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Chemical compound From Wikipedia, the free encyclopedia
Longifolene is the common (or trivial) chemical name of a naturally occurring, oily liquid hydrocarbon found primarily in the high-boiling fraction of certain pine resins. The name is derived from that of a pine species from which the compound was isolated,[1] Chemically, longifolene is a tricyclic sesquiterpene. This molecule is chiral, and the enantiomer commonly found in pines and other higher plants exhibits a positive optical rotation of +42.73°. The other enantiomer (optical rotation −42.73°) is found in small amounts in certain fungi and liverworts.
Names | |
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IUPAC name
(1R,2S,7S,9S)- 3,3,7-trimethyl- 8-methylenetricyclo- [5.4.0.02,9]undecane | |
Identifiers | |
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3D model (JSmol) |
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5731712 2044263 4663756 | |
ChEBI |
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ChemSpider | |
ECHA InfoCard | 100.006.812 |
EC Number |
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PubChem CID |
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UNII |
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CompTox Dashboard (EPA) |
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Properties | |
C15H24 | |
Molar mass | 204.36 g/mol |
Density | 0.928 g/cm3 |
Boiling point | 254 °C (489 °F; 527 K) (706 mm Hg) |
Hazards | |
GHS labelling: | |
Danger | |
H304, H317, H410 | |
P261, P272, P273, P280, P301+P310, P302+P352, P321, P331, P333+P313, P363, P391, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Longifolene is also one of two most abundant aroma constituents of lapsang souchong tea, because the tea is smoked over pinewood fires.[2]
Terpentine obtained from Pinus longifolia (obsolete name for Pinus roxburghii Sarg.) contains as much as 20% of longifolene.[3]
The laboratory synthesis of longifolene has attracted much syntheses.[4][5][6][7][8][9][10]
Longifolene total synthesis by Corey.svg |
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The biosynthesis of longifolene begins with farnesyl diphosphate (1) (also called farnesyl pyrophosphate) by means of a cationic polycyclization cascade. Loss of the pyrophosphate group and cyclization by the distal alkene gives intermediate 3, which by means of a 1,3-hydride shift gives intermediate 4. After two additional cyclizations, intermediate 6 produces longifolene by a 1,2-alkyl migration.
It reacts with borane to give the derivative dilongifolylborane, which is a chiral hydroborating agent.[11]
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