Sabinene

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Sabinene[1]
Sabinene
Names
IUPAC name
4-methylene-1-(1-methylethyl)bicyclo[3.1.0]hexane
Identifiers
  • 3387-41-5 checkY
  • 10408-16-9 (-) checkY
  • 2009-00-9 (+) checkY
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.020.194 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h7,9H,3-6H2,1-2H3 checkY
    Key: NDVASEGYNIMXJL-UHFFFAOYSA-N checkY
  • 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).
checkY verify (what is checkY☒N ?)
Infobox references

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.

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[edit]

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.[4][6]

See also[edit]

  • Thujene, a double bond isomer of sabinene

References[edit]

  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. ^ a b c d e 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. ^ a b 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. doi:10.1016/S0031-9422(97)00741-3. ISSN 0031-9422. PMID 9747540.