| 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 |
Cell cycle regulators; apoptosis pathways. (-)-Syringaresinol inhibits the proliferation of human promyelocytic HL-60 cells through G1 arrest and induction of apoptosis. Its mechanism of action involves cell cycle regulation and activation of apoptotic pathways. The compound also exhibits anti-inflammatory activity by modulating inflammatory mediators. As a lignan, it may interact with various cellular targets involved in cancer cell proliferation and survival.
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| ln Vitro |
(-)-Syringaresinol inhibits the proliferation of human promyelocytic HL-60 cells through G1 arrest and induction of apoptosis. It exhibits anti-inflammatory, antiplasmodial, and antineuroinflammatory activities. The compound has anticancer activity. It decreased the viability of HL-60 cells by inducing G1 arrest. In a direct enantiomer comparison, (+)-syringaresinol significantly upregulated SIRT1 gene expression, while (-)-syringaresinol showed no activity at all.
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| ln Vivo |
In vivo studies of (-)-syringaresinol are limited. As a lignan with anticancer, anti-inflammatory, and antineuroinflammatory activities, it has potential for evaluation in animal models of cancer, inflammation, and neurodegenerative diseases. Its ability to induce G1 arrest and apoptosis in cancer cells suggests potential antitumor efficacy. Further in vivo studies are needed to characterize its pharmacokinetic and pharmacodynamic properties, as well as its efficacy and safety profile.
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| Enzyme Assay |
Non-cell-based assays for (-)-syringaresinol include cell cycle analysis using flow cytometry to assess G1 arrest. Apoptosis assays include caspase activity measurements and detection of apoptotic markers by Western blot. Anti-inflammatory activity can be assessed by measuring inhibition of inflammatory mediators in enzyme assays or cell-based systems. Standard analytical methods including HPLC, NMR, and mass spectrometry are used for compound characterization.
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| Cell Assay |
Cell-based assays for (-)-syringaresinol use human promyelocytic HL-60 cells to assess antiproliferative and pro-apoptotic activities. Cells are treated with the compound at various concentrations, and cell viability is measured using MTT or similar assays. Cell cycle analysis is performed by propidium iodide staining and flow cytometry. Apoptosis is evaluated by Annexin V/PI staining and caspase activity assays. For anti-inflammatory studies, macrophage cell lines are used.
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| Animal Protocol |
In vivo studies of (-)-syringaresinol are limited. Based on its biological activities, potential animal models include: tumor xenograft models for anticancer evaluation; carrageenan-induced paw edema models for anti-inflammatory evaluation; and models of neurodegenerative diseases for antineuroinflammatory evaluation. Standard protocols for these models involve administration of the compound followed by measurement of relevant endpoints.
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| ADME/Pharmacokinetics |
(-)-Syringaresinol has a molecular formula of C₂₂H₂₆O₈ and a molecular weight of 418.44 g/mol. It is soluble in DMSO (90 mg/mL). The compound is a naturally occurring lignan found in Annona montana. It should be stored under recommended conditions. It is intended for research use only.
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| Toxicity/Toxicokinetics |
Specific toxicity data for (-)-syringaresinol are limited. As a natural lignan, it is generally considered to have low toxicity. The compound exhibits anticancer activity by inducing apoptosis in HL-60 cells, indicating biological activity at certain concentrations. Standard laboratory safety practices should be followed when handling this compound.
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| References | |
| Additional Infomation |
(-)-Caumanyl alcohol is the (7β,7'β,8β,8'β)-stereomer of eugenol, and is the enantiomer of (+)-eugenol. It has been reported that (-)-eugenol is found in Magnolia officinalis, Cinnamomum cassia, and other organisms with relevant data.
(-)-Syringaresinol is a naturally occurring lignan found in Annona montana and other plant sources. It inhibits the proliferation of human promyelocytic HL-60 cells through G1 arrest and induction of apoptosis, demonstrating anticancer activity. The compound also possesses anti-inflammatory, antiplasmodial, and antineuroinflammatory activities. In a direct enantiomer comparison, (+)-syringaresinol significantly upregulated SIRT1 gene expression, while (-)-syringaresinol showed no activity. It may be a potential chemotherapeutic agent for cancer treatment and is for research use only. |
| Molecular Formula |
C22H26O8
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|---|---|
| Molecular Weight |
418.44
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| Exact Mass |
418.162
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| CAS # |
6216-81-5
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| Related CAS # |
(+)-Syringaresinol;21453-69-0;Syringaresinol;487-35-4;epi-Syringaresinol;51152-20-6
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| PubChem CID |
11604108
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
594.7±50.0 °C at 760 mmHg
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| Melting Point |
198-199℃
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| Flash Point |
313.5±30.1 °C
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| Vapour Pressure |
0.0±1.7 mmHg at 25°C
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| Index of Refraction |
1.578
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| LogP |
0.71
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
30
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| Complexity |
485
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| Defined Atom Stereocenter Count |
4
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| SMILES |
COC1=CC(=CC(=C1O)OC)[C@H]2[C@@H]3CO[C@H]([C@@H]3CO2)C4=CC(=C(C(=C4)OC)O)OC
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| InChi Key |
KOWMJRJXZMEZLD-WRMVBYCNSA-N
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| InChi Code |
InChI=1S/C22H26O8/c1-25-15-5-11(6-16(26-2)19(15)23)21-13-9-30-22(14(13)10-29-21)12-7-17(27-3)20(24)18(8-12)28-4/h5-8,13-14,21-24H,9-10H2,1-4H3/t13-,14-,21+,22+/m1/s1
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| Chemical Name |
4-[(3R,3aS,6R,6aS)-6-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenol
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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 (238.98 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.97 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 (5.97 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 (5.97 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 | 2.3898 mL | 11.9491 mL | 23.8983 mL | |
| 5 mM | 0.4780 mL | 2.3898 mL | 4.7797 mL | |
| 10 mM | 0.2390 mL | 1.1949 mL | 2.3898 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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