Scopoletin

Base Information

• Chemical Name: Scopoletin
• CAS No.: 92-61-5
• Molecular Formula: C10H8O4
• Molecular Weight: 192.171
• Hs Code.: 29322090
• European Community (EC) Number: 202-171-9
• UNII: KLF1HS0SXJ
• ChEMBL ID: CHEMBL71851
• DSSTox Substance ID: DTXSID0075368
• Metabolomics Workbench ID: 46493
• NCI Thesaurus Code: C126100
• Nikkaji Number: J4.658B
• NSC Number: 405647
• Pharos Ligand ID: 49UFWTUZ8W94
• Wikidata: Q2472366
• Wikipedia: Scopoletin
• Mol file: 92-61-5.mol

Synonyms:Acid, Chrysotropic;Acid, Gelseminic;Chrysotropic Acid;Gelseminic Acid;Methylesculetin;Scopoletin

Chemical Property of Scopoletin

Chemical Property:

• Appearance/Colour: crystalline solid
• Vapor Pressure: 2E-07mmHg at 25°C
• Melting Point: 203-205 °C(lit.)
• Refractive Index: 1.609
• Boiling Point: 413.5 °C at 760 mmHg
• PKA: 7.91±0.20(Predicted)
• Flash Point: 172.4 °C
• PSA: 59.67000
• Density: 1.377 g/cm³
• LogP: 1.50720
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Sightly, Heated), Ethyl Acetate (Slightly, Heated), Methanol (Sightl
• Water Solubility.: Slightly soluble
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 192.04225873
• Heavy Atom Count: 14
• Complexity: 261

Purity/Quality:

≥98% ^*data from raw suppliers

Scopoletin ^*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

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: COC1=C(C=C2C(=C1)C=CC(=O)O2)O
• General Description: Scopoletin is a naturally occurring coumarin derivative with a hydroxyl group at the 7-position and a methoxy group at the 6-position, known by various synonyms such as 7-hydroxy-6-methoxycoumarin and escopoletin. It has been isolated from plant sources like *Xeromphis obovata* and *Atractylodes ovata*, often occurring as glycosides such as scopolin (its 7-β-D-glucopyranoside) or more complex glycosidic derivatives like xeroboside and scopoletin β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside. While its biological activities are not detailed in the provided abstracts, its presence in multiple plant species suggests potential pharmacological relevance.

Technology Process of Scopoletin

There total 46 articles about Scopoletin 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: 94.0%

7-acetoxy-6-methoxycoumarin (56795-51-8) → 7-hydroxy-6-methoxy-2H-1-benzopyran-2-one (92-61-5)

Guidance literature:

With silica-supported phosphomolybdic acid; In methanol; at 20 ℃; for 3h;

DOI:10.1002/adsc.200700292

Reference yield: 93.7%

2,4-dihydroxy-5-methoxybenzaldehyde (51061-83-7) + malonic acid (141-82-2) → 7-hydroxy-6-methoxy-2H-1-benzopyran-2-one (92-61-5)

Guidance literature:

With N,N-dimethyl-aniline; for 4h; Reflux;

Reference yield: 91.6%

2,4-dihydroxy-5-methoxybenzaldehyde (51061-83-7) + Malonic acid monomethyl ester (16695-14-0) → 7-hydroxy-6-methoxy-2H-1-benzopyran-2-one (92-61-5)

Guidance literature:

With N,N-dimethyl-aniline; at 180 ℃; for 6h;

upstream raw materials:

aesculetin

dimethyl sulfate

7-hydroxy-6-methoxy-2-oxo-2H-benzopyran-3-carboxylic acid

7-acetoxy-6-methoxycoumarin

Downstream raw materials:

2,4-dihydroxy-5-methoxybenzoic acid

braylin

aesculetin

methyl iodide

Refernces

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.

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