Skimmin

Base Information

• Chemical Name: Skimmin
• CAS No.: 93-39-0
• Molecular Formula: C15H16O8
• Molecular Weight: 324.287
• UNII: H072F03PQN
• DSSTox Substance ID: DTXSID201018989
• Nikkaji Number: J4.674D
• Wikipedia: Skimmin
• Wikidata: Q15114711
• Metabolomics Workbench ID: 142295
• ChEMBL ID: CHEMBL526377
• Mol file: 93-39-0.mol

Synonyms:skimmin

Chemical Property of Skimmin

Chemical Property:

• Vapor Pressure: 7.68E-17mmHg at 25°C
• Melting Point: 221-222oC
• Refractive Index: 1.661
• Boiling Point: 632 °C at 760 mmHg
• PKA: 12.73±0.70(Predicted)
• Flash Point: 239.3 °C
• PSA: 129.59000
• Density: 1.588 g/cm³
• LogP: -1.02830
• Storage Temp.: 2-8°C
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 324.08451746
• Heavy Atom Count: 23
• Complexity: 466

Purity/Quality:

99% ^*data from raw suppliers

Skimmin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC2=C1C=CC(=O)O2)OC3C(C(C(C(O3)CO)O)O)O
• Isomeric SMILES: C1=CC(=CC2=C1C=CC(=O)O2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• Uses: Skimmin is a useful research chemical with neuroprotective effects.

Technology Process of Skimmin

There total 7 articles about Skimmin 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: 89.0%

7-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]-2H-1-benzopyran-2-one (133476-73-0) → skimmin (93-39-0)

Guidance literature:

With sodium methylate; In methanol; at 5 ℃; for 2h;

DOI:10.1002/ejoc.200700954

Reference yield: 61.0%

7-hydroxy-2H-chromen-2-one (93-35-6) + alpha-D-glucopyranose (492-62-6) → skimmin (93-39-0)

Guidance literature:

7-hydroxy-2H-chromen-2-one; alpha-D-glucopyranose; With di-isopropyl azodicarboxylate; triphenylphosphine; In 1,4-dioxane; at 55 ℃; for 0.25h; Inert atmosphere;

With di-isopropyl azodicarboxylate; triphenylphosphine; In 1,4-dioxane; at 55 ℃; for 0.75h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.0c01549

Reference yield: 40.1%

7-hydroxy-2H-chromen-2-one (93-35-6) → skimmin (93-39-0) + O-[β-D-xylopyranosyl(1->6)-β-D-glucopyranosyl] 7-hydroxycoumarin + umbelliferone 7-O-α-L-rhamnopyranosyl (1->2) β-D-glucopyranoside + umbelliferone 7-O-β-D-glucopyranosyl (1->6) β-D-glucopyranoside

Guidance literature:

With 6-furfurylaminopurine; In ethanol; water; at 25 ℃; for 168000h; Enzymatic reaction;

DOI:10.1016/S0040-4039(02)01138-3

upstream raw materials:

7-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]-2H-1-benzopyran-2-one

UDP-glucose

7-hydroxy-2H-chromen-2-one

alpha-D-glucopyranose

Downstream raw materials:

7-hydroxy-2H-chromen-2-one

D-Glucose

Refernces

• 1、 Xu, Xiping,Yan, Yaru,Huang, Wenqian,Mo, Ting,Wang, Xiaohui,Wang, Juan,Li, Jun,Shi, Shepo,Liu, Xiao,Tu, Pengfei. "Molecular cloning and biochemical characterization of a new coumarin glycosyltransferase CtUGT1 from Cistanche tubulosa". . . Retrieved 2021/07/28.
• 2、 Pandey, Ramesh Prasad,Bashyal, Puspalata,Parajuli, Prakash,Yamaguchi, Tokutaro,Sohng, Jae Kyung. "Two trifunctional leloir glycosyltransferases as biocatalysts for natural products glycodiversification". supporting information. p. 8058 - 8064. Retrieved 2019/10/14.