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Topic summary

Α-Pinene

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Names IUPAC name
(1S,5S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene ((−)-α-Pinene)
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard100.029.161EC Number
  • (−): 232-077-3
KEGG
RTECS number
  • DT7000000 (unspec. isomer)
UNII
UN number2368
  • InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m0/s1
    Key: GRWFGVWFFZKLTI-IUCAKERBSA-N
  • InChI=1/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m0/s1
    Key: GRWFGVWFFZKLTI-IUCAKERBBG
  • C\1=C(\[C@@H]2C[C@H](C/1)C2(C)C)C
Properties C10H16Molar mass136.238 g·mol Appearance Clear colorless liquid Density0.858g/mL (liquid at 20°C) Melting point−62.80 °C; −81.04 °F; 210.35 K Boiling point155 °C (311 °F; 428 K) Very low SolubilityInsoluble in chloroform, diethyl etherSolubility in acetic acidMiscible Solubility in ethanolMiscible Solubility in acetoneMiscible Vapor pressure0.5 kPa −50.7° (1S,5S-Pinene) Hazards Occupational safety and health (OHS/OSH):
Main hazards
Flammable GHS labelling: DangerH226, H302, H304, H315, H317, H410P210, P233, P240, P241, P242, P243, P261, P264, P270, P272, P273, P280, P301+P310, P301+P312, P302+P352, P303+P361+P353, P321, P330, P331, P332+P313, P333+P313, P362, P363, P370+P378, P391, P403+P235, P405, P501NFPA 704 (fire diamond)
3
3
0
Flash point33 °C (91 °F; 306 K) 255 °C (491 °F; 528 K) Explosive limits0.8% v/v (lower)
6% v/v (upper) Lethal dose or concentration (LD, LC): 300-2000 mg/kg (rat, oral)
> 5 g/kg (rabbit, dermal) 625 ppm/min (rat) Safety data sheet (SDS) Fisher ScientificRelated compounds
Related alkene
β-pinene, camphene, 3-carene, limonene
Related compounds
borneol, camphor, terpineol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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α-Pinene is an organic compound of the terpene class. It is one of the two isomers of pinene, the other being β-pinene. An alkene, it contains a strained four-membered ring. It is found in the oils of many species of coniferous trees, notably Pinus and Picea species. It is also found in the essential oil of rosemary (Rosmarinus officinalis), Satureja myrtifolia (also known as Zoufa in some regions), and many species of Seseli. Both enantiomers are known in nature; (1S,5S)- or (−)-α-pinene is more common in European pines, whereas the (1R,5R)- or (+)-α-isomer is more common in North America. The enantiomers' racemic mixture is present in some oils such as eucalyptus oil and orange peel oil.

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