| Size | Price | Stock | Qty |
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| 1mg |
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Daidzein metabolite
Daidzein 4'-beta-D-glucuronide is a phytoestrogen metabolite. It interacts with the estrogen receptor (ER) pathway, which is responsible for its anti-inflammatory, antioxidant, and anti-cancer effects. The compound participates in the regulation of cellular processes and can act as a modulator of specific molecular pathways, influencing gene expression and protein activity within cells. It may also affect cell signaling pathways and cellular metabolism. |
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| ln Vitro |
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-(7-hydroxy-4-oxo-1-benzopyran-3-yl)phenoxy]-2-oxanecarboxylic acid is an isoflavonoid and a glycoside.
In vitro, Daidzein 4'-beta-D-glucuronide has significant effects on various types of cells and cellular processes. It influences cell function by impacting cell signaling pathways, gene expression, and cellular metabolism. As a phytoestrogen metabolite, it has anti-inflammatory, antioxidant, and anti-cancer effects in cell-based assays. It interacts with cellular receptors and enzymes, affecting their function and downstream signaling cascades. The compound is also involved in various biochemical reactions with enzymes and proteins. |
| ln Vivo |
Black soybeans are rich in isoflavones, which have several beneficial health effects. In this study, a validated method based on UHPLC-MS/MS was developed to screen black-soybean metabolites in rat urine, bile, and plasma and to quantify the compounds (daidzein, genistein, glycitein, and daidzin) and their metabolites (daidzein-4'-β-d-glucuronide, genistein-7-β-d-glucuronide, and genistein-4'-β-d-glucuronide) in plasma. Thirty-seven compounds were tentatively detected in the biological samples. The method was fully validated in quantitative experiments, including in assessments of linearity (2.5-100 ng/mL for daidzein, genistein, and glycitein; 10-100 ng/mL for daidzin; 5-3125 ng/mL for genistein-7-β-d-glucuronide; and 5-1562.5 ng/mL for daidzein-4'-β-d-glucuronide and genistein-4'-β-d-glucuronide), matrix effects (85-115%), recovery (80-105%), precision (<10%), and accuracy (<10%). The compounds were stable throughout sample storage, treatment, and analysis. The method was first applied to detect IFs and metabolites in rats after oral administration of black-soybean extract. These results support the potential of this method for successful application in pharmacokinetic studies.[1]
In vivo, Daidzein 4'-beta-D-glucuronide is a major circulating metabolite of daidzein in humans following consumption of soy products. As a phase II glucuronide conjugate, it is more water-soluble than the parent isoflavone, facilitating renal and biliary elimination. The compound retains some biological activity and may contribute to the overall health benefits of soy isoflavones, including potential protection against hormone-dependent cancers, cardiovascular disease, and osteoporosis. |
| Enzyme Assay |
Daidzein 4'-beta-D-glucuronide is used as an analytical standard for LC-MS or HPLC quantification. For in vitro assays, the compound is dissolved in an appropriate organic solvent (e.g., DMSO or methanol) to prepare a stock solution (e.g., 1 mg/mL). It is then diluted into assay buffer for use as a reference standard in enzyme inhibition studies (e.g., UGT activity assays) or for establishing calibration curves in mass spectrometry-based quantification of isoflavone metabolites in biological samples.
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| Cell Assay |
Daidzein 4'-beta-D-glucuronide can be added to cell culture media for studies of isoflavone metabolism and cellular uptake. Cells (e.g., intestinal Caco-2, hepatic HepG2, or breast cancer MCF-7 cells) are cultured in standard medium. The glucuronide metabolite is added at various concentrations (e.g., 0.1-100 uM) for 1-48 hours. Cellular uptake and deconjugation to daidzein can be measured by LC-MS. Effects on estrogen-responsive gene expression can be assessed by qPCR. Cell viability and proliferation are measured by MTT assay.
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| Animal Protocol |
For in vivo animal studies, Daidzein 4'-beta-D-glucuronide can be administered to rodents via oral gavage or intravenous injection. Blood samples are collected at multiple time points, and plasma is analyzed by LC-MS to assess the pharmacokinetics of the glucuronide conjugate. Tissues (liver, kidney, intestine, breast) may be collected to determine tissue distribution and potential deconjugation to the active aglycone daidzein. Urine and bile samples can also be collected for excretion studies.
