Ranunculin

Base Information

• Chemical Name: Ranunculin
• CAS No.: 644-69-9
• Deprecated CAS: 7509-28-6
• Molecular Formula: C11H16 O8
• Molecular Weight: 276.243
• European Community (EC) Number: 211-421-6
• UNII: IBP7446K1O
• DSSTox Substance ID: DTXSID40982977
• Nikkaji Number: J205.922C
• Wikipedia: Ranunculin
• Wikidata: Q1245911
• Metabolomics Workbench ID: 68859
• Mol file: 644-69-9.mol

Synonyms:((2S)-5-oxo-2,5-dihydro-2-furanyl)methyl beta-D-glucopyranoside;ranunculin

Chemical Property of Ranunculin

Chemical Property:

• PSA: 125.68000
• LogP: -2.71550
• XLogP3: -2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 276.08451746
• Heavy Atom Count: 19
• Complexity: 357

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=O)OC1COC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC(=O)O[C@@H]1CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• Uses: Ranunculin is a part of the angiosperm family Ranunculaceae. The compound is used to study the effects of angiotensin II-?induced myocardial hypertrophy of total glycosides.

Technology Process of Ranunculin

There total 5 articles about Ranunculin 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: 85.0%

(2'S)-(5'-oxo-2',5'-dihydrofuran-2'-yl)methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (85846-72-6) → (-)-ranunculin (644-69-9,7509-28-6)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 5h; Heating;

DOI:10.1016/0040-4020(82)87017-8

Reference yield:

(5S)-5-(hydroxymethyl)-5H-furan-2-one (78508-96-0) → (-)-ranunculin (644-69-9,7509-28-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / Ag₂O, anh.CaSO₄, iodine / CHCl₃ / 86 h / Ambient temperature

2: 85 percent / 1.5 percent aq. HCl / dioxane / 5 h / Heating

With hydrogenchloride; calcium sulfate; iodine; silver(l) oxide; In 1,4-dioxane; chloroform;

DOI:10.1016/0040-4020(82)87017-8

Reference yield:

(+)-2,3-O-ethoxymethylene-D-ribonolactone (78508-93-7) → (-)-ranunculin (644-69-9,7509-28-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / 220 °C / 40 Torr

2: 77 percent / Ag₂O, anh.CaSO₄, iodine / CHCl₃ / 86 h / Ambient temperature

3: 85 percent / 1.5 percent aq. HCl / dioxane / 5 h / Heating

With hydrogenchloride; calcium sulfate; iodine; silver(l) oxide; In 1,4-dioxane; chloroform;

DOI:10.1016/0040-4020(82)87017-8

upstream raw materials:

(2'S)-(5'-oxo-2',5'-dihydrofuran-2'-yl)methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

(5S)-5-(hydroxymethyl)-5H-furan-2-one

(+)-2,3-O-ethoxymethylene-D-ribonolactone

D-Ribono-1,4-lactone

Downstream raw materials:

protoanemonin

Refernces