Cryptochlorogenic acid

Base Information

• Chemical Name: Cryptochlorogenic acid
• CAS No.: 905-99-7
• Deprecated CAS: 110025-93-9,35906-35-5,17608-52-5
• Molecular Formula: C₁₆H₁₈O₉
• Molecular Weight: 354.314
• Hs Code.: 2918990090
• UNII: F23DJ84IZ9
• Nikkaji Number: J691.615E,J1.453.979D
• Wikidata: Q104254155,Q27145347,Q105023680
• ChEMBL ID: CHEMBL4203706,CHEMBL3092676
• Mol file: 905-99-7.mol

Synonyms:Cryptochlorogenic acid;905-99-7;4-Caffeoylquinic acid;4-O-Caffeoylquinic acid;4-Cqa;4-o-Caffeoyl quinic acid;Quinic acid 4-O-caffeate;4-O-(3,4-Dihydroxycinnamoyl)-D-quinic acid;F23DJ84IZ9;(3R,5R)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,3,5-trihydroxycyclohexane-1-carboxylic acid;CHEMBL4203706;4-(3,4-Dihydroxycinnamoyl)quinic acid;(1alpha,3alpha,4alpha,5beta)-4-(3-(3,4-(Dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,3,5-trihydroxycyclohexanecarboxylic acid;82638-23-1;87099-73-8;rel-(1S,3R,4S,5R)-4-(((E)-3-(3,4-Dihydroxyphenyl)acryloyl)oxy)-1,3,5-trihydroxycyclohexanecarboxylic acid;4-O-trans-caffeoylquinic acid;MFCD10566638;Cryptochlorogenic-acid;Quinic acid, 4-caffeoyl-;UNII-F23DJ84IZ9;4-O-(E)-caffeoylquinic acid;CHEMBL3092676;Cinnamic acid, 3,4-dihydroxy-, 4-carboxy-2,4,6-trihydroxycyclohexyl ester;Quinic acid, 4-caffeoyl-, E-;SCHEMBL18180782;SCHEMBL20883249;ACon1_000120;CHEBI:75491;HY-N0787;BDBM50455380;s9319;4-O-Caffeoylquinic acid, >=98.0%;AKOS037514601;CCG-268076;CS-3767;NCGC00180861-01;(3R,5R)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,3,5-trihydroxy-cyclohexanecarboxylic acid;BS-17821;PD118874;Cryptochlorogenic acid, analytical standard;4-Caffeoylquinic acid/ Cryptochlorogenic acid;Q-100886;B0B55D52-5101-4E6D-AA67-72D1CECBAA5A;Q27145347;49B68A4C-6EC9-4441-B7D7-E3B740A8CDEC;(1alpha,3R,4alpha,5R)-4-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,3,5-trihydroxycyclohexanecarboxylic acid;(1S,3R,4S,5R)-4-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,3,5-trihydroxycyclohexanecarboxylic acid;1,3beta,5alpha-Trihydroxy-4alpha-(3,4-dihydroxycinnamoyloxy)cyclohexane-1beta-carboxylic acid;CYCLOHEXANECARBOXYLIC ACID, 4-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,3,5-TRIHYDROXY-, (1.ALPHA.,3R,4.ALPHA.,5R)-;Cyclohexanecarboxylic acid, 4-(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-1,3,5-trihydroxy-, (1alpha,3R,4alpha,5R)-;Cyclohexanecarboxylic acid, 4-((3-(3,4-dihydroxyphenyl)-1-oxo-2-1R-propenyl)oxy)-1,3,5-trihydroxy-, (1R-(1alpha,3alpha,4alpha,5beta))-;CYCLOHEXANECARBOXYLIC ACID, 4-((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,3,5-TRIHYDROXY-, (1.ALPHA.,3R,4.ALPHA.,5R)-;Cyclohexanecarboxylic acid, 4-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-1,3,5-trihydroxy-, (1alpha,3R,4alpha,5R)-;Cyclohexanecarboxylic acid, 4-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,3,5-trihydroxy-, (1alpha,3R,4alpha,5R)-;Cyclohexanecarboxylic acid, 4-(3-(3,4-(dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,3,5-trihydroxy-, (1alpha,3alpha,4alpha,5beta)-

Chemical Property of Cryptochlorogenic acid

Chemical Property:

• Refractive Index: 1.69
• Boiling Point: 344.3 °C at 760 mmHg
• PKA: 4.07±0.50(Predicted)
• Flash Point: 256.8 °C
• PSA: 164.75000
• Density: 1.65 g/cm³
• LogP: -0.64590
• Storage Temp.: ?20°C
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 354.09508215
• Heavy Atom Count: 25
• Complexity: 520

Purity/Quality:

95%-98% ^*data from raw suppliers

4-Caffeoylquinic acid/ Cryptochlorogenic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(C(C(CC1(C(=O)O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O
• Isomeric SMILES: C1[C@H](C([C@@H](CC1(C(=O)O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O
• Uses: Cryptochlorogenic acid may be used as a reference standard in the determination of cryptochlorogenic acid in the leaves of Hibiscus sabdariffa using high performance liquid chromatography coupled with mass spectrometry (HPLC-MS). 4-O-Caffeoylquinic acid has been used as a reference compound for the quantification in high performance liquid chromatography-diode array detector (HPLC-DAD).

