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Vicine

Alias: Vicine; 152-93-2; Vicioside; 2,6-Diamino-5-(beta-D-glucopyranosyloxy)-(1H)-pyrimidin-4-one; NSC-95092; COL14PJW3X; C08437; CID 91446;
Cat No.:V32655 Purity: ≥98%
Vicine is an alkaloid glycoside found primarily in broad beans that is toxic to humans and can cause hemolytic anemia.
Vicine
Vicine Chemical Structure CAS No.: 152-93-2
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
50mg
Other Sizes
Official Supplier of:
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Product Description
Vicine is an alkaloid glycoside found primarily in broad beans that is toxic to humans and can cause hemolytic anemia.
Biological Activity I Assay Protocols (From Reference)
Targets
Natural alkaloid glycoside
ln Vivo
Two studies were conducted to investigate the effects of feeding raw and water-soaked vetch seeds to male broiler chicks on performance, organ weights, and blood parameters. Intact and ground vetch seeds were soaked in water (1:5) at room temperature for 24 hours (study 1), and (1:10) at 40 degrees C for 24, 48, and 72 hours, with water change every 12 hours (study 2). In study 1, untreated vetch contained, on dry matter basis, 0.530%, 0.731%, and 0.081% total beta-cyanoalanine (BCA), vicine, and convicine, respectively. Toxins were not appreciably reduced in soaked intact and ground vetch. Diets containing untreated, soaked intact, and soaked ground vetch, each at 0%, 20%, 40%, and 60%, were fed to 7-day-old male broilers until onset of neurotoxicity symptoms. Survival time was not only decreased by BCA level but also by those of vicine and convicine (p <.05). In study 2, 60% of untreated or treated vetch seeds were incorporated in chick diets. Although untreated vetch used in this study contained 32% less BCA but 8% and 81% more vicine and convicine, respectively, yet, the chicks on 60% untreated vetch showed toxicity symptoms earlier than those of study 1. Soaking ground vetch for 48 hours or more reduced BCA and totally removed vicine and convicine. Consequently, birds on 60% ground vetch soaked for 48 and 72 hours survived through the starter period and had mean corpuscular hemoglobin concentration and organ weights comparable to those of control at 4 days post trial. The results indicated that "high levels" of vicine or convicine or both might have shortened the birds' survival time by enhancing the neurotoxicity induced by "lower levels" of BCA[1].
References

[1]. Vicine and convicine in common vetch (Vicia sativa) seeds enhance beta-cyanoalanine toxicity in male broiler chicks. Int J Toxicol. 2002 May-Jun;21(3):201-9.

Additional Infomation
Vicine is a glycoside.
Vicine has been reported in Vicia faba, Vicia narbonensis, and Momordica charantia with data available.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H16N4O7
Molecular Weight
304.2566
Exact Mass
304.101
Elemental Analysis
C, 39.48; H, 5.30; N, 18.41; O, 36.81
CAS #
152-93-2
PubChem CID
135413566
Appearance
White to off-white solid powder
Density
2.2±0.1 g/cm3
Boiling Point
627.4±65.0 °C at 760 mmHg
Melting Point
242-244℃
Flash Point
333.2±34.3 °C
Vapour Pressure
0.0±4.2 mmHg at 25°C
Index of Refraction
1.820
LogP
-2.55
Hydrogen Bond Donor Count
7
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
3
Heavy Atom Count
21
Complexity
494
Defined Atom Stereocenter Count
5
SMILES
O1[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])([C@@]1([H])C([H])([H])O[H])O[H])O[H])O[H])OC1C(N([H])C(N([H])[H])=NC=1N([H])[H])=O
InChi Key
KGNGTSCIQCLKEH-SYCVNHKBSA-N
InChi Code
InChI=1S/C10H16N4O7/c11-7-6(8(19)14-10(12)13-7)21-9-5(18)4(17)3(16)2(1-15)20-9/h2-5,9,15-18H,1H2,(H5,11,12,13,14,19)/t2-,3-,4+,5-,9+/m1/s1
Chemical Name
2,4-diamino-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1H-pyrimidin-6-one
Synonyms
Vicine; 152-93-2; Vicioside; 2,6-Diamino-5-(beta-D-glucopyranosyloxy)-(1H)-pyrimidin-4-one; NSC-95092; COL14PJW3X; C08437; CID 91446;
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: 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)
Solubility Data
Solubility (In Vitro)
DMSO : ~50 mg/mL (~164.33 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.22 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 (8.22 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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (8.22 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.2867 mL 16.4333 mL 32.8666 mL
5 mM 0.6573 mL 3.2867 mL 6.5733 mL
10 mM 0.3287 mL 1.6433 mL 3.2867 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:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
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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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