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Revision as of 12:24, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 466031160 of page Terpinene for the Chem/Drugbox validation project (updated: 'ChemSpiderID', 'ChEBI', 'StdInChI', 'StdInChIKey').		Latest revision as of 03:10, 11 February 2024 edit Maxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,043 edits Used lowercase "cite" template everywhere for consistency, as the majority of instances used lowercase already. Add: bibcode, authors 1-1. Removed parameters. Some additions/deletions were parameter name changes. | Use this bot. | #UCB_Other
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	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{Chembox		{{Chembox
			| Watchedfields = changed
			| verifiedrevid = 470602550
	| Name = Terpinenes		| Name = Terpinenes
			| ImageFileL1_Ref = {{chemboximage|correct|??}}
	| ImageFileL1 = Alpha terpinene.png		| ImageFileL1 = Alpha terpinene.png
	| ImageSizeL1 = 50px		| ImageSizeL1 = 50px
	| ImageCaptionL1 = α-Terpinene		| ImageCaptionL1 = α-Terpinene
			| ImageFileR1_Ref = {{chemboximage|correct|??}}
	| ImageFileR1 = Beta terpinene.png		| ImageFileR1 = Beta terpinene.png
	| ImageSizeR1 = 50px		| ImageSizeR1 = 50px
	| ImageCaptionR1 = β-Terpinene		| ImageCaptionR1 = β-Terpinene
			| ImageFileL2_Ref = {{chemboximage|correct|??}}
	| ImageFileL2 = Gamma terpinene.png		| ImageFileL2 = Gamma terpinene.png
	| ImageSizeL2 = 50px		| ImageSizeL2 = 50px
	| ImageCaptionL2 = γ-Terpinene		| ImageCaptionL2 = γ-Terpinene
	| ImageFileR2 = terpinolene.svg		| ImageFileR2 = terpinolene.svg
	| ImageSizeR2 = 50px		| ImageSizeR2 = 50px
	| ImageCaptionR2 = δ-Terpinene<br>(terpinolene)		| ImageCaptionR2 = δ-Terpinene<br />(terpinolene)
	| IUPACName = α: 4-methyl-1-(1-methylethyl)-1,3-cyclohexadiene<br>β: 4-methylene-1-(1-methylethyl)cyclohexene<br>γ: 4-methyl-1-(1-methylethyl)-1,4-cyclohexadiene<br>δ: 1-methyl-4-(propan-2-ylidene)cyclohex-1-ene		| IUPACName = α: 4-Methyl-1-(1-methylethyl)-1,3-cyclohexadiene<br />β: 4-Methylene-1-(1-methylethyl)cyclohexene<br />γ: 4-Methyl-1-(1-methylethyl)-1,4-cyclohexadiene<br />δ: 1-Methyl-4-(propan-2-ylidene)cyclohex-1-ene
	| IUPACName_hidden = yes
	| OtherNames =		| OtherNames =
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| CASNo = 99-86-5		| CASNo = 99-86-5
	| CASNo_Comment = (α)		| index_label = (α)
	| CASNo_Ref = {{cascite|correct|}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo1 = 99-84-3		| CASNo1 = 99-84-3
	| CASNo1_Comment = (β)		| index1_label = (β)
	| CASNo1_Ref = {{cascite|correct|}}		| CASNo1_Ref = {{cascite|correct|}}
	| CASNo2 = 99-85-4		| CASNo2 = 99-85-4
	| CASNo2_Comment = (γ)		| index2_label = (γ)
	| CASNo2_Ref = {{cascite|correct|}}		| CASNo2_Ref = {{cascite|correct|}}
	| CASNo3 = 586-62-9		| CASNo3 = 586-62-9
	| CASNo3_Comment = (δ)		| index3_label = (δ)
	| CASNo3_Ref = {{cascite|correct|}}		| CASNo3_Ref = {{cascite|correct|}}
			| UNII_Ref = {{fdacite|correct|FDA}}
	| ChemSpiderID = 60205
	| ChEBI = 59159		| UNII = I24X278AP1
			| UNII1_Ref = {{fdacite|correct|FDA}}
