Biochanin A (Synonyms: 4-Methylgenistein; Olmelin)

Name: Biochanin A
Brand: MedChemExpress
SKU: HY-14595
Rating: 5.0 (15 reviews)

Cat. No.: HY-14595 Purity: 99.33%: Data Sheet
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Biochanin A is a naturally occurring fatty acid amide hydrolase (FAAH) inhibitor, which inhibits FAAH with IC₅₀s of 1.8, 1.4 and 2.4 μM for mouse, rat, and human FAAH, respectively.

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

CAS No. : 491-80-5

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10 mM * 1 mL in DMSO ready for reconstitution	In-stock	Estimated Time of Arrival: December 31
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10 mM * 1 mL in DMSO	In-stock	Estimated Time of Arrival: December 31
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Customer Review

Based on 15 publication(s) in Google Scholar

Other Forms of Biochanin A:

Biochanin A (Standard) In-stock

15 Publications Citing Use of MCE Biochanin A

Bio/Physico-chemical Assay

RT-PCR

In Vivo Efficacy Study

: Biochanin A purchased from MedChemExpress. Usage Cited in: Cell Rep Med. 2022 Mar 15;3(3):100561. [Abstract]; Biochanin A (BCA) significantly inhibited DHEA metabolism. LNCaP cells were treated with drugs with the indicated doses and [3H]-DHEA. BCA, biochanin A.

: Biochanin A purchased from MedChemExpress. Usage Cited in: Cell Rep Med. 2022 Mar 15;3(3):100561. [Abstract]; Biochanin A (BCA) increased the thermal stability of 3βHSD1. BCA or DHEA was added to FLAG-3βHSD1-expressing cells. Cell lysates were incubated at different temperatures to determine the stability of 3βHSD1. BCA, 20 μM; DHEA, 20 μM.

: Biochanin A purchased from MedChemExpress. Usage Cited in: Cell Rep Med. 2022 Mar 15;3(3):100561. [Abstract]; The Biochanin A (BCA) probe inhibited 3βHSD1 activity. GST-3βHSD1 (3 μg) was used for the in vitro enzyme activity assays. BCA, 1 μM; BCA probe, 1 μM.

: Biochanin A purchased from MedChemExpress. Usage Cited in: Cell Rep Med. 2022 Mar 15;3(3):100561. [Abstract]; The Biochanin A (BCA) probe directly bound to GST-3βHSD1. GST-3βHSD1 (3 μg) was incubated with the BCA probe with or without DHEA or BCA for pull-down assays.

: Biochanin A purchased from MedChemExpress. Usage Cited in: Cell Rep Med. 2022 Mar 15;3(3):100561. [Abstract]; Biochanin A (BCA) inhibited DHEA-induced AR target gene expression. VCaP cells were treated with the indicated drugs. DHEA, 100 nM; DHT, 1 nM.

: Biochanin A purchased from MedChemExpress. Usage Cited in: Cell Rep Med. 2022 Mar 15;3(3):100561. [Abstract]; Biochanin A (BCA) suppressed pregnenolone- but not progesterone-induced xenograft growth. Xenografts were generated with C4-2 cells. BCA, 50 mg/kg.

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Biological Activity
Protocol
Purity & Documentation
References
Customer Review

Description

Biochanin A is a naturally occurring fatty acid amide hydrolase (FAAH) inhibitor, which inhibits FAAH with IC₅₀s of 1.8, 1.4 and 2.4 μM for mouse, rat, and human FAAH, respectively.

IC₅₀ & Target

IC50: 1.8 μM (mouse FAAH), 1.4 μM (rat FAAH), 2.4 μM (human FAAH)^[1]

