tetracaffeoylquinic acid

Base Information

• Chemical Name: tetracaffeoylquinic acid
• CAS No.: 13613-42-8
• Molecular Formula: C₁₇H₂₀O₉
• Molecular Weight: 368.34
• Mol file: 13613-42-8.mol

Synonyms:

Chemical Property of tetracaffeoylquinic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tetracaffeoylquinic acid

There total 11 articles about tetracaffeoylquinic 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: 69.0%

(1R,3R,4S,5R)-5-[3-(4-acetoxy-3-methoxyphenyl)-acryloyloxy]-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-hydroxycyclohexanecarboxylic acid methyl ester → tetracaffeoylquinic acid (1899-29-2,13613-42-8,29587-85-7,53905-80-9,62929-69-5,82659-66-3,82659-67-4,82659-68-5,87099-72-7,87099-75-0,89886-27-1,40242-06-6)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃; for 96h; Inert atmosphere;

DOI:10.1016/j.tetasy.2013.06.002

Reference yield: 67.0%

ethyl (1S,3R,4R,5R)-3-[3-(4-acetoxy-3-methoxyphenyl)acryloyloxy]-4,5-O-isopropylidene-1-quinate → 3-O-feruloyl-D-quinic acid (1899-29-2,13613-42-8,29587-85-7,40242-06-6,62929-69-5,82659-66-3,82659-67-4,82659-68-5,87099-72-7,87099-75-0,89886-27-1,53905-80-9)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; at 25 ℃; for 144h; Inert atmosphere;

DOI:10.1016/j.tetasy.2013.06.002

Reference yield:

D-(-)-quinic acid (77-95-2) → tetracaffeoylquinic acid (1899-29-2,13613-42-8,29587-85-7,53905-80-9,62929-69-5,82659-66-3,82659-67-4,82659-68-5,87099-72-7,87099-75-0,89886-27-1,40242-06-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 10-camphorsufonic acid / methanol / Inert atmosphere; Reflux

1.2: Inert atmosphere; Reflux

2.1: dmap; pyridine / dichloromethane / 20 °C / Inert atmosphere

3.1: hydrogenchloride / tetrahydrofuran; water / 96 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; dmap; 10-camphorsufonic acid; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/j.tetasy.2013.06.002

upstream raw materials:

4-acetoxyferuloyl chloride

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

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

3-(4-acetoxy-3-methoxyphenyl)prop-2-enoic acid

Downstream raw materials:

3-O-feruloylquinic acid methyl ester

methyl ferulate