			| UNII1 = DV74J5RW4Y
			| UNII2_Ref = {{fdacite|correct|FDA}}
			| UNII2 = 4YGF4PQP49
			| UNII3_Ref = {{fdacite|correct|FDA}}
			| UNII3 = N9830X5KSL
			| ChemSpiderID = 7182
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
			| ChemSpiderID1 = 60205
			| ChemSpiderID2 = 7181
			| ChEBI_Ref = {{ebicite|correct|EBI}}
			| ChEBI = 10334
			| ChEBI1 = 59159
			| ChEBI2 = 10577
			| ChEBI3 = 9457
			| EC_number = 202-795-1
			| EC_number1 = 202-793-0
			| EC_number2 = 202-794-6
			| EC_number3 = 209-578-0
			| KEGG = C09898
			| KEGG2 = C09900
			| KEGG3 = C06075
			| PubChem = 7462
			| PubChem1 = 66841
			| PubChem2 = 7461
			| PubChem3 = 11463
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h6,8H,3-5,7H2,1-2H3		| StdInChI = 1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h6,8H,3-5,7H2,1-2H3
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = SCWPFSIZUZUCCE-UHFFFAOYSA-N		| StdInChIKey = SCWPFSIZUZUCCE-UHFFFAOYSA-N
			| InChI1=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h6,8H,3-5,7H2,1-2H3
	| PubChem =
			| InChIKey1 = SCWPFSIZUZUCCE-UHFFFAOYSA-N
	| SMILES = CC1=CC=C(C(C)C)CC1
			| InChI2=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,7-8H,5-6H2,1-3H3
	| SMILES_Comment = (α)
			| InChIKey2 = YKFLAYDHMOASIY-UHFFFAOYSA-N
	| SMILES1 = C=C1CC=C(C(C)C)CC1
			| InChI3=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4H,5-7H2,1-3H3
	| SMILES1_Comment = (β)
			| InChIKey3 = MOYAFQVGZZPNRA-UHFFFAOYSA-N
	| SMILES2 = CC1=CCC(C(C)C)=CC1
			| SMILES = CC1=CC=C(C(C)C)CC1
	| SMILES2_Comment = (γ)
	| SMILES3 = C/C(C)=C1CCC(C)=CC/1		| SMILES1 = C=C1CC=C(C(C)C)CC1
			| SMILES2 = CC1=CCC(C(C)C)=CC1
	| SMILES3_Comment = (δ)
			| SMILES3 = C/C(C)=C1CCC(C)=CC/1
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C=10|H=16		| C=10 | H=16
	| Appearance =		| Appearance =
	| Density = α: 0.8375 g/cm<sup>3</sup><br>β: 0.838 g/cm<sup>3</sup><br>γ: 0.853 g/cm<sup>3</sup>		| Density = α: 0.8375 g/cm<sup>3</sup><br />β: 0.838 g/cm<sup>3</sup><br />γ: 0.853 g/cm<sup>3</sup>
	| MeltingPt = α: 60-61 °C		| MeltingPt = α: 60-61 °C
	| BoilingPt = α: 173.5-174.8 °C<br>β: 173-174 °C<br>γ: 183 °C		| BoilingPt = α: 173.5-174.8 °C<br />β: 173-174 °C<br />γ: 183 °C
	| Solubility = }}		| Solubility = }}
	| Section3 = {{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards =		| MainHazards =
	| FlashPt =		| FlashPt =
	| Autoignition = }}		| AutoignitionPt = }}
	}}		}}
			The '''terpinenes''' are a group of ]ic hydrocarbons that are classified as ]s. They each have the same molecular formula and carbon framework, but they differ in the position of carbon-carbon double bonds. α-Terpinene has been isolated from ] and ] oils, and from other natural sources. β-Terpinene has no known natural source but has been prepared from ]. γ-Terpinene and δ-terpinene (also known as '''terpinolene''') have been isolated from a variety of plant sources. They are all colorless liquids with a turpentine-like odor.<ref name=UllmannEgg>{{cite encyclopedia|author=M. Eggersdorfer |chapter=Terpenes|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a26_205|isbn=3-527-30673-0}}</ref>
