Difference between revisions of "Ferulic acid"

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Latest revision as of 17:16, 6 October 2019

Ferulic acid
Ferulic acid sample watchglass.jpg
OTC ferulic acid sample
Names
IUPAC name
(E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoic acid
Other names
3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid
3-(4-hydroxy-3-methoxyphenyl)acrylic acid
3-methoxy-4-hydroxycinnamic acid
4-hydroxy-3-methoxycinnamic acid
(2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid
(E)-ferulic acid
Coniferic acid
trans-Ferulic acid
Properties
C10H10O4
Molar mass 194.18 g/mol
Appearance White or pale yellow solid
Odor Dry plant-like
Melting point 168–172 °C (334–342 °F; 441–445 K)
Boiling point Decomposes
0.078 g/100 ml
Solubility Poorly soluble in DMF, DMSO, ethanol, methanol
Vapor pressure 2.69·10-6 mmHg at 25 °C
Acidity (pKa) 4.61
Hazards
Safety data sheet Sigma-Aldrich
Lethal dose or concentration (LD, LC):
7,900 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Ferulic acid is a hydroxycinnamic acid, an organic compound. It is an abundant phenolic phytochemical found in plant cell walls, covalently bonded as side chains to molecules such as arabinoxylans.

Salts of this acid are called ferulates.

Properties

Chemical

As a component of lignin, ferulic acid is a precursor in the manufacture of other aromatic compounds.

Physical

Ferulic acid is an off-white crystalline solid, with a faint dry plant-like odor. It is sparingly soluble in water.

Availability

Ferulic acid can be bought from various natural product stores, and it's quite pure. Some soapmaking suppliers will also sell it.

Ferulic acid is found in a number of vegetable sources, and occurs in particularly high concentrations in popcorn and bamboo shoots. It is a major metabolite of chlorogenic acids in humans along with caffeic and isoferulic acid.

It can be extracted from wheat bran and maize bran using concentrated alkali.[1]

Preparation

Ferulic acid can be prepared from caffeic acid.

Projects

Handling

Safety

Ferulic acid is relative harmless and doesn't show toxicity even at high doses. Though it may irritate the nose if inhaled, it's not classified as known allergen.

Storage

In closed plastic bottles.

Disposal

No special disposal is required. Discard it as you wish.

Ferulic acid is converted by certain strains of yeast, notably strains used in brewing of wheat beers, such as Saccharomyces delbrueckii (Torulaspora delbrueckii), to 4-vinyl guaiacol (2-methoxy-4-vinylphenol) which gives beers such as Weissbier and Wit their distinctive "clove" flavour.

References

  1. https://www.sciencedirect.com/science/article/pii/S0308814609001010?via%3Dihub

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