6468-96-8

Basic information

• Product Name: 3-PHENYLUMBELLIFERONE
• Synonyms: 3-PHENYLUMBELLIFERONE;3-PHENYL-7-HYDROXYCOUMARIN;AKOS BBS-00006093;7-HYDROXY-3-PHENYLCOUMARIN;3-PHENYLUMBELLIFERONE, FOR FLUOR-ESCENCE;7-HYDROXY-3-PHENYLCOUMARIN (3-PHENYLUMBELLIFERONE);7-Hydroxy-3-phenyl-2H-benzopyran-2-one;7-Hydroxy-3-phenyl-2H-1-benzopyran-2-one
• CAS NO: 6468-96-8
• Molecular Formula: C₁₅H₁₀O₃
• Molecular Weight: 238.24
• EINECS: 256-589-9
• Mol File: 6468-96-8.mol
• Article Data: 34

Chemical Properties

• Melting Point: 206-210 °C(lit.)
• Boiling Point: 471.8 °C at 760 mmHg
• Flash Point: 210.1 °C
• Appearance: /
• Density: 1.34 g/cm³
• Vapor Pressure: 1.59E-09mmHg at 25°C
• Refractive Index: 1.666
• Solubility: DMF: soluble
• PKA: 7.80±0.20(Predicted)
• BRN: 384125
• CAS DataBase Reference: 3-PHENYLUMBELLIFERONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PHENYLUMBELLIFERONE(6468-96-8)
• EPA Substance Registry System: 3-PHENYLUMBELLIFERONE(6468-96-8)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 22-24/25-45-37/39-36/37/39-27-26
• WGK Germany: 3
• F: 8
• Hazardous Substances Data: 6468-96-8(Hazardous Substances Data)

Usage

General Description

3-Phenylumbelliferone is a chemical compound used extensively in cellulose research due to its fluorescent properties, making it easier to monitor the processes involved in cellular activities. Its molecular formula is C16H12O3 and it is characterized by pale yellow crystalline properties. It has other variations such as coumarin and is also known for its sweet-smelling hawthorn-like scent. Toxicity studies indicate that high concentrations of 3-Phenylumbelliferone may pose certain hazards, however, its toxicity level is generally considered low. More scientific research is necessary to further understand its full chemical properties and potential applications.

InChI:InChI=1/C15H10O3/c16-12-7-6-11-8-13(10-4-2-1-3-5-10)15(17)18-14(11)9-12/h1-9,16H

Upstream product

• 17838-69-6 ethyl 3-oxo-2-phenylpropanoate 
• 108-46-3 recorcinol 
• 73591-12-5 3-benzoyloxy-2-phenyl-acrylonitrile 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 1074-12-0 phenylglyoxal hydrate 
• 100-34-5 benzene diazonium chloride 
• 129742-35-4 4-[(tert-butyldimethylsilyl)oxy]-2-hydroxybenzaldehyde 
• 62-53-3 aniline 
• 103-82-2 phenylacetic acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 779-27-1 7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid 
• 98-80-6 phenylboronic acid 
• 100-63-0 phenylhydrazine 

Downstream Products

• 116557-43-8 6-bromo-7-hydroxy-3-phenyl-coumarin 
• 672938-07-7 8-bromo-7-hydroxy-3-phenyl-coumarin 
• 672938-12-4 6,8-dibromo-7-hydroxy-3-phenyl-coumarin 
• 2555-22-8 3-phenyl-7-methoxycoumarin 
• 903854-84-2 7-(2-bromoethoxy)-3-phenyl-2H-chromen-2-one 

Relevant articles and documents

Dual Role of Oxoaldehydes: Divergent Synthesis of 3-Aryl- and 3-Aroylcoumarins

A facile and efficient synthetic approach to various valuable 3-aryl- and 3-aroylcoumarins by the direct arylation and aroylation of coumarins with glyoxals in a metal-free manner is presented. The aryl glyoxal is for the first time recognized to serve as an aryl surrogate in addition to its role as an aroyl transfer reagent via a simple switch in reaction conditions. The approach accommodates a broad substrate scope and high yields of the two types of cross-coupling reactions starting from identical starting materials.

Chlorophyll-catalyzed photochemical regioselective coumarin C-H arylation with diazonium salts

This communication describes the development of a mild method for the cross-coupling of the C3-position of coumarin with an array of diazonium salts mediated by chlorophyll as a biocatalyst via visible light catalysis. A natural pigment such as chlorophyll is used as a green photosensitizer and environmentally benign catalyst. This general and easy procedure provides a transition-metal-free alternative for the formation of 3-aryl coumarin derivatives at room temperature with good to excellent yields. This journal is

1,2,3,4-Tetrahydroisoquinoline/2H-chromen-2-one conjugates as nanomolar P-glycoprotein inhibitors: Molecular determinants for affinity and selectivity over multidrug resistance associated protein 1

A series of coniugates bearing a 1,2,3,4-tetrahydroisoquinoline motif linked to substituted 7-hydroxy-2H-chromen-2-ones was synthesized and assayed through calcein-AM test in Madin-Darby Canine Kidney (MDCK) cells overexpressing P-glycoprotein (P-gp) and closely related multidrug resistance associated protein 1 (MRP1) to probe the interference with efflux mechanisms mediated by P-gp and MRP1, respectively. A number of substituents at C3 and C4 of coumarin nucleus along with differently sized and shaped spacers was enrolled to investigate the effects of focused structural modifications over affinity and selectivity. Linker length and flexibility played a key role in enhancing P-gp affinity as proved by the most potent P-gp modulator (3h, IC50 = 70 nM). A phenyl ring within the spacer (3k, 3l, 3o) and bulkier groups (Br in 3r, Ph in 3u) at coumarin C3 led to derivatives showing nanomolar activity (160 nM 50 350). Molecular docking calculations carried out on a human MDR1 homology model structure contributed to gain insights into the ligands’ binding modes. Some compounds (3d, 3h, 3l, 3r, 3t, 3u) reversed MDR thereby restoring doxorubicin cytotoxicity when co-administered with the drug into MDCK-MDR1 cells.