			==Production and uses==
			α-Terpinene is produced industrially by acid-catalyzed rearrangement of α-]. It has perfume and flavoring properties but is mainly used to confer pleasant odor to industrial fluids. Hydrogenation gives the saturated derivative ].<ref name=UllmannEgg/>
			==Biosynthesis of α-terpinene==
			–197}}</ref>]]
			The biosynthesis of α-terpinene and other terpenoids starts with the isomerization of ] to ] (LPP). LPP then forms a resonance-stabilized cation by loss of the pyrophosphate group. Cyclization is then completed thanks to this more favorable stereochemistry of the LPP cation, yielding a terpinyl cation.<ref>{{cite journal |doi=10.1021/acs.chemrev.7b00287|title=Structural and Chemical Biology of Terpenoid Cyclases |year=2017 |last1=Christianson |first1=David W. |journal=Chemical Reviews |volume=117 |issue=17 |pages=11570–11648 |pmid=28841019 |pmc=5599884 }}</ref> Finally, a 1,2-hydride shift via a ] produces the terpinen-4-yl cation. It is the loss of a hydrogen from this cation that generates α-terpinene.
			== Plants that produce terpinene ==
			* '']''<ref name=cceo>{{cite journal
			| last = Li
			| first = Rong
			|author2=Zi-Tao Jiang
			| title = Chemical composition of the essential oil of Cuminum cyminum L. from China
			| journal = Flavour and Fragrance Journal
			| volume = 19
			| issue = 4
			| pages = 311–313
			| year = 2004
			| doi = 10.1002/ffj.1302
			}}</ref><ref name=unec>{{cite journal
			| last1 = Wang
			| first1 = Lu
			| 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 = 72–77
			| year = 2009
			| doi = 10.1016/j.aca.2009.05.030
			| pmid = 19576388
			| last2 = Wang
			| first2 = Z
			| last3 = Zhang
			| first3 = H
			| last4 = Li
			| first4 = X
			| last5 = Zhang
			| first5 = H | bibcode = 2009AcAC..647...72W
			|display-authors=etal}}</ref><ref name=aacc>{{cite journal
			| last1 = Iacobellis
			| first1 = Nicola S.
			| title = Antibacterial Activity of Cuminum cyminum L. and Carum carvi L. Essential Oils
			| journal = Journal of Agricultural and Food Chemistry
			| volume = 53
			| issue = 1
			| pages = 57–61
			| year = 2005
			| doi = 10.1021/jf0487351
			| pmid = 15631509
			| last2 = Lo Cantore
			| first2 = P
			| last3 = Capasso
			| first3 = F
			| last4 = Senatore
			| first4 = F |display-authors=etal}}</ref>
			* '']''
			* '']'' <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|bibcode=2004BioSE..32..875H |issn=0305-1978}}</ref>
			* '']''
			*'']''<ref>{{cite journal|last1=Shahwar|first1=Muhammad Khuram|last2=El-Ghorab|first2=Ahmed Hassan|last3=Anjum|first3=Faqir Muhammad|last4=Butt|first4=Masood Sadiq|last5=Hussain|first5=Shahzad|last6=Nadeem|first6=Muhammad|date=2012-07-01|title=Characterization of Coriander (Coriandrum sativum L.) Seeds and Leaves: Volatile and Non Volatile Extracts|journal=International Journal of Food Properties|volume=15|issue=4|pages=736–747|doi=10.1080/10942912.2010.500068|issn=1094-2912|doi-access=free}}</ref>
			== References ==
			{{Reflist}}
			]
			]
			]
			]