Caffeoylmalic acid

Caffeoylmalic acid
Chemical structure of 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 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 4816367
PubChem CID
  • 6124299
UNII
  • 8EY7S5QS7D checkY
CompTox Dashboard (EPA)
  • DTXSID301031926 Edit this at Wikidata
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
  • C1=CC(=C(C=C1C=CC(=O)OC(CC(=O)O)C(=O)O)O)O
Properties
Chemical formula
 C13H12O8
Molar mass 296.231 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

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

References

  1. ^ Budzianowski J (January 1990). "Caffeoylmalic and two pyrrole acids from Parietaria officinalis". Phytochemistry. 29 (10): 3299–301. doi:10.1016/0031-9422(90)80203-S.
  2. ^ Hahn R, Nahrstedt A (February 1993). "Hydroxycinnamic Acid Derivatives, Caffeoylmalic and New Caffeoylaldonic Acid Esters, from Chelidonium majus". Planta Medica. 59 (1): 71–5. doi:10.1055/s-2006-959608. PMID 17230338.
  3. ^ Farahpour, MR (January 2015). "Antinociceptive and anti-inflammatory activities of hydroethanolic extract of Urtica dioica" (PDF). Int. J. Biol. Pharm. Allied Sci. 4 (1): 165–167 – via Google Scholar.
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Types of hydroxycinnamic acids
Aglycones
Precursor
  • Cinnamic acid
Monohydroxycinnamic acids
(Coumaric acids)
  • p-Coumaric acid
  • o-Coumaric acid
  • m-Coumaric acid
Dihydroxycinnamic acids
Trihydroxycinnamic acids
O-methylated forms
others
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
Glycosides
  • Ferulic acid glucoside
  • p-Coumaric acid glucoside
  • 1-Sinapoyl-D-glucose
Tartaric acid esters
Other esters
with caffeic acid
Caffeoyl phenylethanoid
glycoside (CPG)
  • Echinacoside
  • Calceolarioside A, B, C, F
  • Chiritoside A, B, C
  • Cistanoside A, B, C, D, E, F, G, H
  • Conandroside
  • Myconoside
  • Pauoifloside
  • Plantainoside A
  • Plantamajoside
  • Tubuloside B
  • Verbascoside (Isoverbascoside, 2′-Acetylverbascoside)
Oligomeric forms
Dimers
Trimers
Tetramers
  • Tetraferulic acids
Conjugates with
coenzyme A (CoA)
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