Cellular Effect

Cell Line	Type	Value	Description	References
A-431	IC₅₀	3 x 10^-1 μg/mL Compound: 6	Inhibition of EGFR in human A431 cells Inhibition of EGFR in human A431 cells	[PMID: 1479375]
A549	ED₅₀	19.77 μg/mL Compound: 12	Cytotoxicity against human A549 cells after 7 days Cytotoxicity against human A549 cells after 7 days	[PMID: 8201311]
A549	IC₅₀	> 100 μM Compound: 16	Cytotoxicity against human A549 cells after 72 hrs by MTT assay Cytotoxicity against human A549 cells after 72 hrs by MTT assay	[PMID: 18440233]
B16-BL6	IC₅₀	> 100 μM Compound: 16	Cytotoxicity against mouse B16-BL6 cells after 72 hrs by MTT assay Cytotoxicity against mouse B16-BL6 cells after 72 hrs by MTT assay	[PMID: 18440233]
BALB/3T3	IC₅₀	219.5 μM Compound: 10	Growth inhibition of BALB/c mouse cloned 3T3/A31 cells after 72 hrs by nigrosin assay Growth inhibition of BALB/c mouse cloned 3T3/A31 cells after 72 hrs by nigrosin assay	[PMID: 10096863]
GES1	IC₅₀	> 32 μM Compound: 2	Cytotoxicity against human GES1 cells assessed as cell viability measured after 72 hrs by MTT assay Cytotoxicity against human GES1 cells assessed as cell viability measured after 72 hrs by MTT assay	[PMID: 33581557]
GES1	IC₅₀	> 32 μM Compound: 53	Cytotoxicity against human GES1 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay Cytotoxicity against human GES1 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay	[PMID: 33619958]
HEK293	IC₅₀	9.9 μM Compound: 22	Inhibition of human recombinant 17beta-HSD2 expressed in HEK293 cell lysate assessed as conversion of radiolabeled estrone to estradiol Inhibition of human recombinant 17beta-HSD2 expressed in HEK293 cell lysate assessed as conversion of radiolabeled estrone to estradiol	[PMID: 18533708]
HT-1080	IC₅₀	> 100 μM Compound: 16	Cytotoxicity against human HT1080 cells after 72 hrs by MTT assay Cytotoxicity against human HT1080 cells after 72 hrs by MTT assay	[PMID: 18440233]
HT-29	ED₅₀	28.38 μg/mL Compound: 12	Cytotoxicity against human HT-29 cells after 7 days Cytotoxicity against human HT-29 cells after 7 days	[PMID: 8201311]
HeLa	IC₅₀	> 100 μM Compound: 16	Cytotoxicity against human HeLa cells after 72 hrs by MTT assay Cytotoxicity against human HeLa cells after 72 hrs by MTT assay	[PMID: 18440233]
Ishikawa	EC₅₀	0.42 μM Compound: BCA, Biochanin A	Estrogenic activity at estrogen receptor in human Ishikawa cells assessed as induction of alkaline phosphatase expression after 72 hrs by microplate reader Estrogenic activity at estrogen receptor in human Ishikawa cells assessed as induction of alkaline phosphatase expression after 72 hrs by microplate reader	[PMID: 22464681]
MCF7	EC₅₀	0.21 μM Compound: BCA, Biochanin A	Antiproliferative activity against estrogen-deficient human MCF7 cells after 72 hrs by MTT assay Antiproliferative activity against estrogen-deficient human MCF7 cells after 72 hrs by MTT assay	[PMID: 22464681]
MCF7	ED₅₀	5.49 μg/mL Compound: 12	Cytotoxicity against human MCF7 cells after 7 days Cytotoxicity against human MCF7 cells after 7 days	[PMID: 8201311]
MCF7	IC₅₀	10 μM Compound: Biochanin A	Antiproliferative activity against human MCF7 cells assessed as inhibition of cell growth incubated for 6 days by SRB assay Antiproliferative activity against human MCF7 cells assessed as inhibition of cell growth incubated for 6 days by SRB assay	[PMID: 33257172]
MCF7	IC₅₀	40 μg/mL Compound: Biochanin A	Antiproliferative activity against human MCF7 cells assessed as inhibition of cell growth incubated for 2 days by WST-1 assay Antiproliferative activity against human MCF7 cells assessed as inhibition of cell growth incubated for 2 days by WST-1 assay	[PMID: 33257172]
MCF7	IC₅₀	40 μg/mL Compound: Biochanin A	Inhibition of DNA synthesis in human MCF7 cells incubated for 4 days by BrdU incorporation assay Inhibition of DNA synthesis in human MCF7 cells incubated for 4 days by BrdU incorporation assay	[PMID: 33257172]
MGC-803	IC₅₀	2.95 μM Compound: 53	Antiproliferative activity against human MGC-803 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay Antiproliferative activity against human MGC-803 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay	[PMID: 33619958]
MGC-803	IC₅₀	6.77 μM Compound: 2	Antiproliferative activity against human MGC-803 cells assessed as reduction in cell viability after 72 hrs by MTT assay Antiproliferative activity against human MGC-803 cells assessed as reduction in cell viability after 72 hrs by MTT assay	[PMID: 33581557]
MGC-803	IC₅₀	6.77 μM Compound: 53	Antiproliferative activity against human MGC-803 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay Antiproliferative activity against human MGC-803 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay	[PMID: 33619958]
Macrophage cell line	CC₅₀	50.4 μM Compound: BChA	Cytotoxicity in human monocyte-derived macrophages assessed as reduction in cell viability incubated for 3 days by alamar blue dye based assay Cytotoxicity in human monocyte-derived macrophages assessed as reduction in cell viability incubated for 3 days by alamar blue dye based assay	[PMID: 28964936]

