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
3D model (Jmol)	Interactive image
ChEBI	CHEBI:27794
PubChem	736186
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	194.18 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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] An analysis of propolis from Henan, China found sinapinic acid, isoferulic acid, caffeic acid and chrysin, with the first three compounds demonstrating antibacterial properties.^[2]

In food

Ferulic acid is found in pineapple flesh.^[3]

References

↑ 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.
↑ Qiao Z; Chen R (August 1991). "[Isolation and identification of antibiotic constituents of propolis from Henan]". Zhongguo Zhong Yao Za Zhi (in Chinese). 16 (8): 481–2, 512. PMID 1804186.
↑ Phenolic profiles of pineapple fruits (Ananas comosus L. Merrill) Influence of the origin of suckers. Edwige Sopie Yapo, Hilaire Tanoh Kouakou, Laurent kouakou kouakou, Justin Yatty Kouadio, Patrice Kouamé andjean-Michel Mérillon, Australian Journal of Basic and Applied Sciences, 2011, 5(6), pages 1372-1378

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

Ferulic acid glucoside
p-Coumaric acid glucoside
1-Sinapoyl-D-glucose

Tartaric acid esters

Caftaric acid
Cichoric acid (dicaffeoyltartaric acid)
Coutaric acid
Fertaric acid
Grape reaction product (caftaric acid conjugated with glutathione)

Other esters
with caffeic acid

Caffeoylmalic acid
Ethyl caffeate
Methyl caffeate
Caffeic acid phenethyl ester (CAPE)
Rosmarinic acid (ester with 3,4-dihydroxyphenyllactic acid)

Caffeoyl phenylethanoid
glycoside (CPG)

Echinacoside
Calceolarioside A, B, C and F
Chiritoside A, B and C
Cistanoside A, B, C, D, E, F, G an H
Conandroside
Myconoside
Pauoifloside
Plantainoside A
Plantamajoside
Tubuloside B
Verbascoside (Isoverbascoside, 2'-Acetylverbascoside)

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

Conjugates with
coenzyme A (CoA)

This article is issued from Wikipedia - version of the 7/20/2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.