2,5-Dihydroxycinnamic acid

2,5-Dihydroxycinnamic acid
Names

Preferred IUPAC name (2E)-3-(2,5-Dihydroxyphenyl)prop-2-enoic acid
Other names (2E)-3-(2,5-Dihydroxyphenyl)acrylic acid, grevillic acid
Identifiers
CAS Number	38489-67-7^Y 636-01-1 (non-specific)^Y
3D model (JSmol)	Interactive image
ChemSpider	6442618
PubChem CID	181581
UNII	6EHK92QE99^Y
InChI InChI=1S/C9H8O4/c10-7-2-3-8(11)6(5-7)1-4-9(12)13/h1-5,10-11H,(H,12,13) Key: JXIPYOZBOMUUCA-UHFFFAOYSA-N
SMILES C1=CC(=C(C=C1O)C=CC(=O)O)O
Properties
Chemical formula	C₉H₈O₄
Molar mass	180.159 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

2,5-Dihydroxycinnamic acid is a hydroxycinnamic acid derivative. It is an isomer of caffeic acid.

Preparation

2,5-Dihydroxycinnamic acid is produced by Elbs persulfate oxidation of o-coumaric acid.^[1]^[2]

^ Cain, J.C.; Greenaway, A.J. (1907). "Abstracts of Papers on Organic chemistry". Journal of the Chemical Society, Abstracts. 92: A741–A812. doi:10.1039/CA9079200741.
^ Otto, Neubauer; Flatow, L. (1907). "Synthesen von Alkaptonsäuren". Zeitschrift für Physiologische Chemie. 52 (3–4): 375–398. doi:10.1515/bchm2.1907.52.3-4.375.

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-<i>O</i>-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′-<i>O</i>-4″-Triferulic acid
Tetramers	Tetraferulic acids

Conjugates with
coenzyme A (CoA)

This article about an aromatic compound is a stub. You can help Wikipedia by expanding it.

This page was last edited on 2 April 2024, at 18:48