| 词条 | Pinene | |||||||||||||||||||||||||
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 446720672 | Name = Pinene | ImageFile = Alpha-pinen.svg | ImageSize = 150px | ImageName = Pinene | IUPACName = (1S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene (1S,5S)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptane | OtherNames = |Section1={{Chembox Identifiers | SMILES = CC1=CCC2CC1C2(C)C | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 80-56-8 | CASNo_Comment = (unspecified) | CASNo2_Ref = {{cascite|changed|??}} | CASNo2 = 7785-70-8 | CASNo2_Comment = (1R-α) | CASNo3_Ref = {{cascite|changed|??}} | CASNo3 = 7785-26-4 | CASNo3_Comment = (1S-α) | CASNo4_Ref = {{cascite|changed|??}} | CASNo4 = 2437-95-8 | CASNo4_Comment = ((±)-α) | CASNo5_Ref = {{cascite|changed|??}} | CASNo5 = 18172-67-3 | CASNo5_Comment = (β) | RTECS = |Section2={{Chembox Properties | Formula = C10H16 | MolarMass = 136.24 g/mol | Appearance = Liquid | Density = 0,86 g·cm−3 (alpha, 15 °C)[1][2] | Solubility = Practically insoluble in water | MeltingPtC = −62 to −55 | MeltingPt_notes = (alpha)[1] | BoilingPtC = 155 to 156 | BoilingPt_notes = (alpha)[1] }} Pinene (C10H16) is a bicyclic monoterpene chemical compound.{{Ref|Mann}} There are two structural isomers of pinene found in nature: α-pinene and β-pinene. As the name suggests, both forms are important constituents of pine resin; they are also found in the resins of many other conifers, as well as in non-coniferous plants such as camphorweed (Heterotheca)[3] and big sagebrush (Artemisia tridentata). Both isomers are used by many insects in their chemical communication system. The two isomers of pinene constitute the major component of turpentine. Isomers
Biosynthesisα-Pinene and β-pinene are both produced from geranyl pyrophosphate, via cyclisation of linaloyl 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.[4] PlantsAlpha-pinene is the most widely encountered terpenoid in nature[5] and is highly repellant to insects.[6]Alpha-pinene appears in conifers and numerous other plants.[9] Pinene is a major component of the essential oils of Sideritis spp. (ironwort)[7] and Salvia spp. (sage).[8] Cannabis also contains alpha-pinene[9] and beta-pinene.[10] Resin from Pistacia terebinthus (commonly known as terebinth or turpentine tree) is rich in pinene. Pine nuts produced by pine trees contain pinene.[9]Makrut lime fruit peel contains an essential oil comparable to lime fruit peel oil; its main components are limonene and β-pinene.[11]The racemic mixture of the two forms of pinene is found in some oils like eucalyptus oil.[12] UsageIn chemical industry, selective oxidation of pinene with some catalysts gives many compounds for perfumery, such as artificial odorants. An important oxidation product is verbenone, along with pinene oxide, verbenol, and verbenyl hydroperoxide.[13] Pinenes are the primary constituents of turpentine. The use of pinene as a biofuel in spark ignition engines has been explored.[14] Pinene dimers have been shown to have heating values comparable to the rocket fuel JP-10.[4] References1. ^1 2 {{GESTIS|ZVG=491170|CAS=80-56-8|Name=alpha-Pinen|Date=07-January-2016}} 2. ^{{GESTIS|ZVG=492888|Name=beta-Pinen|Date=07-January-2016}} 3. ^Lincoln, D.E., B.M. Lawrence. 1984. The volatile constituents of camphorweed, Heterotheca subaxillaris. Phytochemistry 23(4):933-934 4. ^1 {{Cite journal|last=Sarria|first=Stephen|last2=Wong|first2=Betty|last3=Martín|first3=Hector García|last4=Keasling|first4=Jay D.|last5=Peralta-Yahya|first5=Pamela|date=2014-07-18|title=Microbial Synthesis of Pinene|journal=ACS Synthetic Biology|volume=3|issue=7|pages=466–475|doi=10.1021/sb4001382|pmid=24679043}}{{open access}} 5. ^Noma Y, Asakawa Y (2010). Biotransformation of monoterpenoids by microorganisms, insects, and mammals. In: Baser KHC, Buchbauer G (eds). Handbook of Essential Oils: Science, Technology, and Applications. CRC Press: Boca Raton, Florida, pp. 585–736. 6. ^{{cite journal |authors=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 |url= |pmid=19729299}} 7. ^Kose EO, Deniz IG, Sarikurkcu C, Aktas O, Yavuz M (2010). 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. Food Chem Toxicol 48: 2960–2965. 8. ^Ozek G, Demirci F, Ozek T, Tabanca N, Wedge DE, Khan SI et al. (2010). Gas chromatographic-mass spectrometric analysis of volatiles obtained by four different techniques from Salvia rosifolia Sm., and evaluation for biological activity. J Chromatog 1217: 741–748. 9. ^1 2 {{cite journal |author=Russo, E. B |title=Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects |journal=British Journal of Pharmacology |volume=163 |issue=7 |pages=1344–1364 |year=2011 |doi=10.1111/j.1476-5381.2011.01238.x |pmid=21749363 |pmc=3165946}} 10. ^{{Cite journal|last=Hillig|first=Karl W|date=October 2004|title=A chemotaxonomic analysis of terpenoid variation in Cannabis|url=http://linkinghub.elsevier.com/retrieve/pii/S0305197804001012|journal=Biochemical Systematics and Ecology|volume=32|issue=10|pages=875–891|doi=10.1016/j.bse.2004.04.004|issn=0305-1978}} 11. ^{{cite journal|last=Kasuan|first=Nurhani|url=http://www.ukm.my/mjas/v17_n3/Nurhani.pdf|journal=Malyasian Journal of Analytical Sciences|title=Extraction of Citrus hystrix D.C. (Kaffir Lime) Essential Oil Using Automated Steam Distillation Process: Analysis of Volatile Compounds|volume=17|issue=3|pages=359–369|year=2013}} 12. ^{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/alpha-pinene#section=Top|title=ALPHA-PINENE|last=Pubchem|website=pubchem.ncbi.nlm.nih.gov|language=en|access-date=2017-11-14}} 13. ^{{cite journal |author=U. Neuenschwander| journal =ChemSusChem| title=Mechanism of the Aerobic Oxidation of α-Pinene | volume=3| issue=1| date=2010| pages = 75–84 |language=German |doi=10.1002/cssc.200900228| pmid =20017184}} 14. ^{{Cite journal|last=Raman|first=Vallinayagam|last2=Sivasankaralingam|first2=Vedharaj|last3=Dibble|first3=Robert|last4=Sarathy|first4=S. Mani|date=2016-10-17|title=α-Pinene - A High Energy Density Biofuel for SI Engine Applications|url=http://papers.sae.org/2016-01-2171/|language=English|location=Warrendale, PA}} Bibliography
3 : Monoterpenes|Cyclobutanes|Cyclohexenes |
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