Grundinformationen
- Standard-SMILES
Cc1cc(=O)oc2cc(O)ccc12- InChIKey
HSHNITRMYYLLCV-UHFFFAOYSA-N- Summenformel
- C10H8O3
- Durchschnittliche Molmasse
- 176,17 g/mol
- Monoisotopische Masse
- 176,04734412
Überblick
Beta-methylumbelliferone appears as colorless crystals. Insoluble in water. (NTP, 1992)
Namen und Bezeichner
- Bevorzugter Name
- 4-Methylumbelliferone
- IUPAC
- 7-hydroxy-4-methylchromen-2-one
- Lokaler Name
- Hymecromon
- Englischer Name
- 4-Methylumbelliferone
- Summenformel
- C10H8O3
- Molmasse
- 176.17
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
90-33-5- PubChem CID
- 5280567
- DTXSID
DTXSID8025670- ChEMBL
CHEMBL12208- ChEBI
CHEBI:17224- UNII
- 3T5NG4Q468
- EC Number
- 201-986-7
- Nikkaji
- J1.763.999D、J3.914D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,9
- Polarare Oberfläche (TPSA)
- 46,5 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 13
- Formalladung
- 0
- Komplexität
- 257
Experimentelle und physikochemische Eigenschaften
Chemical Classes
Other Classes -> Other Aromatic Compounds
Industrial compound
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals
Physical Description
Beta-methylumbelliferone appears as colorless crystals. Insoluble in water. (NTP, 1992)
Colorless solid; [CAMEO] Off-white powder; [Acros Organics MSDS]
Solid
Physikochemische Eigenschaften
- Schmelzpunkt
- 188.5 · 188.5-190 °C(lit.)
- Siedepunkt
- 267.77 °C · 267.77°C (rough estimate)
- Dichte
- 1.1958 · 1.1958 (rough estimate)
- Brechungsindex
- 1.5036 · 1.5036 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Practically insoluble in water; slightly soluble in ethanol, ether,chloroform; soluble inmethanol
- Aggregatzustand
- Crystalline Powder
- pka
- 7.79 · 7.79(at 25℃)
- Farbe
- off-white to yellow
- Wasserlöslichkeit
- slightly soluble
- Merck
- 14 · 14,4854
- BRN
- 142217 · 142217
- Stabilität
- Stable. Combustible. Incompatible with strong oxidizing agents.
- Major Application
- color filter, electroluminescent displays, document security processes, lasers, integrated circuits, liquid crystal displays, surface brightening composition, oil products, teeth whitening agent, lysosomal enzyme assay, substrate for lipase, determining protein-protein-interactions in living cells, Antitrypanosomal, antileishmanial, anticancer, antiHIV, antimalarial, antibacterial, antifungal
- InChI
- 1S/C10H8O3/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5,11H,1H3
- InChIKey
- HSHNITRMYYLLCV-UHFFFAOYSA-N
- SMILES
- CC1=CC(=O)Oc2cc(O)ccc12
- LogP
- 2.37 · 2.370 (est)
- CAS Datenbank
- 90 · 90-33-5(CAS DataBase Reference)
- NIST chemische Informationen
- 7 · Coumarin, 7-hydroxy-4-methyl-(90-33-5)
- EPA chemische Informationen
- 4 · 4-Methylumbelliferone (90-33-5)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 340 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Chemical: 2H-1-Benzopyran-2-one, 7-hydroxy-4-methyl-
2H-1-Benzopyran-2-one, 7-hydroxy-4-methyl-: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
An irritant; [NTP] Causes tearing, ptosis, and altered sleep time in oral lethal-dose studies of mice and rats; Causes changes in liver and pituitary weights in 26-week constant oral studies of rats; [RTECS] An irritant; Harmful by inhalation and skin absorption; [Acros Organics MSDS]
Sicherheit und Schutzausrüstung
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Sicherheitsdaten
- wgk
- 2
- tsca
- TSCA listed
- hs_code
- 29329990
- RTECS-Nr.
- GN7000000
- risk_code
- 36/37/38-20/21/22
- Toxizität
- LD50 oral in rat: 3850mg/kg
- hazard_code
- Xi,Xn
- hazard_note
- Irritant
- safety_code
- 26-37/39-36
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
MeSH Pharmacological Classification
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)
Verwendung und Herstellung
Uses
Used as an analytical reagent, fluorescent indicator, and antispasmodic drug; [Merck Index] Used in tunable lasers; [NTP]
Use (kg; approx.) in Germany (2009): >2500
Anwendungen
Verwenden4-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.
Darstellung
synthetische4-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.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: 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.
Zugehörige Reaktionen
Verknüpfte Notizen
Wird geladen…