Β-Pinene

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
CAS Number	127-91-3 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:50025 Y
ChEMBL	ChEMBL501351 Y
ChemSpider	14198 Y
DrugBank	DB15574
ECHA InfoCard	100.004.430
EC Number	204-872-5
KEGG	C09882 Y
PubChem CID	14896
UNII	4MS8VHZ1HJ Y
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 Y Key: WTARULDDTDQWMU-UHFFFAOYSA-N 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
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[1]
Boiling point	165–167 °C; 329–332 °F; 438–440 K[2]
Thermochemistry
Std enthalpy of combustion (ΔcH⦵298)	−6214.1±2.9 kJ/mol[1]
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). Y verify (what is YN ?) Infobox references

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:

• Cuminum cyminum^[6][7]
• Humulus lupulus^[8]
• Pinus pinaster^[5]
• Clausena anisata
• Cannabis sativa^[9]
• Piper nigrum^[10]
• Myristica fragans .^[10]
• Citrus aurantiifolia^[10]
• Pistacia lentiscus^[10]

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

Uses

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 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

1. "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. 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. 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. 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.