In Vitro

Biochanin A inhibits the hydrolysis of 0.5 μM AEA by mouse, rat and human FAAH with IC₅₀ s of 1.8, 1.4 and 2.4 μM respectively. FAAH is inhibited by Biochanin A with a pIC₅₀ value of 6.21±0.02, corresponding to an IC₅₀ value of 0.62 μM. Biochanin A produces significant inhibition of the URB597-sensitive tritium retention at high nanomolar-low micromolar concentrations. Experiments are run with human FAAH and 0.5 μM [³H]AEA with assay conditions giving these higher utilization rates, the activity is still inhibited by Biochanin A, Genistein, Formononetin and Daidzein in the low micromolar range (IC₅₀s of 6.0, 8.4, 12 and 30 μM, respectively)^[1].

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

In Vivo

Biochanin A is tested at doses of 30, 100 and 300 μg. The highest dose also reduced formalin-induced ERK phosphorylation in a manner antagonized by AM251. Thus, Biochanin A behaved like URB597 after local administration to the paw. In anaesthetized mice, URB597 (30 μg i.pl.) and Biochanin A (100 μg i.pl.) both inhibit the spinal phosphorylation of extracellular signal-regulated kinase produced by the intraplantar injection of formalin. The effects of both compounds are significantly reduced by the CB1 receptor antagonist/inverse agonist AM251 (30 μg i.pl.). Biochanin A (15 mg/k i.v.) does not increase brain AEA concentrations, but produces a modest potentiation of the effects of 10 mg/kg i.v. AEA in the tetrad test. Biochanin A (15 mg/kg i.v.) is without effects on its own, but significantly potentiates the effects of AEA (10 mg/kg i.v.)^[1].

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

Molecular Weight

284.26

Formula

C₁₆H₁₂O₅

CAS No.

491-80-5

Appearance

Solid

Color

White to yellow

SMILES

OC1=C2C(OC=C(C3=CC=C(OC)C=C3)C2=O)=CC(O)=C1

Structure Classification

Initial Source

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	2 years
	-20°C	1 year

Solvent & Solubility

In Vitro:

DMSO : ≥ 50 mg/mL (175.90 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

*"≥" means soluble, but saturation unknown.

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	3.5179 mL	17.5895 mL	35.1791 mL
5 mM	0.7036 mL	3.5179 mL	7.0358 mL
10 mM	0.3518 mL	1.7590 mL	3.5179 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)

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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: ≥ 2.5 mg/mL (8.79 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 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% Corn Oil
Solubility: ≥ 2.5 mg/mL (8.79 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 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 (25.0 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

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

Please enter your animal formula composition:

DMSO +

Tween-80 +

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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: 99.33%

Select Batch:

Data Sheet (279 KB) SDS (393 KB)

COA (247 KB) HNMR (253 KB) RP-HPLC (244 KB) MS (68 KB)

Handling Instructions (2659 KB)

References

[1]. Thors L, et al. Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase. Br J Pharmacol. 2010 Jun;160(3):549-60. [Content Brief]

