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 | |
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3D model (
JSmol)
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|
ChEBI |
|
ChemSpider | |
ECHA InfoCard | 100.029.170 |
EC Number |
|
PubChem
CID
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UNII |
|
CompTox Dashboard (
EPA)
|
|
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Properties | |
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] |
Practically insoluble in water | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Pinene is a collection of unsaturated bicyclic monoterpenes. Two geometric isomers of pinene are found in nature, α-pinene and β-pinene. Both are chiral. As the name suggests, pinenes are found in pines. Specifically, pinene is the major component of the liquid extracts of conifers. [3] Pinenes are also found in many non-coniferous plants such as camphorweed ( Heterotheca) [4] and big sagebrush ( Artemisia tridentata).
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 |
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]
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]
β-Pinene can be converted to α-pinene in the presence of strong bases. [14]
Selective oxidation of pinene occurs at the allylic position to give verbenone, along with pinene oxide, as well as verbenol and its hydroperoxide. [15] [16]
Hydrogenation of pinene gives pinane, precursor to a useful pinane hydroperoxide.
The hydroboration of α-pinene has been extensively examined. With borane-dimethylsulfide, two equivalents of α-pinene react to give (diisopinocampheyl)borane. [17] Reaction with 9-BBN gives the reagent called alpine borane. This sterically crowded chiral trialkylborane can stereoselectively reduce aldehydes in what is known as the Midland Alpine borane reduction. [18]
Pinenes, especially α, are the primary constituents of turpentine, a nature-derived solvent and fuel. [3]
The use of pinene as a biofuel in spark ignition engines has been explored. [19] Pinene dimers have been shown to have heating values comparable to the jet fuel JP-10. [5]
{{
cite journal}}
: CS1 maint: multiple names: authors list (
link)
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 | |
| |
3D model (
JSmol)
|
|
ChEBI |
|
ChemSpider | |
ECHA InfoCard | 100.029.170 |
EC Number |
|
PubChem
CID
|
|
UNII |
|
CompTox Dashboard (
EPA)
|
|
| |
Properties | |
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] |
Practically insoluble in water | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Pinene is a collection of unsaturated bicyclic monoterpenes. Two geometric isomers of pinene are found in nature, α-pinene and β-pinene. Both are chiral. As the name suggests, pinenes are found in pines. Specifically, pinene is the major component of the liquid extracts of conifers. [3] Pinenes are also found in many non-coniferous plants such as camphorweed ( Heterotheca) [4] and big sagebrush ( Artemisia tridentata).
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 |
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]
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]
β-Pinene can be converted to α-pinene in the presence of strong bases. [14]
Selective oxidation of pinene occurs at the allylic position to give verbenone, along with pinene oxide, as well as verbenol and its hydroperoxide. [15] [16]
Hydrogenation of pinene gives pinane, precursor to a useful pinane hydroperoxide.
The hydroboration of α-pinene has been extensively examined. With borane-dimethylsulfide, two equivalents of α-pinene react to give (diisopinocampheyl)borane. [17] Reaction with 9-BBN gives the reagent called alpine borane. This sterically crowded chiral trialkylborane can stereoselectively reduce aldehydes in what is known as the Midland Alpine borane reduction. [18]
Pinenes, especially α, are the primary constituents of turpentine, a nature-derived solvent and fuel. [3]
The use of pinene as a biofuel in spark ignition engines has been explored. [19] Pinene dimers have been shown to have heating values comparable to the jet fuel JP-10. [5]
{{
cite journal}}
: CS1 maint: multiple names: authors list (
link)