Sinapyl alcohol

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Structural formula
Structural formula of sinapyl alcohol
General
Surname Sinapyl alcohol
other names
  • 4- (3-hydroxyprop-1-enyl) -2,6-dimethoxyphenol
  • 4-hydroxy-3,5-dimethoxycinnamyl alcohol
  • Sinapine alcohol
  • Syringenin
Molecular formula C 11 H 14 O 4
Brief description

Solid

External identifiers / databases
CAS number 537-33-7
EC number 664-272-8
ECHA InfoCard 100.190.507
PubChem 5280507
ChemSpider 4444145
Wikidata Q418975
properties
Molar mass 210.23 g mol −1
Physical state

firmly

Melting point

61-65 ° C

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
EUH: 066
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Sinapyl alcohol ( trans -3,5-dimethoxy-4-hydroxycinnamic alcohol) is a chemical compound from the group of phenylpropanoids or cinnamic acid derivatives.

Occurrence

Sinapyl alcohol occurs naturally alongside cumaryl alcohol and coniferyl alcohol as a monomer of lignin (the supporting polymer of plants and wood). Sinapyl alcohol is the main component of lignin in hardwood. The biosynthesis of sinapyl alcohol is carried out in a multi-stage process in which in Phenylpropanstoffwechsel from phenylalanine or tyrosine trans-cinnamic acid is formed by hydroxylation and methylation to sinapinic acid is reacted. This in turn is reduced to sinapyl alcohol via the sinapine aldehyde . It is also the biosynthesis from an aldehyde stage by coniferylaldehyde 5-hydroxylase (Cald5H), subsequent methylation by 5-hydroxyconiferylaldehyde- O -methyltransferase (AldOMT) and ultimately reduction by sinapyl alcohol dehydrogenase (SAD).

properties

Sinapyl alcohol is an air-sensitive solid. The technical product contains up to 20% ethyl acetate .

Individual evidence

  1. ↑ a b c d e data sheet Sinapyl alcohol, technical grade, 80% from Sigma-Aldrich , accessed on July 22, 2011 ( PDF ).
  2. ↑ Gerhard Richter: Metabolic physiology of plants . Thieme, Stuttgart, 1997, ISBN 978-3-13-442006-7 ( page 373 in the Google book search).
  3. ↑ Peter Schopfer, Axel Brennicke: Plant Physiology . Spektrum Akademischer Verlag, 2010, ISBN 978-3-8274-2351-1 ( page 363 in the Google book search).
  4. ↑ Helge Scharnhop: Investigations on the biosynthesis of aromatic secondary metabolites in cell structures of Sorbus aucuparia L. and Centaurium erythraea RAFN . Cuvillier, E, 2008, ISBN 978-3-86727-665-8 ( page 19 in the Google book search).