longifolene
Sign in to saveAlso known as (+)-Longifolen, kuromatsuene, junipene, [1S-(1alpha,3abeta,4alpha,8abeta)]-decahydro-4,8,8-trimethyl-9-methylene-1,4-methanoazulene, (1S,3aR,4S,8aS)-4,8,8-trimethyl-9-methylenedecahydro-1,4-methanoazulene, d-longifolene, (1S,3aR,4S,8aS)-(+)-decahydro-4,8,8-trimethyl-9-methylene-1,4-methanoazulene
Longifolene is a common sesquiterpene. It is an 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. It is a tricyclic chiral molecule. 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. ==Occurrence== Terpentine obtained from Pinus longifolia (obsolete name for Pinus roxburghii Sarg.) contains as much as
Wikidata facts
- Mass
- 204.188
Show 4 more facts
- Commons category
- Longifolene
- chemical formula
- C₁₅H₂₄
- canonical SMILES
- CC1(CCCC2(C3C1C(C2=C)CC3)C)C
- isomeric SMILES
- C[C@]12CCCC([C@@H]3[C@H]1CC[C@@H]3C2=C)(C)C
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Article
5 sectionsContents
- Occurrence
- Biosynthesis
- Synthesis and related chemistry
- References
- External links
Longifolene is a common sesquiterpene. It is an 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. It is a tricyclic chiral molecule. 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. ==Occurrence== Terpentine obtained from Pinus longifolia (obsolete name for Pinus roxburghii Sarg.) contains as much as 20% of longifolene.
Longifolene is also one of two most abundant aroma constituents of lapsang souchong tea, because the tea is smoked over pinewood fires. ==Biosynthesis== 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.