Chlorogenic Acid

Base Information

• Chemical Name: Chlorogenic Acid
• CAS No.: 202650-88-2
• Molecular Formula: C16H18O9
• Molecular Weight: 354.314
• European Community (EC) Number: 206-325-6
• UNII: 318ADP12RI
• DSSTox Substance ID: DTXSID101318952
• Nikkaji Number: J954.882C,J108.009A
• Wikipedia: Chlorogenic_acid
• Wikidata: Q421964
• NCI Thesaurus Code: C116073
• Pharos Ligand ID: FWDZD69K7KQU
• Metabolomics Workbench ID: 38262
• ChEMBL ID: CHEMBL284616
• Mol file: 202650-88-2.mol

Synonyms:3 Caffeoylquinic Acid;3-Caffeoylquinic Acid;Acid, 3-Caffeoylquinic;Acid, Chlorogenic;Chlorogenic Acid

Chemical Property of Chlorogenic Acid

Chemical Property:

• Boiling Point: 665.0±55.0 °C(Predicted)
• PKA: 3.90±0.50(Predicted)
• PSA: 164.75000
• Density: 1.65±0.1 g/cm3(Predicted)
• LogP: -0.64590
• 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: 534

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O
• Isomeric SMILES: C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O
• Recent ClinicalTrials: Effect of Chlorogenic Acid on Patients With Impaired Glucose Tolerance

Technology Process of Chlorogenic Acid

There total 12 articles about Chlorogenic 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: 91.0%

C26H30O11 → 3-caffeoylquinic acid (202650-88-2)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 20 ℃;

DOI:10.1002/1099-0690(200103)2001:6<1137::AID-EJOC1137>3.0.CO;2-2

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

upstream raw materials:

(1S)-1-ethoxycarbonyloxy-3c-(3,4-dihydroxy-trans-cinnamoyloxy)-4t,5t-dihydroxy-cyclohexane-r-carboxylic acid methyl ester

caffeic acid

D-(-)-quinic acid

Trimethylsilyltetra-O-trimethylsilylchinat

Downstream raw materials:

3-caffeoylchinasaeure permethyl

1,3,4,3',4'-pentaacetylchlorogenic acid

caffeic acid

quinone of 5-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.