Sabinene

Last updated
Sabinene [1]
(+-)-Sabinene Structural Formulea V.1.svg
Names
IUPAC name
4-methylene-1-(1-methylethyl)bicyclo[3.1.0]hexane
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.020.194 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h7,9H,3-6H2,1-2H3 Yes check.svgY
    Key: NDVASEGYNIMXJL-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h7,9H,3-6H2,1-2H3
    Key: NDVASEGYNIMXJL-UHFFFAOYAW
  • C=C2C1CC1(C(C)C)CC2
Properties
C10H16
Molar mass 136.23 g/mol
Density 0.844 g/mL at 20 °C g/cm3
Boiling point 163 to 164 °C (325 to 327 °F; 436 to 437 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Sabinene is a natural bicyclic monoterpene with the molecular formula C10H16. It is isolated from the essential oils of a variety of plants including Marjoram, [2] holm oak (Quercus ilex) and Norway spruce (Picea abies). It has a strained ring system with a cyclopentane ring fused to a cyclopropane ring.

Contents

Sabinene is one of the chemical compounds that contributes to the spiciness of black pepper and is a major constituent of carrot seed oil. It also occurs in tea tree oil at a low concentration. It is also present in the essential oil obtained from nutmeg, [3] Laurus nobilis , and Clausena anisata .

Biosynthesis

Sabinene, a bicyclic monoterpene, is present in the (+) and (-) enantiomers. [4] It is biosynthesized from the common terpenoid precursor, geranyl pyrophosphate (GPP) that undergoes polycyclization catalyzed by sabinene synthase (SabS). [4] [5] GPP is formed from the terpenoid synthesis pathway with the starter units, isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP). The starter units, IPP and DMAPP, can be synthesized from either the mevalonate (MVA) or the methylerythritol 4-phosphate (MEP) pathway. [4] With the head-to-tail condensation of IPP and DMAPP catalyzed by GPP synthase, GPP is formed. Sabinene synthase (SabS) then catalyzes the ionization and isomerization of GPP to form 3R-linalyl pyrophosphate. [4] [6] Further ionization and cyclization results in the formation of sabinene.

With the biosynthesis catalyzed by sabinene synthase, the precursor, geranyl pyrophosphate, undergoes isomerization and cyclization to form sabinene. Sabinene BIosynthesis.jpg
With the biosynthesis catalyzed by sabinene synthase, the precursor, geranyl pyrophosphate, undergoes isomerization and cyclization to form sabinene.

See also

Related Research Articles

<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">Dimethylallyl pyrophosphate</span> Chemical compound

Dimethylallyl pyrophosphate is an isoprenoid precursor. It is a product of both the mevalonate pathway and the MEP pathway of isoprenoid precursor biosynthesis. It is an isomer of isopentenyl pyrophosphate (IPP) and exists in virtually all life forms. The enzyme isopentenyl pyrophosphate isomerase catalyzes isomerization between DMAPP and IPP.

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

Geranyl pyrophosphate (GPP), also known as geranyl diphosphate (GDP), is the pyrophosphate ester of the terpenoid geraniol. Its salts are colorless. It is a precursor to many natural products.

Farnesyl pyrophosphate (FPP), also known as farnesyl diphosphate (FDP), is an intermediate in the biosynthesis of terpenes and terpenoids such as sterols and carotenoids. It is also used in the synthesis of CoQ, as well as dehydrodolichol diphosphate.

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 (monocyclic and bicyclic). 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.

The enzyme (+)-δ-cadinene synthase catalyzes the chemical reaction

<span class="mw-page-title-main">Bornyl diphosphate synthase</span>

In enzymology, bornyl diphosphate synthase (BPPS) (EC 5.5.1.8) is an enzyme that catalyzes the chemical reaction

The enzyme (–)-endo-Fenchol synthase (EC 4.2.3.10) catalyzes the chemical reaction

The enzyme sabinene-hydrate synthase (EC 4.2.3.11) catalyzes the chemical reaction

The enzyme monoterpenyl-diphosphatase (EC 3.1.7.3) catalyzes the reaction

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

Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Iridoids decrease the growth rates of many generalist herbivores.

