| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
Estrogen receptors (ERα, ERβ); antioxidant pathways. (+)-Secoisolariciresinol is a plant lignan that is metabolized by intestinal microbiota to the mammalian lignans enterodiol and enterolactone. These metabolites have estrogenic activity by binding to estrogen receptors and antioxidant activity by scavenging free radicals. The compound's mechanism of action is primarily mediated through its metabolites rather than the parent compound itself. Lignans are known for their potential health benefits including anticancer, cardioprotective, and hormone-balancing effects.
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| ln Vitro |
(+)-Secoisolariciresinol exhibits antioxidant activity by scavenging free radicals and reducing oxidative stress. The compound is metabolized to enterodiol and enterolactone, which have estrogenic activity and can bind to estrogen receptors. The compound's specific in vitro activities depend on the concentrations tested and the assay systems used. Further studies are needed to fully characterize its activity profile.
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| ln Vivo |
In vivo studies of (+)-secoisolariciresinol are primarily related to its metabolism to mammalian lignans. Following oral administration, the compound is metabolized by intestinal microbiota to enterodiol and enterolactone, which are absorbed systemically. These metabolites have been studied for their potential health benefits including anticancer, cardioprotective, and hormone-balancing effects. The compound's effects in vivo are mediated through its metabolites.
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| Enzyme Assay |
Non-cell-based assays for (+)-secoisolariciresinol include antioxidant assays such as DPPH radical scavenging, ABTS, and FRAP assays. Estrogen receptor binding can be assessed using competitive binding assays with radiolabeled estradiol. Standard analytical methods including HPLC, NMR, and mass spectrometry are used for compound characterization and purity assessment.
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| Cell Assay |
Cell-based assays for (+)-secoisolariciresinol use various cell lines to assess its biological activities. Estrogen receptor activity is assessed using MCF-7 breast cancer cells (ER-positive) or reporter gene assays with an estrogen response element (ERE)-luciferase construct. For antioxidant studies, cells are exposed to oxidative stress inducers and treated with the compound, and intracellular ROS levels are measured. The compound's effects on cell proliferation and apoptosis can be assessed in cancer cell lines.
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| Animal Protocol |
In vivo studies of (+)-secoisolariciresinol have been conducted in animal models to study its metabolism and health effects. The compound is administered orally, and its metabolites enterodiol and enterolactone are measured in plasma, urine, and tissues. Potential animal models include: ovariectomized rat models for estrogenic effects; and tumor xenograft models for anticancer evaluation. Standard protocols for these models involve administration of the compound followed by measurement of relevant endpoints.
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| ADME/Pharmacokinetics |
(+)-Secoisolariciresinol has a molecular formula of C₂₀H₂₆O₆ and a molecular weight of approximately 362.42 g/mol. The CAS number is 145265-02-7. It is a plant lignan found in various dietary sources including flaxseed. The compound is metabolized by intestinal microbiota to the mammalian lignans enterodiol and enterolactone. It should be stored under recommended conditions. It is intended for research use only.
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| Toxicity/Toxicokinetics |
Specific toxicity data for (+)-secoisolariciresinol are limited. As a natural lignan found in dietary sources, it is generally considered to have low toxicity. Lignans are widely consumed in the human diet and are generally recognized as safe. Standard laboratory safety practices should be followed when handling this compound, including the use of personal protective equipment. It is intended for research use only.
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| References | |
| Additional Infomation |
(+)-secoisolariciresinol is the enantiomer of secoisolariciresinol, having the (+)-(2S,3S)- configuration. It is the enantiomer of (-)-secoisolariciresinol. (+)-secoisolariciresinol has been reported to exist in Phyllanthus lawii, Phyllanthus oxyphyllus, and other organisms with relevant data.
(+)-Secoisolariciresinol is a naturally occurring lignan compound found in various plant sources, including flaxseed (Linum usitatissimum) and other dietary sources. Lignans are a class of polyphenolic compounds known for their diverse biological activities, including antioxidant, anticancer, and hormone-balancing effects. Secoisolariciresinol is metabolized by intestinal microbiota to the mammalian lignans enterodiol and enterolactone, which have estrogenic activity. The compound is used as a reference standard for the identification and quantification of lignans in plant extracts and for research purposes. It is for research use only. |
| Molecular Formula |
C20H26O6
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|---|---|
| Molecular Weight |
362.417
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| Exact Mass |
362.172
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| CAS # |
145265-02-7
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| PubChem CID |
6336781
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| Appearance |
White to off-white solid
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| LogP |
2.5
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
9
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| Heavy Atom Count |
26
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| Complexity |
357
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| Defined Atom Stereocenter Count |
2
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| SMILES |
COC1=C(C=CC(=C1)C[C@H](CO)[C@H](CC2=CC(=C(C=C2)O)OC)CO)O
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| InChi Key |
PUETUDUXMCLALY-HZPDHXFCSA-N
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| InChi Code |
InChI=1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16-/m1/s1
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| Chemical Name |
(2S,3S)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol
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| Synonyms |
(+)-Secoisolariciresinol
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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: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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: 50 mg/mL (137.96 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.90 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 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 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to 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 (6.90 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 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (6.90 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7592 mL | 13.7961 mL | 27.5923 mL | |
| 5 mM | 0.5518 mL | 2.7592 mL | 5.5185 mL | |
| 10 mM | 0.2759 mL | 1.3796 mL | 2.7592 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.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT01276704 | Terminated | Drug: Placebo Drug: secoisolariciresinol |
Breast Cancer | Carol Fabian, MD | January 2011 | Phase 2 |
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