macrocarpene lyase (decyclizing). This enzyme catalyses the following chemical reaction

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.

β-Cyclocitral Chemical compound

β-Cyclocitral (beta-cyclocitral) is an apocarotenoid derived from the C7 oxidation of β-carotene. This apocarotenoid has revived interest due to its roles in plant development. β-cyclocitral has been found endogenously in a variety of organisms including plants, cyanobacteria, fungi and animals. β-Cyclocitral is a volatile compound that contributes to the aroma of various fruits, vegetables and ornamental plants. In plants, β-cyclocitral was found to be an important regulator in root development.

References

  1. "MetaCyc bisabolene biosynthesis (engineered)". biocyc.org. Retrieved 2018-05-28.
  2. Aldrich, J.R.; Numata, H.; Borges, M.; Bin, F.; Waite, G.K.; Lusby, W.R. (1993). "Artifacts and pheromone blends from Nezara spp. and other stink bug (Heteroptera: Pentatomidae)". Zeitschrift für Naturforschung. 48C (1–2): 73–79. doi: 10.1515/znc-1993-1-214 . S2CID   40523228. Archived from the original on 2013-04-08. Retrieved 2013-10-22.
  3. Lu, F.; Teal, P.E. (2001). "Sex pheromone components in oral secretions and crop of male Caribbean fruit flies, Anastrepha suspensa (Loew)". Archives of Insect Biochemistry and Physiology. 48 (3): 144–154. doi:10.1002/arch.1067. PMID   11673844.
  4. Spakowicz, Daniel J.; Strobel, Scott A. (2015). "Biosynthesis of hydrocarbons and volatile organic compounds by fungi: bioengineering potential". Applied Microbiology and Biotechnology. 99 (12): 4943–4951. doi:10.1007/s00253-015-6641-y. PMC   4677055 . PMID   25957494.
  5. "pubchem/alpha-Bisabolene".
  6. "pubchem/beta-Bisabolene".
  7. Bisabolene derived sesquiterpenoid biosynthesis Archived November 2, 2010, at the Wayback Machine
  8. (−)-β-bisabolene, flavornet.org
  9. "Alternative Diesel Fuel from Biosynthetic Bisabolene". 13 August 2014.