4-Methylumbelliferone

Modify Date: 2025-08-20 10:11:42

4-Methylumbelliferone Structure
4-Methylumbelliferone structure
 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 Chinese USA Flash Point 174.5ºC

 Use of 4-Methylumbelliferone


4-Methylumbelliferone is a hyaluronic acid biosynthesis inhibitor with antitumoral and antimetastatic effects.

 Names

Name 4-Methylumbelliferone
Synonym More Synonyms

 4-Methylumbelliferone Biological Activity

Description 4-Methylumbelliferone is a hyaluronic acid biosynthesis inhibitor with antitumoral and antimetastatic effects.
Related Catalog
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
Storage condition -20°C Freezer
Stability Stable. Combustible. Incompatible with strong oxidizing agents.
Water Solubility slightly soluble

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GN7000000
CHEMICAL NAME :
Coumarin, 7-hydroxy-4-methyl-
CAS REGISTRY NUMBER :
90-33-5
BEILSTEIN REFERENCE NO. :
0142217
LAST UPDATED :
199710
DATA ITEMS CITED :
15
MOLECULAR FORMULA :
C10-H8-O3
MOLECULAR WEIGHT :
176.18
WISWESSER LINE NOTATION :
T66 BOVJ E1 IQ

HEALTH HAZARD DATA

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

 Synthetic Route

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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
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