5-Caffeoylshikimic acid

Base Information

• Chemical Name: 5-Caffeoylshikimic acid
• CAS No.: 73263-62-4
• Deprecated CAS: 1656981-79-1
• Molecular Formula: C16H16 O8
• Molecular Weight: 336.298
• UNII: 5U399BD0RZ
• DSSTox Substance ID: DTXSID501312675
• Metabolomics Workbench ID: 70422
• Nikkaji Number: J139.306E
• Wikidata: Q27105553
• Wikipedia: Dactylifric_acid
• Mol file: 73263-62-4.mol

Synonyms:5-O-caffeoylshikimic acid

Chemical Property of 5-Caffeoylshikimic acid

Chemical Property:

• Vapor Pressure: 5.28E-17mmHg at 25°C
• Boiling Point: 635.1°C at 760 mmHg
• PKA: 4.27±0.70(Predicted)
• Flash Point: 236.5°C
• PSA: 144.52000
• Density: 1.6g/cm³
• LogP: 0.15930
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 336.08451746
• Heavy Atom Count: 24
• Complexity: 540

Purity/Quality:

≥98% ^*data from raw suppliers

5-O-Caffeoylshikimicacid ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C=C1C(=O)O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O
• Isomeric SMILES: C1[C@H]([C@@H]([C@@H](C=C1C(=O)O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O

Technology Process of 5-Caffeoylshikimic acid

There total 9 articles about 5-Caffeoylshikimic 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:

p-coumaroylshikimic acid → 5-O-caffeoyl-shikimic acid (73263-62-4)

Guidance literature:

With NADPH; In aq. phosphate buffer; at 30 ℃; for 3h; pH=7.5; Enzymatic reaction;

DOI:10.1016/j.bbrc.2018.01.075

Reference yield:

shikimic acid (138-59-0) + 3,4-diacetoxycinnamoyl chloride (98631-72-2,82592-68-5) → 4-O-caffeoylshikimic acid (1177319-06-0) + 3-O-caffeoylshikimic acid (1178525-55-7) + 5-O-caffeoyl-shikimic acid (73263-62-4)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1021/jf904537z

Reference yield:

(3aR,7R,7aS)-7-[(E)-3-(2,2-Diphenyl-benzo[1,3]dioxol-5-yl)-acryloyloxy]-2,2-dimethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid → 5-trans-caffeoylshikimic acid (73263-62-4)

Guidance literature:

In acetic acid; at 100 ℃; for 2h;

DOI:10.1248/cpb.30.3219

upstream raw materials:

methyl 3,4-O-isopropylideneshikimate

shikimic acid

3,4-diacetoxycinnamoyl chloride

methyl shikimate

Downstream raw materials:

caffeic acid

shikimic acid

(E)-3-(2,2-diphenylbenzo[d][1,3]dioxolen-5-yl) acrylic acid