Camphene

Chemical compound From Wikipedia, the free encyclopedia

Camphene is a bicyclic organic compound. It is one of the most pervasive monoterpenes. As with other terpenes, it is insoluble in water, flammable, colorless, and has a pungent smell.[2] It is a minor constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil, neroli, ginger oil, valerian, and mango.[3] It is produced industrially by isomerization of the more common alpha-pinene using a solid acid catalyst such as titanium dioxide.[4]

Quick Facts Names, Identifiers ...
Camphene
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Names
Preferred IUPAC name
2,2-Dimethyl-3-methylidenebicyclo[2.2.1]heptane
Other names
2,2-Dimethyl-3-methanylidenebicyclo[2.2.1]heptane
2,2-Dimethyl-3-methylenebicyclo[2.2.1]heptane
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.123
EC Number
  • 201-234-8
KEGG
RTECS number
  • EX1055000
UNII
UN number 2319 1325
  • InChI=1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3 Y
    Key: CRPUJAZIXJMDBK-UHFFFAOYSA-N Y
  • InChI=1/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3
    Key: CRPUJAZIXJMDBK-UHFFFAOYAL
  • C1(=C)C(C)(C)C2CC1CC2
Properties
C10H16
Molar mass 136.238 g·mol−1
Appearance White or colorless solid[1]
Density 0.842 g/cm3[1]
Melting point 51 to 52 °C (124 to 126 °F; 324 to 325 K)[1]
Boiling point 159 °C (318 °F; 432 K)[1]
Practically insoluble[1]
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS09: Environmental hazard
Warning
H226, H228, H319, H410
P210, P233, P240, P241, P242, P243, P264, P273, P280, P303+P361+P353, P305+P351+P338, P337+P313, P370+P378, P391, P403+P235, P501
Flash point 40 °C (104 °F; 313 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Camphene is used in the preparation of fragrances and as a food additive for flavoring. These include isobornyl acetate.

Biosynthesis

Camphene is biosynthesized from linalyl pyrophosphate via a sequence of carbocationic intermediates.[5]

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Biosynthesis of camphene (one enantiomer) from linalyl pyrophosphate.[5]

References

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