Tribuloside

Base Information

• Chemical Name: Tribuloside
• CAS No.: 22153-44-2
• Molecular Formula: C₃₀H₂₆O₁₃
• Molecular Weight: 594.529
• DSSTox Substance ID: DTXSID50436355
• Nikkaji Number: J650.629A
• Wikidata: Q82251628
• Pharos Ligand ID: YK64Q8G4YG9W
• Metabolomics Workbench ID: 139440
• ChEMBL ID: CHEMBL499705
• Mol file: 22153-44-2.mol

Synonyms:Tribuloside;cis-Tiliroside;163956-16-9;22153-44-2;Kaempferol-3-O-(6''-O-cis-coumaryl)glucoside;CHEMBL499705;[(2R,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (Z)-3-(4-hydroxyphenyl)prop-2-enoate;(Z)-((2R,3S,4S,5R,6S)-6-((5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl 3-(4-hydroxyphenyl)acrylate;DTXSID50436355;AKOS015965157;FS-7626;AC-20516;AC-34365;HY-126422;CS-0103784;E88866

Chemical Property of Tribuloside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 135 - 140 °C (methanol)
• Refractive Index: 1.759
• Boiling Point: 943.887 °C at 760 mmHg
• PKA: 6.20±0.40(Predicted)
• Flash Point: 311.861 °C
• PSA: 216.58000
• Density: 1.687 g/cm³
• LogP: 1.72540
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 8
• Exact Mass: 594.13734088
• Heavy Atom Count: 43
• Complexity: 1040

Purity/Quality:

99% ^*data from raw suppliers

Tribuloside ^*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)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)O)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1/C=C\C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)O)O)O)O

Technology Process of Tribuloside

There total 5 articles about Tribuloside 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: 67.0%

6''-O-p-coumaroylastragalin heptaacetate (256442-36-1) → astragalin (480-10-4) + trans-tiliroside (22153-44-2,68170-52-5,72691-81-7,104641-16-9,20316-62-5,163956-16-9)

Guidance literature:

With sodium methylate; In methanol; chloroform; for 2h; Ambient temperature;

DOI:10.1002/hlca.19810640630

Reference yield:

kaempferol 3-O-(3'',6''-di-O-E-p-coumaroyl)-β-D-glucopyranoside (74712-68-8) → astragalin (480-10-4) + p-Coumaric Acid (7400-08-0,50940-26-6) + trans-tiliroside (22153-44-2,68170-52-5,72691-81-7,104641-16-9,20316-62-5,163956-16-9)

Guidance literature:

With sodium hydroxide; at 50 - 60 ℃;

DOI:10.1007/BF00638772

Reference yield:

Tiliroside (20316-62-5,68170-52-5,72691-81-7,104641-16-9,22153-44-2,163956-16-9) → trans-tiliroside (22153-44-2,68170-52-5,72691-81-7,104641-16-9,20316-62-5,163956-16-9)

Guidance literature:

With iodine; In d⁽⁴⁾-methanol; at 50 ℃; for 0.0333333h; Green chemistry;

DOI:10.1016/j.tetlet.2015.11.050

upstream raw materials:

trans-tiliroside

6''-O-p-coumaroylastragalin heptaacetate

kaempferol 3-O-(3'',6''-di-O-E-p-coumaroyl)-β-D-glucopyranoside

Tiliroside

Downstream raw materials:

trans-tiliroside

astragalin

p-Coumaric Acid

D-Glucose