Ferulic acid

Ferulic acid

Names
IUPAC name (E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoic acid
Other names 2-propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)- ferulic acid 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 Ferulate Coniferic acid trans-ferulic acid (E)-ferulic acid
Identifiers
CAS Number	1135-24-6 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17620 Y
ChEMBL	ChEMBL32749 Y
ChemSpider	393368 Y
DrugBank	DB07767 Y
ECHA InfoCard	100.013.173
PubChem	445858
InChI InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+ Y Key: KSEBMYQBYZTDHS-HWKANZROSA-N Y InChI=1/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+ Key: KSEBMYQBYZTDHS-HWKANZROBE
SMILES COc1cc(ccc1O)/C=C/C(=O)O
Properties
Chemical formula	C10H10O4
Molar mass	194.18 g/mol
Appearance	Crystalline Powder
Melting point	168 to 172 °C (334 to 342 °F; 441 to 445 K)
Solubility in water	0.78 g/L
Acidity (pKa)	3.46
Hazards
NFPA 704	1 2 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Ferulic acid is a hydroxycinnamic acid, a type of organic compound. It is an abundant phenolic found in plant cell wall components such as arabinoxylans as covalent side chains. It is related to trans-cinnamic acid. As a component of lignin, ferulic acid is a precursor in the manufacture of other aromatic compounds. The etymology is from the genus Ferula, referring to the giant fennel (Ferula communis).

As a building block of lignocelluloses, such as pectin and lignin, ferulic acid is ubiquitous in the plant kingdom.

Ferulic acid is found in the seeds of coffee, apple, artichoke, peanut, and orange, as well as in both seeds and cell walls of commelinid plants (such as rice, wheat, oats, the Chinese water chestnut (Eleocharis dulcis) and pineapple). Often in the form of chlorogenic acid.

In cereals, ferulic acid is localized in the bran the hard outer layer of grain. In wheat, phenolic compounds are mainly found in the form of insoluble bound ferulic acid and be relevant to resistance to wheat fungal diseases. The highest known concentration of ferulic acid glucoside has been found in flax seed (4.1 ± 0.2 g/kg). It is also found in barley grain.

Asterid Eudicot plants can also produce ferulic acid. The tea brewed from the leaves of yacón (Smallanthus sonchifolius), a plant traditionally grown in the Northern and Central Andes, contains quantities of ferulic acid. In legumes, the white bean variety navy bean is the richest source of ferulic acid among the common bean (Phaseolus vulgaris) varieties. It is also found in horse grams (Macrotyloma uniflorum).