6093-67-0

Basic information

• Product Name: 5-Hydroxycoumarin
• Synonyms: 5-Hydroxycoumarin;5-Hydroxy-2H-1-benzopyran-2-one;5-hydroxy-2H-chromen-2-one
• CAS NO: 6093-67-0
• Molecular Formula: C₉H₆O₃
• Molecular Weight: 162.14214
• Mol File: 6093-67-0.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 358.672 °C at 760 mmHg
• Flash Point: 168.723 °C
• Appearance: /
• Density: 1.403 g/cm³
• Vapor Pressure: 1.21E-05mmHg at 25°C
• Refractive Index: 1.64
• CAS DataBase Reference: 5-Hydroxycoumarin(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hydroxycoumarin(6093-67-0)
• EPA Substance Registry System: 5-Hydroxycoumarin(6093-67-0)

Safety Data

• Hazardous Substances Data: 6093-67-0(Hazardous Substances Data)

Usage

General Description

5-Hydroxycoumarin, also known as umbelliferone, is a chemical compound found in various plants such as the umbellifers (Apiaceae) and the Rutaceae family. It is a lactone and a coumarin derivative with a white crystalline appearance and a characteristic sweet odor. 5-Hydroxycoumarin is utilized in the production of perfumes, as a fluorescent whitening agent in textiles, and as a precursor for the synthesis of other pharmaceuticals and fragrances. It also possesses antioxidant, anti-inflammatory, and anti-microbial properties, making it a valuable compound in the fields of medicine and cosmetics. However,

InChI:InChI=1/C9H6O3/c10-7-2-1-3-8-6(7)4-5-9(11)12-8/h1-5,10H

Upstream product

• 91136-61-7 2-oxo-2H-chromen-5-yl acetate 
• 90947-66-3 5-hydroxycoumarin-3-carboxylic acid 
• 84632-12-2 5-methoxy-2-oxo-2H-chromene-3,8-dicarboxylic acid 
• 39503-30-5 3-formyl-2-hydroxy-4-methoxy-benzoic acid methyl ester 
• 91-64-5 coumarin 
• 154424-13-2 (E)-3-(2,6-dimethoxy-phenyl)-acrylic acid methyl ester 
• 700-44-7 6-methoxysalicylaldehyde 
• 387-46-2 2,6-dihydroxybenzaldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 873974-01-7 5-methoxy-2-oxo-2H-chromene-3,8-dicarboxylic acid-3-ethyl ester-8-methyl ester 
• 39503-26-9 5-carbomethoxy-6-hydroxysalicylaldehyde 
• 3392-97-0 2,6-dimethoxybenzaldehyde 
• 471-25-0 Propiolic acid 
• 108-46-3 recorcinol 

Downstream Products

• 141234-13-1 5-<(E)-3-(4,5-dihydro-5,5-dimethyl-4-oxo-2-furanyl)-2-butenyloxy>-coumarin 
• 17235-14-2 (Z)-4-(o-hydroxyphenyl)-2-methylbut-3-en-2-ol 
• 184351-95-9 5-Hydroxy-6-iodo-chromen-2-one 
• 4412-93-5 bakuchicin 
• 184352-04-3 5-Hydroxy-6-vinyl-chromen-2-one 
• 184352-10-1 6-(2,2-Dimethoxy-ethyl)-5-hydroxy-chromen-2-one 
• 150598-44-0 5-[(2-oxo-2H-1-benzopyran-5-yl)oxy]pentanoic acid ethyl ester 
• 150598-37-1 trifluoromethanesulfonic acid 2-oxo-2H-1-benzopyran-5-yl ester 
• 1092459-85-2 5-butoxycoumarin 
• 1092459-83-0 5-ethoxycoumarin 
• 1092459-86-3 5-pentoxycoumarin 
• 1092459-87-4 5-octoxycoumarin 
• 79326-07-1 5-(benzyloxy)-2H-chromen-2-one 
• 1092459-84-1 5-propoxycoumarin 

Relevant articles and documents

Metal-free, Br?nsted acid-mediated synthesis of coumarin derivatives from phenols and propiolic acids

A novel synthesis of coumarin derivatives by Br?nsted acid-mediated condensation and intramolecular cyclization of phenols and propiolic acids was reported. This transformation requires the use of TfOH in place of a conventional metal mediator, and it occurs under mild conditions and provides rapid access to coumarin derivatives in good yields.

Synthetic models related to methoxalen and menthofuran-cytochrome P450 (CYP) 2A6 interactions. Benzofuran and coumarin derivatives as potent and selective inhibitors of CYP2A6

Human microsomal cytochrome P450 (CYP) 2A6 contributes extensively to nicotine detoxication but also activates tobacco-specific procarcinogens to mutagenic products. We prepared a series of benzofuran and coumarin derivatives that have inhibitory effects on the activity of human CYP2A6. The reported compounds methoxalen and menthofuran had potent inhibitory effects on the activity of CYP2A6 with IC50 values of 0.47 μM and 1.27 μM, respectively. Synthetic benzofuran (4-methoxybenzofuran: IC50=2.20 μM) and coumarin (5-methoxycoumarin: IC50=0.13 μM and 6-methoxycoumarin: IC50=0.64 μM) derivatives, which have more selective effects than those of methoxalen and menthofuran, exhibited comparable activities against CYP2A6. These compounds can be used as a lead compounds in the design of CYP2A6 inhibitor drugs to reduce smoking and tobacco-related cancers.

Intramolecular conjugate addition of α,β-unsaturated lactones having an alkanenitrile side chain: Stereocontrolled construction of carbocycles with quaternary carbon atoms

An efficient method for constructing carbocycles with all-carbon quaternary stereocenters has been developed on the basis of a stereoselective cyclization reaction of ,-unsaturated lactones having an alkanenitrile side chain. Treatment of the substrate with lithium hexamethyldisilazide (LiHMDS) in the presence of triisopropylsilyl chloride (TIPSCl) led to the generation of the corresponding -cyano carbanion species which readily underwent an intramolecular conjugate addition reaction. It was found that thecombined use of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and triethylamine is also effective for the cyclization reaction without using a strong base. Interestingly, different ste-reochemical outcomes were observed in the two cyclization methods. Georg Thieme Verlag Stuttgart - New York.