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3-Carene

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Carene
Carene
Names
Preferred IUPAC name
3,7,7-Trimethylbicyclo[4.1.0]hept-3-ene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.033.367 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h6-8H,4-5H2,1-3H3 checkY
    Key: KALFVDDBBPRATR-UHFFFAOYSA-N checkY
  • InChI=1/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h6-8H,4-5H2,1-3H3
    Key: KALFVDDBBPRATR-UHFFFAOYAY
  • CC2(C)C\1CCC(C)/C=C/12
Properties
C10H16
Molar mass 136.238 g·mol−1
Density 0.86 g/cm3 (20 °C)[1]
Boiling point 170–172 °C (338–342 °F; 443–445 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Carene, or delta-3-carene, is a bicyclic monoterpene consisting of fused cyclohexene and cyclopropane rings. It occurs as a constituent of turpentine,[2] with a content as high as 42% depending on the source. Carene has a sweet and pungent odor.[3] A colorless liquid, it is not soluble in water, but miscible with fats and oils.[3] It is chiral, occurring naturally both as the racemate and enantio-enriched forms.

Reactions and uses

Treatment with peracetic acid gives 3,4-caranediol. Pyrolysis over ferric oxide induces rearrangement, giving p-cymene. Carene is used in the perfume industry and as a chemical intermediate.[2]

References

  1. ^ a b Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ a b "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2005. doi:10.1002/14356007.a26_205. {{cite encyclopedia}}: Unknown parameter |authors= ignored (help)
  3. ^ a b Merck Index (12th ed.). 1996. p. 300. 1885.