Technology Process of Cryptochlorogenic acid

There total 7 articles about Cryptochlorogenic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

neochlorogenic acid (327-97-9,534-61-2,906-33-2,15016-60-1,15076-00-3,29587-84-6,32719-11-2,72690-58-5,77209-78-0,82659-69-6,82659-70-9,82659-71-0,82690-55-9,93451-45-7,93451-46-8) → 3-O-(cis-caffeoyl)quinic acid (32719-11-2) + (1S,3R,4R,5R)-5-[3-(3,4-dihydroxyphenyl)-2-hydroxypropanoyl]-1,4,5-trihydroxycyclohexanecarboxylic acid (1258222-08-0) + (1S,3R,4R,5R)-5-[3-(3,4-dihydroxyphenyl)-3-hydroxypropanoyl]-1,4,5-trihydroxycyclohexanecarboxylic acid (1258222-09-1) + caffeic acid (331-39-5,501-16-6) + D-(-)-quinic acid (77-95-2) + 4-O-caffeoylquinic acid (905-99-7,6049-17-8,17608-52-5,82638-22-0,82638-23-1,87099-76-1,87099-73-8) + 3-caffeoylquinic acid (202650-88-2)

Guidance literature:

In water; at 100 ℃; for 0.333333h;

DOI:10.1021/jf103373t

Reference yield:

neochlorogenic acid (327-97-9,534-61-2,906-33-2,15016-60-1,15076-00-3,29587-84-6,32719-11-2,72690-58-5,77209-78-0,82659-69-6,82659-70-9,82659-71-0,82690-55-9,93451-45-7,93451-46-8) → 3-O-(cis-caffeoyl)quinic acid (32719-11-2) + (1S,3R,4R,5R)-5-[3-(3,4-dihydroxyphenyl)-2-hydroxypropanoyl]-1,4,5-trihydroxycyclohexanecarboxylic acid (1258222-08-0) + (1S,3R,4R,5R)-5-[3-(3,4-dihydroxyphenyl)-3-hydroxypropanoyl]-1,4,5-trihydroxycyclohexanecarboxylic acid (1258222-09-1) + caffeic acid (331-39-5,501-16-6) + D-(-)-quinic acid (77-95-2) + 4-O-caffeoylquinic acid (905-99-7,6049-17-8,17608-52-5,82638-22-0,82638-23-1,87099-76-1,87099-73-8) + 4,5-di-O-caffeoylquinic acid (14534-61-3,17912-89-9,89886-28-2,89886-29-3,89886-30-6,89886-31-7,102851-07-0,102851-08-1,136088-12-5,57378-72-0) + 3-caffeoylquinic acid (202650-88-2)

Guidance literature:

In water; at 200 ℃; for 0.166667h;

DOI:10.1021/jf103373t

Reference yield:

neochlorogenic acid (327-97-9,534-61-2,906-33-2,15016-60-1,15076-00-3,29587-84-6,32719-11-2,72690-58-5,77209-78-0,82659-69-6,82659-70-9,82659-71-0,82690-55-9,93451-45-7,93451-46-8) → (1S,3R,4R,5R)-5-[3-(3,4-dihydroxyphenyl)-2-hydroxypropanoyl]-1,4,5-trihydroxycyclohexanecarboxylic acid (1258222-08-0) + (1S,3R,4R,5R)-5-[3-(3,4-dihydroxyphenyl)-3-hydroxypropanoyl]-1,4,5-trihydroxycyclohexanecarboxylic acid (1258222-09-1) + caffeic acid (331-39-5,501-16-6) + D-(-)-quinic acid (77-95-2) + 4-O-caffeoylquinic acid (905-99-7,6049-17-8,17608-52-5,82638-22-0,82638-23-1,87099-76-1,87099-73-8)

Guidance literature:

In water; for 0.166667h; Microwave irradiation; Reflux;

DOI:10.1021/jf103373t

upstream raw materials:

3-caffeoylquinic acid

(E)-3,4-di-O-acetylcaffeoyl chloride

(1R,3R,4S,5R)-3-[(tert-butyldimethylsilyl)oxy]-1,4-dihydroxy-6-oxa-bicyclo[3.2.1]octan-7-one

neochlorogenic acid

Downstream raw materials:

cis-4-O-caffeoylquinic acid

Refernces

• 1、 Dawidowicz, Andrzej L.,Typek, Rafal. "Thermal stability of 5-o-caffeoylquinic acid in aqueous solutions at different heating conditions". experimental part. p. 12578 - 12584. Retrieved 2011/10/30.
• 2、 Sefkow, Michael,Kelling, Alexandra,Schilde, Uwe. "First efficient syntheses of 1-, 4-, and 5-caffeoylquinic acid". . p. 2735 - 2742. Retrieved 2007/10/03.