beta-Pinene

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β-Pinene
Beta-pinen.svg
(1S)-(-)-beta-pinene-2D-projected-skeletal.png
(1S)-(−)-beta-pinene-from-xtal-3D-balls.png
Names
IUPAC names
6,6-Dimethyl-2-methylidenebicyclo[3.1.1]heptane
Pin-2(10)-ene
Other names
6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptane
2(10)-Pinene
Nopinene
Pseudopinene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.430 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3 checkY
    Key: WTARULDDTDQWMU-UHFFFAOYSA-N checkY
  • InChI=1/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3
    Key: WTARULDDTDQWMU-UHFFFAOYAW
  • C1(=C)C2CC(CC1)C2(C)C
Properties
C10H16
Molar mass 136.238 g·mol−1
Appearance Colorless liquid
Density 0.872 g/mL
Melting point −61.54 °C; −78.77 °F; 211.61 K[1]
Boiling point 165–167 °C; 329–332 °F; 438–440 K[2]
Thermochemistry
−6214.1±2.9 kJ/mol[1]
Hazards
R-phrases (outdated) R10 R36 R37 R38
S-phrases (outdated) S26 S36
NFPA 704 (fire diamond)
1
3
0
Flash point 36 °C (97 °F; 309 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

beta-Pinene (β-pinene) is a monoterpene, an organic compound found in plants. It is one of the two isomers of pinene, the other being α-pinene. It is colorless liquid soluble in alcohol, but not water. It has a woody-green pine-like smell.

This is one of the most abundant compounds released by forest trees.[3] If oxidized in air, the allylic products of the pinocarveol and myrtenol family prevail.[4]

Sources[edit]

Many plants from many botanical families contain the compound, including:

References[edit]

  1. ^ a b "β-Pinene". National Institute of Standards and Technology. Retrieved January 29, 2018.
  2. ^ "(−)-β-Pinene". Sigma-Aldrich. Retrieved January 29, 2018.
  3. ^ Geron, C., et al. (2000). A review and synthesis of monoterpene speciation from forests in the United States. Atmospheric Environment 34(11), 1761-81.
  4. ^ a b Neuenschwander, U.; Meier, E.; Hermans, I. (2011). "Peculiarities of β-pinene autoxidation". ChemSusChem. 4 (11): 1613–21. doi:10.1002/cssc.201100266. PMID 21901836.
  5. ^ Li, Rong; Jiang, Zi-Tao (2004). "Chemical composition of the essential oil of Cuminum cyminum L. From China". Flavour and Fragrance Journal. 19 (4): 311–313. doi:10.1002/ffj.1302.
  6. ^ Wang, L.; Wang, Z.; Zhang, H.; Li, X.; Zhang, H. (2009). "Ultrasonic nebulization extraction coupled with headspace single drop microextraction and gas chromatography-mass spectrometry for analysis of the essential oil in Cuminum cyminum L". Analytica Chimica Acta. 647 (1): 72–7. doi:10.1016/j.aca.2009.05.030. PMID 19576388.
  7. ^ Tinseth, G. The Essential Oil of Hops: Hop Aroma and Flavor in Hops and Beer. Archived 2013-11-11 at the Wayback Machine Brewing Techniques January/February 1994. Accessed July 21, 2010.
  8. ^ Hillig, Karl W (October 2004). "A chemotaxonomic analysis of terpenoid variation in Cannabis". Biochemical Systematics and Ecology. 32 (10): 875–891. doi:10.1016/j.bse.2004.04.004. ISSN 0305-1978.