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 ; (β): 99-84-3 ; (γ): 99-85-4 ; (δ): 586-62-9 ;
3D model ( JSmol)	(α): Interactive image; (β): Interactive image; (γ): Interactive image; (δ): Interactive image;
ChEBI	(α): CHEBI:10334 ; (β): CHEBI:59159; (γ): CHEBI:10577; (δ): CHEBI:9457;
ChemSpider	(α): 7182 ; (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 ; (β): DV74J5RW4Y ; (γ): 4YGF4PQP49 ; (δ): N9830X5KSL ;
	InChI 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 ; (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). verify (what is ?) 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]

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]