Rhein Acyl-β-D-glucuronide

Base Information

• Chemical Name: Rhein Acyl-β-D-glucuronide
• CAS No.: 190605-03-9
• Molecular Formula: C₂₁H₁₆O₁₂
• Molecular Weight: 460.351
• Mol file: 190605-03-9.mol

Synonyms:Rhein Acyl-β-D-glucuronide;1-(9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylate) β-D-Glucopyranuronic Acid;Rhein-acyl-beta-D-glucuronide min. 91%

Chemical Property of Rhein Acyl-β-D-glucuronide

Chemical Property:

• PSA: 208.12000
• LogP: -1.07780

Purity/Quality:

97% ^*data from raw suppliers

RheinAcyl-β-D-glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A metabolite of Rhein (R318500).

Technology Process of Rhein Acyl-β-D-glucuronide

There total 3 articles about Rhein Acyl-β-D-glucuronide 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:

C21H16O12*C4H9NO → rhein acyl glucuronide (190605-03-9)

Guidance literature:

With Amberlyst A-15; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/acs.jafc.6b01872

Reference yield:

1,8-dihydroxy-3-carboxy-anthraquinone (478-43-3) → rhein acyl glucuronide (190605-03-9)

Guidance literature:

Multi-step reaction with 3 steps

1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-methyl-morpholine / acetonitrile; tetrahydrofuran / 8 h / 20 °C / Inert atmosphere

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; morpholine / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

3: Amberlyst A-15 / tetrahydrofuran / 1 h / 20 °C

With morpholine; 4-methyl-morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; acetonitrile;

DOI:10.1021/acs.jafc.6b01872

Reference yield:

allyl glucuronate (698358-03-1) → rhein acyl glucuronide (190605-03-9)

Guidance literature:

Multi-step reaction with 3 steps

1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-methyl-morpholine / acetonitrile; tetrahydrofuran / 8 h / 20 °C / Inert atmosphere

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; morpholine / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

3: Amberlyst A-15 / tetrahydrofuran / 1 h / 20 °C

With morpholine; 4-methyl-morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; acetonitrile;

DOI:10.1021/acs.jafc.6b01872

upstream raw materials:

1,8-dihydroxy-3-carboxy-anthraquinone

allyl glucuronate