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4-Hydroxycoumarin

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-H2007

  • Specification : 98%

  • CAS number : 1076-38-6

  • Formula : C9H6O3

  • Molecular Weight : 162.144

  • PUBCHEM ID : 54682930

  • Volume : 20mg

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Catalogue Number

BF-H2007

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

162.144

Appearance

Powder

Botanical Source

synthesis

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

C1=CC=C2C(=C1)C(=CC(=O)O2)O

Synonyms

4-Monohydroxycoumarin/4-hydroxy-2H-benzopyran-2-one/4-hydroxy-2-chromenone/4-Hydroxy-2H-chromen-2-one/Benzotertonicacid/4-Coumaryl alcohol/4-Hydroxy Coumarin/4-HYDROXYCUMARIN/4-Coumarinol/4-Hydroxy-2H-1-benzopyran-2-one/HydroxyCoumarin/COUMARIN KIT/4-Hydroxycoumarine/4-Hydroxycoumarin/benzotetronic acid/2H-1-Benzopyran-2-one, 4-hydroxy-/COUMARINOL/4-hydroxy-coumari

IUPAC Name

4-hydroxychromen-2-one

Density

1.4±0.1 g/cm3

Solubility

Flash Point

165.4±20.7 °C

Boiling Point

352.4±42.0 °C at 760 mmHg

Melting Point

211-213 °C(lit.)

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2932200000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:1076-38-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30697671

Abstract

4-Hydroxycoumarins are some of the most versatile heterocyclic scaffolds and are frequently applied in the synthesis of various organic compounds. 4-Hydroxycoumarin-based compounds are important among heterocyclic structures due to their biological and pharmaceutical activities. In this study, we provide an overview on the recent applications of 4-hydroxycoumarin in multicomponent reactions for the synthesis of various heterocyclic compounds during the time period of 2015-2018.

KEYWORDS

4-Hydroxycoumarin; Heterocycles; Multicomponent reaction; Synthesis.

Title

The Molecular Diversity Scope of 4-hydroxycoumarin in the Synthesis of Heterocyclic Compounds via Multicomponent Reactions

Author

Ghodsi Mohammadi Ziarani 1 , Razieh Moradi 2 , Tahereh Ahmadi 3 , Parisa Gholamzadeh 3

Publish date

2019 Nov

PMID

28587908

Abstract

Acyl-CoAs are essential intermediates in the biosynthetic pathways of a number of industrially and pharmaceutically important molecules. When these pathways are reconstituted in a heterologous microbial host for metabolic engineering purposes, the acyl-CoAs may be subject to undesirable hydrolysis by the host’s native thioesterases, resulting in a waste of cellular energy and decreased intermediate availability, thus impairing bioconversion efficiency. 4-hydroxycoumarin (4HC) is a direct synthetic precursor to the commonly used oral anticoagulants (e.g. warfarin) and rodenticides. In our previous study, we have established an artificial pathway for 4HC biosynthesis in Escherichia coli, which involves the thioester intermediate salicoyl-CoA. Here, we utilized the 4HC pathway as a demonstration to examine the negative effect of salicoyl-CoA degradaton, identify and inactivate the responsible thioesterase, and eventually improve the 4HC production. We screened a total of 16 E. coli thioesterases and tested their hydrolytic activity towards salicoyl-CoA in vitro. Among all the tested candidate enzymes, YdiI was found to be the dominant contributor to the salicoyl-CoA degradation in E. coli. Remarkably, the ydiI knockout strain carrying the 4HC pathway exhibited an up to 300% increase in 4HC production. An optimized 4HC pathway construct introduced in the ydiI knockout strain led to the accumulation of 935mg/L of 4HC in shake flasks, which is about 1.5 folds higher than the wild-type strain. This study demonstrates a systematic strategy to alleviate the undesirable hydrolysis of thioester intermediates, allowing production enhancement for other biosynthetic pathways with similar issues.

KEYWORDS

4-Hydoxycoumarin; Acyl-CoAs; Salicoyl-CoA degradation; Thioester; Thioesterase.

Title

Elevating 4-hydroxycoumarin Production Through Alleviating Thioesterase-Mediated salicoyl-CoA Degradation

Author

Xiaolin Shen 1 , Monika Mahajani 2 , Jia Wang 1 , Yaping Yang 3 , Qipeng Yuan 1 , Yajun Yan 4 , Yuheng Lin 5

Publish date

2017 Jul

PMID

32080255

Abstract

Mosquito-borne diseases like malaria are a major public health problem in tropical countries, such as Madagascar. Female Anopheles mosquito vectors the human malaria parasites (Plasmodium spp.) and is important indicator in malaria surveillance activities. Among the various means of vector control in Madagascar, the use of attractants for mass trapping of target species could be an alternative to insecticides. The aim of this study is to evaluate whether 4-hydroxycoumarin can be used as an attractant for anthropophilic Anopheles spp. vectors of malaria. For this, a field study was conducted using CDC light traps in the village of Ambohidray, Madagascar. 16 days of trapping was conducted and four replicates nights were performed for each product tested. 4-hydroxycoumarin, octenol and two types of blend of these products were tested. The results showed that 4-hydroxycoumarin (2 mg) have a significant attractive effect on Anopheles spp. and significant selectivity towards Anopheles gambiae s.l, and Anopheles mascarensis which are both significant malaria vectors in Madagascar. A synergy of 4-hydroxycoumarin with octenol was found to attract these mosquito vectors. A significant decrease in vector populations was observed during this experiment. These results suggest that 4-hydroxycoumarin could be useful for malaria surveillance and the control of vector populations.

Title

Field Assessment of 4-hydroxycoumarin as an Attractant for Anthropophilic Anopheles Spp. Vectors of Malaria in Madagascar

Author

Tovo Mbolatiana Andrianjafy 1 2 , Voahangy Vestalys Ramanandraibe 1 , Elodie Toavina Andrianarijaona 2 , Niry Hasinandrianina Ramarosandratana 2 , Lala Harivelo Ravaomanarivo 2 , Patrick Mavingui 1 3 , Marc Lemaire 4 5

Publish date

2020 Feb 20


Description :

4-Hydroxycoumarin, a coumarin derivative, is one of the most versatile heterocyclic scaffolds and is frequently applied in the synthesis of various organic compounds. 4-Hydroxycoumarin possesses both electrophilic and nucleophilic properties. 4-Hydroxycoumarin derivatives are employed as the anticoagulant, antibacterial, antifungal, antiviral, antitumor, antiprotozoal, insecticidal, antimycobacterial, antimutagenic, antioxidant, anti-inflammatory agents, HIV protease inhibitors and tyrosine kinase inhibitors[1].