Nonivamide CAS NO.2444-46-4

Min.Order: 10 Milligram
Payment Terms: T/T
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Product Details

Keywords

Nonivamide
2444-46-4
standard supplier in China

Quick Details

ProName: Nonivamide
CasNo: 2444-46-4
Molecular Formula: C17H27NO3
Appearance: detailed see specifications
Application: analysis,activity test,Botanical Refer...
DeliveryTime: 1-3?working?days?after?confirming?the?...
PackAge: According to the clients requirement.
Port: China main port
ProductionCapacity: 1 Metric Ton/Day
Purity: ≥98%
Storage: Store at 2~8°C
Transportation: by air or by ocean shipping
LimitNum: 10 Milligram
Plant of Origin: Chinese herbal medicine
Testing Method: NMR/MS/HPLC
Product Ecification: 1mg-1kg
Heavy Metal: <10ppm
Voluntary Standards: company standard
Storage: Store in dry, dark and ventilated plac...
PackAge: Brown vial HDPE plastic bottle

Superiority

Hubei CuiRan Biotechnology Co., Ltd is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine，Traditional Chinese Medicine), Natural Active Pharmaceutical Ingredients worldwide. From small quantities for R&D or reference standard, to large quantities for customizing or manufacturing, Biopurify emphasizes on consistent and reliable services for his customers.
With excellent quality products and good service, we have clients from more than dozens countries and regions, and we pride ourselves in providing our customers with a total satisfaction experiences.
We are doing our best to be your reliable partner for high quality Phytochemicals and Reference Standards from china.

Our main services:
A. Supply active ingredients and reference standards ofTraditional Chinese Medicine, from mgs to kgs scale.
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR, CM and PD services from lab scale, pilot scale to commercial scale(GMP is also available)
E.Traditional Chinese Medicine compounds library

1.Provide traditional Chinese medicine reference materials and natural active ingredients;
2.More than 2200 compounds are available for selection, continuously building high-quality natural product libraries for drug research and development;
3.Provide various screening libraries and more inhibitor products;
4.Provide separation and structural determination of natural products;
5.Laboratory scale pilot to commercial scale collaborative research and process development services.More than 180 experiences in phytochemistry (still increasing)
Each product has passed very strict testing (NMR/MS/HPLC)
Agents from many countries

General tips：For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging：1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition：Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Details

Chemical Properties of Nonivamide

Cas No.	2444-46-4	SDF
PubChem ID	2998	Appearance	White-beige powder
Formula	C₁₇H₂₇NO₃	M.Wt	293.40
Type of Compound	Alkaloids	Storage	Desiccate at -20°C
Synonyms	Nonanoic acid vanillylamide; Nonivamide; 8-Nordihydrocapsaicin; Pelargonic acid vanillylamide; Pseudocapsaicin; N-Vanillylpelargonamide
Solubility	DMSO : 100 mg/mL (340.83 mM; Need ultrasonic)
Chemical Name	N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide
SMILES	CCCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
Standard InChIKey	RGOVYLWUIBMPGK-UHFFFAOYSA-N
Standard InChI	InChI=1S/C17H27NO3/c1-3-4-5-6-7-8-9-17(20)18-13-14-10-11-15(19)16(12-14)21-2/h10-12,19H,3-9,13H2,1-2H3,(H,18,20)
General tips	For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging	1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment.
Shipping Condition	Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Nonivamide

The fruits of Capsicum annuum L.

Biological Activity of Nonivamide

Description

Nonivamide, present in chili peppers, is commonly manufactured synthetically and used as a food additive to add pungency to seasonings, flavorings, and spice blends. Nonivamide and capsaicin are novel skin permeation enhancers for indometacin. Nonivamide has antioxidant, anti-obesity, and anti-inflammatory effects, it reduces energy intake, enhances energy metabolism, decreases serum triacylglycerol content, and inhibits adipogenesis via activation of the transient receptor potential cation channel subfamily V member 1 (TRPV1).

Targets

In vitro

Protective effect and relation structure-activity of nonivamide and iododerivatives in several models of lipid oxidation.[Pubmed: 19497416]

Chem Biol Interact. 2009 Jul 15;180(2):183-92.

The introduction of an iodine atom on the vanillyl moiety of Nonivamide causes a switch in the vanilloid activity (TRPV1 antagonism versus TRPV1 desensitization) and nullifies the aversive properties of capsaicinoids. In the present study we investigated the effect of iodination in the vanillyl moiety on the antioxidant activity of capsaicinoids.
METHODS AND RESULTS:
To this aim, we have compared the protective effects of Nonivamide and three iododerivatives, 2-iodoNonivamide (2IN), 5-iodoNonivamide (5IN), and 6-iodoNonivamide (6IN) in a series of in vitro models of lipid oxidation, namely the autoxidation and the FeCl(3)-mediated oxidation of linoleic acid at 37 degrees C and the thermal (140 degrees C), solvent-free oxidation of cholesterol. All tested compounds could protect linoleic acid and cholesterol against oxidative degradation, the order of potency being: Nonivamide>5IN>6IN approximately 2IN. Our results show that, in general, the introduction of an iodine atom on the vanillyl moiety of Nonivamide causes a decrease in the antioxidant activity, and this effect is sensitive to the position of iodine on the aromatic ring, with 5IN substantially retaining the efficacy of Nonivamide to protect linoleic and cholesterol against free radical attack. Moreover, the pre-treatment with 5IN, at noncytotoxic concentrations, significantly preserved LDL from Cu(2+)-induced oxidative damage at 37 degrees C for 2h, inhibiting the reduction of polyunsaturated fatty acids and cholesterol and the increase of their oxidative products.
CONCLUSIONS:
The results of the present work suggest that 5IN exerts useful antioxidant properties in different in vitro systems of lipid peroxidation. This, coupled to its lacks of pungency and TRPV1 inhibiting properties, qualifies this phenolic compound as an attractive candidate for further investigations in vivo.

