Coumaryl alcohol

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of cumaryl alcohol
Structure of ( E ) -cumaryl alcohol
General
Surname Coumaryl alcohol
other names
  • p -Cumaryl alcohol
  • 3- (4-hydroxyphenyl) -2-propen-1-ol
  • 4-hydroxy cinnamon alcohol
  • 4 - [( E ) -3-hydroxyprop-1-enyl] phenol
  • 4- (3-hydroxy-1-propen-1-yl) phenol
Molecular formula C 9 H 10 O 2
Brief description

Solid

External identifiers / databases
CAS number
  • 20649-40-5 ( E ) -cumaryl alcohol
  • 124076-60-4 ( Z ) -cumaryl alcohol
  • 3690-05-9 (unspec.)
PubChem 5280535
ChemSpider 4444166
Wikidata Q420084
properties
Molar mass 150.18 g mol −1
Physical state

firmly

Melting point

124 ° C

solubility

in alcohol, ether, acetone and benzene

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 .

Cumaryl alcohol is a chemical compound from the group of phenylpropanoids or cinnamon alcohol derivatives.

Occurrence

Cumaryl alcohol, together with the other two monomers sinapyl alcohol and coniferyl alcohol, forms the basis of lignin , the support polymer of plants and wood. Cumaryl alcohol is more present in the lignin of grasses and less in the lignin of trees.

Manufacturing

The biosynthesis of cumaryl alcohol takes place in the plant in the phenylpropane metabolism , a multi-stage process in which trans- cinnamic acid is formed from phenylalanine or tyrosine . This is converted to coumaric acid by hydroxylation and then reduced to cumaryl alcohol via the aldehyde stage.

Technically, cumaryl alcohol can be produced by the enzymatic oxidation of 4-allyphenol .

Fatty acid - ester of Cumarylalkohols are the basis of the epicuticular waxes , which the surface of apples protect.

Individual evidence

  1. ^ A b c Robert C. Weast, Ph.D: Handbook of Chemistry and Physics . 66th edition. CRC Press, 1985, ISBN 0-8493-0466-0 .
  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. ↑ Gerhard Richter: Metabolic physiology of plants . Thieme, Stuttgart, 1997, ISBN 978-3-13-442006-7 ( page 373 in the Google book search).
  4. ↑ Peter Schopfer, Axel Brennicke: Plant Physiology . Spektrum Akademischer Verlag, 2010, ISBN 978-3-8274-2351-1 ( page 363 in the Google book search).
  5. ↑ Patent EP0710289B1 : Process for Producing 4-Hydroxy-Cinnamyl Alcohol. ‌
  6. ↑ Patent DE69401755T2 : Process for the production of 4-hydroxy- cinnamon alcohols . ‌