Pinene

Names
IUPAC names (1S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene (1S,5S)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptane
Identifiers
CAS Number	(unspecified): 1330-16-1 Y (1R-α): 7785-70-8 Y (1S-α): 7785-26-4 Y ((±)-α): 80-56-8 Y (β): 18172-67-3 Y
3D model (JSmol)	(unspecified): Interactive image
ChEBI	(unspecified): CHEBI:17187 (1R-α): CHEBI:28261 (1S-α): CHEBI:28660 ((±)-α): CHEBI:36740 (β): CHEBI:50025
ChemSpider	(1R-α): 74205 (1S-α): 389795 ((±)-α): 6402 (β): 14198
ECHA InfoCard	100.029.170
EC Number	(1R-α): 232-087-8
PubChem CID	(1R-α): 82227 (1S-α): 15837102 ((±)-α): 6654 (β): 14896
UNII	(unspecified): 996299PUKB Y (1R-α): H6CM4TWH1W Y (1S-α): TZR3GM95PR Y ((±)-α): JPF3YI7O34 Y (β): AFN153A7SU Y
CompTox Dashboard (EPA)	(unspecified): DTXSID7041671
SMILES (unspecified): CC1=CCC2CC1C2(C)C
Properties
Chemical formula	C10H16
Molar mass	136.24 g/mol
Appearance	Liquid
Density	0,86 g·cm−3 (alpha, 15 °C)[1][2]
Melting point	−62 to −55 °C (−80 to −67 °F; 211 to 218 K) (alpha)[1]
Boiling point	155 to 156 °C (311 to 313 °F; 428 to 429 K) (alpha)[1]
Solubility in water	Practically insoluble in water
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Pinene (C₁₀H₁₆) is a bicyclic monoterpene chemical compound. There are two structural isomers of pinene found in nature: α-pinene and β-pinene. As the name suggests, both forms are important constituents of pine resin; they are also found in the resins of many other conifers, as well as in non-coniferous plants such as camphorweed (Heterotheca)^[3] and big sagebrush (Artemisia tridentata). Both isomers are used by many insects in their chemical communication system. The two isomers of pinene, especially α, constitute the major component of turpentine.^[4]

Isomers

skeletal formula
perspective view	X		X
ball-and-stick model	X		X
name	(1R)-(+)-α-pinene	(1S)-(−)-α-pinene	(1R)-(+)-β-pinene	(1S)-(−)-β-pinene
CAS number	7785-70-8	7785-26-4	19902-08-0	18172-67-3

Biosynthesis

α-Pinene and β-pinene are both produced from geranyl pyrophosphate, via cyclisation of linaloyl pyrophosphate followed by loss of a proton from the carbocation equivalent. Researchers at the Georgia Institute of Technology and the Joint BioEnergy Institute have been able to synthetically produce pinene with a bacterium.^[5]

Plants

Alpha-pinene is the most widely encountered terpenoid in nature^[6] and is highly repellent to insects.^[7]

Alpha-pinene appears in conifers and numerous other plants.^[8] Pinene is a major component of the essential oils of Sideritis spp. (ironwort)^[9] and Salvia spp. (sage).^[10] Cannabis also contains alpha-pinene^[8] and beta-pinene.^[11] Resin from Pistacia terebinthus (commonly known as terebinth or turpentine tree) is rich in pinene. Pine nuts produced by pine trees contain pinene.^[8]

Makrut lime fruit peel contains an essential oil comparable to lime fruit peel oil; its main components are limonene and β-pinene.^[12]

The racemic mixture of the two forms of pinene is found in some oils like eucalyptus oil.^[13]

Reactions

Selective oxidation of pinene occurs at the allylic position to give verbenone, along with pinene oxide, as well as verbenol and its hydroperoxide.^[14]

• Pinenes are the primary constituents of turpentine.
• The use of pinene as a biofuel in spark ignition engines has been explored.^[15]
• Pinene dimers have been shown to have heating values comparable to the jet fuel JP-10.^[5]