Pinane

Pinane
Identifiers
3D model (JSmol)
1847301
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.790 Edit this at Wikidata
EC Number
  • 207-467-1
  • trans: 229-978-9
UNII
UN number 3295
  • InChI=1S/C10H18/c1-7-4-5-8-6-9(7)10(8,2)3/h7-9H,4-6H2,1-3H3
    Key: XOKSLPVRUOBDEW-UHFFFAOYSA-N
  • trans: InChI=1S/C10H18/c1-7-4-5-8-6-9(7)10(8,2)3/h7-9H,4-6H2,1-3H3/t7-,8-,9-/m0/s1
    Key: XOKSLPVRUOBDEW-CIUDSAMLSA-N
  • cis: InChI=1S/C10H18/c1-7-4-5-8-6-9(7)10(8,2)3/h7-9H,4-6H2,1-3H3/t7-,8+,9+/m1/s1
    Key: XOKSLPVRUOBDEW-VGMNWLOBSA-N
  • CC1CCC2CC1C2(C)C
  • trans: C[C@H]1CC[C@H]2C[C@@H]1C2(C)C
  • cis: C[C@@H]1CC[C@H]2C[C@@H]1C2(C)C
Properties
C10H18
Molar mass 138.254 g·mol−1
Appearance colorless liquids
Boiling point 167.2 – 168 °C (cis)
164 °C (trans)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pinane describes a pair of isomeric hydrocarbons. The isomers, actually diastereomers, are both chiral. They are the cis and trans isomers arising from the hydrogenation of the terpenes pinene. Both isomers undergo reaction with air (autoxidation) to give 2-pinane hydroperoxides.[1] Partial reduction of these isomers gives 2-pinanol.[2] Pyrolysis of pinane gives dimethyloctadienes,[3] which can be further transformed into the fragrance chemical dihydromyrcenol.[4]

Formation of dimethyloctadienes

References

  1. ^ Erman, Mark B.; Kane, Bernard J. (2008). "Chemistry Around Pinene and Pinane: A Facile Synthesis of Cyclobutanes and Oxatricyclo-Derivative of Pinane from cis- and trans-Pinanols". Chemistry & Biodiversity. 5 (6): 910–919. doi:10.1002/cbdv.200890104. PMID 18618388. S2CID 24782774.
  2. ^ Eggersdorfer, Manfred (2000). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN 3527306730.
  3. ^ Sagorin, Gilles; Cazeils, Emmanuel; Basset, Jean-François; Reiter, Maud (2021). "From Pine to Perfume". CHIMIA. 75 (9): 780–787. doi:10.2533/chimia.2021.780. PMID 34526184.
  4. ^ Naves, Y -R (1968). "Progress in the Synthesis of Perfumes Based on Pinenes". Russian Chemical Reviews. 37 (10): 779–788. Bibcode:1968RuCRv..37..779N. doi:10.1070/RC1968v037n10ABEH001703.

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