| Size | Price | Stock | Qty |
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| 1mg |
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| Other Sizes |
| Targets |
Syk kinase (Spleen Tyrosine Kinase) and Phospholipase Cgamma (PLCgamma). Linocinnamarin targets the Syk/PLCgamma signaling pathway, which is critical for antigen-stimulated degranulation in immune cells such as mast cells and basophils. By inactivating this pathway, the compound inhibits downstream signaling events including intracellular calcium mobilization and ROS generation, leading to suppression of inflammatory responses. Its primary mechanism is the direct inhibition of Syk activation.
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| ln Vitro |
Linocinnamarin inhibits antigen-stimulated degranulation by inactivating the Syk/phospholipase Cgamma (PLCgamma) pathways. It suppresses antigen-stimulated spleen tyrosine kinase (Syk) activation, which is a key early signaling event in immune cell activation. The compound also inhibits antigen-stimulated increases in intracellular free Ca2+ concentration and ROS generation. These in vitro activities demonstrate its ability to modulate immune cell function and reduce inflammatory responses. The compound's anti-inflammatory effects are mediated through inhibition of Syk/PLCgamma signaling rather than direct neutralization of inflammatory mediators.
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| ln Vivo |
In vivo anti-inflammatory studies have been conducted using rat hind paw inflammation models. Linocinnamarin exhibited statistically significant inhibition of hind paw inflammation at a minimally effective dose of 10 mg/kg. PK parameters and % Syk inhibition were extrapolated from rat whole blood PK/PD curve fits. These findings confirm the in vivo efficacy of Linocinnamarin as an anti-inflammatory agent and support its mechanism of action involving Syk inhibition. Further studies in other animal models of inflammation and allergic disease would be valuable.
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| Enzyme Assay |
Sykinase inhibition assay: The in vitro activity of Linocinnamarin can be evaluated using a Syk kinase inhibition assay. Recombinant human Syk kinase is incubated with test compound at varying concentrations (0.001-100 uM) in kinase assay buffer containing ATP and a peptide substrate (e.g., poly(Glu, Tyr) peptide). Following incubation, phosphorylation of the substrate is detected by ELISA or using a fluorescence-based kinase assay kit. IC₅0 values are calculated from the concentration-response curve. Alternatively, molecular docking studies can be performed to predict binding interactions between Linocinnamarin and the Syk active site. This assay has been used to demonstrate that LN directly suppresses Ag-stimulated Syk activation in cell-free systems.
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| Cell Assay |
For degranulation assays, cells (e.g., RBL-2H3 mast cells or human basophils) are sensitized with antigen-specific IgE overnight. Cells are washed and pre-incubated with Linocinnamarin (1-100 uM) for 30-60 minutes. Antigen stimulation is then performed for 30-60 minutes. Degranulation is quantified by measuring release of beta-hexosaminidase (enzyme activity by colorimetric substrate) or histamine (by ELISA). Intracellular Ca2+ concentration is measured using fluorescent Ca2+ indicator dyes (e.g., Fluo-4 AM). ROS generation is assessed using DCFH-DA probe. Syk phosphorylation is analyzed by Western blotting using anti-phospho-Syk antibodies. All experiments should include appropriate positive and negative controls.
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| Animal Protocol |
Animal inflammation models: For the rat hind paw edema model, male rats are administered Linocinnamarin (oral or intraperitoneal, doses ranging from 5-50 mg/kg) 1-2 hours prior to injection of inflammatory agent (carrageenan or compound 48/80). Paw volume is measured using a plethysmometer at 0, 1, 2, 3, 4, and 6 hours post-injection. Percentage inhibition of edema is calculated compared to vehicle control group. For PK/PD studies, blood samples are collected at multiple time points after administration to determine drug concentrations and correlate with Syk inhibition in whole blood ex vivo. The minimally effective dose in this model was found to be 10 mg/kg. IL-6 and TNF-alpha levels in paw tissue or serum are measured by ELISA as secondary endpoints.
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| ADME/Pharmacokinetics |
Linocinnamarin (MW 340.33, formula C1₆H20O₈). Solubility: soluble in DMSO (50 mg/mL). For in vivo administration, formulations using 10% DMSO + 40% PEG300 + 5% Tween 80 + 45% Saline are recommended for achieving working concentrations up to 2-5 mg/mL. Storage: Powder at -20degC (stable for 3 years). In solution at -80degC (stable for 1 year). Pharmacokinetic parameters: In rats, minimally effective dose was 10 mg/kg. PK parameters including Cmax, Tmax, half-life, and oral bioavailability have been studied in rat models and correlated with Syk inhibition using PK/PD modeling. Detailed PK data are available through research publications. The compound has a molecular weight of 679.64 for the glycoside form. However, the aglycone form is reported as C1₆H20O₈, MW 340.33. There is some discrepancy in reported molecular weights in the literature due to the glycoside structure; the biologically active form may be the aglycone.
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| Toxicity/Toxicokinetics |
Based on its natural product origin from Fragaria ananassa (strawberry), which is widely consumed as food, Linocinnamarin is expected to have low acute toxicity at concentrations typically used for research. No significant adverse effects have been reported in animal studies at doses up to 50 mg/kg. Standard safety precautions for laboratory chemicals should be followed. Comprehensive toxicity studies including genotoxicity, reproductive toxicity, and chronic toxicity have not been extensively performed. The compound should not be used for therapeutic purposes in humans.
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| References | |
| Additional Infomation |
It has been reported that methyl 3-[4-(β-D-glucopyranosyl)phenyl]acrylate is found in plants of the genus Euphorbia hirta and flax (Linum usitatissimum), and there is relevant data available.
Linocinnamarin has been studied as a potential therapeutic agent for allergic and inflammatory conditions. The inhibition of antigen-stimulated degranulation and Syk/PLCgamma pathway suggests that Linocinnamarin may be useful for treating conditions such as asthma, allergic rhinitis, atopic dermatitis, and other mast cell-mediated disorders. The compound is not a marketed drug and is currently only available for research use. It can be used as a reference standard for natural product analysis or as a tool compound for studying Syk-dependent signaling pathways. The compound should be stored under appropriate conditions to maintain stability. Additional research is ongoing to explore its full therapeutic potential. |
| Molecular Formula |
C16H20O8
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|---|---|
| Molecular Weight |
340.33
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| Exact Mass |
340.115
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| CAS # |
554-87-0
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| PubChem CID |
12311284
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
591.4±50.0 °C at 760 mmHg
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| Flash Point |
217.4±23.6 °C
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| Vapour Pressure |
0.0±1.7 mmHg at 25°C
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| Index of Refraction |
1.628
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| LogP |
-0.71
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
24
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| Complexity |
432
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| Defined Atom Stereocenter Count |
5
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| SMILES |
O1[C@H]([C@@H]([C@H]([C@@H]([C@H]1CO)O)O)O)OC1C=CC(/C=C/C(=O)OC)=CC=1
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| InChi Key |
KPYQJVYNSWDFQU-ORXIWHNOSA-N
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| InChi Code |
InChI=1S/C16H20O8/c1-22-12(18)7-4-9-2-5-10(6-3-9)23-16-15(21)14(20)13(19)11(8-17)24-16/h2-7,11,13-17,19-21H,8H2,1H3/b7-4+/t11-,13-,14+,15-,16-/m1/s1
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| Chemical Name |
methyl (E)-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoate
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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 | 2.9383 mL | 14.6916 mL | 29.3832 mL | |
| 5 mM | 0.5877 mL | 2.9383 mL | 5.8766 mL | |
| 10 mM | 0.2938 mL | 1.4692 mL | 2.9383 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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