{{Lowercase title}} {{chembox | Watchedfields = changed | Name = β-Pinene | verifiedrevid = 443421864 | ImageFile = Beta-pinen.svg | ImageSize = 130 | ImageFileL1 = (1S)-(-)-beta-pinene-2D-projected-skeletal.png | ImageFileR1 = (1S)-(−)-beta-pinene-from-xtal-3D-balls.png | IUPACName = 6,6-Dimethyl-2-methylidenebicyclo[3.1.1]heptane<br />Pin-2(10)-ene | OtherNames = 6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptane<br />2(10)-Pinene<br />Nopinene<br />Pseudopinene |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 127-91-3 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 501351 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 50025 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID=14198 | DrugBank = DB15574 | EINECS = 204-872-5 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C09882 | PubChem = 14896 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 4MS8VHZ1HJ | InChI = 1/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3 | InChIKey = WTARULDDTDQWMU-UHFFFAOYAW | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = WTARULDDTDQWMU-UHFFFAOYSA-N | SMILES = C1(=C)C2CC(CC1)C2(C)C }} |Section2={{Chembox Properties | C=10 | H=16 | Appearance = Colorless liquid | Density = 0.872 g/mL | MeltingPtK = 211.61 | MeltingPt_ref = <ref name="auto">{{cite web | url = http://webbook.nist.gov/cgi/cbook.cgi?Name=beta-pinene&Units=SI&cTG=on&cIR=on&cTC=on&cTZ=on&cTP=on&cMS=on&cTR=on&cUV=on&cIE=on&cGC=on&cIC=on&cES=on&cDI=on&cSO=on | title = β-Pinene | access-date = January 29, 2018 | publisher = National Institute of Standards and Technology }}</ref> | BoilingPtK = 438-440 | BoilingPt_ref = <ref>{{cite web | url = https://www.sigmaaldrich.com/catalog/product/aldrich/402753?lang=pt&region=BR | title = (−)-β-Pinene | access-date = January 29, 2018 | publisher = Sigma-Aldrich }}</ref> }} |Section3={{Chembox Thermochemistry | DeltaHc = {{val|-6214.1|2.9|u=kJ/mol}}<ref name="auto"/> }} |Section4={{Chembox Hazards | FlashPtC = 36 | NFPA-H = 1 | NFPA-F = 3 | NFPA-R = 0 | GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}}{{GHS09}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|226|304|315|317|410}} | PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|272|273|280|301+310|302+352|303+361+353|321|331|332+313|333+313|362|363|370+378|391|403+235|405|501}} }} }}

'''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.<ref>{{citation | editor=Arza Seidel|display-editors=etal| author=Charles S. Sell | chapter=Terpenoids | title=Kirk-Othmer Chemical Technology of Cosmetics | year=2013 | pages=247–374|publisher=John Wiley & Sons | isbn=978-1-118-40692-2}}</ref> 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.<ref>{{cite journal|last=Geron |first=C. |display-authors=etal |date=2000 |url=https://hero.epa.gov/reference/19095/|archive-url=https://web.archive.org/web/20210228065359/https://hero.epa.gov/hero/index.cfm/reference/details/reference_id/19095|url-status=live|archive-date=2021-02-28|title=A review and synthesis of monoterpene speciation from forests in the United States |journal=Atmospheric Environment |volume=34 |issue=11 |pages=1761–1781}}</ref> If oxidized in air, the allylic products of the pinocarveol and myrtenol family prevail.<ref name=herm>{{cite journal | pmid = 21901836| year = 2011| last1 = Neuenschwander| first1 = U.| last2 = Meier| first2 = E.| last3 = Hermans| first3 = I.| title = Peculiarities of β-pinene autoxidation| journal = ChemSusChem| volume = 4| issue = 11| pages = 1613–21| doi = 10.1002/cssc.201100266}}</ref>

