5-(3,4-Dihydro-5,7-dihydroxy-4-oxo-2H-1-benzopyran-2-yl)-2-methoxyphenyl beta-D-glucopyranosiduronic acid

Base Information

• Chemical Name: 5-(3,4-Dihydro-5,7-dihydroxy-4-oxo-2H-1-benzopyran-2-yl)-2-methoxyphenyl beta-D-glucopyranosiduronic acid
• CAS No.: 1237479-05-8
• Molecular Formula: C₂₂H₂₂O₁₂
• Molecular Weight: 478.409
• Hs Code.: 2938909090
• Mol file: 1237479-05-8.mol

Synonyms:5-(3,4-Dihydro-5,7-dihydroxy-4-oxo-2H-1-benzopyran-2-yl)-2-methoxyphenyl beta-D-glucopyranosiduronic acid

Chemical Property of 5-(3,4-Dihydro-5,7-dihydroxy-4-oxo-2H-1-benzopyran-2-yl)-2-methoxyphenyl beta-D-glucopyranosiduronic acid

Chemical Property:

• PSA: 192.44000
• LogP: 0.08390

Purity/Quality:

95% ^*data from raw suppliers

rac-Hesperetin3’-O-β-D-Glucuronide(MixtureofDiastereomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: rac-Hesperetin 3’-O-β-D-Glucuronide is one of the most abundant metabolites of rac-Hesperetin (H289501); a derivative of Hesperidine (H281185) with potential antihyperglycemic activity.

Technology Process of 5-(3,4-Dihydro-5,7-dihydroxy-4-oxo-2H-1-benzopyran-2-yl)-2-methoxyphenyl beta-D-glucopyranosiduronic acid

There total 3 articles about 5-(3,4-Dihydro-5,7-dihydroxy-4-oxo-2H-1-benzopyran-2-yl)-2-methoxyphenyl beta-D-glucopyranosiduronic acid 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: 30.0%

7-O-benzoylhesperetin 3'-O-[methyl (2'',3'',4''-tri-O-acetyl)-β-D-glucopyranosyl uronate] (1237479-01-4) → hesperetin 3'-O-β-D-glucuronide (1237479-05-8)

Guidance literature:

7-O-benzoylhesperetin 3'-O-[methyl (2'',3'',4''-tri-O-acetyl)-β-D-glucopyranosyl uronate]; With water; sodium carbonate; at 0 - 20 ℃; for 5h; Inert atmosphere;

In water; pH=Ca. 6; Inert atmosphere;

DOI:10.1021/jf1010403

Reference yield:

(S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone (520-33-2,41001-90-5,69097-99-0) → hesperetin 3'-O-β-D-glucuronide (1237479-05-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridine / 20 °C / Cooling with ice

2.1: boron trifluoride diethyl etherate / dichloromethane / 20 °C / Molecular sieve; Inert atmosphere; Cooling with ice

3.1: water; sodium carbonate / 5 h / 0 - 20 °C / Inert atmosphere

3.2: Dowex 50WX₄-50 H(+) form / pH Ca_. 6 / Inert atmosphere

With pyridine; boron trifluoride diethyl etherate; water; sodium carbonate; In dichloromethane;

DOI:10.1021/jf1010403

Reference yield:

7-O-benzoylhesperetin (1237478-97-5) + methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucuronate → hesperetin 3'-O-β-D-glucuronide (1237479-05-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 20 °C / Molecular sieve; Inert atmosphere; Cooling with ice

2.1: water; sodium carbonate / 5 h / 0 - 20 °C / Inert atmosphere

2.2: Dowex 50WX₄-50 H(+) form / pH Ca_. 6 / Inert atmosphere

With boron trifluoride diethyl etherate; water; sodium carbonate; In dichloromethane;

DOI:10.1021/jf1010403

upstream raw materials:

7-O-benzoylhesperetin

7-O-benzoylhesperetin 3'-O-[methyl (2'',3'',4''-tri-O-acetyl)-β-D-glucopyranosyl uronate]

(S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone

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