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| *'']''<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> | *'']''<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> | ||
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| == References == | == References == | ||
Latest revision as of 22:33, 20 January 2025
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| Names | |||
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| IUPAC names
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 | |||
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| ECHA InfoCard | 100.029.440 
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SMILES
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| Properties | |||
| Chemical formula | C10H16 | ||
| Molar mass | 136.238 g·mol | ||
| Density | α: 0.8375 g/cm β: 0.838 g/cm γ: 0.853 g/cm | ||
| Melting point | α: 60-61 °C | ||
| Boiling point | α: 173.5-174.8 °C β: 173-174 °C γ: 183 °C | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
Infobox references
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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
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
- Melaleuca alternifolia
- Cannabis
- Origanum syriacum
- Coriandrum sativum
- Monarda fistulosa
References
- ^ M. Eggersdorfer (2005). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN 3-527-30673-0.
- Dewick, P. M. (2009). Medicinal Natural Products: A Biosynthetic Approach. United Kingdom: John Wiley & Sons. pp. 187–197.
- Christianson, David W. (2017). "Structural and Chemical Biology of Terpenoid Cyclases". Chemical Reviews. 117 (17): 11570–11648. doi:10.1021/acs.chemrev.7b00287. PMC 5599884. PMID 28841019.
- Li, Rong; Zi-Tao Jiang (2004). "Chemical composition of the essential oil of Cuminum cyminum L. from China". Flavour and Fragrance Journal. 19 (4): 311–313. doi:10.1002/ffj.1302.
- Wang, Lu; Wang, Z; Zhang, H; Li, X; Zhang, H; et al. (2009). "Ultrasonic nebulization extraction coupled with headspace single drop microextraction and gas chromatography–mass spectrometry for analysis of the essential oil in Cuminum cyminum L.". Analytica Chimica Acta. 647 (1): 72–77. Bibcode:2009AcAC..647...72W. doi:10.1016/j.aca.2009.05.030. PMID 19576388.
- Iacobellis, Nicola S.; Lo Cantore, P; Capasso, F; Senatore, F; et al. (2005). "Antibacterial Activity of Cuminum cyminum L. and Carum carvi L. Essential Oils". Journal of Agricultural and Food Chemistry. 53 (1): 57–61. doi:10.1021/jf0487351. PMID 15631509.
- Hillig, Karl W (October 2004). "A chemotaxonomic analysis of terpenoid variation in Cannabis". Biochemical Systematics and Ecology. 32 (10): 875–891. Bibcode:2004BioSE..32..875H. doi:10.1016/j.bse.2004.04.004. ISSN 0305-1978.
- Shahwar, Muhammad Khuram; El-Ghorab, Ahmed Hassan; Anjum, Faqir Muhammad; Butt, Masood Sadiq; Hussain, Shahzad; Nadeem, Muhammad (2012-07-01). "Characterization of Coriander (Coriandrum sativum L.) Seeds and Leaves: Volatile and Non Volatile Extracts". International Journal of Food Properties. 15 (4): 736–747. doi:10.1080/10942912.2010.500068. ISSN 1094-2912.