Hymecromon

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Gefahrenhinweise

  H303：May be harmfulif swallowed

  H315：Verursacht Hautreizungen.

  H319：Verursacht schwere Augenreizung.

  H335：Kann die Atemwege reizen.

• Sicherheit

  P261：Einatmen von Staub vermeiden.

  P304+P340：BEI EINATMEN: Die Person an die frische Luft bringen und für ungehinderte Atmung sorgen.

  P305+P351+P338：BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

  P405：Unter Verschluss aufbewahren.

4-Methylumbelliferone Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
  R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.

• S-Sätze Betriebsanweisung:

  S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
  S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
  S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.

• Chemische Eigenschaften

  Off-white to yellow crystals. Soluble in ethanol, acetic acid, alkali solutions, and ammonia. Slightly soluble in hot water, ether, and chloroform. Exhibits blue fluorescence when exposed to concentrated sulfuric acid.

• Originator

  Odeston,Merck

• Verwenden

  4-methylumbelliferone (4-MU) is a dietary supplement that inhibits hyaluronic acid (HA) synthesis. HA is a prominent component of the extracellular matrix at many sites of chronic inflammation, including type 1 diabetes (T1D), multiple sclerosis, and numerous malignancies. 4-MU is an already approved drug in Europe and Asia called “hymecromone” where it is used to treat biliary spasm.

• Definition

  ChEBI: 4-methylumbelliferone is a hydroxycoumarin that is umbelliferone substituted by a methyl group at position 4. It has a role as an antineoplastic agent and a hyaluronic acid synthesis inhibitor. It is functionally related to an umbelliferone.

• synthetische

  4-Methylumbelliferone is obtained by the cyclization reaction between resorcinol and ethyl acetate. Concentrated sulfuric acid is cooled to below 10 ° C, and a solution prepared from resorcinol and ethyl acetate is slowly added to the stirring solution. After dropping it completely, let it stand for 12 hours. Then, the reaction mixture is added into ice-cold water. The precipitate is filtered out and purified with a dilute sodium hydroxide solution and dilute sulfuric acid to obtain the final product.

• Manufacturing Process

  Resorcin reacted with 3-oxo-butyric acid ethyl ester in the presence sulfuric acid and phosphorous pentaoxide and 4-methyl-7-hydroxycoumarine (hymecromone) was obtained.

• Therapeutic Function

  Choleretic, Spasmolytic, Sunscreen agent

• Allgemeine Beschreibung

  4-Methylumbelliferone is a useful indicator for nitric acid determination and enzyme activity investigation. It emits fluorescence in alkaline solution and Standard for the fluorometric determination of enzyme activity. Highly fluorescent in alkaline solution. Fluorescence: max Abs. l = 360nm, max. Em. l = 449nm; pH > 9.

• Air & Water Reaktionen

  Insoluble in water.

• Brandgefahr

  Flash point data for 4-Methylumbelliferone are not available. 4-Methylumbelliferone is probably combustible.

• Pharmazeutische Anwendungen

  4-Methylumbelliferone is primarily used in synthesizing medicinal compounds and as a building block for fluorescent probes. Applications include synthesis of:
  coumarin triazole derivatives as potential antimicrobial agents.
  coumarin salen-based fluorescence sensors for Mg2+ detection.
  pyranocoumarin derivatives as anti-hyperglycemic and anti-dyslipidemic agents.
  coumarin piperazine derivatives as potential multireceptor atypical antipsychotics.
  4-methylumbelliferyl T-antigen as a substrate for endo-α-N-acetylgalactosaminidase.

• Biologische Aktivität

  4-methylumbelliferone is a hyaluronic acid (ha) synthesis inhibitor. the activation of has2 and the over-production of ha are existed in many metastatic tumor cell lines. increased synthesis of ha is often associated with increased metastatic potential and invasivity in tumor cells.

• Sicherheitsprofil

  Moderately toxic by ingestion and intraperitoneal routes. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes.

• in vitro

  4-methylumbelliferone (mu), an inhibitor of ha synthesis, has been studied as a potential anti-tumor drug on account of inhibiting the growth of primary tumors and distant metastasis of tumor cells. the mechanism still needs to be clarified, although several studies revealed that the anticancer effects of mu are mediated by inhibition of ha signal pathway. in a previous study the regulation of ha synthesis was demonstrated by ceramide, and now show how mu activated nsmase2 generates ceramides and mediates mu modulated inhibition of ha synthesis (cell migration and invasion, and apoptosis of tumor cells). using a ha enriched mouse oligodendroglioma cell line g26-24, it was found that mu elevated the activity of nsmase2 and enhanced ceramide levels, which in turn potentiated phosphatase pp2a activity. further, the activated pp2a decreased phosphorylation of akt, reduced activities of ha synthase2 (has2) and calpains, and blocked both the synthesis of ha, and the migration and invasion of g26-24 tumor cells. in addition, mu mediated ceramide induced activation of p53 and caspase-3, decreased sirt1 expression and deduced g26-24 viability. the mechanism of the mu anticancer therefore initially involves nsmase2/ceramide/pp2a/akt/has2/caspase-3/p53/sirt1 and the calpain signaling pathway, indicating that ceramides play a important role in the ability of a tumor to become aggressively metastatic and grow [1].

• target

  P450 (e.g. CYP17) | NADPH-oxidase | PKC | ROS

• IC 50

  0.4 mm

• läuterung methode

  Purify it by recrystallisation from EtOH. It is very slightly soluble in cold H2O (solubility at 37o is 0.22%), slightly soluble in Et2O and CHCl3, but soluble in MeOH and AcOH. It has a blue fluorescence in aqueous EtOH and has UV: 221, max 251 and 322.5nm (MeOH). The IR has 3077 br, 1667, 1592, 1385, 1267, 1156, 1130 and 1066 cm-1.max The acetate has m 153-154o. [Woods & Sapp J Org Chem 27 3703 1962, Beilstein 18 III/IV 332, 18/1 V 439.]

• Einzelnachweise

  [1] qin j, kilkus j, dawson g. the hyaluronic acid inhibitor 4-methylumbelliferone is an nsmase2 activator-role of ceramide in mu anti-tumor activity. biochim biophys acta. 2016 feb;1861(2):78-90.
  [2] Mustafa, Yasser Fakri et al. “4-Methylumbelliferone And Its Derived Compounds: A Brief Review Of Their Cytotoxicity.” The Egyptian Journal of Chemistry (2021): 0-0.
  [3] Essa, Marwa Labib et al. “Dual targeting nanoparticles based on hyaluronic and folic acids as a promising delivery system of the encapsulated 4-Methylumbelliferone (4-MU) against invasiveness of lung cancer in vivo and in vitro.” International journal of biological macromolecules (2022): n. pag.

4-Methylumbelliferone Upstream-Materialien And Downstream Produkte

Hymecromon Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global(663)Suppliers

90-33-5, 4-Methylumbelliferone Verwandte Suche: