Sabinene

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Sabinene[1]
Sabinene
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 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 ?)

Sabinene is a natural bicyclic

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

Sabinene, a bicyclic monoterpene, is present in the (+) and (-)

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

  • Thujene, a double bond isomer of sabinene

References

  1. ^ Beilstein. 5, IV, 451
  2. S2CID 99578528
    .
  3. PMID 5615546
    .
  4. ^
    S2CID 27685411
    .
  5. PMID 12941302
    .
  6. ^
    PMID 9747540
    .


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