4-Hydroxycoumarin

Name: 4-Hydroxycoumarin
Brand: MedChemExpress
SKU: HY-N6856
Rating: 4.5 (1 reviews)

Cat. No.: HY-N6856 Purity: 99.96%: FAQs
Data Sheet SDS COA Handling Instructions

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4-Hydroxycoumarin is an orally active coumarin derivative, one of the most versatile heterocyclic scaffolds, often used in the synthesis of various organic compounds. 4-Hydroxycoumarin possesses both electrophilic and nucleophilic properties. 4-Hydroxycoumarin is an HIV protease inhibitor and tyrosine kinase inhibitor. 4-Hydroxycoumarin has anti-inflammatory, antibacterial and anti-tumor effects.

For research use only. We do not sell to patients.

4-Hydroxycoumarin Chemical Structure

CAS No. : 1076-38-6

Size	Price	Stock	Quantity

Free Sample (0.1 - 0.5 mg)		Apply Now
Solid + Solvent (Highly Recommended)
10 mM * 1 mL in DMSO ready for reconstitution	USD 27	In-stock	Estimated Time of Arrival: December 31
Solution
10 mM * 1 mL in DMSO	USD 27	In-stock	Estimated Time of Arrival: December 31
Solid
50 g	USD 25	In-stock	Estimated Time of Arrival: December 31
> 100 g		Get quote

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Based on 1 publication(s) in Google Scholar

Other Forms of 4-Hydroxycoumarin:

4-Hydroxycoumarin (Standard) Get quote

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Biological Activity
Purity & Documentation
References
Customer Review

Description

Cellular Effect

Cell Line	Type	Value	Description	References
EA.hy 926	EC₅₀	> 200 μM Compound: 3, 4-HC	Cytotoxicity against human EAhy926 cells assessed as reduction in cell viability after 48 hrs by MTT assay Cytotoxicity against human EAhy926 cells assessed as reduction in cell viability after 48 hrs by MTT assay	[PMID: 24721833]
EA.hy 926	EC₅₀	> 200 μM Compound: 3, 4-HC	Cytotoxicity against human EAhy926 cells assessed as reduction in cell viability after 72 hrs by MTT assay Cytotoxicity against human EAhy926 cells assessed as reduction in cell viability after 72 hrs by MTT assay	[PMID: 24721833]
LNCaP	EC₅₀	100.51 μM Compound: 3, 4-HC	Cytotoxicity against human LNCAP cells assessed as reduction in cell viability after 48 hrs by MTT assay Cytotoxicity against human LNCAP cells assessed as reduction in cell viability after 48 hrs by MTT assay	[PMID: 24721833]
LNCaP	EC₅₀	120.27 μM Compound: 3, 4-HC	Cytotoxicity against human LNCAP cells assessed as reduction in cell viability after 72 hrs by MTT assay Cytotoxicity against human LNCAP cells assessed as reduction in cell viability after 72 hrs by MTT assay	[PMID: 24721833]
MCF7	EC₅₀	> 200 μM Compound: 3, 4-HC	Cytotoxicity against human MCF7 cells assessed as reduction in cell viability after 48 hrs by MTT assay Cytotoxicity against human MCF7 cells assessed as reduction in cell viability after 48 hrs by MTT assay	[PMID: 24721833]
MCF7	EC₅₀	199.82 μM Compound: 3, 4-HC	Cytotoxicity against human MCF7 cells assessed as reduction in cell viability after 72 hrs by MTT assay Cytotoxicity against human MCF7 cells assessed as reduction in cell viability after 72 hrs by MTT assay	[PMID: 24721833]
MCF7	GI₅₀	95.34 μM Compound: 4a	Cytotoxicity against human MCF7 cells assessed as cell growth inhibition after 48 hrs by SRB assay Cytotoxicity against human MCF7 cells assessed as cell growth inhibition after 48 hrs by SRB assay	[PMID: 28041801]
MDA-MB-231	EC₅₀	> 200 μM Compound: 3, 4-HC	Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability after 48 hrs by MTT assay Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability after 48 hrs by MTT assay	[PMID: 24721833]
MDA-MB-231	EC₅₀	100.26 μM Compound: 3, 4-HC	Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability after 72 hrs by MTT assay Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability after 72 hrs by MTT assay	[PMID: 24721833]
PC-3	EC₅₀	150.46 μM Compound: 3, 4-HC	Cytotoxicity against human PC3 cells assessed as reduction in cell viability after 48 hrs by MTT assay Cytotoxicity against human PC3 cells assessed as reduction in cell viability after 48 hrs by MTT assay	[PMID: 24721833]
PC-3	EC₅₀	173.31 μM Compound: 3, 4-HC	Cytotoxicity against human PC3 cells assessed as reduction in cell viability after 72 hrs by MTT assay Cytotoxicity against human PC3 cells assessed as reduction in cell viability after 72 hrs by MTT assay	[PMID: 24721833]
SK-MEL-28	IC₅₀	1.3 μM Compound: 9	Anticancer activity against human SK-MEL-28 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay Anticancer activity against human SK-MEL-28 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay	[PMID: 37197457]
SK-MEL3	IC₅₀	2.1 μM Compound: 9	Anticancer activity against human SK-MEL3 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay Anticancer activity against human SK-MEL3 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay	[PMID: 37197457]
TK-10	GI₅₀	> 100 μM Compound: 4a	Cytotoxicity against human TK10 cells assessed as cell growth inhibition after 48 hrs by SRB assay Cytotoxicity against human TK10 cells assessed as cell growth inhibition after 48 hrs by SRB assay	[PMID: 28041801]
U-937	EC₅₀	> 200 μM Compound: 3, 4-HC	Cytotoxicity against human U937 cells assessed as reduction in cell viability after 48 hrs by Alamar blue assay Cytotoxicity against human U937 cells assessed as reduction in cell viability after 48 hrs by Alamar blue assay	[PMID: 24721833]
U-937	EC₅₀	164.12 μM Compound: 3, 4-HC	Cytotoxicity against human U937 cells assessed as reduction in cell viability after 72 hrs by Alamar blue assay Cytotoxicity against human U937 cells assessed as reduction in cell viability after 72 hrs by Alamar blue assay	[PMID: 24721833]
UACC-62	GI₅₀	83.6 μM Compound: 4a	Cytotoxicity against human UACC62 cells assessed as cell growth inhibition after 48 hrs by SRB assay Cytotoxicity against human UACC62 cells assessed as cell growth inhibition after 48 hrs by SRB assay	[PMID: 28041801]

