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Nonivamide

Catalog No. T1321 CAS 2444-46-4

Synonyms: Nonanoic acid vanillylamide, Pelargonic acid vanillylamide, Vanillyl-N-nonylamide, Pseudocapsaicin

Nonivamide (Nonanoic acid vanillylamide) is found in herbs and spices. Nonivamide is an alkaloid from Capsicum species Nonivamide is a flavoring ingredient. Nonivamide is an organic compound and a capsaicinoid. It is an amide of pelargonic acid and vanillylamine. It is present in chili peppers, but is commonly manufactured synthetically. It is more heat-stable than capsaicin.

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Nonivamide, CAS 2444-46-4

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100 mg	In stock	$ 50.00
500 mg	In stock	$ 68.00
5 g	In stock	$ 97.00
1 mL * 10 mM (in DMSO)	In stock	$ 50.00

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Purity: 99.21%

Purity: 97.61%

Biological Description

Chemical Properties

Storage & Solubility Information

Description	Nonivamide (Nonanoic acid vanillylamide) is found in herbs and spices. Nonivamide is an alkaloid from Capsicum species Nonivamide is a flavoring ingredient. Nonivamide is an organic compound and a capsaicinoid. It is an amide of pelargonic acid and vanillylamine. It is present in chili peppers, but is commonly manufactured synthetically. It is more heat-stable than capsaicin.
In vitro	Nonivamide, a synthetic derivate of natural capsaicin, has an effective antifouling activity. Capsaicin exhibits 4d-EC50 values of 5.5±0.5 mg/L, 23±2 mg/L, 6.9±0.2 mg/L, and 15.6±0.4 mg/L in static toxicity tests conducted using Pseudomonas putida, Lake Erie bacteria, Vibrio natriegens, and Vibrio parahaemolyticus, respectively. A significant growth inhibitory effect (p<0.01) is observed in the group treated with 1 mg/L of Nonivamide for 4 d, and the EC50 value (4 d-EC50) is 5.1 mg/L[1]. Nonivamide treatment causes calcium release from the ER and altered the transcription of growth arrest- and DNA damage-inducible transcript 3 (GADD153), GADD45α, GRP78/BiP, ATF3, CCND1, and CCNG2) in a manner comparable with prototypical ER stress-inducing agents. ER calcium flux is evaluated by pretreating cells with 2.5 μM thapsigargin for 5 min followed by addition of 2.5 μM Nonivamide. Treatment of TRPV1-overexpressing cells with 2.5 μM Nonivamide produces marked increases in cytosolic calcium due to release of calcium from ER stores. Treatment of TRPV1-overexpressing cells with 1 μM Nonivamide causes an approximate 50% loss in cell viability after a 24-h period. BEAS-2B cells treated with 100 and 200 μM Nonivamide also exhibits a shift in the relative amount of EIF2α-P and an increase in the expression of GADD153 mRNA and protein[2]. Treatment with Nonivamide reduces lipid accumulation to a similar extent as CAP; the effects are not different from the effects after CAP treatment at any of the tested concentrations. Compared to untreated control cells, treatment with Nonivamide decreases lipid accumulation by 5.34±1.03% (P<0.05) at 0.01 μM up to 10.4±2.47% (P<0.001) at 1 μM[3].
Cell Research	Nonivamide is dissolved in ethanol to 1,000× stock solutions freshly each time and final ethanol concentration during the assays never exceeded 0.2% (v/v)[3]. In the MTT assay, the reduction of yellow tetrazolium salt MTT to a purple formazan by mitochondrial and ER enzymes is used as a measure for cell viability. Cells are seeded in 96‐well plates and treated with 1?nM-10?μM CAP or Nonivamide with or without addition of 25-100?μM BCH or the corresponding ethanol concentration (0.1-0.2% (v/v), solvent control) for 12 days after initiation of differentiation. Cell culture media is exchanged every second day. On Day 12, 100?μL of the MTT working reagent (0.83?mg/mL MTT diluted in PBS/serum-free media (1:5)), is added to each well, and cells are incubated at 37°C for approximately 15?min. The MTT working solution is removed and the purple formazan formed during incubation is dissolved in 150?μL DMSO per well. Absorbance is measured at 550?nm with 690?nm as reference wavelength using multiwell plate reader. The number of metabolically active cells is calculated relative to untreated control cells or the corresponding solvent control (100%)[3].
Source	Natural Products > Solanaceae > Capsicum

Synonyms	Nonanoic acid vanillylamide, Pelargonic acid vanillylamide, Vanillyl-N-nonylamide, Pseudocapsaicin
Molecular Weight	293.4
Formula	C17H27NO3
CAS No.	2444-46-4

Storage

Powder: -20°C for 3 years | In solvent: -80°C for 1 year

Solubility Information

DMSO: 53 mg/mL(180.6 mM)

References and Literature

1. Zhou J, et al. Toxic effects of environment-friendly antifoulant Nonivamide on Phaeodactylum tricornutum. Environ Toxicol Chem. 2013 Apr;32(4):802-9. 2. Thomas KC, et al. Transient receptor potential vanilloid 1 agonists cause endoplasmic reticulum stress and cell death in human lung cells. J Pharmacol Exp Ther. 2007 Jun;321(3):830-8. 3. Rohm, B., Holik, A., Kretschy, N., Somoza, M., Ley, J., & Widder, S. et al. (2015). Nonivamide Enhances miRNA let-7d Expression and Decreases Adipogenesis PPARγ Expression in 3T3-L1 Cells. Journal Of Cellular Biochemistry, 116(6), 1153-1163. doi: 10.1002/jcb.25052

Citations

1. Zhang B, Zhao J, Wang Z, et al. Identification of Multi-Target Anti-AD Chemical Constituents From Traditional Chinese Medicine Formulae by Integrating Virtual Screening and In Vitro Validation. Frontiers in Pharmacology. 2021：1781

Related compound libraries

This product is contained In the following compound libraries：

Membrane Protein-targeted Compound Library Drug Repurposing Compound Library Anti-Cancer Clinical Compound Library Traditional Chinese Medicine Monomer Library Anti-Cancer Drug Library ReFRAME Related Library RO5 Drug-like Natural Product Library Clinical Compound Library Human Endogenous Metabolite Compound Library Plus Ion Channel Inhibitor Library

Related Products

Related compounds with same targets

WS-12 GSK2798745 Capsaicin TRPM4-IN-2 SB 452533 NGD-8243 (+)-Camphor JT010

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Keywords

Nonivamide 2444-46-4 Membrane transporter/Ion channel TRP/TRPV Channel TRP Channel Inhibitor Nonanoic acid vanillylamide Pelargonic acid vanillylamide inhibit Transient receptor potential channels Vanillyl-N-nonylamide Pseudocapsaicin inhibitor

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