Esculetin

Base Information

• Chemical Name: Esculetin
• CAS No.: 305-01-1
• Molecular Formula: C9H6O4
• Molecular Weight: 178.144
• Hs Code.: 29322090
• Mol file: 305-01-1.mol

Synonyms:Coumarin,6,7-dihydroxy- (8CI);6,7-Dihydroxy-2-benzopyrone;6,7-Dihydroxycoumarin;Aesculetin;Asculetine;Cichorigenin;Cichoriin aglycon;Esculin aglycon;NSC 26428;

Chemical Property of Esculetin

Chemical Property:

• Appearance/Colour: yellowish crystalline powder
• Vapor Pressure: 0.000164mmHg at 25°C
• Melting Point: 271-273 °C(lit.)
• Refractive Index: 1.594
• Boiling Point: 469.7 °C at 760 mmHg
• PKA: 1.71(at 25℃)
• Flash Point: 201.4 °C
• PSA: 70.67000
• Density: 1.563 g/cm³
• LogP: 1.20420
• Storage Temp.: 2-8°C
• Solubility.: Solubility Almost insoluble in boiling water, ether; soluble in
• Water Solubility.: slightly soluble

Purity/Quality:

99% ^*data from raw suppliers

Esculetin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: antifungal, hepatoprotective, IL-1 inhibitor In filters for absorption of ultraviolet light. In the presence of esculetin and HA14-1 (sc-205911) expression of the death receptor 4 (DR4) has been observed to be upregulated and extracellular-regulated kinase (ERK) to be activated. Other studies suggest that esculetin upregulates death receptor 5 (DR5) protein expression, and enhances TRAIL-induced apoptosis. It also inhibits the activity of 12-LO (12-lipoxygenase), and decreases leukotriene biosynthesis during 5-LO inhibition.

Technology Process of Esculetin

There total 41 articles about Esculetin 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: 100.0%

6-hydroxy-7-phenylmethoxy-2H-1-benzopyran-2-one (895-61-4) → aesculetin (305-01-1)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In methanol; Product distribution / selectivity;

Reference yield: 85.0%

malic acid (617-48-1,78644-42-5) + 1,2,4-triacetoxybenzene (613-03-6) → aesculetin (305-01-1)

Guidance literature:

With sulfuric acid; for 2h; Heating;

Reference yield: 84.4%

ayapin (494-56-4) → aesculetin (305-01-1)

Guidance literature:

ayapin; aluminum tri-bromide; In ethanethiol; at 0 - 20 ℃;

With hydrogenchloride; In water; at 0 - 20 ℃; Product distribution / selectivity;

upstream raw materials:

7-hydroxy-2H-chromen-2-one

malic acid

1,2,4-triacetoxybenzene

1,2,4-Trihydroxybenzene

Downstream raw materials:

2-oxo-2H-chromene-6,7-diyl diacetate

6-hydroxy-7-phenylmethoxy-2H-1-benzopyran-2-one

6,7-bis-benzyloxy-coumarin

6-benzoyloxy-7-hydroxy-coumarin

Refernces

• 1、 Dean,Taylor. "-". . p. 114. Retrieved 1966.
• 2、 Sigmund. "-". . p. 657. Retrieved 1910.
• 3、 Singh, Sarita,Agarwal, Karishma,Iqbal, Hina,Yadav, Pankaj,Yadav, Deepika,Chanda, Debabrata,Tandon, Sudeep,Khan, Feroz,Gupta, Anil Kumar,Gupta, Atul. "Synthesis and evaluation of substituted 8,8-dimethyl-8H-pyrano[2,3-f]chromen-2-one derivatives as vasorelaxing agents". . . Retrieved 2020.
• 4、 Schmidt,E.. "-". . p. 324. Retrieved 1898.
• 5、 Borges,Pinto. "Synthesis of coumarins and derivatives. Biomimetic synthesis of esculetin and halogenated derivatives". . p. 1061 - 1068. Retrieved 1992.
• 6、 Sang, Dayong,Yue, Huaxin,Zhao, Zhengdong,Yang, Pengtao,Tian, Juan. "Anchimerically Assisted Selective Cleavage of Acid-Labile Aryl Alkyl Ethers by Aluminum Triiodide and N, N-Dimethylformamide Dimethyl Acetal". . p. 6429 - 6440. Retrieved 2020/07/14.