Terpinene

Terpinenes

α-Terpinene

β-Terpinene

γ-Terpinene

δ-Terpinene
(terpinolene)

Names

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

Identifiers

CAS Number

(α): 99-86-5^Y
(β): 99-84-3^Y
(γ): 99-85-4^Y
(δ): 586-62-9^Y

3D model (JSmol)

ChEBI

(α): CHEBI:10334^Y
(β): CHEBI:59159
(γ): CHEBI:10577
(δ): CHEBI:9457

ChemSpider

(α): 7182^N
(β): 60205
(γ): 7181

ECHA InfoCard

100.029.440

EC Number

(α): 202-795-1
(β): 202-793-0
(γ): 202-794-6
(δ): 209-578-0

KEGG

(α): C09898
(γ): C09900
(δ): C06075

PubChem CID

(α): 7462
(β): 66841
(γ): 7461
(δ): 11463

UNII

(α): I24X278AP1^Y
(β): DV74J5RW4Y^Y
(γ): 4YGF4PQP49^Y
(δ): N9830X5KSL^Y

InChI

InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h6,8H,3-5,7H2,1-2H3^Y
Key: SCWPFSIZUZUCCE-UHFFFAOYSA-N^Y
(β): InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h6,8H,3-5,7H2,1-2H3
Key: SCWPFSIZUZUCCE-UHFFFAOYSA-N
(γ): InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,7-8H,5-6H2,1-3H3
Key: YKFLAYDHMOASIY-UHFFFAOYSA-N
(δ): InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4H,5-7H2,1-3H3
Key: MOYAFQVGZZPNRA-UHFFFAOYSA-N

SMILES

(α): CC1=CC=C(C(C)C)CC1
(β): C=C1CC=C(C(C)C)CC1
(γ): CC1=CCC(C(C)C)=CC1
(δ): C/C(C)=C1CCC(C)=CC/1

Properties

Chemical formula

C₁₀H₁₆

Molar mass

136.238 g·mol⁻¹

Density

α: 0.8375 g/cm³
β: 0.838 g/cm³
γ: 0.853 g/cm³

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 [77 °F], 100 kPa).

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Infobox references

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.^[1]

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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.^[1]

Biosynthesis of α-terpinene

Biosynthetic pathway to alpha-terpinene from geranyl pyrophosphate.^[2]

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.^[3] 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

References

^ ^a ^b 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.

This page was last edited on 11 February 2024, at 03:10

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