α-Pinene
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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.[2] An alkene, it contains a reactive four-membered ring. It is found in the oils of many species of many coniferous trees, notably the Pinus and Picea species. It is also found in the essential oil of rosemary (Rosmarinus officinalis) and Satureja myrtifolia (also known as Zoufa in some regions).[3][4] 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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Names | |||
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IUPAC name
(1S,5S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene ((−)-α-Pinene) | |||
Identifiers | |||
3D model (JSmol) |
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ChEBI |
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ChemSpider |
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ECHA InfoCard | 100.029.161 | ||
EC Number |
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KEGG |
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PubChem CID |
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RTECS number |
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UNII |
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UN number | 2368 | ||
CompTox Dashboard (EPA) |
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Properties | |||
C10H16 | |||
Molar mass | 136.238 g·mol−1 | ||
Appearance | Clear colorless liquid | ||
Density | 0.858 g/mL (liquid at 20 °C) | ||
Melting point | −62.80 °C; −81.04 °F; 210.35 K[1] | ||
Boiling point | 155 °C (311 °F; 428 K)[1] | ||
Very low | |||
Solubility | Insoluble in chloroform, diethyl ether | ||
Solubility in acetic acid | Miscible | ||
Solubility in ethanol | Miscible | ||
Solubility in acetone | Miscible | ||
Vapor pressure | 0.5 kPa | ||
Chiral rotation ([α]D) |
−50.7° (1S,5S-Pinene) | ||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards |
Flammable | ||
GHS labelling: | |||
Danger | |||
H226, H302, H304, H315, H317, H410 | |||
P210, 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, P501 | |||
NFPA 704 (fire diamond) | |||
Flash point | 33 °C (91 °F; 306 K) | ||
255 °C (491 °F; 528 K) | |||
Explosive limits | 0.8% v/v (lower) 6% v/v (upper) | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) |
300-2000 mg/kg (rat, oral) > 5 g/kg (rabbit, dermal) | ||
LC50 (median concentration) |
625 ppm/min (rat) | ||
Safety data sheet (SDS) | Fisher Scientific | ||
Related 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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