Camphene
Not to be confused with camphine, a lamp fuel.
Camphene[1][2]
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Names
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Preferred IUPAC name
2,2-Dimethyl-3-methylidenebicyclo[2.2.1]heptane
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Other names
2,2-Dimethyl-3-methanylidenebicyclo[2.2.1]heptane 2,2-Dimethyl-3-methylenebicyclo[2.2.1]heptane
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Identifiers
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ChEBI
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ChEMBL
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ChemSpider
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ECHA InfoCard
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100.001.123
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EC Number
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KEGG
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RTECS number
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UNII
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UN number
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2319 1325
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InChI=1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3 YKey: CRPUJAZIXJMDBK-UHFFFAOYSA-N YInChI=1/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3 Key: CRPUJAZIXJMDBK-UHFFFAOYAL
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Properties
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C10H16
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Molar mass
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136.238 g·mol−1
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Appearance
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White or colorless solid[3]
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Density
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0.842 g/cm3[3]
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Melting point
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51 to 52 °C (124 to 126 °F; 324 to 325 K)[3]
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Boiling point
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159 °C (318 °F; 432 K)[3]
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Practically insoluble[3]
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Hazards
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GHS labelling:
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Warning
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H226, H228, H319, H410
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P210, P233, P240, P241, P242, P243, P264, P273, P280, P303+P361+P353, P305+P351+P338, P337+P313, P370+P378, P391, P403+P235, P501
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Flash point
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40 °C (104 °F; 313 K)
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[4] It is a minor constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil, neroli, ginger oil, valerian, and mango.[5] It is produced industrially by isomerization of the more common alpha-pinene using a solid acid catalyst such as titanium dioxide.[6]
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.[7]
References
- ^ IUCLID Datasheet[permanent dead link]
- ^ Fisher Scientific MSDS
- ^ a b c d e Merck Index, 11th Edition, 1736
- ^ Eggersdorfer, Manfred (2000). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN 978-3527306732.
- ^ 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.
- ^ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
- ^ a b 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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