Chemistry:Camphene
From HandWiki
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| Names | |||
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| 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)
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| ChEBI | |||
| ChEMBL | |||
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PubChem CID
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| UNII | |||
| UN number | 2319 1325 | ||
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| Properties | |||
| C10H16 | |||
| Molar mass | 136.238 g·mol−1 | ||
| Appearance | white or colorless solid[3] | ||
| Density | 0.842 g/cm3[3] | ||
| Melting point | 51 to 52 °C (124 to 126 °F; 324 to 325 K)[3] | ||
| Boiling point | 159 °C (318 °F; 432 K)[3] | ||
| Practically insoluble[3] | |||
| Hazards | |||
| GHS pictograms |   
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| GHS Signal word | Warning | ||
| H226, H228, H319, H410 | |||
| P210, P233, P240, P241, P242, P243, P264, P273, P280, P303+361+353, P305+351+338, P337+313, P370+378, P391, P403+235, 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). | |||
 verify (what is   ?)
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| Infobox references | |||
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
Biosynthesis of camphene (one enantiomer) from linalyl pyrophosphate.[7]
Camphene is biosynthesized from linalyl pyrophosphate via a sequence of carbocationic intermediates.[7]
References
- ↑ IUCLID Datasheet[yes|permanent dead link|dead link}}]
- ↑ Fisher Scientific MSDS
- ↑ 3.0 3.1 3.2 3.3 3.4 Merck Index, 11th Edition, 1736
- ↑ Eggersdorfer, Manfred (2000). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205.
- ↑ 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.
- ↑ 7.0 7.1 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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