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| ADME/Pharmacokinetics |
As a phase II metabolite, Daidzein 4'-beta-D-glucuronide has different PK properties compared to the aglycone daidzein. Following daidzein consumption, the glucuronide conjugate appears in plasma within 1-2 hours and reaches peak concentrations by 4-8 hours. The half-life is approximately 6-8 hours. The glucuronide is more water-soluble and has reduced membrane permeability compared to daidzein. It is eliminated primarily via renal excretion, with some biliary excretion and enterohepatic recirculation.
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| Toxicity/Toxicokinetics |
Daidzein 4'-beta-D-glucuronide is a naturally occurring metabolite and is considered to have low toxicity. Daidzein and its metabolites are generally recognized as safe at dietary intake levels from soy products. The compound is stored at 4degC, sealed, away from moisture. For research use, standard laboratory safety precautions (gloves, safety glasses) are recommended. No specific acute toxicity data is available for this glucuronide metabolite. Not intended for human consumption.
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| References |
[1]. Zhang J, et al. Metabolite Identification and Pharmacokinetic Profiling of Isoflavones from Black Soybean in Rats Using Ultrahigh-Performance Liquid Chromatography with Linear-Ion-Trap-Orbitrap and Triple-Quadrupole Tandem Mass Spectrometry. J Agric Food Chem. 2018 Dec 12;66(49):12941-12952.
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| Additional Infomation |
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-(7-hydroxy-4-oxo-1-benzopyran-3-yl)phenoxy]-2-oxacyclohexanecarboxylic acid is an isoflavone compound and also a glycoside.
Daidzein 4'-beta-D-glucuronide is not a drug but a research-use endogenous metabolite and analytical standard. It has no approved therapeutic status. It is used as a reference standard for analytical research, quality control, and pharmaceutical reference standard applications. The compound is associated with daidzein metabolism studies and is important for understanding the bioavailability and biological activity of dietary isoflavones. It is also used to study UGT-mediated phase II metabolism and enterohepatic circulation of phytoestrogens. |
| Molecular Formula |
C21H18O10
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|---|---|
| Molecular Weight |
430.36
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| Exact Mass |
430.09
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| CAS # |
264236-77-3
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| PubChem CID |
23930394
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| Appearance |
Typically exists as White to off-white solid at room temperature
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| LogP |
0.436
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
10
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
31
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| Complexity |
715
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| Defined Atom Stereocenter Count |
5
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| SMILES |
OC1C=CC2C(C(C3C=CC(O[C@@H]4O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]4O)=CC=3)=COC=2C=1)=O
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| InChi Key |
ATUYSKUVHUPXBV-ZFORQUDYSA-N
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| InChi Code |
InChI=1S/C21H18O10/c22-10-3-6-12-14(7-10)29-8-13(15(12)23)9-1-4-11(5-2-9)30-21-18(26)16(24)17(25)19(31-21)20(27)28/h1-8,16-19,21-22,24-26H,(H,27,28)/t16-,17-,18+,19-,21+/m0/s1
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| Chemical Name |
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-(7-hydroxy-4-oxochromen-3-yl)phenoxy]oxane-2-carboxylic acid
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| Synonyms |
Daidzein 4'-O-glucuronide; DAIDZEIN 4'-BETA-D-GLUCURONIDE; Daidzein 4'-; A-D-Glucuronide; Daidzein 4'-b-D-Glucuronide; (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-(7-hydroxy-4-oxochromen-3-yl)phenoxy]oxane-2-carboxylic acid; 4-(7-Hydroxy-4-oxo-4H-1-benzopyran-3-yl)phenyl ss-D-Glucopyranosiduronic Acid;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.3236 mL | 11.6182 mL | 23.2364 mL | |
| 5 mM | 0.4647 mL | 2.3236 mL | 4.6473 mL | |
| 10 mM | 0.2324 mL | 1.1618 mL | 2.3236 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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