4-甲基伞形酮 , 4-Methylumbelliferone

Chemopreventive and therapeutic agent for prostate cancer; fluorescent.

4-Methylumbelliferone (4-ΜU) is a synthetic coumarin with diverse biological activities. It inhibits hyaluronic acid synthesis in PC3-ML and DU145 cells (IC50s = ~0.4 mM for both). 4-MU inhibits the growth of PC3-ML, DU145, C4-2B, LNCaP, and LAPC-4 prostate cancer cells (IC50s = 0.2-0.4 mM) and invasion and chemotactic motility of PC3-ML and DU145 cells in vitro. It reduces tumor growth and microvessel density in a PC3-ML mouse xenograft model when administered at doses of 225 and 450 mg/kg twice per day. 4-ΜU is active against H. pylori and V. cholerae in vitro (MICs = 59 and 100-200 μg/ml, respectively). Derivatives and conjugates of 4-ΜU have been used as fluorogenic substrates to measure enzyme activity. Upon enzymatic cleavage, 4-ΜU is released and its fluorescence can be used to quantify enzyme activity. 4-MU fluorescence is pH-dependent with excitation maxima of 320 and 360 nm at low (1.97-6.72) and high pH (7.12-10.3), respectively, and an emission maximum ranging from 445 to 455 nm, increasing as pH decreases.

4-Methylumbelliferone analytical standard provided with chromatographic purity, to be used as reference material for qualitative determination.

Hymecromone, also known as 4-mu or himecromona, belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. Hymecromone exists as a solid, slightly soluble (in water), and a very weakly acidic compound (based on its pKa). Hymecromone exists in all eukaryotes, ranging from yeast to humans. Hymecromone participates in a number of enzymatic reactions. In particular, hymecromone can be biosynthesized from umbelliferone. Hymecromone is also a parent compound for other transformation products, including but not limited to, 4-methylumbelliferyl alpha-L-arabinoside, 4-methylumbelliferyl alpha-D-galactoside, and 4-methylumbelliferyl beta-D-galactoside.

Beta-methylumbelliferone appears as colorless crystals. Insoluble in water. (NTP, 1992)

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 derives from an umbelliferone.

Title: Hymecromone

CAS Registry Number: 90-33-5

CAS Name: 7-Hydroxy-4-methyl-2H-1-benzopyran-2-one

Additional Names: 7-hydroxy-4-methylcoumarin; 7-hydroxy-4-methyl-2-oxo-3-chromene; 4-methylumbelliferone; b-methylumbelliferone; imecromone; 4-MU

Trademarks: Bilcolic (Unifa); Biliton H (Berlin-Chemie); Cantabilin (Formenti); Cantabiline; Cholonerton (Dolorgiet); Cholspasmin (Lipha); Cumarote C (Towa Yakuhin); Himecol (Kissei); Medilla (Omega); Mendiaxon (Roland)

Molecular Formula: C10H8O3

Molecular Weight: 176.17

Percent Composition: C 68.18%, H 4.58%, O 27.25%

Literature References: Prepd from resorcinol and ethyl acetoacetate: Pechmann, Duisberg, Ber. 16, 2119 (1883); Russell, Frye, Org. Synth. 21, 23 (1941); Woods, Sapp, J. Org. Chem. 27, 3703 (1962). Use in determn of nitric acid: F. J. Welcher, Organic Analytical Reagents vol. 1 (Van Nostrand, New York, 1947) pp 214-215.

Properties: Crystals from alc, mp 194-195° (Woods, Sapp), formerly reported as 185-186° (Pechmann, Duisberg). uv max (methanol): 221, 251, 322.5 nm. Blue fluorescence in alcohol + water. Sol in methanol, glacial acetic acid; slightly sol in ether, chloroform. Practically insol in cold water.

Melting point: mp 194-195° (Woods, Sapp)

Absorption maximum: uv max (methanol): 221, 251, 322.5 nm

Use: Analytical reagent.

Therap-Cat: Choleretic; antispasmodic.

Keywords: Antispasmodic; Choleretic.

COA:

Product name: 4-Methylumbelliferone 

CAS: 90-33-5          M.F.: C₁₀H₈O₃        M.W._: 176.17