Capsaicin and nonivamide as novel skin permeation enhancers for indomethacin.[Pubmed: 11113638]

Eur J Pharm Sci. 2001 Jan;12(3):195-203.

METHODS AND RESULTS:
The study was conducted in vitro to investigate the changes of indomethacin transdermal permeation pretreated by capsaicin and Nonivamide, two compounds chemically similar to Azone. The combined effect of low frequency ultrasound (20 kHz) and enhancers on the indomethacin permeation was also evaluated. The experimental data demonstrated that capsaicin and Nonivamide significantly enhanced the flux of indomethacin across nude mouse skin. Enhancement effects of both analogues were very similar and depended predominantly on the concentration tested. Histological examination coupled with visual scores indicated the safety of capsaicin and Nonivamide on skin structure.
CONCLUSIONS:
Simultaneous application of ultrasound and enhancers significantly increased skin permeation of indomethacin compared with either ultrasound or enhancers alone. Better effect was obtained by the combination with capsaicin than Nonivamide.

Protocol of Nonivamide

Kinase Assay

Nonivamide enhances miRNA let-7d expression and decreases adipogenesis PPARγ expression in 3T3-L1 cells.[Pubmed: 25704235 ]

J Cell Biochem. 2015 Jun;116(6):1153-63.

Red pepper and its major pungent principle, capsaicin (CAP), have been shown to be effective anti-obesity agents by reducing energy intake, enhancing energy metabolism, decreasing serum triacylglycerol content, and inhibiting adipogenesis via activation of the transient receptor potential cation channel subfamily V member 1 (TRPV1). However, the binding of CAP to the TRPV1 receptor is also responsible for its pungent sensation, strongly limiting its dietary intake.
METHODS AND RESULTS:
Here, the effects of a less pungent structural CAP-analog, Nonivamide, on adipogenesis and underlying mechanisms in 3T3-L1 cells were studied. Nonivamide was found to reduce mean lipid accumulation, a marker of adipogenesis, to a similar extent as CAP, up to 10.4% (P < 0.001). Blockage of the TRPV1 receptor with the specific inhibitor trans-tert-butylcyclohexanol revealed that the anti-adipogenic activity of Nonivamide depends, as with CAP, on TRPV1 receptor activation. In addition, in cells treated with Nonivamide during adipogenesis, protein levels of the pro-adipogenic transcription factor peroxisome-proliferator activated receptor γ (PPARγ) decreased.
CONCLUSIONS:
Results from miRNA microarrays and digital droplet PCR analysis demonstrated an increase in the expression of the miRNA mmu-let-7d-5p, which has been associated with decreased PPARγ levels.

Cell Research

Nonivamide, a capsaicin analogue, exhibits anti-inflammatory properties in peripheral blood mononuclear cells and U-937 macrophages.[Pubmed: 27666931 ]

Mol Nutr Food Res. 2017 Feb;61(2).

Inflammation-related diseases are a worldwide problem. The counteraction of inflammation with compounds activating the trigeminal nerve is one strategy to fight these diseases. Known trigeminally active compounds found in black or red pepper are the tingling t-pellitorine, the pungent capsaicin, and the less pungent Nonivamide. The presented study compares the anti-inflammatory potential of Nonivamide to the two known anti-inflammatory compounds, elucidating the mechanism of action and the role of transient receptor protein (TRP) channels.
METHODS AND RESULTS:
Primary peripheral blood mononuclear cells (PBMCs) and U-937 macrophages were stimulated with 1 μg/mL LPS from Escherichia coli (EC-LPS) to induce inflammation. Nonivamide attenuated the EC-LPS induced release of IL-6 and TNF-α in PBMCs and U-937 macrophages determined by magnetic bead kit analysis. This anti-inflammatory mechanism was independent from nuclear factor-kappa B pathway but mitogen-activated protein kinase (MAPK) pathway may be involved. In addition, cotreatment of U-937 with the trigeminally active compound and an antagonist of TRPV1 or TRPA1 abolished the anti-inflammatory activity.
CONCLUSIONS:
Nonivamide possessed similar anti-inflammatory potential as capsaicin and t-pellitorine. In U-937 macrophages, the tested compounds exploited an anti-inflammatory effect by inhibiting the EC-LPS induced activation of the MAPK pathway. In addition, the TRP channel activation plays a role in the anti-inflammatory capacity of capsaicin and Nonivamide.

Preparing Stock Solutions of Nonivamide

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	3.4083 mL	17.0416 mL	34.0832 mL	68.1663 mL	85.2079 mL
5 mM	0.6817 mL	3.4083 mL	6.8166 mL	13.6333 mL	17.0416 mL
10 mM	0.3408 mL	1.7042 mL	3.4083 mL	6.8166 mL	8.5208 mL
50 mM	0.0682 mL	0.3408 mL	0.6817 mL	1.3633 mL	1.7042 mL
100 mM	0.0341 mL	0.1704 mL	0.3408 mL	0.6817 mL	0.8521 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.