Ferulic acid

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Structural formula
Structure of ferulic acid
Structural formula of trans -ferulic acid
General
Surname Ferulic acid
other names
  • 4-hydroxy-3-methoxycinnamic acid
  • Coniferic acid
  • FERULIC ACID ( INCI )
Molecular formula C 10 H 10 O 4
Brief description

yellowish odorless solid

External identifiers / databases
CAS number
  • 1135-24-6
  • 537-98-4 [( E ) -isomer]
  • 1014-83-1 [( Z ) -isomer]
EC number 214-490-0
ECHA InfoCard 100.013.173
PubChem 445858
ChemSpider 393368
DrugBank DB07767
Wikidata Q417362
properties
Molar mass 194.19 g mol −1
Physical state

firmly

density

1.14 g cm −3

Melting point

169-173 ° C

solubility

soluble in water

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
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 .

Ferulic acid (more precisely trans -Ferulasäure ) is an organic compound , the (or its ester ) in various plants (eg. B. Stinkasant , dill , rice , grasses) occurs. See also the plant genus Ferula . It plays a role in the synthesis of lignin in the cell walls of plants.

Chemical properties

Ferulic acid belongs to the group of phenolic acids . The curcumin of turmeric is derived from its structure . Of course, it occurs almost exclusively in the trans form. Only beans contain a higher proportion of cis -ferulic acid, with some researchers assuming that the cis -form only arises when the plant samples are stored.

use

Ferulic acid is used as a raw material for the production of vanillin and antimicrobial substances for soaps, fragrances and cosmetics.

Importance in beer preparation

Ferulic acid has a decisive influence on the later sensory characteristics of the beer , especially in the preparation of wheat beer.

Occurrence of ferulic acid: Ferulic acid is bound to the insoluble pentosans in malt , there to arabinose side chains. Barley malt has a higher proportion of bound ferulic acid than wheat malt; analogously, higher values ​​are found in barley malt seasonings.

Influence during mashing : During mashing, there is the greatest influence on the release of ferulic acid (during malting only through hydrolytic pentosan degradation). Favorable mashing temperatures of 37–47 ° C cause a significant increase in ferulic acid, 44 ° C is an optimal temperature. Through the breakdown of the arabinoxylan by the endo- and exo-xylanases (optimum 45 ° C) and arabinosidases (40–45 °) C) the ferulic acid is released. A reduction in the mash pH below 5.7 slows down the degradation.

Fermentation : Top-fermenting yeast has the property of forming 4-vinylguajacol from ferulic acid as a precursor, which is a typical wheat beer aroma and is reminiscent of cloves. During fermentation, the ferulic acid is decarboxylated to form 4-vinylguaiacol, in wheat beer yeast in amounts of approx. 0.5–3.0 ppm. The formation is less due to the usual temperatures of 15-25 ° C during fermentation than to the vessels and yeast systems used. Multiple yeast management by harvesting in the upright cylinder-conical fermentation tank has a negative impact on the formation of 4-vinylguaiacol due to increased static pressure, which also has a general effect on the formation of esters and stress on the yeast cells. The desirable range of 4-vinylguaiacol formed is 1.2-1.7 ppm.

Individual evidence

  1. Entry on FERULIC ACID in the CosIng database of the EU Commission, accessed on May 13, 2020.
  2. a b c d e Entry on ferulic acid in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
  3. Carl L. Yaws; Thermophysical Properties of Chemicals and Hydrocarbons; ISBN 978-0-8155-1596-8 .
  4. ^ Albert Gossauer: Structure and reactivity of biomolecules , Verlag Helvetica Chimica Acta, Zurich, 2006, p. 385, ISBN 978-3-906390-29-1 .
  5. Tokusoglu Ozlem: Fruit and Cereal Bioactives: Sources, Chemistry, and Applications . CRC Press, 2011, ISBN 978-1-4398-0665-4 ( page 63 in the Google book search).
  6. Cesar G. Fraga: Plant phenolics and human health . Wiley, 2009, ISBN 978-0-470-28721-7 ( page 67 in the Google book search).