Pelargonidin 3-glucoside

Base Information

• Chemical Name: Pelargonidin 3-glucoside
• CAS No.: 18466-51-8
• Molecular Formula: C₂₁H₂₁O₁₀*Cl
• Molecular Weight: 468.845
• UNII: 8H1WZY9R6P
• DSSTox Substance ID: DTXSID00939866
• Wikipedia: Callistephin
• Wikidata: Q27116710
• Mol file: 18466-51-8.mol

Synonyms:callistephin;pelargonidin 3-glucoside;pelargonidin-3-glucopyranoside;pelargonidin-3-glucoside

Chemical Property of Pelargonidin 3-glucoside

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 173.21000
• Density: g/cm³
• LogP: -2.31960
• Storage Temp.: −20°C
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 468.0823246
• Heavy Atom Count: 32
• Complexity: 585

Purity/Quality:

98%,99%, ^*data from raw suppliers

Pelargonidin 3-Glucoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=[O+]C3=CC(=CC(=C3C=C2OC4C(C(C(C(O4)CO)O)O)O)O)O)O.[Cl-]
• Isomeric SMILES: C1=CC(=CC=C1C2=[O+]C3=CC(=CC(=C3C=C2O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O.[Cl-]
• Uses: Pelargonidin 3-O-β-glucopyranoside is a naturally occurring anthocyanin found in strawberries and other fruits and flowers. Pelargonidin 3-O-β-glucopyranoside is known to exert potential antiinflammatory, anti-adhesive, anti-estrogenic, and angiotensin-converting enzyme inhibitory activities. Pelargonidin 3-Glucoside is also the glucoside of Pelargonidin (P218500), an potential antidiabetic agent. Pelargonidin 3-O-β-glucopyranoside is a naturally occurring anthocyanin found in strawberries and other fruits and flowers. Pelargonidin 3-O-β-glucopyranoside is known to exert potential antiinflammat ory, anti-adhesive, anti-estrogenic, and angiotensin-converting enzyme inhibitory activities. Pelargonidin 3-Glucoside is also the glucoside of Pelargonidin (P218500), an potential antidiabetic agent.

Technology Process of Pelargonidin 3-glucoside

There total 10 articles about Pelargonidin 3-glucoside 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:

UDP-glucose (133-89-1) + pelargonidin chloride (134-04-3) → pelargonidin-3-O-glucoside (18466-51-8,125410-44-8)

Guidance literature:

With Glycine max (L_.) Merr_. cv. Clark His₆-UDP-glucose:flavonoid 3-O-glucosyltransferase; at 30 ℃; for 0.05h; pH=8; regiospecific reaction; aq. buffer;

DOI:10.1016/j.phytochem.2010.05.009

Reference yield:

5,7-Diacetoxy-2-(4-acetoxy-phenyl)-3-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-chromenylium; chloride → pelargonidin-3-glucoside chloride (18466-51-8,125410-44-8)

Guidance literature:

With hydrogenchloride; potassium hydroxide; In methanol; water; for 3h; Yield given; Ambient temperature;

DOI:10.1002/hlca.19940770616

Reference yield:

4'-acetoxy-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)acetophenone (164329-27-5) → pelargonidin-3-glucoside chloride (18466-51-8,125410-44-8)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl gas / ethyl acetate / 48 h / -10 °C

2: 1.) KOH; 2.) 1M HCl / H₂O; methanol / 3 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; In methanol; water; ethyl acetate;

DOI:10.1002/hlca.19940770616

upstream raw materials:

2-formyl-3,5-dihydroxyphenyl benzoate

4'-acetoxy-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)acetophenone

4-(2-hydroxyacetyl)phenyl acetate

4-acetyloxyacetophenone

Downstream raw materials:

4-hydroxy-benzoic acid

Refernces

• 1、 Dangles, Olivier,Elhajji, Hakima. "145. Synthesis of 3-Methoxy- and 3-(β-D-Glucopyranosyloxy)flavylium Ions. Influence of the Flavylium Substitution Pattern on the Reactivity of Anthocyanins in Aqueous Solution". . p. 1595 - 1610. Retrieved 2007/10/02.