Structure via PubChem · Public domain (PubChem)
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
In the Vinony graph
Within Vinony's link graph, longifolene is referenced by 86 other articles, and connects out to fungi, International Standard Book Number and Pinus.
It sits within the topics Chembox having GHS data, Chembox image size set and Chemical articles with multiple CAS registry numbers.
Its subject is documented across 12 Wikipedia language editions.
Chemical data
- Formula
- C15H24
- Molecular weight
- 204.35 g/mol
- IUPAC name
- (1R,2S,7S,9S)-3,3,7-trimethyl-8-methylidenetricyclo[5.4.0.02,9]undecane
- SMILES
- C[C@]12CCCC([C@@H]3[C@H]1CC[C@@H]3C2=C)(C)C
- InChIKey
- PDSNLYSELAIEBU-GUIRCDHDSA-N
- XLogP
- 5.1
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Has part
- hydrogen
- 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
via Wikidata · CC0
~2 min read
Encyclopedic overview
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.
Excerpted from Wikipedia’s “longifolene” article, available under the CC BY-SA 4.0 licence.