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

* ''Cuminum cyminum''<ref name=li>{{cite journal | doi = 10.1002/ffj.1302| title = Chemical composition of the essential oil of ''Cuminum cyminum'' L. From China| year = 2004| last1 = Li| first1 = Rong| last2 = Jiang| first2 = Zi-Tao| journal = Flavour and Fragrance Journal| volume = 19| issue = 4| pages = 311–313}}</ref><ref>{{cite journal | pmid = 19576388 | year = 2009 | last1 = Wang | first1 = L. | last2 = Wang | first2 = Z. | last3 = Zhang | first3 = H. | last4 = Li | first4 = X. | last5 = Zhang | first5 = H. | title = Ultrasonic nebulization extraction coupled with headspace single drop microextraction and gas chromatography-mass spectrometry for analysis of the essential oil in ''Cuminum cyminum'' L. | journal = Analytica Chimica Acta | volume = 647 | issue = 1 | pages = 72–7 | doi = 10.1016/j.aca.2009.05.030 }}</ref> *''Humulus lupulus''<ref>{{cite web|last=Tinseth |first=G. |url=http://morebeer.com/brewingtechniques/library/backissues/issue2.1/tinseth.html |title=The Essential Oil of Hops: Hop Aroma and Flavor in Hops and Beer. |archive-url=https://web.archive.org/web/20131111102913/http://morebeer.com/brewingtechniques/library/backissues/issue2.1/tinseth.html |url-status=live |archive-date=2013-11-11 }} ''Brewing Techniques'' January/February 1994. Accessed July 21, 2010.</ref> * ''Pinus pinaster''<ref name=herm/> * ''Clausena anisata'' * ''Cannabis sativa''<ref>{{Cite journal|last=Hillig|first=Karl W|date=October 2004|title=A chemotaxonomic analysis of terpenoid variation in ''Cannabis''|journal=Biochemical Systematics and Ecology|volume=32|issue=10|pages=875–891|doi=10.1016/j.bse.2004.04.004|issn=0305-1978}}</ref> * ''Piper nigrum''<ref name=":0">{{Cite book |last=Santana de Oliveira |first=Mozaniel |title=Essential oils: applications and trends in food science and technology |date=2022 |publisher=Springer |isbn=978-3-030-99476-1 |location=Cham, Switzerland}}</ref> * ''Myristica fragrans''<ref name=":0" /> * ''Citrus aurantiifolia''<ref name=":0" /> * ''Pistacia lentiscus''<ref name=":0" /> The clear compound is produced by distillation of turpentine oils.<ref name=":1">{{Cite book |last1=Surburg |first1=Horst |title=Common fragrance and flavor materials: preparation, properties and uses |last2=Panten |first2=Johannes |date=2016 |publisher=Wiley-VCH Verlag GmbH & Co. KGaA |isbn=978-3-527-33160-4 |edition=6th completely revised and updated |location=Weinheim}}</ref>

==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<ref>{{Cite book |last=Opdyke |first=D. L. J. |url=https://books.google.com/books?id=IDkvBQAAQBAJ |title=Monographs on Fragrance Raw Materials: A Collection of Monographs Originally Appearing in Food and Cosmetics Toxicology |date=2013-10-22 |publisher=Elsevier |isbn=978-1-4831-4797-0 |language=en}}</ref>).<ref>{{Cite book |last=Mattiello |first=Joseph J. |url=https://books.google.com/books?id=2GouxJ7nsuYC |title=Protective and Decorative Coatings |date=1945 |publisher=U.S. Government Printing Office |language=en}}</ref>

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.<ref name=":1" /><ref>{{Cite book |last=Opdyke |first=D. L. J. |url=https://books.google.com/books?id=IDkvBQAAQBAJ |title=Monographs on Fragrance Raw Materials: A Collection of Monographs Originally Appearing in Food and Cosmetics Toxicology |date=2013-10-22 |publisher=Elsevier |isbn=978-1-4831-4797-0 |language=en}}</ref>

==References== {{reflist}}

{{DEFAULTSORT:Pinene, beta-}} Category:Flavors Category:Perfume ingredients Category:Vinylidene compounds Category:Monoterpenes Category:Bicyclic compounds Category:Cyclobutanes