Camphene

Title: Camphene
CAS Registry Number: 79-92-5
CAS Name: 2,2-Dimethyl-3-methylenebicyclo[2.2.1]heptane
Additional Names: 2,2-dimethyl-3-methylenenorbornane; 3,3-dimethyl-2-methylenenorcamphane
Molecular Formula: C10H16
Molecular Weight: 136.23
Percent Composition: C 88.16%, H 11.84%
Literature References: Occurs in many essential oils, such as turpentine (levo and dextro forms), in cypress oil (dextro form), in camphor oil from species of Lauraceae (dextro), in bergamot oil, in oil of citronella, neroli, ginger, valerian. Reviews on isolation, preparation and properties: J. L. Simonsen, The Terpenes vol. II (Cambridge Univ. Press, 1949) pp 280-322; E. Guenther, The Essential Oils vol. II (Van Nostrand, 1949) pp 66-70. Synthesis: G. W. Hana, H. Koch, Ber. 111, 2527 (1968).
Derivative Type: dl-Form
Properties: Cubic crystals from alcohol. Large dodecahedra by slow sublimation. Volatilizes on exposure to air. Insipid odor. mp 51-52°. bp760 158.5-159.5°; bp100 92.4°; bp16 55-56°. d454 0.8422. nD54 1.45514. Practically insol in water. Moderately sol in alcohol; sol in ether, cyclohexane, cyclohexene, dioxane, chloroform.
Melting point: mp 51-52°
Boiling point: bp760 158.5-159.5°; bp100 92.4°; bp16 55-56°
Index of refraction: nD54 1.45514
Density: d454 0.8422
Derivative Type: d-Form
Properties: mp 52°. [a]D17 +103.5° (c = 9.67 in ether). d450 0.8486. nD50 1.4605.
Melting point: mp 52°
Optical Rotation: [a]D17 +103.5° (c = 9.67 in ether)
Index of refraction: nD50 1.4605
Density: d450 0.8486
Derivative Type: l-Form
Properties: mp 52°. [a]D21 -119.11° (c = 2.33 in benzene). d454 0.8422. nD40 1.4620.
Melting point: mp 52°
Optical Rotation: [a]D21 -119.11° (c = 2.33 in benzene)
Index of refraction: nD40 1.4620
Density: d454 0.8422
Camphoric Acid Camphotamide Camylofine Canadine Candelilla Wax

Camphene[1][2]
Camphene.png Camphene BS.png
Identifiers
CAS number 79-92-5 YesY
PubChem 6616
ChemSpider 6364 YesY
UNII G3VG94Z26E YesY
EC number 201-234-8
KEGG C06076 YesY
ChEBI CHEBI:3830 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H16
Molar mass 136.23 g mol−1
Appearance Crystalline 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
R-phrases R11 R36/37/38 R50/53
S-phrases S16 S26 S29 S37/39 S57
Flash point 40 °C; 104 °F; 313 K
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Camphene is bicyclic monoterpene. It is nearly insoluble in water, but very soluble in common organic solvents. It volatilizes readily at room temperature 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, and valerian. 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. Its mid-19th century use as a fuel for lamps was limited by its explosiveness.