Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Terpinene: Difference between pages

| Watchedfields = changed

| verifiedrevid = 470602550

| ImageFileL1_Ref = {{chemboximage|correct|??}}

| ImageSizeL1 = 50px

| ImageCaptionL1 = α-Terpinene

| ImageFileR1_Ref = {{chemboximage|correct|??}}

| ImageSizeR1 = 50px

| ImageCaptionR1 = β-Terpinene

| ImageFileL2_Ref = {{chemboximage|correct|??}}

| ImageSizeL2 = 50px

| ImageCaptionL2 = γ-Terpinene

| ImageSizeR2 = 50px

| 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

|Section1={{Chembox Identifiers

| CASNo = 99-86-5

| index_label = (α)

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo1 = 99-84-3

| index1_label = (β)

| CASNo1_Ref = {{cascite|correct|}}

| CASNo2 = 99-85-4

| index2_label = (γ)

| CASNo2_Ref = {{cascite|correct|}}

| CASNo3 = 586-62-9

| index3_label = (δ)

| CASNo3_Ref = {{cascite|correct|}}

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

| 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}}

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| InChI1=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h6,8H,3-5,7H2,1-2H3

| InChIKey1 = SCWPFSIZUZUCCE-UHFFFAOYSA-N

| InChI2=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,7-8H,5-6H2,1-3H3

| InChIKey2 = YKFLAYDHMOASIY-UHFFFAOYSA-N

| InChI3=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4H,5-7H2,1-3H3

| InChIKey3 = MOYAFQVGZZPNRA-UHFFFAOYSA-N

| SMILES = CC1=CC=C(C(C)C)CC1

| SMILES1 = C=C1CC=C(C(C)C)CC1

| SMILES2 = CC1=CCC(C(C)C)=CC1

| SMILES3 = C/C(C)=C1CCC(C)=CC/1

|Section2={{Chembox Properties

| C=10 | H=16

| Appearance =

| Density = α: 0.8375 g/cm³<br />β: 0.838 g/cm³<br />γ: 0.853 g/cm³

| MeltingPt = α: 60-61 °C

| BoilingPt = α: 173.5-174.8 °C<br />β: 173-174 °C<br />γ: 183 °C

| Solubility = }}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

The '''terpinenes''' are a group of [[isomer]]ic hydrocarbons that are classified as [[monoterpene]]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 [[cardamom]] and [[marjoram]] oils, and from other natural sources. β-Terpinene has no known natural source but has been prepared from [[sabinene]]. 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-[[pinene]]. It has perfume and flavoring properties but is mainly used to confer pleasant odor to industrial fluids. Hydrogenation gives the saturated derivative [[P-Menthane|''p''-menthane]].<ref name=UllmannEgg/>

==Biosynthesis of α-terpinene==

[[File:TerpineneBiosyn.svg|thumb|left|170px|Biosynthetic pathway to alpha-terpinene from geranyl pyrophosphate.<ref>{{cite book | author = Dewick, P. M. | year = 2009 | title = Medicinal Natural Products: A Biosynthetic Approach | url = https://archive.org/details/medicinalnatural00dewi_880 | url-access = limited | location = United Kingdom | publisher = John Wiley & Sons | pages = [https://archive.org/details/medicinalnatural00dewi_880/page/n193 187]–197}}</ref>]]

The biosynthesis of α-terpinene and other terpenoids starts with the isomerization of [[geranyl pyrophosphate]] to [[linalyl pyrophosphate]] (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 [[Wagner-Meerwein rearrangement]] produces the terpinen-4-yl cation. It is the loss of a hydrogen from this cation that generates α-terpinene.

== Plants that produce terpinene ==

* ''[[Cuminum cyminum]]''<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>

* ''[[Melaleuca alternifolia]]''

* ''[[Cannabis]]'' <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>

* ''[[Origanum syriacum]]''

*''[[Coriandrum sativum]]''<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}}

[[Category:Monoterpenes]]

[[Category:Dienes]]

[[Category:Cyclohexenes]]

[[Category:Cyclohexadienes]]