Longifolene

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(+)-Longifolene
Longifolene
Names
IUPAC name
(1R,2S,7S,9S)- 3,3,7-trimethyl- 8-methylenetricyclo- [5.4.0.02,9]undecane
Identifiers
3D model (
JSmol
)
5731712 2044263 4663756
ChEBI
ChemSpider
ECHA InfoCard
 100.006.812 Edit this at Wikidata
EC Number
  • (+): 207-491-2
UNII
  • InChI=1S/C15H24/c1-10-11-6-7-12-13(11)14(2,3)8-5-9-15(10,12)4/h11-13H,1,5-9H2,2-4H3/t11-,12-,13+,15-/m1/s1 ☒N
    Key: PDSNLYSELAIEBU-GUIRCDHDSA-N ☒N
  • (+): C[C@]12CCCC([C@@H]3[C@H]1CC[C@@H]3C2=C)(C)C
  • (−): C[C@@]12CCCC([C@H]3[C@@H]1CC[C@H]3C2=C)(C)C
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:
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
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 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

liverworts
.

Longifolene is also one of two most abundant

aroma constituents of lapsang souchong tea, because the tea is smoked over pinewood fires.[2]

Occurrence and syntheses

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
Longifolene total synthesis by Corey.svg
Longifolene total synthesis by Corey.svg

Biosynthesis

The biosynthesis of longifolene begins with

1,3-hydride shift gives intermediate 4. After two additional cyclizations, intermediate 6 produces longifolene by a 1,2-alkyl migration
.

The biosynthesis of Longifolene
The biosynthesis of Longifolene

Reactions

It reacts with borane to give the derivative dilongifolylborane, which is a chiral hydroborating agent.[11]

References

  1. ^ Naffa, P.; Ourisson, G. Bulletin de la Société chimique de France, 1954, 1410.
  2. ^ Shan-Shan Yao； Wen-Fei Guo； YI Lu； Yuan-Xun Jiang, "Flavor Characteristics of Lapsang Souchong and Smoked Lapsang Souchong,a Special Chinese Black Tea with Pine Smoking Process", Journal of Agricultural and Food Chemistry, Vol. 53, No.22, (2005)[permanent dead link]
  3. ISBN 978-3527306732
    .
  4. doi:10.1021/ja01057a039
    .
  5. doi:10.1021/ja00775a044
    .
  6. doi:10.1021/ja00849a062
    .
  7. doi:10.1021/ja00476a071
    .
  8. doi:10.1021/jo00206a049
    .
  9. doi:10.1021/ja00167a105
    .
  10. J. Org. Chem.
    2005, 70, 5139 -5143.
  11. doi:10.1021/ar00063a004
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Longifolene&oldid=1159811304"