Βべーた-Pinene: Difference between revisions

{{DISPLAYTITLE:βべーた-Pinene}}

| verifiedrevid = 443421864

| ImageFile = Beta-pinen.svg

| 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}}

| PubChem = 14896

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 4MS8VHZ1HJ

|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べーた-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べーた-Pinene | access-date = January 29, 2018 | publisher = [[Sigma-Aldrich]] }}</ref>

| Solubility =

|Section3={{Chembox Thermochemistry

| DeltaHc = {{val|-6214.1|2.9|u=kJ/mol}}<ref name="auto"/>

}}

|Section4={{Chembox Hazards

| MainHazards =

| FlashPtC = 36

| AutoignitionPtC =

| 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べーた-Pinene''' is a [[monoterpene]], an organic compound found in plants. It is one of the two [[isomer]]s of [[pinene]], the other being [[alpha-Pinene|αあるふぁ-pinene]]. It is a [[color]]less [[liquid]] [[solubility|soluble]] in [[ethanol|alcohol]], but not [[water]]. It has a [[wood]]y-green [[pine]]-like [[odour|smell]].

βべーた-Pinene is one of the most abundant compounds released by forest trees.<ref>Geron, C., et al. (2000). [http://hero.epa.gov/index.cfm?action=reference.details&reference_id=19095 A review and synthesis of monoterpene speciation from forests in the United States.] ''Atmospheric Environment'' 34(11), 1761-81.</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べーた-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>Tinseth, G. [http://morebeer.com/brewingtechniques/library/backissues/issue2.1/tinseth.html The Essential Oil of Hops: Hop Aroma and Flavor in Hops and Beer.] {{Webarchive|url=https://web.archive.org/web/20131111102913/http://morebeer.com/brewingtechniques/library/backissues/issue2.1/tinseth.html |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>

* ''[[Black pepper|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|Myristica fragans .]]''<ref name=":0" />

* ''[[Key lime|Citrus aurantiifolia]]''<ref name=":0" />

* ''[[Pistacia lentiscus]]''<ref name=":0" />

The clear compund is produced by [[distillation]] of [[Turpentine|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=6. completely revised and updated |location=Weinheim}}</ref>

==Uses==

{{expand section|date=October 2023}}

βべーた-Pinene is used in fragrances and essential oils. It is also used in the production of other [[Aroma compound|aroma compounds]], such as [[myrcene]] and [[nerol]] (got by careful fractional distillation of crude nerol got 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>). The myrcene is got by pyrolysis of αあるふぁ-Pinene or βべーた-Pinene.<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> Reacting with [[formaldehyde]], result is nopol. When nopol is [[Acetylation|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>

[[Category:Vinylidene compounds]]

[[Category:Bicyclic compounds]]

[[Category:Cyclobutanes]]