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:

• General Description: Esculetin (6,7-dihydroxycoumarin) is a bioactive coumarin derivative formed through the photo-degradation of caffeic acid or the enzymatic hydroxylation of umbelliferone by polyphenol oxidase. It serves as an intermediate in coumarin biosynthesis and exhibits substrate activity for tyrosinase, being further oxidized to o-quinone. Esculetin also demonstrates vasorelaxant properties, with derivatives showing enhanced pharmacological effects. Additionally, its formation can be influenced by metal ions like Pb(II) and Cu(II), which promote its production during caffeic acid photodegradation.

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:

isoscopoletin

Scoparone

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

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

Refernces

Synthesis of 2(1H)-quinolinone derivatives and their inhibitory activity on the release of 12(S)-hydroxyeicosatetraenoic acid (12-HETE) from platelets

10.1248/cpb.43.1724

The researchers synthesized numerous 2(1H)-quinolinone derivatives and identified 3,4-dihydro-6-[3-(1-o-tolylimidazol-2-yl)sulfinylpropoxy]-2(1H)-quinolinone (Sk) as a potent inhibitor of 12-HETE release, surpassing esculetin in potency. Further investigation into the enantiomers of Sk revealed that (S)-(+)-Sk exhibited the best pharmacological profile and was selected for further development. The study discusses structure-activity relationships and concludes that (S)-(+)-Sk has the optimal structure for inhibitory activity. Key chemicals used in the synthesis process include cilostazol, esculetin, various 2(1H)-quinolinone derivatives, and reagents such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), m-chloroperbenzoic acid (mCPBA), and cumene hydroperoxide.

10.1016/S0040-4020(01)92484-6

The research aims to elucidate the structures of several natural coumarins found in Ptaeroxylon obliquum (sneezewood) and synthesize them from aesculetin (5). The study confirms the structures of three coumarins (1-3) through UV, NMR, and IR spectroscopy, and demonstrates their interconversion via Claisen rearrangement. The key chemicals involved include aesculetin (5), scopoletin (6), and various derivatives such as 7-mono-ether (8) and 3,3-dimethylallyl bromide. The researchers synthesized coumarin 1 from scopoletin and used pyrolysis to produce obliquetin (2), nieshoutin (3), and an unexpected out-of-ring rearrangement product, 10. Methylation of 10 yielded rutacultin (11). The study concludes that the biogenesis of these coumarins might follow a similar pathway involving Claisen rearrangements, providing valuable insights into the natural synthesis of these compounds and their potential applications.