2-pinanol

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Structural formula
Structural formula of the cis isomer of 2-pinanol.
Structural formula of the trans isomer of 2-pinanol.
Stereoisomers (left: cis , right: trans )
General
Surname 2-pinanol
other names
  • Pinan-2-ol
  • 2,6,6-trimethylbicyclo [3.1.1] heptan-2-ol
Molecular formula C 10 H 18 O
Brief description

colorless solid

External identifiers / databases
CAS number
  • 473-54-1
  • 4948-28-1 ( cis -form)
  • 4948-29-2 ( trans form)
  • 35408-04-9 [(1 R , 2 R ) form]
  • 35519-42-7 [(1 R , 2 S ) form]
EC number 207-466-6
ECHA InfoCard 100.006.789
PubChem 10128
Wikidata Q61472915
properties
Molar mass 154.28 g mol −1
Physical state

firmly

Melting point
  • 78-79.2 ° C ( cis isomer)
  • 58–59 ° C ( trans isomer)
boiling point
  • 90–91 ° C ( cis isomer at 1.5 kPa)
  • 88–89 ° C ( trans isomer at 0.12 kPa)
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2-pinanol is a chemical compound from the group of monoterpenes .

Extraction and presentation

2-Pinanol can be obtained by hydration (addition of water) of α- pinene , β-pinene or a mixture of isomers. It can also be obtained by oxidizing pinane in the presence of a base such as sodium hydroxide and a radical initiator such as AIBN . cis -2-pinanol is produced industrially by the catalytic hydrogenation of 2-pinane hydroperoxide . Alternatively, 2-pinane hydroperoxide can be treated with sodium sulfide in aqueous sodium hydroxide or with sodium methoxide . cis -2-pinanol can also be obtained directly from pinane by air oxidation in the presence of alkalis, such as sodium hydroxide, at 80 to 100.degree.

properties

2-Pinanol is a colorless solid, the cis -isomer having a camphor- like odor.

use

2-pinanol is used as a flavoring agent. It is also used as an intermediate in the production of terpene alcohols such as α-fenchol and linalool . The pyrolysis of 2-pinanol at 500 ° C yields linalool. (-) - Linalool is formed from (+) - cis - and (-) - trans -2-pinanol, and (+) - linalool from (-) - cis - and (+) - trans -2-pinanol.

Individual evidence

  1. ↑ a b c d e f g Ullmann's Encyclopedia of Industrial Chemistry . John Wiley & Sons, 2003, ISBN 3-527-30385-5 , pp. 661 ( limited preview in Google Book search).
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ↑ a b Entry on 2-pinanol in the Hazardous Substances Data Bank , accessed on February 4, 2019.
  4. ↑ Patent US3723542A : Process for producing 2-pinanol. Applied on January 23, 1970 , published February 27, 1973 , inventor: R. Risco, S. Lemberg. Accessed on 4 February of 2019.
  5. ^ Connolly / Hill: Dictionary of Terpenoids . CRC Press, 1991, ISBN 0-412-25770-X , pp. 140 ( limited preview in Google Book search).
  6. ↑ Yoshifumi Yuasa, Akira Nagakura, Haruki Tsuruta: A Convenient Synthesis of α-Fenchol from trans-2-Pinanol Using a Solid Acid Catalyst . In: Journal of Essential Oil Research . tape 8 , no. 5 , 1996, pp. 517-520 , doi : 10.1080 / 10412905.1996.9700679 .
  7. ↑ Eberhard Breitmaier: Terpene flavors, fragrances, pharmaceuticals, pheromones . John Wiley & Sons, 2012, ISBN 978-3-527-66048-3 ( limited preview in Google Book Search).
  8. ↑ Janne Leiner et al. : Thermal Behavior of Pinan-2-ol and Linalool . In: Molecules . tape 18 , no. 7 , July 2013, p. 8358-8375 , doi : 10.3390 / molecules18078358 , PMC 6269951 (free full text).