Terpinene

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title: "Terpinene" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["monoterpenes", "dienes", "cyclohexenes", "cyclohexadienes"] topic_path: "general/monoterpenes" source: "https://en.wikipedia.org/wiki/Terpinene" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 470602550 | Name = Terpinenes | ImageFileL1_Ref = | ImageFileL1 = Alpha terpinene.png | ImageSizeL1 = 50px | ImageCaptionL1 = α-Terpinene | ImageFileR1_Ref = | ImageFileR1 = Beta terpinene.png | ImageSizeR1 = 50px | ImageCaptionR1 = β-Terpinene | ImageFileL2_Ref = | ImageFileL2 = Gamma terpinene.png | ImageSizeL2 = 50px | ImageCaptionL2 = γ-Terpinene | ImageFileR2 = terpinolene.svg | ImageSizeR2 = 50px | ImageCaptionR2 = δ-Terpinene (terpinolene) | IUPACName = α: 4-Methyl-1-(1-methylethyl)-1,3-cyclohexadiene β: 4-Methylene-1-(1-methylethyl)cyclohexene γ: 4-Methyl-1-(1-methylethyl)-1,4-cyclohexadiene δ: 1-Methyl-4-(propan-2-ylidene)cyclohex-1-ene | OtherNames = |Section1={{Chembox Identifiers | CASNo = 99-86-5 | index_label = (α) | CASNo_Ref = | CASNo1 = 99-84-3 | index1_label = (β) | CASNo1_Ref = | CASNo2 = 99-85-4 | index2_label = (γ) | CASNo2_Ref = | CASNo3 = 586-62-9 | index3_label = (δ) | CASNo3_Ref = | UNII_Ref = | UNII = I24X278AP1 | UNII1_Ref = | UNII1 = DV74J5RW4Y | UNII2_Ref = | UNII2 = 4YGF4PQP49 | UNII3_Ref = | UNII3 = N9830X5KSL | ChemSpiderID = 7182 | ChemSpiderID_Ref = | ChemSpiderID1 = 60205 | ChemSpiderID2 = 7181 | ChEBI_Ref = | 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 = | StdInChI = 1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h6,8H,3-5,7H2,1-2H3 | StdInChIKey_Ref = | 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 | 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 β: 0.838 g/cm3 γ: 0.853 g/cm3 | MeltingPt = α: 60-61 °C | BoilingPt = α: 173.5-174.8 °C β: 173-174 °C γ: 183 °C | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }}

The terpinenes are a group of isomeric hydrocarbons that are classified as monoterpenes. 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.

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.

Biosynthesis of α-terpinene

::figure[src="https://upload.wikimedia.org/wikipedia/commons/9/98/TerpineneBiosyn.svg" caption="pages = [https://archive.org/details/medicinalnatural00dewi_880/page/n193 187]–197}}"] ::

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. 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{{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 | 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}}{{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 | bibcode = 2005JAFC...53...57I |display-authors=etal}}
  • Melaleuca alternifolia
  • Cannabis
  • Origanum syriacum
  • Coriandrum sativum
  • Monarda fistulosa

References

References

  1. {{cite encyclopedia. M. Eggersdorfer. (2005). Wiley-VCH
  2. Dewick, P. M.. (2009). "Medicinal Natural Products: A Biosynthetic Approach". John Wiley & Sons.
  3. (2017). "Structural and Chemical Biology of Terpenoid Cyclases". Chemical Reviews.
  4. Hillig, Karl W. (October 2004). "A chemotaxonomic analysis of terpenoid variation in Cannabis". Biochemical Systematics and Ecology.
  5. (2012-07-01). "Characterization of Coriander (Coriandrum sativum L.) Seeds and Leaves: Volatile and Non Volatile Extracts". International Journal of Food Properties.

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monoterpenesdienescyclohexenescyclohexadienes