In Vitro

4-Hydroxycoumarin (0, 50, 160, 500 μM, 24 h) disrupts the actin cytoskeleton in B16-F10 melanoma cells but not in B82 fibroblasts. However, they can reduce their adhesion and motility to extracellular matrix proteins^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Viability Assay^[2]

Cell Line:	B16-F10, B82
Concentration:	0, 50, 160, 500 μM
Incubation Time:	24 h
Result:	Had no appreciable effect on cell viability.

Western Blot Analysis ^[2]

Cell Line:	B16-F10
Concentration:	0, 50, 160, 500 μM
Incubation Time:	24 h
Result:	Reduced the adhesion to ECM proteins and the tyrosine phosphorylation of several proteins in a concentration-dependent manner. Inhibited the migration at 500 μM.

In Vivo

4-Hydroxycoumarin (10, 20 or 40 mg/kg/day, oral gavage) can effectively inhibit tumor growth and improve survival rate in melanoma mice^[3].
4-Hydroxycoumarin (5, 10, 25, 50 mg/kg/ day, Oral gavage) can significantly reduce symptoms in a rat model of trinitrobenzene sulfonic acid-induced colitis^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:	Mouse melanoma model^[3]
Dosage:	10, 20 or 40 mg/kg
Administration:	i.g.
Result:	Reduced >85% of the number of pulmonary tumors. Diminished the tumor size from day 22 and increased survival time at 10 mg/kg/day.

Animal Model:	Rat colitis model ^[4]
Dosage:	5, 10, 25, 50 mg/kg
Administration:	p.o.
Result:	Reduced damage score and extension of the lesion at doses of 10 and 25 mg/kg. Counteracted GSH content and reduced AP activity at a dose of 5 mg/kg. Showed a good recovery of the intestinal cytoarchitecture at doses of 5 and 25 mg/kg.

