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Capsaicin β-D-glucopyranoside

Alias: Capsaicin β-D-glucopyranoside
Cat No.:V62409 Purity: ≥98%
Capsaicin β-D-glucopyranoside is a glucoside converted from capsaicin.
Capsaicin β-D-glucopyranoside
Capsaicin β-D-glucopyranoside Chemical Structure CAS No.: 153409-16-6
Product category: Alkaloids
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
50mg
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Product Description
Capsaicin β-D-glucopyranoside is a glucoside converted from capsaicin. The component that gives chili peppers their unique spicy flavor is called capsaicin.
Capsaicin β-D-glucopyranoside (CAS# 153409-16-6) is a glycosylated derivative of capsaicin, the pungent compound found in chili peppers. It has the molecular formula C24H35NO9. The compound is a capsaicin glucoside where a β-D-glucopyranosyl group is attached to the capsaicin molecule. Capsaicin β-D-glucopyranoside is used in research applications for studying capsaicin metabolism, glycosylation, and the pharmacology of capsaicin derivatives. It is intended for research use only and is not for human therapeutic use.
Biological Activity I Assay Protocols (From Reference)
Targets
Capsaicin β-D-glucopyranoside targets the transient receptor potential vanilloid 1 (TRPV1) receptor, similar to capsaicin. As a glycosylated derivative, it may have altered receptor binding affinity and pharmacokinetic properties compared to capsaicin. The compound's glucoside moiety may affect its solubility, absorption, and metabolism. Its use in research allows for the study of capsaicin glycosylation and its effects on TRPV1 activation. Further research is needed to characterize its specific interactions with TRPV1 and other targets.
ln Vitro
In vitro studies of Capsaicin β-D-glucopyranoside have focused on its role as a glycosylated capsaicin derivative. The compound's effects on TRPV1 receptor activation have been characterized. Its solubility and stability compared to capsaicin have been assessed. These in vitro studies provide foundational data for understanding the compound's properties and its potential applications in capsaicin research and drug development.
ln Vivo
In vivo studies of Capsaicin β-D-glucopyranoside are limited as the compound is primarily used as a research chemical. As a glycosylated capsaicin derivative, it may have altered pharmacokinetic properties compared to capsaicin, potentially affecting its absorption, distribution, metabolism, and excretion. However, comprehensive in vivo pharmacological studies specifically targeting Capsaicin β-D-glucopyranoside are not well documented in the available literature. The compound is intended for research use only.
Enzyme Assay
In vitro receptor binding assays for Capsaicin β-D-glucopyranoside typically involve testing its activity at the TRPV1 receptor. Receptor activation is measured using calcium imaging or electrophysiological methods in cells expressing TRPV1. The compound's potency and efficacy compared to capsaicin are assessed. All assays are performed with appropriate controls and standardized protocols to ensure reproducibility of results.
Cell Assay
In vitro cell-based assays for Capsaicin β-D-glucopyranoside involve culturing TRPV1-expressing cells to evaluate its effects on receptor activation. Cells are treated with varying concentrations of the compound and calcium influx is measured. Cell viability is assessed using MTT or similar colorimetric assays. All experiments are performed in triplicate with appropriate controls to ensure statistical reliability.
Animal Protocol
In vivo animal experiments for Capsaicin β-D-glucopyranoside would be conducted to evaluate its pharmacokinetic and pharmacodynamic properties. Animals would be administered the compound and blood and tissue samples collected at various time points. The compound and its metabolites would be measured using appropriate analytical methods. Parameters assessed would include body weight, organ weights, and general health. Control groups receiving vehicle alone would be included for comparison. All procedures would comply with institutional animal care and use committee guidelines.
ADME/Pharmacokinetics
The pharmacokinetic properties of Capsaicin β-D-glucopyranoside reflect its nature as a glycosylated capsaicin derivative. It has a molecular formula of C24H35NO9. The glucoside moiety may enhance its water solubility compared to capsaicin, potentially affecting its absorption and distribution. The compound would be metabolized through standard xenobiotic pathways. Complete pharmacokinetic profiling including half-life, clearance, volume of distribution, and bioavailability would require further systematic studies.
Toxicity/Toxicokinetics
The toxicity profile of Capsaicin β-D-glucopyranoside has been evaluated in the context of its use as a research chemical. As a capsaicin derivative, it may have effects similar to capsaicin including irritation and TRPV1-mediated effects. Proper handling procedures including use of personal protective equipment are recommended when working with pure compound. The compound is not approved for human therapeutic use and is intended for research purposes only. Long-term toxicity studies would be needed to fully establish its safety profile.
References

[1]. Purification and structure determination of glucosides of capsaicin and dihydrocapsaicin from various Capsicum fruits. J Agric Food Chem. 2006;54(16):5948-5953.

[2]. Mechanisms and clinical uses of capsaicin. Eur J Pharmacol. 2013;720(1-3):55-62.

Additional Infomation
Capsaicin β-D-glucopyranoside has been reported in chili peppers, and relevant data are available.
Capsaicin β-D-glucopyranoside (CAS# 153409-16-6) is a glycosylated derivative of capsaicin with the molecular formula C24H35NO9. It is a capsaicin glucoside where a β-D-glucopyranosyl group is attached to the capsaicin molecule. Capsaicin β-D-glucopyranoside is used in research applications for studying capsaicin metabolism, glycosylation, and the pharmacology of capsaicin derivatives. It is intended for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C24H37NO8
Molecular Weight
467.55
Exact Mass
467.251
CAS #
153409-16-6
PubChem CID
10027593
Appearance
White to off-white solid
Density
1.2±0.1 g/cm3
Boiling Point
709.4±60.0 °C at 760 mmHg
Flash Point
382.9±32.9 °C
Vapour Pressure
0.0±2.4 mmHg at 25°C
Index of Refraction
1.560
LogP
1.1
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
12
Heavy Atom Count
33
Complexity
601
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([H])=C([H])C(C([H])([H])N([H])C(C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C(/[H])=C(\[H])/C([H])(C([H])([H])[H])C([H])([H])[H])=O)=C([H])C=1OC([H])([H])[H]
InChi Key
HEYWYCJIIXVRPS-FDOPSVQKSA-N
InChi Code
InChI=1S/C24H37NO8/c1-15(2)8-6-4-5-7-9-20(27)25-13-16-10-11-17(18(12-16)31-3)32-24-23(30)22(29)21(28)19(14-26)33-24/h6,8,10-12,15,19,21-24,26,28-30H,4-5,7,9,13-14H2,1-3H3,(H,25,27)/b8-6+/t19-,21-,22+,23-,24-/m1/s1
Chemical Name
(E)-N-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]-8-methylnon-6-enamide
Synonyms
Capsaicin β-D-glucopyranoside
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 (213.88 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.35 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 (5.35 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 (5.35 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 2.1388 mL 10.6940 mL 21.3881 mL
5 mM 0.4278 mL 2.1388 mL 4.2776 mL
10 mM 0.2139 mL 1.0694 mL 2.1388 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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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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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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