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

Juvabione, historically known as the paper factor, is the methyl ester of todomatuic acid. Both are sesquiterpenes (C15) found in the wood of true firs of the genus Abies. They occur naturally as part of a mixture of sesquiterpenes based upon the bisabolane scaffold. Sesquiterpenes of this family are known as insect juvenile hormone analogues (IJHA) because of their ability to mimic juvenile activity in order to stifle insect reproduction and growth. These compounds play important roles in conifers as the second line of defense against insect induced trauma and fungal pathogens.

Patchoulol synthase (EC 4.2.3.70) is an enzyme with systematic name (2E,6E)-farnesyl-diphosphate diphosphate-lyase (patchoulol-forming). This enzyme catalyses the following chemical reaction

(+)-Car-3-ene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-car-3-ene-forming]. This enzyme catalyses the following chemical reaction

1,8-Cineole synthase (EC 4.2.3.108, 1,8-cineole cyclase, geranyl pyrophoshate:1,8-cineole cyclase, 1,8-cineole synthetase) is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase (cyclizing, 1,8-cineole-forming). This enzyme catalyses the following chemical reaction

(–)-Sabinene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (–)-sabinene-forming]. This enzyme catalyses the following chemical reaction

(+)-Sabinene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-sabinene-forming]. This enzyme catalyses the following chemical reaction

(+)-camphene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-camphene-forming]. This enzyme catalyses the following chemical reaction

(–)-α-Pinene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (–)-α-pinene-forming]. This enzyme catalyses the following chemical reaction

(+)-α-pinene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-α-pinene-forming]. This enzyme catalyses the following chemical reaction

References

  1. ↑ Beilstein . 5, IV, 451
  2. ↑ Verma, Ram S.; Padalia, Rajendra C.; Chauhan, Amit; Verma, Rajesh K.; Ur Rahman, Laiq; Singh, Anand (2016). "Changes in the Essential Oil Composition of Origanum majoranaL. During Post Harvest Drying". Journal of Essential Oil Bearing Plants. 19 (6): 1547–1552. doi:10.1080/0972060X.2014.935039. S2CID   99578528.
  3. ↑ Shulgin, A. T.; Sargent, T.; Naranjo, C. (1967). "The Chemistry and Psychopharmacology of Nutmeg and of Several Related Phenylisopropylamines" (pdf). Psychopharmacology Bulletin. 4 (3): 13. PMID   5615546.
  4. 1 2 3 4 5 Cao, Yujin; Zhang, Haibo; Liu, Hui; Liu, Wei; Zhang, Rubing; Xian, Mo; Liu, Huizhou (2018-02-01). "Biosynthesis and production of sabinene: current state and perspectives". Applied Microbiology and Biotechnology. 102 (4): 1535–1544. doi:10.1007/s00253-017-8695-5. ISSN   1432-0614. PMID   29264773. S2CID   27685411.
  5. ↑ Peters, R.J.; Croteau, R. B. (2003-09-15). "Alternative termination chemistries utilized by monoterpene cyclases: chimeric analysis of bornyl diphosphate, 1,8-cineole, and sabinene synthases". Archives of Biochemistry and Biophysics. 417 (2): 203–211. doi:10.1016/S0003-9861(03)00347-3. ISSN   0003-9861. PMID   12941302.
  6. 1 2 Adam, K. P.; Croteau, R. (1998-09-28). "Monoterpene Biosynthesis in the Liverwort Conocephalum Conicum: Demonstration of Sabinene Synthase and Bornyl Diphosphate Synthase in Honour of Professor G. H. Neil Towers 75th Birthday". Phytochemistry. 49 (2): 475–480. Bibcode:1998PChem..49..475A. doi:10.1016/S0031-9422(97)00741-3. ISSN   0031-9422. PMID   9747540.


This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.