3-p-Coumaroylquinic acid

Base Information

• Chemical Name: 3-p-Coumaroylquinic acid
• CAS No.: 87099-71-6
• Molecular Formula: C16H18O8
• Molecular Weight: 338.314
• UNII: 1AF7V9VW0S
• DSSTox Substance ID: DTXSID301344004
• Nikkaji Number: J238.609G,J302.610H
• Wikidata: Q104938518
• Mol file: 87099-71-6.mol

Synonyms:2-coumaroylquinic acid;o-coumaroylquinic acid

Chemical Property of 3-p-Coumaroylquinic acid

Chemical Property:

• PSA: 144.52000
• LogP: -0.35150
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 338.10016753
• Heavy Atom Count: 24
• Complexity: 496

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
• 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
• Uses: 5-O-Coumaroylquinic Acid is a butanol extract and a chemical constituent of Amygdalus persica L. flower, used as medicine and food. 5-O-Coumaroylquinic Acid is a flavonoid with antioxidant properties.

Technology Process of 3-p-Coumaroylquinic acid

There total 36 articles about 3-p-Coumaroylquinic 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: 77.3%

quinic acid bisacetonide (209965-31-1) + 4-hydroxycinnamic acid chloride (108608-03-3) → trans-3-p-coumaroylquinic acid (1899-30-5,5746-55-4,32451-86-8,32719-13-4,82659-64-1,82659-65-2,82889-89-2,87099-71-6,87099-74-9)

Guidance literature:

quinic acid bisacetonide; 4-hydroxycinnamic acid chloride; With pyridine; In dichloromethane;

With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃;

Reference yield: 77.0%

ethyl 5-O-acetyl-p-coumaroyl-3,4-O-isopropylidenequinate → 5-O-p-coumaroylquinic acid (5746-55-4,32451-86-8,32719-13-4,82659-64-1,82659-65-2,82889-89-2,87099-71-6,87099-74-9,1899-30-5)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃; for 144h;

DOI:10.1016/j.tetasy.2017.01.015

Reference yield:

(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone (32384-42-2) → 5-O-p-coumaroylquinic acid (5746-55-4,32451-86-8,32719-13-4,82659-64-1,82659-65-2,82889-89-2,87099-71-6,87099-74-9,1899-30-5)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium ethanolate / Inert atmosphere

2: dmap; pyridine / dichloromethane / 24 h / 20 °C

3: hydrogenchloride; water / tetrahydrofuran / 144 h / 20 °C

With pyridine; hydrogenchloride; dmap; water; sodium ethanolate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetasy.2017.01.015

upstream raw materials:

(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone

ethyl (3aR,5R,7R,7aS)-5,7-dihydroxy-2,2-dimethylhexahydro-benzo[1,3]dioxole-5-carboxylate

para-coumaric acid

3-(4-acetoxyphenyl)acrylic acid

Downstream raw materials:

(Z)-p-coumaric acid

p-Coumaric Acid