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N-Vanillyldecanamide

Alias: Decanamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-; N-Vanillyldecanamide
Cat No.:V26783 Purity: ≥98%
N-Vanillyldecanamide, a capsaicinoid compound extracted from Capsicum annuum fruits, significantly reduced free radical length in alfalfa seedlings in a dose-dependent fashion.
N-Vanillyldecanamide
N-Vanillyldecanamide Chemical Structure CAS No.: 31078-36-1
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
N-Vanillyldecanamide, a capsaicinoid compound extracted from Capsicum annuum fruits, significantly reduced free radical length in alfalfa seedlings in a dose-dependent fashion.
N-Vanillyldecanamide (CAS#: 31078-36-1), also known as capsaicinamide or nonivamide, is a capsaicinoid compound extracted from Capsicum annuum fruits. It is a derivative of capsaicin, the compound responsible for the spicy taste of chili peppers. N-Vanillyldecanamide exhibits analgesic and anti-inflammatory properties, making it of interest in pain management research. It significantly reduces free radical length in alfalfa seedlings in a dose-dependent fashion.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary target of N-Vanillyldecanamide is the transient receptor potential vanilloid type 1 (TRPV1) channel, which is involved in the perception of pain and temperature. By acting on TRPV1, it can modulate pain signaling pathways. Its effects are similar to those of capsaicin, but it may have distinct pharmacological properties.
ln Vitro
In vitro, N-Vanillyldecanamide has been shown to significantly reduce free radical length in alfalfa seedlings in a dose-dependent fashion. This suggests antioxidant activity. It also exhibits analgesic and anti-inflammatory properties in various in vitro models. Its activity at TRPV1 receptors can be assessed using calcium imaging or electrophysiological techniques in cells expressing TRPV1.
ln Vivo
Capsaicin
In vivo, N-Vanillyldecanamide has been studied for its analgesic and anti-inflammatory effects. As a capsaicinoid, it may produce similar effects to capsaicin, including pain relief and anti-inflammatory actions. Specific in vivo study protocols for N-Vanillyldecanamide are not extensively detailed in the available literature, but it is commonly used as a reference compound in pain research.
Enzyme Assay
In vitro enzyme/receptor binding assays for N-Vanillyldecanamide typically involve radioligand binding studies using cells or membrane preparations expressing TRPV1 receptors. Competitive binding assays are performed using a radiolabeled capsaicin analog to determine the compound's affinity for TRPV1. Functional assays, such as calcium influx measurements, can also be used to assess its agonistic or antagonistic activity at the receptor.
Cell Assay
In vitro cellular assays for N-Vanillyldecanamide are conducted in cell lines expressing TRPV1 or in primary sensory neurons. Cells are treated with the compound, and calcium influx is measured using fluorescent indicators to assess TRPV1 activation. Cytotoxicity and cell viability assays can be performed to evaluate its safety profile. Its antioxidant activity can be assessed by measuring free radical scavenging in cell-based or cell-free systems.
Animal Protocol
In vivo animal studies for N-Vanillyldecanamide are typically conducted in rodent models of pain and inflammation. The compound is administered orally, intraperitoneally, or topically, and its analgesic effects are assessed using standard pain tests such as the hot plate test, tail flick test, or formalin test. Anti-inflammatory activity can be evaluated in models of acute or chronic inflammation.
ADME/Pharmacokinetics
D pharmacokinetic properties of N-Vanillyldecanamide indicate it has a molecular weight of 307.43 and a molecular formula of C18H29NO3. It is soluble in DMSO at concentrations up to approximately 250 mg/mL. For in vivo studies, it can be formulated in vehicles such as 10% DMSO + 40% PEG300 + 5% Tween 80 + 45% saline. The powder should be stored at -20°C for up to 3 years.
Toxicity/Toxicokinetics
Toxicological information for N-Vanillyldecanamide is limited. As a capsaicinoid, it may cause irritation and burning sensations at high concentrations. Its safety profile would need to be carefully evaluated for therapeutic applications. Standard toxicology studies, including acute toxicity, skin irritation, and sensitization tests, would be required for clinical development.
References

[1]. Capsaicinoids from hot pepper ( Capsicum annuum L.) and their phytotoxic effect on seedling growth of lettuce ( Lactuca sativa L.). Nat Prod Res. 2020 Jun;34(11):1597-1601.

Additional Infomation
It has been reported that chili peppers (Capsicum annuum) contain n-vanillyldecanoamide, and relevant data is available. See also: Chili powder (partial).
N-Vanillyldecanamide is a capsaicinoid compound with analgesic and anti-inflammatory properties. It is also known as nonivamide. It is used in research as a tool for studying TRPV1-mediated pain pathways and as a reference compound for capsaicin-related studies. It is not approved for clinical use and is available from research chemical suppliers.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C18H29NO3
Molecular Weight
307.43
Exact Mass
307.215
CAS #
31078-36-1
PubChem CID
169252
Appearance
White to off-white solid powder
Density
1.027g/cm3
Boiling Point
502.9ºC at 760mmHg
Flash Point
257.9ºC
Index of Refraction
1.511
LogP
4.548
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
11
Heavy Atom Count
22
Complexity
296
Defined Atom Stereocenter Count
0
InChi Key
QLHTWDQJPOTDMV-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H29NO3/c1-3-4-5-6-7-8-9-10-18(21)19-14-15-11-12-16(20)17(13-15)22-2/h11-13,20H,3-10,14H2,1-2H3,(H,19,21)
Chemical Name
N-[(4-hydroxy-3-methoxyphenyl)methyl]decanamide
Synonyms
Decanamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-; N-Vanillyldecanamide
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 : ~250 mg/mL (~813.19 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 2.08 mg/mL (6.77 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
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 (6.77 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.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (6.77 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 20.8 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 3.2528 mL 16.2639 mL 32.5277 mL
5 mM 0.6506 mL 3.2528 mL 6.5055 mL
10 mM 0.3253 mL 1.6264 mL 3.2528 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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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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