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456055

Sigma-Aldrich

Camphene

95%

Synonym(s):

(±)-Camphene, 2,2-Dimethyl-3-methylenebicyclo[2.2.1]heptane, 2,2-Dimethyl-3-methylenenorbornane, 2,2-Dimethyl-3-methylidenebicyclo[2.2.1]heptane, 2-Methylene-3,3-dimethylbicyclo[2.2.1]heptane, 3,3-Dimethyl-2-methylenenorbornane, 3,3-Dimethyl-2-methylenenorcamphane, DL-Camphene

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About This Item

Empirical Formula (Hill Notation):
C10H16
CAS Number:
79-92-5
Molecular Weight:
136.23
EC Number:
201-234-8
MDL number:
MFCD00066603
UNSPSC Code:
12352100
PubChem Substance ID:
24869106
NACRES:
NA.22

Quality Level

100

Assay

95%

form

solid

bp

159-160 °C (lit.)

mp

48-52 °C (lit.)

density

0.85 g/mL at 25 °C (lit.)

SMILES string

[H][C@]12CC[C@]([H])(C1)C(C)(C)C2=C

InChI

1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3/t8-,9+/m0/s1

InChI key

CRPUJAZIXJMDBK-DTWKUNHWSA-N

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General description

Camphene is abicyclic monoterpene and a constituent of many essential oils derived fromvarious plants such as Alpinia speciosa, Xanthium strumariumleaves, needles of Pinus uncinata, and Pinus uliginosa.(5)

Application

Camphene can be used as a reactant to synthesize:
  • Isobornyl carboxylates by silica-supported tungstophosphoric acid-catalyzed liquid-phase esterification of C2-C6 fatty acids.
  • Hydroaminated camphene via intermolecular anti-Markovnikov hydroamination reaction with N-hydroxyphthalimide and triethyl phosphite in the presence of dilauroyl peroxide as an initiator.
  • Camphene oxide via methyltrioxorhenium-catalyzed epoxidation in the presence of H2O2 as an oxidant and pyrazole as a Lewis base adduct.
  • Isobornyl alkyl ethers using alcohols via cation exchange resin-catalyzed alkoxylation.

Signal Word

Danger

Hazard Statements

H228,H319,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Flam. Sol. 1

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 2

Flash Point(F)

78.8 °F - DIN 51755 Part 1

Flash Point(C)

26 °C - DIN 51755 Part 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW7368
0000188887
MKCS8585
0000258592
0000178665

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Radosław Bonikowski et al.
Natural product communications, 10(2), 371-373 (2015-04-30)
The compositions of mountain pine (Pinus uncinata) and peat-bog pine (P. uliginosa) needle essential oils were investigated. Enantiomeric compositions of selected monoterpene hydrocarbons were also examined. Respectively, fifty-three and seventy-six components of the essential oils were identified using GC-MS and
Dendritic growth kinetics and structure II. Camphene.
Rubinstein ER and Glicksman ME.
Journal of Crystal Growth, 112(1), 97-110 (1991)
Young J Hong et al.
Organic & biomolecular chemistry, 8(20), 4589-4600 (2010-08-21)
Based on quantum chemical studies, mechanisms to form bornyl diphosphate from geranyl diphosphate are suggested. While bornyl diphosphate is usually proposed to be generated via combination of the pyrophosphate group with a secondary bornyl cation, quantum chemical computations indicate that
A Sunesson et al.
Applied and environmental microbiology, 61(8), 2911-2918 (1995-08-01)
Five fungal species, Aspergillus versicolor, Penicillium commune, Cladosporium cladosporioides, Paecilomyces variotii, and Phialophora fastigiata, were cultivated on two media, malt extract agar and dichloran glycerol agar. Culture flasks provided with inlet and outlet tubes were used and purified, and humidified
Magdalena Ceborska et al.
Carbohydrate polymers, 91(1), 110-114 (2012-10-10)
The separation of isomeric monoterpenes, camphene and fenchene by complexation with β-cyclodextrin is presented. Both of the monoterpenes form complexes with β-cyclodextrin (as shown by both gas chromatography and (1)H NMR) with similar stability constants nevertheless it is possible to
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