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

3D model (JSmol)

Interactive image

ChEBI

CHEBI:3830^Y

ChEMBL

ChEMBL2268550

ChemSpider

6364^Y

ECHA InfoCard

100.001.123

EC Number

201-234-8

KEGG

C06076^Y

PubChem CID

6616

RTECS number

EX1055000

UNII

G3VG94Z26E^Y

UN number

2319 1325

CompTox Dashboard (EPA)

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 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 [77 °F], 100 kPa).

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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.

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Transcription

Biosynthesis

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

References

^ IUCLID Datasheet^{[permanent dead link]}
^ 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. ISBN 978-3527306732.
^ 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.
^ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
^ ^a ^b 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.

This page was last edited on 8 March 2024, at 14:43

Camphene

From Wikipedia, the free encyclopedia

YouTube Encyclopedic

Transcription

Biosynthesis

References