Camphene

Camphene[1][2] |

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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 racemate
* [1] 5794-03-6]] \+ enantiomer
* 5794-04-7 \- enantiomer

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:3830 Y

ChEMBL |

* ChEMBL2268550

ChemSpider |

* 6364 Y

EC Number |

* 201-234-8

KEGG |

* C06076 Y

PubChem CID

* 6616

RTECS number |

* EX1055000

UNII |

* G3VG94Z26E Y

UN number | 2319 1325

InChI

* InChI=1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3 Y

Key: CRPUJAZIXJMDBK-UHFFFAOYSA-N Y

* 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[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]

Solubility in water

| Practically insoluble[3]
Hazards
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H226, H228, H319, 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).

Y verify (what is YN ?)
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

File:CampheneBiosyn.svg

Biosynthesis of camphene (one enantiomer) from linalyl pyrophosphate.[7]

Camphene is biosynthesized from linalyl pyrophosphate via a sequence of carbocationic intermediates.[7]

## References

1. ↑ IUCLID Datasheet[yes|permanent dead link|dead link}}]
2. ↑ Fisher Scientific MSDS
3. ↑ 3.0 3.1 3.2 3.3 3.4 Merck Index, 11th Edition, 1736
4. ↑ Eggersdorfer, Manfred (2000). "Ullmann's Encyclopedia of Industrial Chemistry". 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. ↑ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
7. ↑ 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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*[CID]: Compound ID
*[H226]: Flammable liquid and vapour
*[H228]: Flammable solid
*[H319]: Causes serious eye irritation
*[H410]: Very toxic to aquatic life with long lasting effects
*[P210]: Keep away from heat/sparks/open flames/hot surfaces – No smoking
*[P233]: Keep container tightly closed
*[P240]: Ground/bond container and receiving equipment
*[P241]: Use explosion-proof electrical/ventilating/light/…/equipment
*[P242]: Use only non-sparking tools
*[P243]: Take precautionary measures against static discharge
*[P264]: Wash … thoroughly after handling
*[P273]: Avoid release to the environment
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P337+313]: Get medical advice/attention
*[P370+378]: In case of fire: Use … for extinction
*[P391]: Collect spillage
*[P403+235]: Store in a well ventilated place. Keep cool
*[P501]: Dispose of contents/container to …