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Sinapine

Cat No.:V32101 Purity: =99.93%
Sinapine is an alkaloid extracted from the seeds of Brassicaceae species.
Sinapine
Sinapine Chemical Structure CAS No.: 18696-26-9
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of Sinapine:

  • Sinapine thiocyanate
  • Sinapine hydroxide
Official Supplier of:
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Top Publications Citing lnvivochem Products
Purity & Quality Control Documentation

Purity: =99.93%

Product Description
Sinapine is an alkaloid extracted from the seeds of Brassicaceae species. Sinapine has anti~inflammatory, antioxidant, anti-tumor, anti-angiogenic and radioprotective effects. Sinapine is also an acetylcholinesterase (AChE) inhibitor and has been utilized in study/research of Alzheimer's disease (AD), ataxia, myasthenia gravis and Parkinson's disease (PD).
Biological Activity I Assay Protocols (From Reference)
Targets
Acetylcholinesterase (AChE); P-glycoprotein (P-gp)
ln Vitro
In cardiomyocytes, sinapine (6 or 60 μM; 1 hour) counteracts the oxidative stress caused by H2O2 and antimycin A on the mitochondria [1]. With relatively low toxicity, sinapine (10-200 μM; 24 h) suppresses Caco-2 cell proliferation in a dose-dependent manner [3]. By causing a reduction in P-glycoprotein (P-gp), sinapine (10-200 μM; 24 hours) stimulates the accumulation of doxorubicin in Caco-2 cells [3]. The phosphorylation of ERK1/2 and FRS2α is considerably reduced by sinapine (10-200 μM; 24 hours) [3].
ln Vivo
By altering the makeup of the intestinal microbiota in mice, sinapine lowers the incidence of non-alcoholic fatty liver disease [2].
Cell Assay
The Caco-2 cells are seeded into a 96-well plate with 8000 cells/well for 24 h. After incubation with different doses of Sinapine (0-200 μM), doxorubicin, or both for 24 h, the medium is discarded. Cell survival after exposure to Sinapine alone or a combination of Sinapine and the anti-tumor agent doxorubicin is examined by MTT colorimetric assay[3].
Animal Protocol
Rats: Sixty male Sprague-Dawley rats (95 g) are randomly allotted to 6 groups of 10 rats each and reared in individual cages. Six groups of 10 growing rats each are fed ad libitum for 15 days one of six diets: diet A, rapeseed (3.80 g of sinapine/kg DM); diet B, ethanol/water-extracted rapeseed (0.48 g of sinapine); diet C, control diet; diet G, control diet+3.74 g of extracted sinapine; diet H, control diet + 3.72 g of sinapine+other phenolic compounds; or diet I, control diet+the hydrolysis products of sinapine and other phenolic compounds. The rats are weighed at 8 a.m. on days 1, 4, 8, 11 and 15 of the trial. After sacrifice the gut contents are eliminated to permit determination of empty body weight gain (EBWG). The distribution, refusal and intake of each rat are recorded every day[4].
References
[1]. Boulghobra D, et, al. Sinapine, but not sinapic acid, counteracts mitochondrial oxidative stress in cardiomyocytes. Redox Biol. 2020 Jul;34:101554.
[2]. Li Y, et, al. Sinapine reduces non-alcoholic fatty liver disease in mice by modulating the composition of the gut microbiota. Food Funct. 2019 Jun 19;10(6):3637-3649.
[3]. Guo Y, et al. Sinapine as an active compound for inhibiting the proliferation of Caco-2 cells via downregulation of P-glycoprotein. Food Chem Toxicol. 2014 May;67:187-92.
[4]. Yates K, et, al. Determination of sinapine in rapeseed pomace extract: Its antioxidant and acetylcholinesterase inhibition properties. Food Chem. 2019 Mar 15;276:768-775.
[4]. Valorization of rapeseed meal. 5. Effects of sinapine and other phenolic compounds on food intake and nutrient utilization in growing rats. Reprod Nutr Dev. 1987;27(4):781-90.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H24NO5
Molecular Weight
310.3655
Exact Mass
310.16
Elemental Analysis
C, 61.92; H, 7.79; N, 4.51; O, 25.77
CAS #
18696-26-9
Related CAS #
Sinapine thiocyanate;7431-77-8;Sinapine hydroxide;122-30-5
Appearance
Off-white to yellow solid
Source
Seeds of the cruciferous species
LogP
1.67
tPSA
64.99
SMILES
O(C(/C(/[H])=C(\[H])/C1C([H])=C(C(=C(C=1[H])OC([H])([H])[H])O[H])OC([H])([H])[H])=O)C([H])([H])C([H])([H])[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]
InChi Key
HUJXHFRXWWGYQH-UHFFFAOYSA-O
InChi Code
InChI=1S/C16H23NO5/c1-17(2,3)8-9-22-15(18)7-6-12-10-13(20-4)16(19)14(11-12)21-5/h6-7,10-11H,8-9H2,1-5H3/p+1
Chemical Name
Ethanaminium, 2-((3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl)oxy)-N,N,N-trimethyl-
HS Tariff Code
2934.99.9001
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)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~322.21 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.70 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 20.8 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: ≥ 2.08 mg/mL (6.70 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 20.8 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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.2220 mL 16.1098 mL 32.2196 mL
5 mM 0.6444 mL 3.2220 mL 6.4439 mL
10 mM 0.3222 mL 1.6110 mL 3.2220 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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