| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
Estrogen receptors (ERα and ERβ) with weak affinity; also may interact with antioxidant response elements via Nrf2 activation. However, specific high-affinity targets have not been fully characterized. It likely acts as a modulator of cellular redox status and may influence hormone-sensitive pathways.
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|---|---|
| ln Vitro |
(R)-Isomucronulatol shows concentration-dependent DPPH radical scavenging activity (IC₅₀ ~ 50-80 µM) and inhibits lipid peroxidation in linoleic acid models. In cell-free systems, it also reduces ferric ions (FRAP assay) and exhibits moderate ABTS radical cation scavenging. It does not show significant cytotoxicity in normal cells at concentrations up to 100 µM, but may weakly stimulate proliferation of MCF-7 breast cancer cells at low doses, indicating potential estrogenic activity.
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| ln Vivo |
In vivo data are scarce; however, related isoflavonoids have shown estrogenic effects in ovariectomized rats. No specific animal studies for (R)-isomucronulatol are published. It is presumed to be metabolized by gut microbiota similar to other isoflavans, producing active metabolites that may exert systemic effects. Further research is needed to establish its in vivo efficacy and safety.
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| Enzyme Assay |
DPPH and ABTS radical scavenging assays are conducted in 96-well plates; the compound is dissolved in methanol or DMSO and mixed with radicals; absorbance is measured at 517 nm or 734 nm, respectively, after 30 minutes. FRAP assay measures ferric reducing power at 593 nm. For estrogen receptor binding, competitive displacement of [³H]estradiol using recombinant ERα/ERβ is performed with Scatchard analysis to determine relative binding affinity.
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| Cell Assay |
Estrogen-sensitive MCF-7 breast cancer cells are cultured in phenol red-free medium with charcoal-stripped serum. Cells are treated with (R)-isomucronulatol (0.1-100 µM) for 48-72 hours, and proliferation is assessed by MTT or BrdU incorporation. For antioxidant studies, cells are pre-treated with the compound then exposed to H₂O₂ (200 µM) for 1 hour; intracellular ROS is measured by DCFH-DA fluorescence. Cytotoxicity is evaluated in HepG2 or normal fibroblast cell lines.
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| Animal Protocol |
No specific animal models are reported. However, based on its isoflavan structure, potential studies could include ovariectomized rat models to assess estrogenic effects on bone density and uterine weight, or high-fat diet mice to evaluate metabolic benefits. Dosing would be oral gavage (10-50 mg/kg/day) for 4-8 weeks, with endpoints including serum lipid profiles, antioxidant enzyme activities, and histopathology.
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| ADME/Pharmacokinetics |
Absorption is likely moderate after oral administration due to glycoside metabolism; however, as an aglycone, it may be absorbed in the small intestine. It is subject to phase II metabolism (sulfation and glucuronidation) and microbial degradation in colon. Half-life and bioavailability are unknown but expected to be similar to other isoflavans (~2-4 hours). Plasma protein binding is moderate.
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| Toxicity/Toxicokinetics |
Based on its natural origin and lack of reported adverse effects, (R)-isomucronulatol is presumed to have low acute toxicity. No LD₅₀ values are available. In cell culture, it does not induce significant cytotoxicity up to 100 µM. Chronic toxicity studies have not been conducted, but typical isoflavonoids are well-tolerated at dietary intake levels. Standard laboratory precautions are sufficient for handling.
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| References | |
| Additional Infomation |
(R)-Verbassilol has been reported to exist in Astragalus falcatus, Astragalus mongholicus, and other organisms for which relevant data are available.
See also: Verbassilol (note moved to). (R)-Isomucronulatol is a minor phytochemical used primarily as an analytical reference standard for quality control of herbal extracts. It is not intended for pharmaceutical development but serves as a research tool for studying phytoestrogen mechanisms, antioxidant pathways, and structure-activity relationships among isoflavans. Its occurrence in traditional medicinal plants warrants further investigation into potential health benefits. |
| Molecular Formula |
C17H18O5
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|---|---|
| Molecular Weight |
302.32
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| Exact Mass |
302.115
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| CAS # |
64474-51-7
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| Related CAS # |
Isomucronulatol; 52250-35-8
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| PubChem CID |
10380176
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| Appearance |
White to off-white solid
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| Boiling Point |
426.8 °C at 760 mmHg
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| Melting Point |
152-153 °C
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| Source |
Originated from plants: Leguminosae Sphaerophysa salsula (Pall.) DC.
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| LogP |
2.833
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
22
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| Complexity |
363
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| Defined Atom Stereocenter Count |
1
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| SMILES |
COC1=C(C(=C(C=C1)C2CC3=C(C=C(C=C3)O)OC2)O)OC
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| InChi Key |
NQRBAPDEZYMKFL-NSHDSACASA-N
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| InChi Code |
InChI=1S/C17H18O5/c1-20-14-6-5-13(16(19)17(14)21-2)11-7-10-3-4-12(18)8-15(10)22-9-11/h3-6,8,11,18-19H,7,9H2,1-2H3/t11-/m0/s1
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| Chemical Name |
(3R)-3-(2-hydroxy-3,4-dimethoxyphenyl)-3,4-dihydro-2H-chromen-7-ol
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| Synonyms |
(-)-Isomucronulatol; (R)-Isomucronulatol; 2H-1-Benzopyran-7-ol
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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) |
DMSO: ~100 mg/mL (~330.8 mM; with ultrasonication)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.27 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), Clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (25.0 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.27 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), Clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (25.0 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (8.27 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), Clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (25.0 mg/mL) to 900 μL of corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.3078 mL | 16.5388 mL | 33.0775 mL | |
| 5 mM | 0.6616 mL | 3.3078 mL | 6.6155 mL | |
| 10 mM | 0.3308 mL | 1.6539 mL | 3.3078 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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