cis -abienol

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Structural formula
Structural formula of Abienol
General
Surname Cis-abienol
other names
  • ( Z ) -Labda-12,14-dien-8-ol
  • ( Z ) -abienol
  • (12 Z ) -abienol
Molecular formula C 20 H 34 O
Brief description

white to pale yellow, waxy solid

External identifiers / databases
CAS number 17990-16-8
PubChem 643723
ChemSpider 558833
Wikidata Q27137053
properties
Molar mass 290.49 g · mol -1
Physical state

firmly

Melting point

39 ° C

solubility

little in chloroform and ethyl acetate

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 .

cis- abienol is a chemical compound and belongs to the group of labdanes , wherein the labdane -Grundgerüst by double bonds at the positions C-12 and C-14 and by a hydroxy group is modified at the position C-eighth There is consequently a diterpene - alcohol ( terpenoid ). The isomer trans -Abienol, which has an ( E ) - stereochemistry at C-12, is of little importance.

Occurrence and extraction

Balsam fir ( Abies balsamea )

Abienol is a natural substance and occurs in a wide variety of plants, among other things as the main component of the aromatic substance oleoresin in the balsam fir ( Abies balsamea ), in the Banks pine ( Pinus banksiana ), in the black spruce ( Picea mariana ) or in Virginian Tobacco ( Nicotiana tabacum) , from which it can also be obtained by extraction . It occurs mainly on the leaf surface.

use

Abienol serves as an inhibitor of tobacco Verwelkungskrankheit ( English Wilt Disease ). Furthermore, it is a starting compound for the production of fragrances and flavors . For this reason, Abienol is often used as a starting product in the perfume industry. In the laboratory it is mainly used in the synthesis of diols . The smell is described as wooden, amber, and balsamic.

Individual evidence

  1. ↑ a b c d Entry on (+) - cis-Abienol at Toronto Research Chemicals , accessed on April 8, 2018 ( PDF ).
  2. ↑ Data sheet (+) - cis-Abienol, SC-479393 , from Santa Cruz Biotechnology Inc., accessed on April 9, 2018 ( PDF ).
  3. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  4. ^ Entry on cis-Abienol in Chemical Entities of Biological Interest (ChEBI), accessed on April 9, 2018.
  5. ↑ P. Zerbe et al .: Bifunctional cis-abienol synthase from Abies balsamea discovered by transcriptome sequencing and its implications for diterpenoid fragrance production . In: The Journal of Biological Chemistry . tape 287 , 2012, p. 12121-12131 , doi : 10.1074 / jbc.M111.317669 .
  6. ↑ a b c Entry on cis-Abienol . The Goodscent Company, accessed April 9, 2018.
  7. ↑ Entry on Abienol in the MeSH of the NIH US National Library of Medicine , accessed April 9, 2018.
  8. ↑ V. Vontimitta et al .: Analysis of a Nicotiana tabacum L. genomic region controlling two leaf surface chemistry traits . In: Journal of Agricultural and Food Chemistry . tape 58 , 2010, p. 294-300 , doi : 10.1021 / jf903256h .
  9. ^ S. Seo et al .: Identification of natural diterpenes that inhibit bacterial wilt disease in tobacco, tomato and Arabidopsis . In: Plant & Cell Physiology . tape 53 , 2012, p. 1432-1444 , doi : 10.1093 / pcp / pcs085 .
  10. ↑ T. Hieda et al .: Microbial transformation of cis-abienol . In: Agricultural and Biological Chemistry . tape 46 , 1982, pp. 2249-2255 , doi : 10.1080 / 00021369.1982.10865428 .