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. 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. If oxidized in air, the allylic products of the pinocarveol and myrtenol family prevail.

Sources

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

The clear compound is produced by distillation of turpentine oils.

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).

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.

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.