Caffeoylmalic Acid

Base Information

• Chemical Name: Caffeoylmalic Acid
• CAS No.: 53755-04-7
• Molecular Formula: C₁₃H₁₂O₈
• Molecular Weight: 296.233
• UNII: 8EY7S5QS7D
• DSSTox Substance ID: DTXSID301031926
• Nikkaji Number: J715.941B,J2.310.725B
• Wikipedia: Caffeoylmalic_acid
• Wikidata: Q18379746
• Metabolomics Workbench ID: 43771
• ChEMBL ID: CHEMBL393293
• Mol file: 53755-04-7.mol

Synonyms:caffeoylmalic acid

Chemical Property of Caffeoylmalic Acid

Chemical Property:

• Vapor Pressure: 3.03E-13mmHg at 25°C
• Boiling Point: 557.1°Cat760mmHg
• PKA: 2.57±0.23(Predicted)
• Flash Point: 213.6°C
• PSA: 141.36000
• Density: 1.589g/cm³
• LogP: 0.58210
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 296.05321734
• Heavy Atom Count: 21
• Complexity: 430

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C=CC(=O)OC(CC(=O)O)C(=O)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1/C=C/C(=O)OC(CC(=O)O)C(=O)O)O)O

Technology Process of Caffeoylmalic Acid

There total 5 articles about Caffeoylmalic 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: 88.0%

C17H16O10 → Caffeoyl-L-malic acid (39015-77-5,92344-57-5,94730-42-4,149197-97-7,53755-04-7,423170-79-0)

Guidance literature:

With hydrogenchloride; In water; acetone; for 5h; Inert atmosphere; Reflux;

DOI:10.1080/00397911.2011.633252

Reference yield: 51.5%

dimethyl (2S)-2-({(2E)-3-[3,4-bis(acetyloxy)phenyl]prop-2-enoyl}oxy)butanedioate (1364479-79-7) → Caffeoyl-L-malic acid (39015-77-5,92344-57-5,94730-42-4,149197-97-7,53755-04-7,423170-79-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; for 6h; enantioselective reaction; Inert atmosphere; Reflux;

DOI:10.1002/cbdv.201100341

Reference yield:

caffeic acid anhydride tetraacetate (102876-69-7) → Caffeoyl-L-malic acid (39015-77-5,92344-57-5,94730-42-4,149197-97-7,53755-04-7,423170-79-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 48 h / 20 °C

2: trifluoroacetic acid / dichloromethane / 48 h / 20 °C

3: hydrogenchloride / water; acetone / 5 h / Inert atmosphere; Reflux

With pyridine; hydrogenchloride; trifluoroacetic acid; In dichloromethane; water; acetone;

DOI:10.1080/00397911.2011.633252

upstream raw materials:

dimethyl (2S)-2-({(2E)-3-[3,4-bis(acetyloxy)phenyl]prop-2-enoyl}oxy)butanedioate

caffeic acid anhydride tetraacetate

Refernces

• 1、 Lorenz, Peter,Duckstein, Sarina,Conrad, Juergen,Knoedler, Matthias,Meyer, Ulrich,Stintzing, Florian C.. "An approach to the chemotaxonomic differentiation of two European Dog's mercury species: Mercurialis annua L. and M. perennis L.". experimental part. p. 282 - 297. Retrieved 2012/05/04.