β-Pinene

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
CAS Number	127-91-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:50025 ;
ChEMBL	ChEMBL501351 ;
ChemSpider	14198 ;
DrugBank	DB15574;
ECHA InfoCard	100.004.430
EC Number	204-872-5;
KEGG	C09882 ;
PubChem CID	14896;
UNII	4MS8VHZ1HJ ;
CompTox Dashboard (EPA)	DTXSID7027049 ;
	InChI InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3 Key: WTARULDDTDQWMU-UHFFFAOYSA-N ; 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;
	SMILES C1(=C)C2CC(CC1)C2(C)C;
Properties
Chemical formula	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
Boiling point	165–167 °C; 329–332 °F; 438–440 K
Thermochemistry
Std enthalpy of; combustion (ΔcH⦵298)	−6214.1±2.9 kJ/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H304, H315, H317, H410
Precautionary statements	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)	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). verify (what is ?) Infobox references

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 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

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

The clear compound is produced by distillation of turpentine oils.^[14]

Uses

β-Pinene is used in 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 myrcene^[15]).^[16]

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.^[14]^[17]

References

1 2 "β-Pinene". National Institute of Standards and Technology. Retrieved January 29, 2018.
↑ "(−)-β-Pinene". Sigma-Aldrich. Retrieved January 29, 2018.
↑ 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
↑ Geron, C.; et al. (2000). "A review and synthesis of monoterpene speciation from forests in the United States". Atmospheric Environment. 34 (11): 1761–1781. Bibcode:2000AtmEn..34.1761G. doi:10.1016/S1352-2310(99)00364-7. Archived from the original on 2021-02-28.
1 2 Neuenschwander, U.; Meier, E.; Hermans, I. (2011). "Peculiarities of β-pinene autoxidation". ChemSusChem. 4 (11): 1613–21. Bibcode:2011ChSCh...4.1613N. doi:10.1002/cssc.201100266. PMID 21901836.
↑ 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.
↑ 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. Bibcode:2009AcAC..647...72W. doi:10.1016/j.aca.2009.05.030. PMID 19576388.
↑ 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.
↑ Hillig, Karl W (October 2004). "A chemotaxonomic analysis of terpenoid variation in Cannabis". Biochemical Systematics and Ecology. 32 (10): 875–891. Bibcode:2004BioSE..32..875H. doi:10.1016/j.bse.2004.04.004. ISSN 0305-1978.
1 2 3 4 Santana de Oliveira, Mozaniel (2022). Essential oils: applications and trends in food science and technology. Cham, Switzerland: Springer. ISBN 978-3-030-99476-1.
↑ Kaya, Ayla; Demirci, Bora; Baser, K. Husnu Can (January 2010). "Composition of the essential oil of Seseli campestre Besser growing in Northwest Anatolia". Turkish Journal of Pharmaceutical Sciences. 7 (2): 162 – via Academia.edu.
↑ Baser, K. Husnu Can; Ozek, Temel; Kurkcuoglu, M.; Aytaç, Zeki (January–February 2000). "Essential Oil of Seseli campestre Besser". Journal of Essential Oil Research. 12 (1): 105–107. doi:10.1080/10412905.2000.9712054 – via Academia.edu.
↑ Vaglica, Alessandro; Maggio, Antonella; Badalamenti, Natale; Bruno, Maurizio; Lauricella, Marianna; Occhipinti, Chiara; D’Anneo, Antonella (2024-02-28). "Seseli tortuosum L. subsp. tortuosum Essential Oils and Their Principal Constituents as Anticancer Agents". Plants. 13 (5): 680. Bibcode:2024Plnts..13..678V. doi:10.3390/plants13050678. ISSN 2223-7747. PMC 10935401. PMID 38475524.
1 2 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.
↑ 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.
↑ Mattiello, Joseph J. (1945). Protective and Decorative Coatings. U.S. Government Printing Office.
↑ 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.

[auto-1] 1 2 "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): 1761–1781. Bibcode:2000AtmEn..34.1761G. doi:10.1016/S1352-2310(99)00364-7. Archived from the original on 2021-02-28.

[herm-5] 1 2 Neuenschwander, U.; Meier, E.; Hermans, I. (2011). "Peculiarities of β-pinene autoxidation". ChemSusChem. 4 (11): 1613–21. Bibcode:2011ChSCh...4.1613N. doi:10.1002/cssc.201100266. PMID 21901836.

[li-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. Bibcode:2009AcAC..647...72W. 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): 875–891. Bibcode:2004BioSE..32..875H. doi:10.1016/j.bse.2004.04.004. ISSN 0305-1978.

[:0-10] 1 2 3 4 Santana de Oliveira, Mozaniel (2022). Essential oils: applications and trends in food science and technology. Cham, Switzerland: Springer. ISBN 978-3-030-99476-1.

[:24-11] Kaya, Ayla; Demirci, Bora; Baser, K. Husnu Can (January 2010). "Composition of the essential oil of Seseli campestre Besser growing in Northwest Anatolia". Turkish Journal of Pharmaceutical Sciences. 7 (2): 162 – via Academia.edu.

[:26-12] Baser, K. Husnu Can; Ozek, Temel; Kurkcuoglu, M.; Aytaç, Zeki (January–February 2000). "Essential Oil of Seseli campestre Besser". Journal of Essential Oil Research. 12 (1): 105–107. doi:10.1080/10412905.2000.9712054 – via Academia.edu.

[13] Vaglica, Alessandro; Maggio, Antonella; Badalamenti, Natale; Bruno, Maurizio; Lauricella, Marianna; Occhipinti, Chiara; D’Anneo, Antonella (2024-02-28). "Seseli tortuosum L. subsp. tortuosum Essential Oils and Their Principal Constituents as Anticancer Agents". Plants. 13 (5): 680. Bibcode:2024Plnts..13..678V. doi:10.3390/plants13050678. ISSN 2223-7747. PMC 10935401. PMID 38475524.

[:1-14] 1 2 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.

[15] 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.

[16] Mattiello, Joseph J. (1945). Protective and Decorative Coatings. U.S. Government Printing Office.

[17] 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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