Caffeoylmalic acid

Caffeoylmalic acid
Names

IUPAC name 2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxybutanedioic acid
Other names (+)-(E)-caffeoyl-L-malic acid
Identifiers
CAS Number	39015-77-5
3D model (Jmol)	Interactive image
ChemSpider	4816367
PubChem	6124299
InChI InChI=1S/C13H12O8/c14-8-3-1-7(5-9(8)15)2-4-12(18)21-10(13(19)20)6-11(16)17/h1-5,10,14-15H,6H2,(H,16,17)(H,19,20)/b4-2+ Key: PMKQSEYPLQIEAY-DUXPYHPUSA-N InChI=1/C13H12O8/c14-8-3-1-7(5-9(8)15)2-4-12(18)21-10(13(19)20)6-11(16)17/h1-5,10,14-15H,6H2,(H,16,17)(H,19,20)/b4-2+ Key: PMKQSEYPLQIEAY-DUXPYHPUBQ
SMILES C1=CC(=C(C=C1C=CC(=O)OC(CC(=O)O)C(=O)O)O)O
Properties
Chemical formula	C₁₃H₁₂O₈
Molar mass	296.23 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

Caffeoylmalic acid is a hydroxycinnamic acid ester found in the leaves and flowers of Parietaria officinalis.^[1] It is also found in Chelidonium majus^[2] and Urtica dioica.^[3]

References

↑ Caffeoylmalic and two pyrrole acids from Parietaria officinalis. Jaromir Budzianowski, Phytochemistry, 1990, Volume 29, Issue 10, pages 3299–3301, doi:10.1016/0031-9422(90)80203-S
↑ Hydroxycinnamic Acid Derivatives, Caffeoylmalic and New Caffeoylaldonic Acid Esters, from Chelidonium majus. Hahn R and Nahrstedt A, Planta Med., February 1993, volume 59, issue 1, pages 71-75, PMID 17230338
↑ Rheumatic Pain Treatment With Stinging Nettle (Urticae Folium/Herba). S. Chrubasik and P. Shvartzman (article)

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

Tartaric acid esters

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

Conjugates with
coenzyme A (CoA)

This article is issued from Wikipedia - version of the 11/1/2015. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.