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{{Short description|Oily organic chemical found in plants}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 383401219 |
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| verifiedrevid = 446720672 |
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| Name = Pinene |
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| Name = Pinene |
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| ImageFile = Alpha-pinen.png |
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| ImageFile = Alpha-pinen.svg |
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| ImageSize = 150px |
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| ImageSize = 150px |
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| ImageName = Pinene |
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| ImageName = Pinene |
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| IUPACName = (1''S'',5''S'')-2,6,6-trimethylbicyclohept-2-ene or (1''S'',5''S'')-6,6-dimethyl-2-methylenebicycloheptane |
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| IUPACName = (1''S'',5''S'')-2,6,6-trimethylbicyclohept-2-ene <br/> (1''S'',5''S'')-6,6-dimethyl-2-methylenebicycloheptane |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| SMILES = |
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| SMILES = CC1=CCC2CC1C2(C)C |
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| index_label = (mixture) |
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| CASNo_Ref = {{cascite}} |
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| index2_label = (1''R''-α) |
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| CASNo=80-56-8 |
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| index3_label = (1''S''-α) |
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| CASOther = (unspecified)<br> (1''R''-α)<br> (1''S''-α)<br> ((±)-α)<br> (β) |
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| index4_label = (1''R''-β) |
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| RTECS = |
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| index5_label = (1''S''-β) |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 1330-16-1 |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| CASNo2 = 7785-70-8 |
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| CASNo3_Ref = {{cascite|correct|CAS}} |
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| CASNo3 = 7785-26-4 |
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| CASNo4_Ref = {{cascite|correct|CAS}} |
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| CASNo4 = 19902-08-0 |
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| CASNo5_Ref = {{cascite|correct|CAS}} |
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| CASNo5 = 18172-67-3 |
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| ChEBI = 17187 |
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| ChEBI2 = 28261 |
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| ChEBI3 = 28660 |
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| ChEBI5 = 50025 |
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| ChemSpiderID2 = 74205 |
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| ChemSpiderID3 = 389795 |
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| ChemSpiderID4 = 8466294 |
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| ChemSpiderID5 = 14198 |
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| EC_number2 = 232-087-8 |
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| PubChem2 = 82227 |
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| PubChem3 = 15837102 |
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| PubChem4 = 10290825 |
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| PubChem5 = 440967 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 996299PUKB |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2 = H6CM4TWH1W |
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| UNII3_Ref = {{fdacite|correct|FDA}} |
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| UNII3 = TZR3GM95PR |
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| UNII4_Ref = {{fdacite|correct|FDA}} |
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| UNII4 = IGO73S04D5 |
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| UNII5_Ref = {{fdacite|correct|FDA}} |
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| UNII5 = AFN153A7SU |
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| RTECS = |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>10</sub>H<sub>16</sub> |
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| Formula = C<sub>10</sub>H<sub>16</sub> |
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| MolarMass = 136.24 g/mol |
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| MolarMass = 136.24 g/mol |
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| Appearance = Liquid |
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| Appearance = Liquid |
