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โ‡ฑ ฮฒ-Pinene - Wikipedia

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ฮฒ-Pinene
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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 ๐Ÿ‘ 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 ๐Ÿ‘ check
    Y
    Key: WTARULDDTDQWMU-UHFFFAOYSA-N ๐Ÿ‘ check
    Y
  • 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 gยทmolโˆ’1
Appearance Colorless liquid
Density 0.872 g/mL
Melting point โˆ’61.54 ยฐC; โˆ’78.77 ยฐF; 211.61 K[1]
Boiling point 165โ€“167 ยฐC; 329โ€“332 ยฐF; 438โ€“440 K[2]
Thermochemistry
Std enthalpy of
combustion (ฮ”cHโฆต298)
 โˆ’6214.1ยฑ2.9 kJ/mol[1]
Hazards
GHS labelling:
๐Ÿ‘ GHS02: Flammable
๐Ÿ‘ GHS07: Exclamation mark
๐Ÿ‘ GHS08: Health hazard
๐Ÿ‘ GHS09: 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)
Flash point 36 ยฐC (97 ยฐF; 309 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 ยฐC [77 ยฐF], 100 kPa).
Chemical compound

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

ฮฒ-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

[edit]

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

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

Uses

[edit]

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

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

References

[edit]
  1. ^ a b "ฮฒ-Pinene". National Institute of Standards and Technology. Retrieved January 29, 2018.
  2. ^ "(โˆ’)-ฮฒ-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. 247โ€“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): 1761โ€“1781. Archived from the original on 2021-02-28.
  5. ^ a b Neuenschwander, U.; Meier, E.; Hermans, I. (2011). "Peculiarities of ฮฒ-pinene autoxidation". ChemSusChem. 4 (11): 1613โ€“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): 311โ€“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): 72โ€“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 from the original on 2013-11-11. 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): 875โ€“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 (6th 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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