70831-56-0

Basic information

• Product Name: Cichoric acid
• Synonyms: (2r,3r)-2,3-bis[[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid;(2R,3R)-2,3-BIS[[(2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL]OXY]-BUTANE DIOIC ACID;CHICHORIC ACID;CICHORIC ACID;CICHORINIC ACID;DICAFFEOYL TARTARIC ACID;L-CHICORIC ACID;Cichoric Acid (Chicoric acid)
• CAS NO: 70831-56-0
• Molecular Formula: C₂₂H₁₈O₁₂
• Molecular Weight: 474.37
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 70831-56-0.mol

Chemical Properties

• Melting Point: 206°C(lit.)
• Boiling Point: 785 °C at 760 mmHg
• Flash Point: 272.9 °C
• Appearance: /
• Density: 1.641 g/cm³
• Vapor Pressure: 5.86E-26mmHg at 25°C
• Refractive Index: 1.726
• Storage Temp.: −20°C
• PKA: 1.42±0.25(Predicted)
• CAS DataBase Reference: Cichoric acid(CAS DataBase Reference)
• NIST Chemistry Reference: Cichoric acid(70831-56-0)
• EPA Substance Registry System: Cichoric acid(70831-56-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-42/43
• Safety Statements: 22-36/37-45-24/25
• WGK Germany: 3
• RTECS: EJ9852090
• Hazardous Substances Data: 70831-56-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m0/s1

Upstream product

• 147-71-7 D-tartaric acid 
• 488148-83-0 dibenzyl (+)-(2S,3S)-2,3-bis{3-[3,4-bis(benzyloxy)phenyl]prop-2-enoyloxy}-D-tartrate 
• 331-39-5 caffeic acid 
• 74257-25-3 ethyl caffeate 
• 54429-62-8 (E)-3-(3,4-bis(benzyloxy)phenyl)acrylic acid 
• 203571-40-8 3-(3,4-bis-benzyloxy-phenyl)-acrylic acid ethyl ester 
• 82592-68-5 (E)-3,4-di-O-acetylcaffeoyl chloride 
• 87-69-4 L-Tartaric acid 
• 488148-82-9 dibenzyl (-)-(2R,3R)-2,3-bis{3-[2,3-bis(3,4-dibenzyloxy)phenyl]prop-2-enoyloxy}-L-tartrate 
• 204273-54-1 (2R,3R)-2,3-Bis-[(E)-3-(3,4-diacetoxy-phenyl)-acryloyloxy]-succinic acid di-tert-butyl ester 
• 6537-80-0 caftaric acid 
• 6537-80-0 (-)-chicoric acid 

Downstream Products

• 6537-80-0 cis-chicoric acid 

Relevant articles and documents

A convenient synthesis of the Echinacea-derived immunostimulator and HIV-1 integrase inhibitor (-)-(2R,3R)-chicoric acid

The Echinacea-derived immunostimulator and HIV-1 integrase inhibitor (-)-chicoric acid (=2,3-bis{[3- (3,4-dihydroxyphenyl)-1-oxoprop-2-enyl]oxy}butanedioic acid; 1a) was conveniently prepared via a silane-promoted Pd-mediated chemoselective hydrogenolysis of its perbenzylated derivative 12a, which was generated from an efficient and reliable carbodiimide-mediated coupling reaction between the caffeic acid dibenzyl ether derivative 7 and commercially available (+)-dibenzyl L-tartrate (9a). The other naturally occurring dextrorotatory chicoric acid (1b) can be similarly prepared.

Facile syntheses of (2R,3R)-(-)- and (2S,3S)-(+)-chicoric acids

Practical and efficient syntheses of (2R, 3R)-(-)- and (2S, 3S)(+)- chicoric acids are reported, which may be amenable to analogue preparation.