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| Density = 0,86 g·cm<sup>−3</sup> (alpha, 15 °C)<ref name="GESTIS">{{GESTIS|ZVG=491170|CAS=80-56-8|Name=alpha-Pinen|Date=24. January 2008}}</ref><ref name="GESTIS beta">{{GESTIS|ZVG=492888|Name=beta-Pinen|Date=24. January 2008}}</ref> |
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| Density = 0,86 g·cm<sup>−3</sup> (alpha, 15 °C)<ref name="GESTIS">{{GESTIS|ZVG=491170|CAS=80-56-8|Name=alpha-Pinen|Date=07-January-2016}}</ref><ref name="GESTIS beta">{{GESTIS|ZVG=492888|Name=beta-Pinen|Date=07-January-2016}}</ref> |
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| Solubility = Practically insoluble in water |
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| Solubility = Practically insoluble in water |
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| MeltingPtC = −62 to −55 |
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| MeltingPt = −62–−55 °C (alpha)<ref name="GESTIS"/> |
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| BoilingPt = 155–156 °C (alpha)<ref name="GESTIS"/> |
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| MeltingPt_notes = (alpha)<ref name="GESTIS"/> |
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| BoilingPtC = 155 to 156 |
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| BoilingPt_notes = (alpha)<ref name="GESTIS"/> |
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}} |
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}} |
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}} |
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}} |
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'''Pinene''' (C<sub>10</sub>H<sub>16</sub>) is a bicyclic ] ].{{Ref|Mann}} There are two structural ]s of pinene found in nature: ] and ]. As the name suggests, both forms are important constituents of ] ]; they are also found in the resins of many other ], as well as in non-coniferous ]s. Both isomers are used by many insects in their chemical communication system. |
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'''Pinene''' is a collection of unsaturated bicyclic ]s. Two geometric ]s of pinene are found in nature, ] and ]. Both are chiral. As the name suggests, pinenes are found in ]. Specifically, pinene is the major component of the liquid extracts of ].<ref name=terp>{{Ullmann |doi=10.1002/14356007.a27_267|title=Turpentines |year=2000 |last1=Gscheidmeier |first1=Manfred |last2=Fleig |first2=Helmut |isbn=3527306730 }}</ref> Pinenes are also found in many non-coniferous ]s such as camphorweed ('']'')<ref>{{Cite journal|vauthors=Lincoln DE, Lawrence BM|date=1984|title=The Volatile Constituents of Camphorweed, ''Heterotheca subaxillaris''|journal=Phytochemistry|volume=23|issue=4|pages=933–934|doi=10.1016/S0031-9422(00)85073-6|bibcode=1984PChem..23..933L }}</ref> and big sagebrush ('']''). |
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== Isomers == |
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== Isomers == |
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{| class="wikitable" style="margin:1em auto; text-align:center;" |
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<center> |
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| ''']'''||]||]||]||] |
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{|align="center" class="wikitable" |
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|<center>''']'''</center>||<center>]</center>||<center>]</center>||<center>]</center>||<center>]</center> |
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|<center>'''perspective view'''</center>||<center>X</center>||<center>]</center>||<center>X</center>||<center>]</center> |
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| '''perspective view'''||X||]||X||] |
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|<center>''']'''</center>||<center>X</center>||<center>]</center>||<center>X</center>||<center>]</center> |
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| ''']'''||X||]||X||] |
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|<center>'''name'''</center>||<center>(1''R'')-(+)-α-pinene</center>||<center>(1''S'')-(−)-α-pinene</center>||<center>(1''R'')-(+)-β-pinene</center>||<center>(1''S'')-(−)-β-pinene</center> |
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| '''name'''||(1''R'')-(+)-α-pinene||(1''S'')-(−)-α-pinene||(1''R'')-(+)-β-pinene||(1''S'')-(−)-β-pinene |
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|<center>''']'''</center>||<center>7785-70-8</center>||<center>7785-26-4</center>||<center>19902-08-0</center>||<center>18172-67-3</center> |
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| ''']'''||7785-70-8||7785-26-4||19902-08-0||18172-67-3 |
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</center> |
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== Biosynthesis == |
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== Biosynthesis == |
