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Camphene

From Wikipedia, the free encyclopedia
Not to be confused withcamphine, a lamp fuel.
Camphene
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.001.123Edit this at Wikidata
EC Number
  • 201-234-8
KEGG
RTECS number
  • EX1055000
UNII
UN number2319 1325
  • InChI=1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3 checkY
    Key: CRPUJAZIXJMDBK-UHFFFAOYSA-N checkY
  • 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
  • C1(=C)C(C)(C)C2CC1CC2
Properties
C10H16
Molar mass136.238 g·mol−1
AppearanceWhite or colorless solid[1]
Density0.842 g/cm3[1]
Melting point51 to 52 °C (124 to 126 °F; 324 to 325 K)[1]
Boiling point159 °C (318 °F; 432 K)[1]
Practically insoluble[1]
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS09: Environmental hazard
Warning
H226,H228,H319,H410
P210,P233,P240,P241,P242,P243,P264,P273,P280,P303+P361+P353,P305+P351+P338,P337+P313,P370+P378,P391,P403+P235,P501
Flash point40 °C (104 °F; 313 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Camphene is a bicyclicorganic compound. It is one of the most pervasivemonoterpenes. As with other terpenes, it isinsoluble in water, flammable, colorless, and has a pungent smell.[2] It is a minor constituent of manyessential oils such asturpentine,cypress oil,camphor oil,citronella oil,neroli,ginger oil,valerian, andmango.[3] It is produced industrially by isomerization of the more commonalpha-pinene using asolid acidcatalyst such astitanium dioxide.[4]

Camphene is used in the preparation of fragrances and as a food additive for flavoring. These includeisobornyl acetate.

Biosynthesis

[edit]

Camphene is biosynthesized fromlinalyl pyrophosphate via a sequence ofcarbocationic intermediates.[5]

Biosynthesis of camphene (one enantiomer) from linalyl pyrophosphate.[5]

References

[edit]
  1. ^abcdeMerck Index, 11th Edition,1736
  2. ^Eggersdorfer, Manfred (2000). "Terpenes".Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.doi:10.1002/14356007.a26_205.ISBN 978-3-527-30673-2.
  3. ^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.
  4. ^Sell, Charles S. (2006). "Terpenoids".Kirk-Othmer Encyclopedia of Chemical Technology.doi:10.1002/0471238961.2005181602120504.a01.pub2.ISBN 0471238961.
  5. ^abCroteau, 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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