Kinase Assay ^[1]	For experiments with FAAH, rat liver homogenates, mouse brain homogenates and membranes from COS7 cells transfected with the human enzyme are used. Frozen (−80°C) livers from adult C57BL/6 mice and frozen brains (minus cerebella) from adult Wistar or Sprague-Dawley rats are thawed and homogenized in 20 mM HEPES, 1 mM MgCl₂, pH 7. The homogenates are centrifuged at ~35000×g for 20 min at 4°C. After resuspension in buffer followed by recentrifugation and a second resuspension in buffer, the pellets are incubated at 37°C for 15 min. This incubation is undertaken in order to hydrolyse all endogenous FAAH substrates. The homogenates are then centrifuged as above, recentrifuged and resuspended in 50 mM Tris-HCl buffer, pH 7.4, containing 1 mM EDTA and 3 mM MgCl₂. The homogenates are then frozen at −80°C in aliquots until used for assay. FAAH is assayed in the homogenates and in the COS7 cell membranes using 0.5 µM (unless otherwise stated) [³H]AEA labelled in the ethanolamine part of the molecule. Blank values are obtained by the use of buffer rather than homogenate. In the experiments comparing effects of Biochanin A upon FAAH and FAAH-2, the same assay is used but with 16 nM [³H]oleoylethanolamide ([³H]OEA) as substrate and with an incubation phase at room temperature. The choice of OEA rather than AEA for FAAH-2 is motivated by the relative rates of hydrolysis: OEA is metabolized four times faster than AEA by FAAH-2, whereas for FAAH the rate of hydrolysis of OEA is about a third of that for AEA. When 0.5 µM [³H]AEA is used as substrate, assay conditions for rat brain and mouse liver are chosen so that <10% of added substrate is metabolized. For the human FAAH samples, <5% of the [³H]AEA is metabolized in all cases. For 16 nM [³H]OEA, a limited supply of an expensive ligand meant that optimization is not possible, and the amount of substrate utilized is higher (34±1 and 0.5±0.1% for FAAH and its corresponding mock-transfected, respectively; 40±2 and 21±0.4 for FAAH-2 and its corresponding mock-transfected respectively)^[1]. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Animal Administration ^[1]	Mice^[1] ICR mice are used for the behavioural tests measuring spontaneous activity (over a 10 min testing period), rectal temperature, ring immobility (over a 5 min testing period) and nociceptive threshold (tail flick tests). AEA and Biochanin A are dissolved in a vehicle consisting of ethanol, Emulphor-620 and physiological saline in a ratio of 1:1:18 v/v, and administered i.v. to the animals via the tail vein (injection volume 10 µL/g body weight). The degree of antinociception is expressed as percentage of maximum possible effect (%MPE), defined as [(test-control time)/(10-control time)]×100. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
References	[1]. Thors L, et al. Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase. Br J Pharmacol. 2010 Jun;160(3):549-60. [Content Brief]

Complete Stock Solution Preparation Table

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

DMSO	1 mM	3.5179 mL	17.5895 mL	35.1791 mL	87.9477 mL
	5 mM	0.7036 mL	3.5179 mL	7.0358 mL	17.5895 mL
	10 mM	0.3518 mL	1.7590 mL	3.5179 mL	8.7948 mL
	15 mM	0.2345 mL	1.1726 mL	2.3453 mL	5.8632 mL
	20 mM	0.1759 mL	0.8795 mL	1.7590 mL	4.3974 mL
	25 mM	0.1407 mL	0.7036 mL	1.4072 mL	3.5179 mL
	30 mM	0.1173 mL	0.5863 mL	1.1726 mL	2.9316 mL
	40 mM	0.0879 mL	0.4397 mL	0.8795 mL	2.1987 mL
	50 mM	0.0704 mL	0.3518 mL	0.7036 mL	1.7590 mL
	60 mM	0.0586 mL	0.2932 mL	0.5863 mL	1.4658 mL
	80 mM	0.0440 mL	0.2199 mL	0.4397 mL	1.0993 mL
	100 mM	0.0352 mL	0.1759 mL	0.3518 mL	0.8795 mL

Biochanin A Related Classifications

Help & FAQs

Do most proteins show cross-species activity?
Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

Biochanin A491-80-54-Methylgenistein OlmelinFAAHAutophagyEndogenous MetaboliteFatty acid amide hydrolaseInhibitorinhibitorinhibit

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Biochanin A (Synonyms: 4-Methylgenistein; Olmelin)

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Biochanin A Related Antibodies

15 Publications Citing Use of MCE Biochanin A

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References

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Complete Stock Solution Preparation Table

Biochanin A Related Classifications

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