Isoferulic acid

Isoferulic acid
Names

IUPAC name (E)-3-(3-Hydroxy-4-methoxyphenyl)prop-2-enoic acid
Other names Hesperetic acid 3-(3-Hydroxy-4-methoxyphenyl)acrylic acid Hesperetate Isoferulate
Identifiers
CAS Number	537-73-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27794
ChemSpider	643318
ECHA InfoCard	100.007.889
PubChem CID	736186
UNII	XSQ2K2G7MC^Y
CompTox Dashboard (EPA)	DTXSID901314847 DTXSID501009309, DTXSID901314847
InChI InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+ Key: QURCVMIEKCOAJU-HWKANZROSA-N
SMILES COC1=C(C=C(C=C1)C=CC(=O)O)O
Properties
Chemical formula	C₁₀H₁₀O₄
Molar mass	194.186 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Isoferulic acid is a hydroxycinnamic acid, a type of organic compound. It is an isomer of ferulic acid.

Occurrence in nature

Isoferulic acid can be found, amongst other compounds, in Lobelia chinensis.^[1]

Ferulic acid is found in pineapple flesh.^[2]

^ Chen JX, Huang SH, Wang Y, Shao M, Ye WC (2010). "Studies on the chemical constituents from Lobelia chinensis". Zhong Yao Cai. 33 (11): 1721–4. PMID 21434431.
^ Edwige Sopie Yapo, Hilaire Tanoh Kouakou, Laurent kouakou kouakou, Justin Yatty Kouadio, Patrice Kouamé andjean-Michel Mérillon (2011). "Phenolic profiles of pineapple fruits (Ananas comosus L. Merrill) Influence of the origin of suckers". Australian Journal of Basic and Applied Sciences. 5 (6): 1372–1378.{{cite journal}}: CS1 maint: multiple names: authors list (link)

Types of hydroxycinnamic acids

Aglycones

Precursor	Cinnamic acid
Monohydroxycinnamic acids (Coumaric acids)	p-Coumaric acid o-Coumaric acid m-Coumaric acid
Dihydroxycinnamic acids	Caffeic acid (3,4-dihydroxycinnamic acid) Umbellic acid (2,4-dihydroxycinnamic acid) 2,3-Dihydroxycinnamic acid 2,5-Dihydroxycinnamic acid 3,5-Dihydroxycinnamic acid
Trihydroxycinnamic acids	2,4,5-Trihydroxycinnamic acid 3,4,5-Trihydroxycinnamic acid
O-methylated forms	Ferulic acid 5-Hydroxyferulic acid Isoferulic acid Sinapinic acid
others	Plicatin A Plicatin B

Esters

glycoside-likes

Esters of
caffeic acid
with cyclitols

esters of quinic acid	Chlorogenic acid (3-caffeoylquinic acid) Cryptochlorogenic acid (4-O-caffeoylquinic acid) Neochlorogenic acid (5-O-Caffeoylquinic acid) Cynarine (1,5-dicaffeoylquinic acid) 3,4-dicaffeoylquinic acid 3,5-dicaffeoylquinic acid
esters of shikimic acid	Dactylifric acid (3-O-caffeoylshikimic acid)

Glycosides

Other esters
with caffeic acid

Caffeoyl phenylethanoid
glycoside (CPG)

Oligomeric forms

Dimers	Diferulic acids (DiFA) : 5,5′-Diferulic acid, 8-O-4′-Diferulic acid, 8,5′-Diferulic acid, 8,5′-DiFA (DC), 8,5′-DiFA (BF), 8,8′-Diferulic acid
Trimers	Triferulic acids : 5-5′,8′-O-4″-Triferulic acid
Tetramers	Tetraferulic acids