Undulatoside A

Base Information

• Chemical Name: Undulatoside A
• CAS No.: 58108-99-9
• Molecular Formula: C16H18O9
• Molecular Weight: 354.31
• European Community (EC) Number: 804-186-1
• DSSTox Substance ID: DTXSID501346913
• Nikkaji Number: J1.088.779H
• Wikidata: Q76303597
• Metabolomics Workbench ID: 126812
• ChEMBL ID: CHEMBL2087913
• Mol file: 58108-99-9.mol

Synonyms:Undulatoside A;Staphylin;58108-99-9;5-hydroxy-2-methyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one;UndulatosideA;CHEMBL2087913;SCHEMBL20678163;DTXSID501346913;AKOS040762465;Undulatoside A, >=90% (LC/MS-ELSD)

Chemical Property of Undulatoside A

Chemical Property:

• PSA: 149.82000
• LogP: -1.01430
• XLogP3: 0
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 354.09508215
• Heavy Atom Count: 25
• Complexity: 536

Purity/Quality:

99% ^*data from raw suppliers

Undulatoside A ≥90% (LC/MS-ELSD) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=O)C2=C(C=C(C=C2O1)OC3C(C(C(C(O3)CO)O)O)O)O
• Isomeric SMILES: CC1=CC(=O)C2=C(C=C(C=C2O1)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O

Technology Process of Undulatoside A

There total 4 articles about Undulatoside A 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: 95.0%

5-hydroxy-7-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2-methylchromone (58109-01-6) → 7-O-β-D-glucopyranoside-2-methyl-5,7-dihydroxy-4H-1-benzopyran-4-one (58108-99-9)

Guidance literature:

5-hydroxy-7-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2-methylchromone; With methanol; sodium; at 0 ℃; for 1h;

DOI:10.1016/j.carres.2010.07.029

Reference yield:

eugenin (1013-69-0) → 7-O-β-D-glucopyranoside-2-methyl-5,7-dihydroxy-4H-1-benzopyran-4-one (58108-99-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Aliquat 336; potassium carbonate / chloroform; water / 18 h / 50 °C

2.1: sodium methylate / methanol / 2 h / 20 °C

2.2: Amberlyst-15 resin

With sodium methylate; Aliquat 336; potassium carbonate; In methanol; chloroform; water;

DOI:10.1021/jo102325s

Reference yield:

1-[2,4,6-tris(acetyloxy)phenyl]ethanone (144152-27-2) → 7-O-β-D-glucopyranoside-2-methyl-5,7-dihydroxy-4H-1-benzopyran-4-one (58108-99-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran / Reflux

2.1: Aliquat 336; potassium carbonate / chloroform; water / 18 h / 50 °C

3.1: sodium methylate / methanol / 2 h / 20 °C

3.2: Amberlyst-15 resin

With sodium methylate; Aliquat 336; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol; chloroform; water;

DOI:10.1021/jo102325s

upstream raw materials:

5-hydroxy-7-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2-methylchromone

eugenin

1-[2,4,6-tris(acetyloxy)phenyl]ethanone

2,4,6-trihydroxyacetophenone

Downstream raw materials:

cypellocarpin C

7-O-(2,3,4-tri-O-acetyl-6-trityl-β-D-glucopyranosyl)-5-hydroxy-2-methylchromone

Refernces

• 1、 Hakki, Zalihe,Cao, Benjamin,Heskes, Allison M.,Goodger, Jason Q.D.,Woodrow, Ian E.,Williams, Spencer J.. "Synthesis of the monoterpenoid esters cypellocarpin C and cuniloside B and evidence for their widespread occurrence in Eucalyptus". experimental part. p. 2079 - 2084. Retrieved 2010/10/19.