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α-Pinene and β-pinene are both produced from ], via cyclisation of ] pyrophosphate followed by loss of a proton from the carbocation equivalent. |
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α-Pinene and β-pinene are both produced from ], via cyclisation of ] pyrophosphate followed by loss of a proton from the carbocation equivalent. Researchers at the Georgia Institute of Technology and the Joint BioEnergy Institute have been able to synthetically produce pinene with a bacterium.<ref name=":0">{{Cite journal|vauthors=Sarria S, Wong B, Martín HG, Keasling JD, Peralta-Yahya P|date=2014|title=Microbial Synthesis of Pinene|journal=ACS Synthetic Biology|volume=3|issue=7|pages=466–475|doi=10.1021/sb4001382|pmid=24679043|doi-access=free}}{{open access}}</ref> |
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] |
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] |
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== Usage == |
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==Plants== |
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] is the most widely encountered terpenoid in nature<ref name="noma2010">{{Cite book|url=https://www.taylorfrancis.com/books/e/9780429155666|title=Handbook of Essential Oils: Science, Technology, and Applications|vauthors=Noma Y, Asakawa Y|publisher=CRC Press|year=2010|isbn=9780429155666|veditors=Baser KH, Buchbauer G|edition=2nd|location=Boca Raton, FL|pages=585–736|chapter=Biotransformation of Monoterpenoids by Microorganisms, Insects, and Mammals}}</ref> and is highly repellent to insects.<ref name="nerio2010">{{cite journal |vauthors=Nerio LS, Olivero-Verbel J, Stashenko E |title=Repellent activity of essential oils: a review |journal=Bioresour Technol |volume=101 |issue=1 |pages=372–378 |year=2010 |doi=10.1016/j.biortech.2009.07.048 |pmid=19729299|bibcode=2010BiTec.101..372N }}</ref> |
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In chemical industry, selective oxidation of pinene with some catalysts gives many compounds for ], such as artificial odorants. An important oxidation product is ], along with pinene oxide, verbenol and verbenyl hydroperoxide. |
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<ref> |
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Alpha-pinene appears in ] and numerous other plants.<ref name="russo2011"/> Pinene is a major component of the essential oils of '']'' spp. (ironwort)<ref>{{Cite journal|vauthors=Köse EO, Deniz İG, Sarıkürkçü C, Aktaş Ö, Yavuz M|date=2010|title=Chemical composition, antimicrobial and antioxidant activities of the essential oils of Sideritis erythrantha Boiss. and Heldr. (var. erythrantha and var. cedretorum P.H. Davis) endemic in Turkey|journal=Food and Chemical Toxicology|volume=48|issue=10|pages=2960–2965|doi=10.1016/j.fct.2010.07.033|pmid=20670669}}</ref> and |
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{{Literatur |
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'']'' spp. (sage).<ref>{{Cite journal|display-authors=6|vauthors=Özek G, Demirci F, Özek T, Tabanca N, Wedge DE, Khan SI, Başer KH, Duran A, Hamzaoglu E|date=2010|title=Gas chromatographic-mass spectrometric analysis of volatiles obtained by four different techniques from Salvia rosifolia Sm., and evaluation for biological activity|journal=Journal of Chromatography A|volume=1217|issue=5|pages=741–748|doi=10.1016/j.chroma.2009.11.086|pmid=20015509}}</ref> '']'' also contains alpha-pinene<ref name="russo2011">{{cite journal|vauthors=Russo EB|date=2011|title=Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects|journal=British Journal of Pharmacology|volume=163|issue=7|pages=1344–1364|doi=10.1111/j.1476-5381.2011.01238.x|pmc=3165946|pmid=21749363}}</ref> and ].<ref>{{Cite journal|vauthors=Hillig KW|date=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|bibcode=2004BioSE..32..875H }}</ref> Resin from '']'' (commonly known as terebinth or turpentine tree) is rich in pinene. ] produced by ] trees contain pinene.<ref name="russo2011"/> |
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|Autor=U. Neuenschwander |
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|Titel=Mechanism of the Aerobic Oxidation of α-Pinene |
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] fruit peel contains an essential oil comparable to lime fruit peel oil; its main components are limonene and β-pinene.<ref name="kasuan">{{cite journal|vauthors=Kasuan N|date=2013|title=Extraction of ''Citrus hystrix'' D.C. (Kaffir Lime) Essential Oil Using Automated Steam Distillation Process: Analysis of Volatile Compounds|url=http://www.ukm.my/mjas/v17_n3/Nurhani.pdf|journal=Malaysian Journal of Analytical Sciences|volume=17|issue=3|pages=359–369}}</ref> |
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|Sammelwerk=ChemSusChem |
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|Band=3 |
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The racemic mixture of the two forms of pinene is found in some oils like eucalyptus oil.<ref>{{Cite web|title=alpha-Pinene - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/compound/alpha-pinene#section=Top|access-date=14 Nov 2017|website=PubChem|publisher=]}}</ref> |