Molecular Weight

162.14

Formula

C₉H₆O₃

CAS No.

1076-38-6

Appearance

Solid

Color

White to off-white

SMILES

O=C1C=C(O)C2=CC=CC=C2O1

Structure Classification

Initial Source

Endogenous metabolite

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Store at room temperature 3 years

In solvent	-80°C	2 years
	-20°C	1 year

Solvent & Solubility

In Vitro:

DMSO : 100 mg/mL (616.74 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	6.1674 mL	30.8368 mL	61.6736 mL
5 mM	1.2335 mL	6.1674 mL	12.3347 mL
10 mM	0.6167 mL	3.0837 mL	6.1674 mL

View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

Molarity Calculator
Dilution Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

This equation is commonly abbreviated as: C₁V₁ = C₂V₂

Concentration _(start)

Volume _(start)

Concentration _(final)

Volume _(final)

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.08 mg/mL (12.83 mM); Clear solution

This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Protocol 2

Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 2.08 mg/mL (12.83 mM); Clear solution

This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil
Solubility: ≥ 2.08 mg/mL (12.83 mM); Clear solution

This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage

mg/kg

Animal weight
(per animal)

Dosing volume
(per animal)

μL

Number of animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

DMSO +

Tween-80 +

Saline

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Calculation results:

Working solution concentration: mg/mL

Method for preparing stock solution: mg drug dissolved in μL DMSO (Stock solution concentration: mg/mL).

The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).

Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.

If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.

Purity & Documentation

Purity: 99.96%

Select Batch:

Data Sheet (281 KB) SDS (393 KB)

COA (253 KB) HNMR (234 KB) LCMS (92 KB)

Handling Instructions (2659 KB)

References

[1]. Mohammadi Ziarani G, et al. The molecular diversity scope of 4-hydroxycoumarin in the synthesis of heterocyclic compounds via multicomponent reactions. Mol Divers. 2019 Jan 29. doi: 10.1007/s11030-019-09918-7. [Content Brief]

[2]. Velasco-Velázquez MA, et al. 4-Hydroxycoumarin disorganizes the actin cytoskeleton in B16-F10 melanoma cells but not in B82 fibroblasts, decreasing their adhesion to extracellular matrix proteins and motility. Cancer Lett. 2003 Aug 20;198(2):179-86. [Content Brief]

[3]. Salinas-Jazmín N, et al. Antimetastatic, antineoplastic, and toxic effects of 4-hydroxycoumarin in a preclinical mouse melanoma model. Cancer Chemother Pharmacol. 2010 Apr;65(5):931-40. [Content Brief]

[4]. Luchini AC, et al. Intestinal anti-inflammatory activity of coumarin and 4-hydroxycoumarin in the trinitrobenzenesulphonic acid model of rat colitis. Biol Pharm Bull. 2008 Jul;31(7):1343-50. [Content Brief]

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg

DMSO	1 mM	6.1674 mL	30.8368 mL	61.6736 mL	154.1839 mL
	5 mM	1.2335 mL	6.1674 mL	12.3347 mL	30.8368 mL
	10 mM	0.6167 mL	3.0837 mL	6.1674 mL	15.4184 mL
	15 mM	0.4112 mL	2.0558 mL	4.1116 mL	10.2789 mL
	20 mM	0.3084 mL	1.5418 mL	3.0837 mL	7.7092 mL
	25 mM	0.2467 mL	1.2335 mL	2.4669 mL	6.1674 mL
	30 mM	0.2056 mL	1.0279 mL	2.0558 mL	5.1395 mL
	40 mM	0.1542 mL	0.7709 mL	1.5418 mL	3.8546 mL
	50 mM	0.1233 mL	0.6167 mL	1.2335 mL	3.0837 mL
	60 mM	0.1028 mL	0.5139 mL	1.0279 mL	2.5697 mL
	80 mM	0.0771 mL	0.3855 mL	0.7709 mL	1.9273 mL
	100 mM	0.0617 mL	0.3084 mL	0.6167 mL	1.5418 mL