Ellagic Acid

Base Information

• Chemical Name: Ellagic Acid
• CAS No.: 476-66-4
• Molecular Formula: C14H6O8
• Molecular Weight: 302.197
• Hs Code.: 29322090
• European Community (EC) Number: 207-508-3
• UNII: 19YRN3ZS9P
• ChEMBL ID: CHEMBL6246
• DSSTox Substance ID: DTXSID2020557
• Metabolomics Workbench ID: 38219
• NCI Thesaurus Code: C63641
• Nikkaji Number: J5.977C
• NSC Number: 758198,656272,407286
• Pharos Ligand ID: Y3Z5XWRFRMVJ
• RXCUI: 1358975
• Wikidata: Q422044
• Wikipedia: Ellagic_acid
• Mol file: 476-66-4.mol

Synonyms:Acid, Benzoaric;Acid, Ellagic;Benzoaric Acid;Ellagic Acid

Chemical Property of Ellagic Acid

Chemical Property:

• Appearance/Colour: cream to light yellow crystalline solid
• Vapor Pressure: 2.32E-26mmHg at 25°C
• Melting Point: ≥350 °C
• Refractive Index: 1.894
• Boiling Point: 796.5 °C at 760 mmHg
• Flash Point: 310.1 °C
• PSA: 141.34000
• Density: 2.066 g/cm³
• LogP: 1.31280
• Storage Temp.: Store at RT
• Sensitive.: Air & Light Sensitive
• Solubility.: 1 M NaOH: 10 mg/mL, dark green
• Water Solubility.: <0.1 g/100 mL at 21℃
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 0
• Exact Mass: 302.00626715
• Heavy Atom Count: 22
• Complexity: 475

Purity/Quality:

99% ^*data from raw suppliers

Ellagic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: C1=C2C3=C(C(=C1O)O)OC(=O)C4=CC(=C(C(=C43)OC2=O)O)O
• Recent ClinicalTrials: The Mitopure Challenge to Detect Levels of Urolithin A in Dried Blood Spots
• Recent NIPH Clinical Trials: Effect of pomegranate juice on the pharmacokinetics of midazolam in healthy volunteers.
• Uses: Ellagic Acid is a phenol antioxidant found naturally in various fruits and vegetables. Ellagic Acid was shown to exhibit high levels of hemostatic, antineoplastic, antimutagenic, antiproliferative and antioxidant properties in studies, which suggests its potential health benefits following ellagic acid consumption.

Technology Process of Ellagic Acid

There total 133 articles about Ellagic 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: 86.0%

2,3,7-trihydroxy-8-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)chromeno[5,4,3-cde]chromene-5,10-dione → L-Rhamnose (3615-41-6,478518-52-4) + ellagic acid (476-66-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 80 ℃; for 1h;

DOI:10.1007/s11418-017-1137-y

Reference yield: 83.0%

methyl galloate (99-24-1) → ellagic acid (476-66-4)

Guidance literature:

With boron trifluoride diethyl etherate; bis-[(trifluoroacetoxy)iodo]benzene; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.3762/BJOC.16.169

Reference yield: 77.0%

ellagic acid 3-O-α-L-rhamnopyranosyl-4′-O-α-L-arabinofuranoside → L-arabinose (5328-37-0) + L-Rhamnose (3615-41-6,478518-52-4) + ellagic acid (476-66-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 80 ℃; for 1h;

DOI:10.1007/s11418-017-1137-y

upstream raw materials:

3,4,5-trihydroxybenzoic acid

methyl galloate

Ethyl gallate

N-galloglycine

Downstream raw materials:

tetrabenzylellagic acid

3,3',4,4'-tetra-O-bemzyl-5,5'-di-C-benzylellagic acid

1,1,6-tribenzyl-3,7,8-tris-benzyloxy-1H-chromeno[5,4,3-cde]chromene-2,5,10-trione

2,3,7,8-tetrakis-benzoyloxy-chromeno[5,4,3-cde]chromene-5,10-dione

Refernces

Synthesis and structure-activity relationship study of antidiabetic penta-O-galloyl-D-glucopyranose and its analogues

10.1021/jm060087k

The research investigates the antidiabetic properties of penta-O-galloyl-D-glucopyranose (PGG) and its analogues. The study explores the structure-activity relationship of PGG's R- and α-anomers, which act as insulin mimetics, stimulating glucose transport in adipocytes and reducing blood glucose and insulin levels in diabetic and obese animals. The researchers synthesized and tested various novel compounds, finding that both the glucose core and the galloyl groups are crucial for activity. The galloyl groups linked to positions 1, 2, 3, and 4 of glucose are essential, while the one at position 6 is not. Notably, 6-chloro-6-deoxy-1,2,3,4-tetra-O-galloyl-R-D-glucopyranose (80) exhibited significantly higher glucose transport stimulatory activity than PGG, comparable to insulin. Key chemicals used in the research include PGG, gallic acid, methyl galloate, ellagic acid, and various derivatives of glucose and galloyl groups. The study provides insights into the development of new antidiabetic therapeutics that can address both hyperglycemia and adiposity.