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Α-pinene

α-Pinene
Alpha-Pinene Isomers.svg
(+)-alpha-pinene-3D-balls.png
(+)-α-pinene
(−)-alpha-pinene-3D-balls.png
(−)-α-pinene
Names
IUPAC name
(1S,5S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene ((−)-α-Pinene)
Identifiers
80-56-8 unspecified YesY
7785-70-8 (+)-α-Pinene YesY
7785-26-4 (−)-α-Pinene YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:36740 unspecified N
CHEBI:28660 (−)-α-Pinene N
CHEBI:28261 (+)-α-Pinene N
ChemSpider 389795 YesY
ECHA InfoCard 100.001.175
KEGG C06308 YesY
PubChem 440968
RTECS number DT7000000 (unspec. isomer)
UNII JPF3YI7O34 YesY
Properties
C10H16
Molar mass 136.24 g·mol−1
Appearance Clear colorless liquid
Density 0.858 g/mL (liquid at 20 °C)
Melting point −64 °C (−83 °F; 209 K)
Boiling point 155 °C (311 °F; 428 K)
Very low
Solubility in acetic acid miscible
Solubility in ethanol miscible
Solubility in acetone miscible
−50.7° (1S,5S-Pinene)
Hazards
Main hazards flammable
R-phrases R10 R20/21/22 R36/37/38 R43 R51
S-phrases S16 S26 S36 S37 S60 S61
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 33 °C (91 °F; 306 K)
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).
N  (what is YesYN ?)
Infobox references

α-Pinene is an organic compound of the terpene class, one of two isomers of pinene. It is an alkene and it contains a reactive four-membered ring. It is found in the oils of many species of many coniferous trees, notably the pine. It is also found in the essential oil of rosemary (Rosmarinus officinalis) and Satureja myrtifolia (also known as "Zoufa" in some regions.) 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 racemic mixture is present in some oils such as eucalyptus oil and orange peel oil.

The four-membered ring in α-pinene 1 makes it a reactive hydrocarbon, prone to skeletal rearrangements such as the Wagner-Meerwein rearrangement. For example, attempts to perform hydration or hydrogen halide addition with the alkene functionality typically lead to rearranged products. With concentrated sulfuric acid and ethanol the major products are terpineol 2 and its ethyl ether 3, while glacial acetic acid gives the corresponding acetate ester 4. With dilute acids, terpin hydrate 5 becomes the major product.


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Wikipedia

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