Esculin

Base Information

• Chemical Name: Esculin
• CAS No.: 531-75-9
• Deprecated CAS: 25360-17-2,28633-38-7,29008-74-0,97882-87-6,1078728-35-4,97882-87-6,29008-74-0,1078728-35-4
• Molecular Formula: C15H16O9
• Molecular Weight: 340.287
• Hs Code.: 29389090
• European Community (EC) Number: 208-517-5,686-504-7
• UNII: 1Y1L18LQAF
• ChEMBL ID: CHEMBL482581
• DSSTox Substance ID: DTXSID7045318
• Metabolomics Workbench ID: 53160
• NCI Thesaurus Code: C83696
• Nikkaji Number: J6.981G
• Wikidata: Q376432
• Wikipedia: Aesculin
• Mol file: 531-75-9.mol

Synonyms:Aesculin;Esculin;Esculoside;Venoplant

Chemical Property of Esculin

Chemical Property:

• Appearance/Colour: White to nearly white
• Vapor Pressure: 1.97E-20mmHg at 25°C
• Melting Point: 203 °C
• Refractive Index: -79 ° (C=2.4, 50% Dioxane)
• Boiling Point: 697.7 °C at 760 mmHg
• PKA: 7.00±0.20(Predicted)
• Flash Point: 262.8 °C
• PSA: 149.82000
• Density: 1.679 g/cm³
• LogP: -1.32270
• Storage Temp.: Store at RT.
• Solubility.: methanol: 50 mg/mL hot, clear to very faintly turbid, yello
• Water Solubility.: MODERATELY SOLUBLE
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 340.07943208
• Heavy Atom Count: 24
• Complexity: 495

Purity/Quality:

99% ^*data from raw suppliers

Esculin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, C, Xi
• Hazard Codes: F,C,Xi
• Statements: 11-20/21/22-34-68/20/21/22-36/37/38
• Safety Statements: 26-36/37/39-45-24/25-36/37-16

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=O)OC2=CC(=C(C=C21)OC3C(C(C(C(O3)CO)O)O)O)O
• Isomeric SMILES: C1=CC(=O)OC2=CC(=C(C=C21)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• Description: Aesculin (also Esculin) is a glucoside compound, which occurs naturally in unprocessed seeds, leaves, bark, and flowers of horse chestnut. Aesculin is used for the identification of bacteria, for the treatment of hemorrhoids and venous peripheral diseases. In cosmetics, aesculin was found to be effective in the treatment of aging skin. Owing to its ultraviolet absorbing activity, aesculin is employed in tanning preparations. Aesculin can be also used as a substrate for the detection of ?-gluocosidase activity in polyacrylamide gels.
• Uses: esculin is used as a skin protectant in ointments and creams. This is a glucoside compound originally obtained from the leaves and bark of the horse chestnut tree. esculoside is utilized in formulations for the treatment of cellulite. es culoside is apparently beneficial for impaired microcirculation. Esculin hydrate has been used as a component of sporulation-inducing esculin agar. It has also been used for esculin uptake assay.

Technology Process of Esculin

There total 8 articles about Esculin 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:

C88H56N4(4+)*4Cl(1-)*2C15H16O9 → C88H56N4(4+)*4Cl(1-) + esculin (531-75-9,97882-87-6)

Guidance literature:

With sodium hydrogencarbonate; In water-d2; at 20 ℃; for 18h;

DOI:10.1002/anie.201703357

Reference yield:

6-hydroxy-7-phenylmethoxy-2H-1-benzopyran-2-one (895-61-4) → esculin (531-75-9,97882-87-6)

Guidance literature:

Multi-step reaction with 3 steps

1: aqueous alkaline solution; acetone

2: ammonia; methanol

3: palladium/barium sulfate; methanol / Hydrogenation

With methanol; Pd-BaSO₄; alkaline solution; ammonia; acetone;

DOI:10.1002/ardp.19442820114

Reference yield:

benzyl chloride (100-44-7) → esculin (531-75-9,97882-87-6)

Guidance literature:

Multi-step reaction with 4 steps

1: methanol; potassium carbonate

2: aqueous alkaline solution; acetone

3: ammonia; methanol

4: palladium/barium sulfate; methanol / Hydrogenation

With methanol; Pd-BaSO₄; alkaline solution; ammonia; potassium carbonate; acetone;

DOI:10.1002/ardp.19442820114

upstream raw materials:

7-benzyloxy-6-β-D-glucopyranosyloxy-coumarin

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

benzyl chloride

7-benzyloxy-6-(tetra-O-acetyl-β-D-glucopyranosyloxy)-coumarin

Downstream raw materials:

isoscopoletin

5-ethoxy-2,4-dimethoxy-cinnamic acid methyl ester

aesculetin

D-glucose

Refernces

• 1、 -. "Amphiphile cyclodextrins, preparation and use thereof for solubilizing organized systems and incorporating hydrophobic molecules". . . Retrieved 2008/06/13.