(-)-Syringaresinol
Based on 1 Customer Validation
(-)-Syringaresinol is an orally active isomer of syringaresinol (HY-N8307) found in Annona Montana. (-)-Syringaresinol exhibits antioxidant, anti-inflammatory, and anticancer activities. (-)-Syringaresinol can alleviate ulcerative colitis via the PI3K-Akt/MAPK/Wnt signaling pathway. (-)-Syringaresinol inhibits HL-60 cell proliferation by arresting the G1 phase and inducing apoptosis. (-)-Syringaresinol inhibits LPS (HY-D1056)-induced microglial activation by downregulating the NF-κB p65 signaling pathway and its interaction with ERβ, exerting anti-neuroinflammatory effects.
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- Pureté: 99.93%
- CAS No.: 6216-81-5
- Formule: C22H26O8
- Masse moléculaire:418.44
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Stockage:
4°C, protect from light
* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
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Activité biologique
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Chemical Information
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Solvant et solubilité
- Pureté et documentation
- Références
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Help & FAQs
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Activité biologique
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| A549 | IC50 |
>30 μM
Compound: 7
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Anticancer activity against human A549 cells by SRB assay
Anticancer activity against human A549 cells by SRB assay
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[PMID: 21420296] |
| BV-2 | IC50 |
>100 μM
Compound: 17
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Antineuroinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induced NO production after 24 hrs in presence of LPS by Griess reaction based assay
Antineuroinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induced NO production after 24 hrs in presence of LPS by Griess reaction based assay
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[PMID: 28911817] |
| BV-2 | IC50 |
13.48 μM
Compound: 7
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Antiinflammatory activity in mouse BV2 cells assessed as inhibition of lipopolysaccharide induced NO production
Antiinflammatory activity in mouse BV2 cells assessed as inhibition of lipopolysaccharide induced NO production
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[PMID: 21420296] |
| BV-2 | IC50 |
27.53 μM
Compound: 5; Syringaresinol
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Antineuroinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induced nitric oxide production after 24 hrs by Griess assay
Antineuroinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induced nitric oxide production after 24 hrs by Griess assay
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[PMID: 26774654] |
| Neutrophil | IC50 |
>50 μM
Compound: (-)-syringaresinol
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Antiinflammatory activity in human neutrophils assessed as inhibition of fMLP/Cytochalasin B-induced elastase release
Antiinflammatory activity in human neutrophils assessed as inhibition of fMLP/Cytochalasin B-induced elastase release
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[PMID: 18817445] |
| Neutrophil | IC50 |
>50 μM
Compound: 25
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Antiinflammatory activity in human neutrophils assessed as inhibition of formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B-induced elastase release
Antiinflammatory activity in human neutrophils assessed as inhibition of formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B-induced elastase release
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[PMID: 18211005] |
| Neutrophil | IC50 |
39.87 μM
Compound: 25
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Antiinflammatory activity in human neutrophils assessed as inhibition of formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B-induced superoxide anion generation
Antiinflammatory activity in human neutrophils assessed as inhibition of formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B-induced superoxide anion generation
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[PMID: 18211005] |
| Neutrophil | IC50 |
40.2 μM
Compound: (-)-syringaresinol
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Antiinflammatory activity in human neutrophils assessed as inhibition of fMLP/cytochalasin B-induced superoxide radical anion generation
Antiinflammatory activity in human neutrophils assessed as inhibition of fMLP/cytochalasin B-induced superoxide radical anion generation
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[PMID: 18817445] |
| RAW264.7 | IC50 |
>50 μM
Compound: 9
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Inhibition of LPS-induced IL-1beta production in mouse RAW264.7 cells after 24 hrs by ELISA
Inhibition of LPS-induced IL-1beta production in mouse RAW264.7 cells after 24 hrs by ELISA
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[PMID: 24963714] |
| RAW264.7 | IC50 |
45.6 μM
Compound: 9
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Inhibition of LPS-induced NO production in mouse RAW264.7 cells after 24 hrs by Griess reagent based assay
Inhibition of LPS-induced NO production in mouse RAW264.7 cells after 24 hrs by Griess reagent based assay
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[PMID: 24963714] |
| SK-MEL-2 | IC50 |
14.47 μM
Compound: 7
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Anticancer activity against human SK-MEL-2 cells by SRB assay
Anticancer activity against human SK-MEL-2 cells by SRB assay
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[PMID: 21420296] |
| SK-OV-3 | IC50 |
>30 μM
Compound: 7
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Anticancer activity against human SKOV3 cells by SRB assay
Anticancer activity against human SKOV3 cells by SRB assay
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[PMID: 21420296] |
| XF498 | IC50 |
8.82 μM
Compound: 7
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Anticancer activity against human XF498 cells by SRB assay
Anticancer activity against human XF498 cells by SRB assay
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[PMID: 21420296] |
(-)-Syringaresinol (25-100 μM, 24 h) enhances intestinal epithelial barrier function, reduces levels of TNF-α, IL-6, IFN-γ, and COX-2, increases tight junction protein expression levels in LPS (HY-D1056)-induced Caco-2 cell[1].