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|Nummer=1 |
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|Jahr=2010 |
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== Reactions == |
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|Seiten=75–84 |
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===α-Pinene=== |
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|DOI=10.1002/cssc.200900228 |
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Selective oxidation of α-pinene occurs at the allylic position to give ], along with pinene oxide, as well as verbenol and its hydroperoxide.<ref>{{cite journal|vauthors=Neuenschwander U, Guignard F, Hermans I|date=2010|title=Mechanism of the Aerobic Oxidation of α-Pinene|journal=ChemSusChem|language=de|volume=3|issue=1|pages=75–84|doi=10.1002/cssc.200900228|pmid=20017184|doi-access=free|bibcode=2010ChSCh...3...75N }}</ref><ref>{{cite journal |doi=10.15227/orgsyn.072.0057|title=(1R,5R)-(+)-Verbenone of High Optical Purity |journal=Organic Syntheses |year=1995 |volume=72 |page=57|author=Mark R. Sivik, Kenetha J. Stanton, Leo A. Paquette }}</ref> |
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}} |
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</ref> |
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] |
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α-Pinene can be converted to ] by way of ]. |
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Pinenes are the primary constituents of ]. |
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] of pinene gives ], precursor to a useful pinane]. |
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The ] of α-pinene has been extensively examined. With ], two equivalents of α-pinene react to give (diisopinocampheyl)borane.<ref>{{cite journal |doi=10.15227/orgsyn.092.0026|title=Preparation of Crystalline (Diisopinocampheyl)borane |year=2015 |last1=Abbott |first1=Jason |first2=Christophe|last2=Allais|first3=William R.|last3=Roush| |
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journal=Organic Syntheses |volume=92 |pages=26–37 |doi-access=free }}</ref> Reaction with ] gives the reagent called ]. This sterically crowded ] trialkylborane can ]ly reduce aldehydes in what is known as the ].<ref>{{cite journal |last1=Midland |first1=M. Mark |title=B -3-Pinanyl-9-borabicyclononane |journal=Encyclopedia of Reagents for Organic Synthesis |date=15 April 2001 |doi=10.1002/047084289X.rp173}}</ref> |
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==References== |
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===β-Pinene=== |
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β-Pinene can be converted to α-pinene in the presence of strong bases,<ref>{{cite journal |doi=10.15227/orgsyn.065.0224|title=(a)-b-PINENE BY ISOMERIZATION OF (B)-b-PINENE |journal=Organic Syntheses |year=1987 |volume=65 |page=224|author=Charles A. Brown, Prabhakav K. Jadhav }}</ref> or pyrolysed to produce ] at 400 °C. |
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<references /> |
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# {{Note|Mann}} J. Mann, R. S. Davidson, J. B. Hobbs, D. V. Banthorpe, J. B. Harborne, ''Natural Products'', pp309-311, Addison Wesley Longman Ltd., Harlow, UK, 1994. ISBN 0-582-06009-5. |
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# {{Note|orgsyn}} ], Coll. Vol. 9, p.745 (1998); Vol. 72, p.57 (1995). |
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==External links== |
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==Use== |
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Pinenes, especially α, are the primary constituents of ], a nature-derived solvent and fuel.<ref name=terp/> |
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The use of pinene as a biofuel in ] has been explored.<ref>{{Cite journal|vauthors=Raman V, Sivasankaralingam V, Dibble R, Sarathy SM|date=2016|title=α-Pinene - A High Energy Density Biofuel for SI Engine Applications|journal=SAE Technical Paper|series=SAE Technical Paper Series|volume=1|doi=10.4271/2016-01-2171}}</ref> Pinene ] have been shown to have heating values comparable to the ].<ref name=":0" /> |
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== References == |
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{{reflist}} |
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== Bibliography == |
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* {{cite book|first1=J.|last1=Mann|first2=R. S.|last2=Davidson|first3=J. B.|last3=Hobbs|first4=D. V.|last4=Banthorpe|first5=J. B.|last5=Harborne|title=Natural Products|pages=|publisher=Addison Wesley Longman Ltd.|location=Harlow, UK|year=1994|isbn=978-0-582-06009-8|url-access=registration|url=https://archive.org/details/isbn_9780582060098/page/309}} |
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