ChemicalBook Product Catalog Natural Products Coumarin Scopoletin

Scopoletin

Scopoletin Basic information
Product Name:Scopoletin
Synonyms:ESCULETIN-6-METHYL ETHER;B-METHYLESCULETIN;SCOPOLETIN;MURRAYETIN;AKOS 214-14;SCOPOLETIN 98.0+% T;NSC 405647;SCOPOLETIN (7-HYDROXY-6-METHOXYCOUMARIN)
CAS:92-61-5
MF:C10H8O4
MW:192.17
EINECS:202-171-9
Product Categories:Marker;sy;Inhibitors;Coumarins;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:92-61-5.mol
Scopoletin Structure
Scopoletin Chemical Properties
Melting point 203-205 °C (lit.)
Boiling point 288.14°C (rough estimate)
density 1.2932 (rough estimate)
refractive index 1.5430 (estimate)
storage temp. 2-8°C
solubility Chloroform (Sightly, Heated), Ethyl Acetate (Slightly, Heated), Methanol (Slightly, Heated)
pka7.91±0.20(Predicted)
form Crystalline Powder
color Beige
Water Solubility Slightly soluble
Merck 14,8408
BRN 156296
InChIKeyRODXRVNMMDRFIK-UHFFFAOYSA-N
LogP1.280 (est)
CAS DataBase Reference92-61-5(CAS DataBase Reference)
NIST Chemistry Reference7-Hydroxy-6-methoxy-2h-1-benzopyran-2-one(92-61-5)
EPA Substance Registry SystemScopoletin (92-61-5)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36-37/39
WGK Germany 2
RTECS GN6930000
HS Code 29322090
MSDS Information
ProviderLanguage
6-Methoxyumbelliferone English
SigmaAldrich English
ACROS English
Scopoletin Usage And Synthesis
Chemical PropertiesCrystalline Solid
UsesScopoletin can be used for cosmetics, topical formulations, and foods.
UsesScopoletin is the aglucone of Scopolin. Used for cosmetics, topical formulations, and foods. Dyes and metabolites.
DefinitionChEBI: A hydroxycoumarin that is umbelliferone bearing a methoxy substituent at position 6.
Synthesis Reference(s)The Journal of Organic Chemistry, 27, p. 3083, 1962 DOI: 10.1021/jo01056a023
General DescriptionScopoletin is a coumarin compound and pharmacologically active chemical that is found in various plant species.
Biochem/physiol ActionsScopoletin significantly increases activity of lipoprotein lipase in adipocytes by promoting transcription of the LPL gene. It also partially reverses inhibition of LPL by TNF-α.
Purification MethodsCrystallise it from water, acetic acid or *C6H6/MeOH. It is dimorphic with a second m at 193-195o. It sublimes at 120-130o/12mm. [Beilstein 18 H 99, 18 I 348, 18 II 68, 18 III/IV 1323, 18/3 V 203.]
Scopoletin Preparation Products And Raw materials
Raw materialsAluminum chloride-->N,N-Diethylaniline-->2,4,5-Trimethoxybenzaldehyde-->Ethyl (triphenylphosphoranylidene)acetate
Preparation ProductsEsculetin
7-HYDROXY-8-METHOXYCOUMARIN 3(2',4'-DICHLOROPHENYL)-7-METHOXYCOUMARIN Scopine 7-(3,3'-dimethylallyloxy)-5-hydroxy-6-methoxycoumarin SCOPARONE Methoxy 8-(3-(4-phenyl-1-piperazinyl)propoxy)-7-methoxycoumarin 7-Methoxycoumarin-4-acetyl-His-Gln-Lys-Leu-Val-Phe-Phe-Ala-(2,4-dinitrophenyl)-Lys trifluoroacetate salt 4-HYDROXY MEPHENYTOIN (7-methoxycoumarin-4-yl)-methyl-caged 8-bromoguanosine cyclic 3',5'-monophosphate 5-FORMYL-6-HYDROXY-7-METHOXYCOUMARIN 8-BROMO-7-METHOXYCOUMARIN 3,4-Dihydroxyacetophenone 7-Methoxycoumarin-4-acetyl-[Asn670, Leu671]-Amyloid β/A4 Precursor Protein 770 Fragment 667-674-(2,4-dinitrophenol)Dap 7,8-DIHYDROXY-6-METHOXYCOUMARIN 8-IODO-7-METHOXYCOUMARIN CHLOROPHOSPHONAZO III HYOSCINE HYDROCHLORIDE
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