Camphene

Camphene^[1]^[2]
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
CAS Number	79-92-5 ;
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−1
Appearance	white or colorless solid
Density	0.842 g/cm3
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 pictograms
GHS Signal word	Warning
GHS hazard statements	H226, H228, H319, H400, H410
GHS precautionary statements	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).

Camphene is a bicyclic organic compound. It is one of the most pervasive monoterpenes. As for 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 catalytic isomerization of the more common alpha-pinene. Camphene is used in the preparation of fragrances and as a food additive for flavoring.

Camphene is biosynthesized from geranyl pyrophosphate.^[6]

References

^ IUCLID Datasheet
^ 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.
^ 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.
^ 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. PMID 3392006.

[1] IUCLID Datasheet

[2] Fisher Scientific MSDS

[Merck-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.

[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] 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. PMID 3392006.

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