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Camphene

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Not to be confused with camphine, a lamp fuel.
Camphene
Names
Preferred IUPAC name 2,2-Dimethyl-3-methylidenebicycloheptane
Other names 2,2-Dimethyl-3-methanylidenebicycloheptane
2,2-Dimethyl-3-methylenebicycloheptane
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.123 Edit this at Wikidata
EC Number
  • 201-234-8
KEGG
PubChem CID
RTECS number
  • EX1055000
UNII
UN number 2319 1325
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3Key: CRPUJAZIXJMDBK-UHFFFAOYSA-N
  • InChI=1/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3Key: CRPUJAZIXJMDBK-UHFFFAOYAL
SMILES
  • C1(=C)C(C)(C)C2CC1CC2
Properties
Chemical formula C10H16
Molar mass 136.238 g·mol
Appearance White or colorless solid
Density 0.842 g/cm
Melting point 51 to 52 °C (124 to 126 °F; 324 to 325 K)
Boiling point 159 °C (318 °F; 432 K)
Solubility in water Practically insoluble
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS07: Exclamation markGHS09: Environmental hazard
Signal word Warning
Hazard statements H226, H228, H319, H410
Precautionary statements 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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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. It is a minor constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil, neroli, ginger oil, valerian, and mango. It is produced industrially by isomerization of the more common alpha-pinene using a solid acid catalyst such as titanium dioxide.

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.

Biosynthesis of camphene (one enantiomer) from linalyl pyrophosphate.

References

  1. IUCLID Datasheet
  2. Fisher Scientific MSDS
  3. ^ Merck Index, 11th Edition, 1736
  4. Eggersdorfer, Manfred (2000). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN 978-3527306732.
  5. 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.
  6. Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
  7. ^ 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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