2-Pinanol

2-Pinanol
Names
Other names
2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol
Identifiers
CAS Number
  • 473-54-1
  • trans: 4948-29-2
  • cis: 4948-28-1
3D model (JSmol)
  • Interactive image
  • trans: Interactive image
  • cis: Interactive image
ChemSpider
  • 9723
  • cis: 4933698
ECHA InfoCard 100.006.789 Edit this at Wikidata
EC Number
  • 207-466-6
PubChem CID
  • 10128
  • trans: 1268143
  • cis: 6428289
UNII
  • 5DZK63N3UU
CompTox Dashboard (EPA)
  • DTXSID5029180 Edit this at Wikidata
  • trans: DTXSID8027583
  • cis: DTXSID3027582
InChI
  • InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,11)8(9)6-7/h7-8,11H,4-6H2,1-3H3
    Key: YYWZKGZIIKPPJZ-UHFFFAOYSA-N
  • trans: InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,11)8(9)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8+,10+/m0/s1
    Key: YYWZKGZIIKPPJZ-QXFUBDJGSA-N
  • cis: InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,11)8(9)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8+,10-/m0/s1
    Key: YYWZKGZIIKPPJZ-XKSSXDPKSA-N
  • CC1(C2CCC(C1C2)(C)O)C
  • trans: CC1(C)[C@@H]2C[C@H]1[C@](C)(O)CC2
  • cis: CC1(C)[C@@H]2C[C@H]1[C@@](C)(O)CC2
Properties
Chemical formula
 C10H18O
Molar mass 154.253 g·mol−1
Appearance colorless solid
Melting point 78–79 °C (cis)
58–59 °C (trans
Hazards
GHS labelling:[1]
Pictograms
 GHS06: ToxicGHS07: Exclamation mark
Danger
Hazard statements
 H302, H311, H312, H315, H319
Precautionary statements
 P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P316, P317, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

2-Pinanol is a collection of bicyclic terpenoid derived from the terpene pinene, but containing a tertiary alcohol. Both cis and trans isomers exist. Both are chiral They are produced by deoxygenation of corresponding cis- and trans-2-pinane hydroperoxide, which in turn can be produced by autoxidation of pinane with air.[2] Heating 2-pinanol gives linalool.[3]

References

  1. ^ "2-Pinanol". pubchem.ncbi.nlm.nih.gov.
  2. ^ 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.
  3. ^ Eggersdorfer, Manfred (2000). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN 978-3527306732.