Ferulic acid

Ferulic acid
Names
	Preferred IUPAC name (2E)-3-(4-hydroxy-3-methoxyphenyl)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; Coniferic acid; trans-ferulic acid; (E)-ferulic acid
Identifiers
CAS Number	537-98-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17620 ;
ChEMBL	ChEMBL32749 ;
ChemSpider	393368 ;
DrugBank	DB07767 ;
ECHA InfoCard	100.013.173
PubChem CID	445858;
UNII	AVM951ZWST ;
CompTox Dashboard (EPA)	DTXSID70892035 DTXSID5040673, DTXSID70892035 ;
	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+ Key: KSEBMYQBYZTDHS-HWKANZROSA-N ; 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	194.186 g·mol−1
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)	4.61
Hazards
NFPA 704 (fire diamond)	2 1 0
	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 derivative and a phenolic compound. It is an organic compound with the formula (CH₃O)HOC₆H₃CH=CHCO₂H. The name is derived from the genus Ferula, referring to the giant fennel (Ferula communis). Classified as a phenolic phytochemical, ferulic acid is an amber colored solid. Esters of ferulic acid are found in plant cell walls, covalently bonded to hemicellulose such as arabinoxylans.^[2] Salts and esters derived from ferulic acid are called ferulates.

^ ^a ^b Mota, Fátima L.; Queimada, António J.; Pinho, Simão P.; Macedo, Eugénia A. (August 2008). "Aqueous Solubility of Some Natural Phenolic Compounds" (PDF). Industrial & Engineering Chemistry Research. 47 (15): 5182–5189. doi:10.1021/ie071452o. hdl:10198/1506.
^ De Oliveira, Dyoni Matias; Finger-Teixeira, Aline; Rodrigues Mota, Thatiane; Salvador, Victor Hugo; Moreira-Vilar, Flávia Carolina; Correa Molinari, Hugo Bruno; Craig Mitchell, Rowan Andrew; Marchiosi, Rogério; Ferrarese-Filho, Osvaldo; Dantas Dos Santos, Wanderley (2015). "Ferulic acid: A Key Component in Grass Lignocellulose Recalcitrance to Hydrolysis". Plant Biotechnology Journal. 13 (9): 1224–1232. doi:10.1111/pbi.12292. PMID 25417596.

[Mota-2008-1] Mota, Fátima L.; Queimada, António J.; Pinho, Simão P.; Macedo, Eugénia A. (August 2008). "Aqueous Solubility of Some Natural Phenolic Compounds" (PDF). Industrial & Engineering Chemistry Research. 47 (15): 5182–5189. doi:10.1021/ie071452o. hdl:10198/1506.

[De_Oliveira-2015-2] De Oliveira, Dyoni Matias; Finger-Teixeira, Aline; Rodrigues Mota, Thatiane; Salvador, Victor Hugo; Moreira-Vilar, Flávia Carolina; Correa Molinari, Hugo Bruno; Craig Mitchell, Rowan Andrew; Marchiosi, Rogério; Ferrarese-Filho, Osvaldo; Dantas Dos Santos, Wanderley (2015). "Ferulic acid: A Key Component in Grass Lignocellulose Recalcitrance to Hydrolysis". Plant Biotechnology Journal. 13 (9): 1224–1232. doi:10.1111/pbi.12292. PMID 25417596.

[1]

[2]