3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic acid

Base Information

• Chemical Name: 3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic acid
• CAS No.: 14364-05-7
• Molecular Formula: C₁₅H₁₈O₈
• Molecular Weight: 326.303
• Wikidata: Q27102325
• Mol file: 14364-05-7.mol

Synonyms:Q27102325

Chemical Property of 3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic acid

Chemical Property:

• PSA: 136.68000
• LogP: -1.03690
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 326.10016753
• Heavy Atom Count: 23
• Complexity: 418

Purity/Quality:

Coumaric acid 4-O-glucoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC(=O)O)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1C=CC(=O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O

Technology Process of 3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic acid

There total 19 articles about 3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic 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: 90.0%

methyl 4-[(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl]coumarate (66642-77-1) → E-4-O-β-D-glucopyranosyl-p-coumaric acid (117405-49-9,117405-48-8,14364-05-7)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 8h;

DOI:10.1021/jf071205v

Reference yield: 83.0%

methyl 4-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)coumarate → 4-O-β-D-galactopyranosyl trans-p-coumaric acid (117405-48-8,14364-05-7)

Guidance literature:

With water; sodium hydroxide; In methanol; at 20 ℃; for 1h;

Reference yield: 76.0%

benzyl 4-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)coumarate → 4-O-β-D-galactopyranosyl trans-p-coumaric acid (117405-48-8,14364-05-7)

Guidance literature:

With water; sodium hydroxide; In methanol; at 20 ℃; for 1h;

upstream raw materials:

p-Coumaric Acid

4-O-(6''-O-p-coumaroyl-β-D-glucopyranosyl)-p-coumaric acid

protoplumericin

methyl 4-[(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl]coumarate

Downstream raw materials:

methyl glucosyl-p-coumaroate

Refernces

• 1、 -. "BIVALENT LECA INHIBITORS TARGETING BIOFILM FORMATION OF PSEUDOMONAS AERUGINOSA". . . Retrieved 2021/05/15.
• 2、 Tatsuzawa, Fumi,Takahashi, Narumi,Kato, Kazuhisa,Shinoda, Koichi,Saito, Norio,Honda, Toshio. "Acylated cyanidin glycosides from the pale-violet flowers of Ionopsidium acaule (Desf.) Rchb. (Brassicaceae)". . p. 69 - 76. Retrieved 2013/11/19.