XIV

Camphene

Names
Preferred IUPAC name 2,2-Dimethyl-3-methylidenebicyclo※heptane
Other names 2,2-Dimethyl-3-methanylidenebicyclo※heptane 2,2-Dimethyl-3-methylenebicyclo※heptane
Identifiers
CAS Number	79-92-5 racemate ※ 5794-03-6]] + enantiomer 5794-04-7 - enantiomer
3D model (JSmol)	Interactive image
ChEBI	CHEBI:3830
ChEMBL	ChEMBL2268550
ChemSpider	6364
ECHA InfoCard	100.001.123
EC Number	201-234-8
KEGG	C06076
PubChem CID	6616
RTECS number	EX1055000
UNII	G3VG94Z26E
UN number	2319 1325
CompTox Dashboard (EPA)	DTXSID8026488
InChI InChI=1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3 Key: CRPUJAZIXJMDBK-UHFFFAOYSA-N 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
SMILES C1(=C)C(C)(C)C2CC1CC2
Properties
Chemical formula	C10H16
Molar mass	136.238 g·mol
Appearance	White/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
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). Y verify (what is  ?) 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. 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 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.

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.