(-)-Syringaresinol (0.5-40 μM,24-72 h) reduces cell viability against HL-60 cells (IC50 = 5.8 μM), and has weak cytotoxicity against SNU-1, SK-OV-3, LLC cells (IC50 > 30 μM)[2].
(-)-Syringaresinol (0-20 μM,0-24 h) induces apoptosis, G1 arrest and release of cytochrome c in HL-60 cells[2].
(-)-Syringaresinol (0-200 μM, 24 h) does not exhibit toxic effects on BV2 cells[3].
(-)-Syringaresinol (25-100 μM, 1 h) suppresses LPS-induced proinflammatory mediator production and upregulation of NO production on BV2 cells[3].
(-)-Syringaresinol (25-100 μM, 24 h) increases the expression of M2 marker CD206, but suppressed the expression of M1 marker CD40 in LPS-stimulated BV2 cells[3].
(-)-Syringaresinol (50 μM, 1 h) has anti-inflammatory effects by ERβ in LPS-stimulated BV2 cells[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:LPS-induced Caco-2 cell
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Concentration:25 μM, 50 μM, 100 μM
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Incubation Time:24 h
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Result:Increased expression levels of ZO-1, occludin, claudin-1, and E-cadherin.
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Cell Line:HL-60 cells
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Concentration:1 μM
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Incubation Time:0 h, 4 h, 8 h, 16 h, 24 h
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Result:Arrested in G1, did not change S phase, increased the expressions of p21waf1/cip1 and p27kip1, decreased the expressions of cyclin D1, cyclin D2, and cyclin E as well as cdk2, cdk4 and cdk6.
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Cell Line:HL-60 cells
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Concentration:0 μM, 0.5 μM, 5 μM, 20 μM
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Incubation Time:24 h
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Result:Showed nuclear fragmentation and cell shrinkage, increased the expression of Bax and the ratio of Bax/Bcl-2, decreased the expressions of Bcl-2 and Bcl-XL.
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Cell Line:HL-60 cells
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Concentration:0 μM, 0.5 μM, 5 μM, 20 μM
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Incubation Time:24 h
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Result:Increased cleavage of caspase-9, caspase-3, and PARP.
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Cell Line:BV2 cells
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Concentration:25 μM, 50 μM, 100 μM
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Incubation Time:1 h
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Result:Attenuated the LPS-induced transcription levels of proinflammatory mediator IL-6, IL-1β, TNF-α, iNOS, and COX-2.
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Cell Line:BV2 cells
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Concentration:25 μM, 50 μM, 100 μM
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Incubation Time:1 h
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Result:Downregulated LPS-induced TNF-α and IL-6 levels.
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Cell Line:BV2 cells
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Concentration:25 μM, 50 μM, 100 μM
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Incubation Time:1 h
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Result:Attenuated the LPS-induced COX-2 and iNOS protein expression.
Reduced the LPS-induced activation of NF-κB p65.
(-)-Syringaresinol (60 mg/kg, i.g., once a day, 2 days) reduces inflammatory responses and suppresses astrocytes activation in the hippocampal area and corpus callosum in LPS-stimulated mice model[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:DSS-induced UC mouse model [1]
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Dosage:10 mg/kg, 20 mg/kg, 40 mg/kg,
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Administration:i.g., once a day, 10 days
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Result:Reduced weight loss and DAI scores, increased colon length and reduced colon damage, reduced spleen coefficient.
