CAS 90-33-5|4-Methylumbelliferone
Introduction：Basic information about CAS 90-33-5|4-Methylumbelliferone, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | 4-Methylumbelliferone | ||
|---|---|---|---|
| CAS Number | 90-33-5 | Molecular Weight | 176.16900 |
| Density | 1.319 g/cm3 | Boiling Point | 377.4ºC at 760 mmHg |
| Molecular Formula | C10H8O3 | Melting Point | 188.5-190 °C(lit.) |
| MSDS | ChineseUSA | Flash Point | 174.5ºC |
Names
| Name | 4-Methylumbelliferone |
|---|---|
| Synonym | More Synonyms |
4-Methylumbelliferone BiologicalActivity
| Description | 4-Methylumbelliferone is a hyaluronic acid biosynthesis inhibitor with antitumoral and antimetastatic effects. |
|---|---|
| Related Catalog | Signaling Pathways >>Others >>OthersResearch Areas >>CancerResearch Areas >>Cardiovascular DiseaseNatural Products >>Phenylpropanoids |
| Target | hyaluronic acid[1] |
| In Vitro | 4-Methylumbelliferone (4-MU) affects several key steps of angiogenesis, including endothelial cell proliferation, adhesion, tube formation, and extracellular matrix remodeling. Half-maximal inhibitory concentrations (IC50) values in the proliferation assay are 0.65±0.04 and 0.37±0.03 mM for HMEC and RF-24 endothelial cells, respectively. 4-Methylumbelliferone (2 mM) treatment for 24 h induces apoptosis in 13% of HMEC and 5% of RF-24 cells. The number of adherent endothelial cells decreases by >20% after 24 h of treatment with 1 mM 4-Methylumbelliferone. Minimal inhibitory concentrations in the tube formation assay are 2 and 0.5 mM 4-Methylumbelliferone for HMEC and RF-24, respectively. Matrix metalloproteinase-2 expression is differentially altered upon 4-Methylumbelliferone treatment in both tested endothelial cell lines[1]. |
| Cell Assay | The MTT dye reduction assay in 96-well microplates is used. The assay is dependent on the reduction of MTT by mitochondrial dehydrogenases of viable cells to a blue formazan product, which can be measured spectrophotometrically. Endothelial cells (2.5×103 cells in a total volume of 100 μL of complete medium) are incubated in each well with serial dilutions of 4-Methylumbelliferone (4-MU) (0, 0.5, 1, 1.5 and 2 mM). After 3 days of incubation in the dark (37°C, 5% CO2 in a humid atmosphere), 10 μL of MTT (5 mg/mL in PBS) is added to each well, and the plate is incubated for further a 4 h (37°C). The formazan is dissolved in 150 μL of 0.04 N HCl-2 propanol, and samples are spectrophotometrically measured at 550 nm. All determinations are carried out in quadruplicate, and at least three independent experiments are carried out. IC50 values are calculated as those concentrations of compound yielding 50% cell survival, taking the values obtained for control as 100%[1]. |
| References | [1]. García-Vilas JA, et al. 4-methylumbelliferone inhibits angiogenesis in vitro and in vivo. J Agric Food Chem. 2013 May 1;61(17):4063-71. |
Chemical & Physical Properties
| Density | 1.319 g/cm3 |
|---|---|
| Boiling Point | 377.4ºC at 760 mmHg |
| Melting Point | 188.5-190 °C(lit.) |
| Molecular Formula | C10H8O3 |
| Molecular Weight | 176.16900 |
| Flash Point | 174.5ºC |
| Exact Mass | 176.04700 |
| PSA | 50.44000 |
| LogP | 1.80700 |
| InChIKey | HSHNITRMYYLLCV-UHFFFAOYSA-N |
| SMILES | Cc1cc(=O)oc2cc(O)ccc12 |
| Storage condition | -20°C Freezer |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
| Water Solubility | slightly soluble |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 3850 mg/kg
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - lacrimation Sense Organs and Special Senses (Eye) - ptosis Behavioral - altered sleep time (including change in righting reflex)
- REFERENCE :
- KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 5,1619,1971
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 2550 mg/kg
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - lacrimation Sense Organs and Special Senses (Eye) - ptosis Behavioral - altered sleep time (including change in righting reflex)
- REFERENCE :
- KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 5,1619,1971
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 7200 mg/kg
- TOXIC EFFECTS :
- Behavioral - somnolence (general depressed activity) Skin and Appendages - hair
- REFERENCE :
- KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 5,1619,1971
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 2850 mg/kg
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - lacrimation Sense Organs and Special Senses (Eye) - ptosis Behavioral - altered sleep time (including change in righting reflex)
- REFERENCE :
- KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 5,1619,1971
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 1250 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- PHTXA6 Pharmacology and Toxicology. English translation of FATOAO. (New York, NY) V.20-22, 1957-59. Discontinued. Volume(issue)/page/year: 21,555,1958
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- >10 gm/kg
- TOXIC EFFECTS :
- Behavioral - somnolence (general depressed activity) Skin and Appendages - hair
- REFERENCE :
- KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 5,1619,1971 ** OTHER MULTIPLE DOSE TOXICITY DATA **
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 56 gm/kg/4W-C
- TOXIC EFFECTS :
- Liver - changes in liver weight
- REFERENCE :
- OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 4,1001,1970
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 182 gm/kg/26W-C
- TOXIC EFFECTS :
- Liver - changes in liver weight Endocrine - changes in pituitary weight
- REFERENCE :
- OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 4,1001,1970 ** REPRODUCTIVE DATA **
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 6 gm/kg
- SEX/DURATION :
- female 9-14 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
- REFERENCE :
- GNRIDX Gendai no Rinsho. (Tokyo, Japan) V.1-10, 1967-76(?). Volume(issue)/page/year: 4,413,1970
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 6 gm/kg
- SEX/DURATION :
- female 7-12 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
- REFERENCE :
- GNRIDX Gendai no Rinsho. (Tokyo, Japan) V.1-10, 1967-76(?). Volume(issue)/page/year: 4,403,1970
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 1500 mg/kg
- SEX/DURATION :
- female 7-12 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - stillbirth
- REFERENCE :
- GNRIDX Gendai no Rinsho. (Tokyo, Japan) V.1-10, 1967-76(?). Volume(issue)/page/year: 4,403,1970 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X7017 No. of Facilities: 25 (estimated) No. of Industries: 2 No. of Occupations: 4 No. of Employees: 2001 (estimated) No. of Female Employees: 395 (estimated)
Safety Information
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Gloves |
|---|---|
| Hazard Codes | Xn:Harmful |
| Risk Phrases | R20/21/22;R36/37/38 |
| Safety Phrases | S26-S37/39 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 2 |
| RTECS | GN7000000 |
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Synonyms
| LM 94 |
| 7-hydroxy-4-methyl-coumarin |
| BMU |
| CantabbY |
| Medilla |
| 7-hydroxy-4-methyl-chromen-2-one |
| 4-Methylumbelliferone |
| EINECS 201-986-7 |
| Crodimon |
| 4-methyl-7-hydroxy coumarin |
| Bilcolic |
| Himecol |
| MFCD00006866 |
| 7-hydroxy-4-methyl-2H-chromen-2-one |
| Eurogale |
| 7-Hydroxy-4-methylcoumarin |
