2,3-Dihydroxypropyl 3,4,5-trihydroxybenzoate

Base Information

• Chemical Name: 2,3-Dihydroxypropyl 3,4,5-trihydroxybenzoate
• CAS No.: 87087-60-3
• Molecular Formula: C₁₀H₁₂O₇
• Molecular Weight: 244.201
• DSSTox Substance ID: DTXSID901239764
• Wikidata: Q104396302
• Metabolomics Workbench ID: 48450

Synonyms:1-o-galloylglycerol

Chemical Property of 2,3-Dihydroxypropyl 3,4,5-trihydroxybenzoate

Chemical Property:

• XLogP3: -0.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 244.05830272
• Heavy Atom Count: 17
• Complexity: 245

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1O)O)O)C(=O)OCC(CO)O

Technology Process of 2,3-Dihydroxypropyl 3,4,5-trihydroxybenzoate

There total 4 articles about 2,3-Dihydroxypropyl 3,4,5-trihydroxybenzoate 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: 69.1%

Propyl gallate (121-79-9,56274-95-4) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → 1-O-Galloylglycerol (59634-75-2,87087-60-3)

Guidance literature:

With lipozyme 435; at 55 ℃; for 120h; Temperature; Enzymatic reaction;

DOI:10.1016/j.foodchem.2019.125479

Reference yield:

→ 1-O-Galloylglycerol (59634-75-2,87087-60-3)

Guidance literature:

With tetrahydrofuran; Pd-BaSO₄; at 35 - 40 ℃; Hydrogenation;

Reference yield:

3,4,5-trihydroxybenzoic acid (149-91-7) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → 1-O-Galloylglycerol (59634-75-2,87087-60-3)

Guidance literature:

With toluene-4-sulfonic acid; for 3h;

upstream raw materials:

3,4,5-trihydroxybenzoic acid

glycerol

Propyl gallate

Refernces

Enzymatic synthesis of 1-o-galloylglycerol: Characterization and determination of its antioxidant properties

10.1016/j.foodchem.2019.125479

Siyu Zhang and Casimir C. Akoh investigate the enzymatic synthesis of 1-o-galloylglycerol (GG) using a food-grade lipase (Lipozyme? 435) and optimizes the reaction conditions to achieve a yield of 76.9% ± 1.2%. GG was characterized by various techniques and found to have higher water solubility and hydrophilicity compared to gallic acid (GA) and propyl gallate (PG). The antioxidant properties of GG were evaluated using ferric reducing antioxidant power (FRAP), hydrogen peroxide (H2O2) scavenging, 1,1-diphenyl-2-picrylhydrazyl (DPPH), and 2,2-azinobis (3-ethylbenzthiazoline-6-sulfonic acid) (ABTS+) assays, revealing that GG exhibited superior scavenging capacity compared to GA and PG. The study suggests that GG could serve as a water-soluble antioxidant alternative to GA for food and cosmetic applications, offering enhanced solubility and potentially safer use due to its lower acidity and reduced likelihood of cellular penetration and cytotoxicity.

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