Reduced bacterial levels in the spleen and mesenteric lymph nodes, reduced serum TNF-α, IL-6, IFN-γ and COX-2 levels.
Showed lower epithelial damage, more intact colon tissue and lower inflammatory cell infiltration than the contorl group.
Improved colonic epithelial cell ultrastructure and gradually restored tight and gap junction integrity.
Reduced mRNA expression of Pdgfra, Tgfbr2, Il1r1, Cacna1d, Fn1, Lamc1, Col4a1, Col1a1, Srfp1, Wnt4, Fzd1, and Wnt5b, reduced phosphorylation levels of PI3K, Akt, NF-κB, MAPK, and GSK-3β, as well as β-catenin, increased expression of E-cadherin.
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Animal Model:LPS (100 mg/kg)-stimulated C57BL/6 mice (Male 8-12-week-old) model[3]
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Dosage:60 mg/kg
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Administration:i.g., once a day, 2 days
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Result:Reduced the mRNA levels of IL-6, IL-1β, TNF-α, COX-2, and iNOS in the mouse hippocampal region.
Suppressed LPS-induced astrocytes activation in the hippocampal area and corpus callosum.
Chemical Information
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CAS No. 6216-81-5
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Appearance Solid
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Masse moléculaire 418.44
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Formule C22H26O8
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Color White to off-white
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SMILES
OC1=C(OC)C=C([C@@H]2OC[C@]3([H])[C@@]2([H])CO[C@H]3C4=CC(OC)=C(O)C(OC)=C4)C=C1OC
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Structure Classification
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Initial Source
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Livraison
Room temperature in continental US; may vary elsewhere.
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Stockage
4°C, protect from light
* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)
Solvant et solubilité
DMSO : 100 mg/mL (238.98 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
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, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
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, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
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.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.5 mg/mL (5.97 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.
Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 2.5 mg/mL (5.97 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 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
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:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
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).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL. * In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
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.
Pureté et documentation
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Fiche technique (290 KB)
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SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 KB)
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Instruction de manipulation (2659 KB)
Références
[1]. Liu Y, et al. (-)-Syringaresinol attenuates ulcerative colitis by improving intestinal epithelial barrier function and inhibiting inflammatory responses. Phytomedicine. 2024 Feb;124:155292. [Content Brief]
[2]. Park BY, et al. (-)-Syringaresinol inhibits proliferation of human promyelocytic HL-60 leukemia cells via G1 arrest and apoptosis. Int Immunopharmacol. 2008 Jul;8(7):967-73. [Content Brief]
[3]. Zhang L, et al. (-)-Syringaresinol suppressed LPS-induced microglia activation via downregulation of NF-κB p65 signaling and interaction with ERβ. Int Immunopharmacol. 2021 Oct;99:107986. [Content Brief]
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, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 2.3898 mL | 11.9491 mL | 23.8983 mL | 59.7457 mL |
| 5 mM | 0.4780 mL | 2.3898 mL | 4.7797 mL | 11.9491 mL | |
| 10 mM | 0.2390 mL | 1.1949 mL | 2.3898 mL | 5.9746 mL | |
| 15 mM | 0.1593 mL | 0.7966 mL | 1.5932 mL | 3.9830 mL | |
| 20 mM | 0.1195 mL | 0.5975 mL | 1.1949 mL | 2.9873 mL | |
| 25 mM | 0.0956 mL | 0.4780 mL | 0.9559 mL | 2.3898 mL | |
| 30 mM | 0.0797 mL | 0.3983 mL | 0.7966 mL | 1.9915 mL | |
| 40 mM | 0.0597 mL | 0.2987 mL | 0.5975 mL | 1.4936 mL | |
| 50 mM | 0.0478 mL | 0.2390 mL | 0.4780 mL | 1.1949 mL | |
| 60 mM | 0.0398 mL | 0.1992 mL | 0.3983 mL | 0.9958 mL | |
| 80 mM | 0.0299 mL | 0.1494 mL | 0.2987 mL | 0.7468 mL | |
| 100 mM | 0.0239 mL | 0.1195 mL | 0.2390 mL | 0.5975 mL |
(-)-Syringaresinol Related Classifications
HY-126066 Related Classifications
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