Camphene

Last updated
Camphene
Camphene.png
Camphene BS.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-234-8
KEGG
PubChem CID
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 Yes check.svgY
    Key: CRPUJAZIXJMDBK-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceWhite 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:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
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 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]

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]

Biosynthesis of camphene (one enantiomer) from linalyl pyrophosphate. CampheneBiosyn.svg
Biosynthesis of camphene (one enantiomer) from linalyl pyrophosphate.

References

  1. 1 2 3 4 5 Merck Index , 11th Edition, 1736
  2. ↑ Eggersdorfer, Manfred (2000). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN   978-3-527-30673-2.
  3. ↑ Pino, Jorge A.; Mesa, Judith; Muñoz, Yamilie; Martí, M. Pilar; Marbot, Rolando (2005). "Volatile Components from Mango (Mangifera indicaL.) Cultivars". Journal of Agricultural and Food Chemistry. 53 (6): 2213–2223. doi:10.1021/jf0402633. PMID   15769159.
  4. ↑ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN   0471238961.
  5. 1 2 Croteau, R.; Satterwhite, D. M.; Cane, D. E.; Chang, C. C. (1988). "Biosynthesis of Monoterpenes. Enantioselectivity in the Enzymatic Cyclization of (+)- and (-)-Linalyl Pyrophosphate to (+)- and (-)-Pinene and (+)- and (-)-Camphene". The Journal of Biological Chemistry. 263 (21): 10063–71. doi: 10.1016/S0021-9258(19)81477-1 . PMID   3392006.
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