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β-Pinene

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β-Pinene is a monoterpene, an organic compound found in plants. It is the less abundant of the two isomers of pinene, the other being α-pinene.[3] It is a colorless liquid soluble in alcohol, but not water. It has a woody-green pine-like smell.

β-Pinene
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
DrugBank
ECHA InfoCard 100.004.430 Edit this at Wikidata
EC Number
  • 204-872-5
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
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H226, H304, H315, H317, H410
P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301 P310, P302 P352, P303 P361 P353, P321, P331, P332 P313, P333 P313, P362, P363, P370 P378, P391, P403 P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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 ?)

β-Pinene is one of the most abundant compounds released by forest trees.[4] If oxidized in air, the allylic products of the pinocarveol and myrtenol family prevail.[5]

Sources

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

The clear compound is produced by distillation of turpentine oils.[11]

Uses

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β-Pinene is usedin the production of other aroma compounds. It converts to myrcene upon heating at 500 °C. Nerol is obtained by careful fractional distillation of crude nerol from from myrcene[12]).[13]

Reaction with formaldehyde (Prins reaction) converts β-pinene to nopol. When nopol is acetylated, the result is nopyl acetate, which is used as fragrance material.[11][14]

References

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  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. ^ Charles S. Sell (2013), "Terpenoids", in Arza Seidel; et al. (eds.), Kirk-Othmer Chemical Technology of Cosmetics, John Wiley & Sons, pp. 247–374, ISBN 978-1-118-40692-2
  4. ^ Geron, C., et al. (2000). A review and synthesis of monoterpene speciation from forests in the United States. Atmospheric Environment 34(11), 1761-81.
  5. ^ 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.
  6. ^ 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.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
  10. ^ a b c d Santana de Oliveira, Mozaniel (2022). Essential oils: applications and trends in food science and technology. Cham, Switzerland: Springer. ISBN 978-3-030-99476-1.
  11. ^ a b Surburg, Horst; Panten, Johannes (2016). Common fragrance and flavor materials: preparation, properties and uses (6. completely revised and updated ed.). Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA. ISBN 978-3-527-33160-4.
  12. ^ Opdyke, D. L. J. (2013-10-22). Monographs on Fragrance Raw Materials: A Collection of Monographs Originally Appearing in Food and Cosmetics Toxicology. Elsevier. ISBN 978-1-4831-4797-0.
  13. ^ Mattiello, Joseph J. (1945). Protective and Decorative Coatings. U.S. Government Printing Office.
  14. ^ Opdyke, D. L. J. (2013-10-22). Monographs on Fragrance Raw Materials: A Collection of Monographs Originally Appearing in Food and Cosmetics Toxicology. Elsevier. ISBN 978-1-4831-4797-0.
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