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5-O-Methylvisammioside

Cat No.:V29134 Purity: ≥98%
5-O-Methylvisammioside is a natural compound extracted from parsnips.
5-O-Methylvisammioside
5-O-Methylvisammioside Chemical Structure CAS No.: 84272-85-5
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
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Product Description
5-O-Methylvisammioside is a natural compound extracted from parsnips.
5-O-Methylvisammioside (CAS 84272-85-5) is a naturally occurring coumarin glycoside isolated from Saposhnikovia divaricata. It is also known as 4'-O-β-D-Glucosyl-5-O-methylvisamminol. 5-O-Methylvisammioside has analgesic, antipyretic, anti-inflammatory, and anti-platelet aggregation effects. It is used to explore mechanisms underlying cardiovascular health, immune modulation, and potential therapeutic applications in oxidative stress-related disorders. It is a natural compound that belongs to the class of iridoid glycosides and is found in various plants, including the medicinal plant Uncaria rhynchophylla.
Biological Activity I Assay Protocols (From Reference)
Targets
5-O-Methylvisammioside targets multiple pathways. It has analgesic, antipyretic, anti-inflammatory, and anti-platelet aggregation effects. Its anti-inflammatory effects are likely mediated through inhibition of inflammatory mediators. Its anti-platelet aggregation effects suggest inhibition of platelet activation pathways. Its cardioprotective effects may involve antioxidant and anti-inflammatory mechanisms.
ln Vitro
In vitro, 5-O-Methylvisammioside has analgesic, antipyretic, anti-inflammatory, and anti-platelet aggregation effects. Quantitative in vitro activity data, such as IC50 values for its anti-inflammatory or anti-platelet effects, is not detailed in the publicly available sources.
ln Vivo
In vivo activity data for 5-O-Methylvisammioside is limited in publicly available literature. As a compound with analgesic, antipyretic, anti-inflammatory, and anti-platelet aggregation effects in vitro, it is hypothesized to exhibit similar effects in vivo. It is used in traditional medicine for its therapeutic properties. However, specific in vivo efficacy studies, including pharmacokinetic and pharmacodynamic parameters, have not been detailed in the available sources.
Enzyme Assay
For cell-free assays, the anti-inflammatory activity of 5-O-Methylvisammioside can be measured by assessing its inhibition of inflammatory enzymes such as COX-2 or LOX. Its anti-platelet aggregation activity can be assessed using platelet aggregation assays with platelet-rich plasma. Its antioxidant activity can be measured using DPPH or ABTS radical scavenging assays.
Cell Assay
For in vitro cellular assays, the anti-inflammatory activity of 5-O-Methylvisammioside is assessed in LPS-stimulated macrophages by measuring the production of inflammatory cytokines. Its anti-platelet aggregation effect is assessed in platelet-rich plasma by measuring aggregation induced by agonists such as ADP or collagen.
Animal Protocol
For in vivo studies, 5-O-Methylvisammioside could be administered orally in animal models of inflammation, pain, or thrombosis. In inflammation models, endpoints include inflammatory cytokine levels and tissue histopathology. In pain models, endpoints include pain response in tests such as the hot plate test or formalin test. In thrombosis models, endpoints include platelet aggregation and thrombus formation.
ADME/Pharmacokinetics
5-O-Methylvisammioside (CAS 84272-85-5) has a molecular formula of C22H28O10 and a molecular weight of 452.45 g/mol. It is also known as 4'-O-β-D-Glucosyl-5-O-methylvisamminol. Appearance: typically a powder. Solubility: DMSO and other organic solvents. Storage: typical for natural products (desiccated, protected from light, -20°C). Purity: typically >98% for research use.
Toxicity/Toxicokinetics
No detailed toxicity data is publicly available. As a natural coumarin glycoside from Saposhnikovia divaricata, it is generally considered to have low toxicity, but standard toxicological studies would be required for drug development.
References

[1]. Separation and Purification of Prim-O-glucosylcimifugin and 5-O-methylvisammioside from Saposhnikovia Divaricata by High-speed Counter-current Chromatography. Chinese Journal of Analytical Chemistry, 2009-11.

[2]. RP-HPLC determination of 5-O-methylvisammioside in Fangfeng Tongsheng Wan. Central South Pharmacy, 2012-02.

Additional Infomation
5-O-methylvesamiglycoside is an oxoheterocyclic compound and an organic heterotricyclic compound. It has been reported that 5-O-methylvesamiglycoside exists in Saposhnikovia divaricata, and relevant data are available for reference.
5-O-Methylvisammioside is a research-grade compound and is not approved for therapeutic use. It serves primarily as a pharmacological tool for studying anti-inflammatory, analgesic, and anti-platelet mechanisms. Its mechanism of action involves anti-inflammatory, analgesic, antipyretic, and anti-platelet aggregation effects. It is a natural product from Saposhnikovia divaricata. No clinical trials have been reported.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C22H28O10
Molecular Weight
452.4517
Exact Mass
452.168
CAS #
84272-85-5
PubChem CID
21670038
Appearance
White to off-white solid powder
Density
1.5±0.1 g/cm3
Boiling Point
690.4±55.0 °C at 760 mmHg
Melting Point
148-150ºC
Flash Point
239.1±25.0 °C
Vapour Pressure
0.0±2.3 mmHg at 25°C
Index of Refraction
1.629
LogP
-0.71
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
10
Rotatable Bond Count
5
Heavy Atom Count
32
Complexity
738
Defined Atom Stereocenter Count
6
SMILES
CC1=CC(=O)C2=C(C3=C(C=C2O1)O[C@@H](C3)C(C)(C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC
InChi Key
QVGFPTYGKPLXPK-OOBAEQHESA-N
InChi Code
InChI=1S/C22H28O10/c1-9-5-11(24)16-13(29-9)7-12-10(20(16)28-4)6-15(30-12)22(2,3)32-21-19(27)18(26)17(25)14(8-23)31-21/h5,7,14-15,17-19,21,23,25-27H,6,8H2,1-4H3/t14-,15+,17-,18+,19-,21+/m1/s1
Chemical Name
(2S)-4-methoxy-7-methyl-2-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]-2,3-dihydrofuro[3,2-g]chromen-5-one
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

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 (~110.51 mM)
H2O : ≥ 25 mg/mL (~55.25 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.53 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 (5.53 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 (5.53 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 2.2102 mL 11.0509 mL 22.1019 mL
5 mM 0.4420 mL 2.2102 mL 4.4204 mL
10 mM 0.2210 mL 1.1051 mL 2.2102 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.

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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?
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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:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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