Nonivamide

Modify Date: 2024-01-02 10:57:29

Nonivamide Structure
Nonivamide structure
 Common Name Nonivamide
CAS Number 2444-46-4 Molecular Weight 293.401
Density 1.0±0.1 g/cm3 Boiling Point 450.4±55.0 °C at 760 mmHg
Molecular Formula C17H27NO3 Melting Point 54°C
MSDS Chinese USA Flash Point 226.2±31.5 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Nonivamide


Nonivamide is a agonist, which exhibits 4d-EC50 value of 5.1 mg/L in static toxicity tests.

 Names

Name Nonivamide
Synonym More Synonyms

 Nonivamide Biological Activity

Description Nonivamide is a agonist, which exhibits 4d-EC50 value of 5.1 mg/L in static toxicity tests.
Related Catalog
Target

TRPV1[1]
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 Assay 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].
References

[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, et al. Nonivamide enhances miRNA let-7d expression and decreases adipogenesis PPARγ expression in 3T3-L1 cells. J Cell Biochem. 2015 Jun;116(6):1153-63.

 Chemical & Physical Properties

Density 1.0±0.1 g/cm3
Boiling Point 450.4±55.0 °C at 760 mmHg
Melting Point 54°C
Molecular Formula C17H27NO3
Molecular Weight 293.401
Flash Point 226.2±31.5 °C
Exact Mass 293.199097
PSA 58.56000
LogP 4.38
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.509
Storage condition 2-8°C
Stability Stable. Incompatible with strong oxidizing agents.
Water Solubility methanol: 100 mg/mL, clear to slightly hazy

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RA5955000
CHEMICAL NAME :
Nonanamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-
CAS REGISTRY NUMBER :
2444-46-4
BEILSTEIN REFERENCE NO. :
2144300
LAST UPDATED :
199701
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C17-H27-N-O3
MOLECULAR WEIGHT :
293.45

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
8 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 36,2595,1993

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H317-H319-H335
Precautionary Statements P261-P280-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes T:Toxic
Risk Phrases R25;R36/37/38
Safety Phrases S26-S45
RIDADR UN 3462 6.1/PG 2
WGK Germany 3
RTECS RA5998000
Hazard Class 6.1
HS Code 2924299090

 Synthetic Route

 Customs

HS Code 2924299090
Summary 2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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 Synonyms

N-[(4-hydroxy-3-methoxy-phenyl)methyl]nonanamide
Nonanimidic acid, N-[(4-hydroxy-3-methoxyphenyl)methyl]-, (1Z)-
N-vanillyl-nonanamide
Vanillyl pelargonic amide
(N-(4-Hydroxy-3-methoxybenzyl)nonanamide
Nonivamide
Vanillyl-N-nonylamide
Pseudocapsaicin
Capsaicin (Synthetic)
N-VANILLYLNONANOAMIDE
Nonanamide, N-vanillyl-
Pelargonyl vanillylamide
N-Nonylvanylamide
NonvaMide
Capsaicin std.
nonanoic acid vanillylamide
EINECS 219-484-1
N-(4-Hydroxy-3-methoxybenzyl)nonanamide
Capsaicinoid
N-Pelargonic Acid Vanillylamide
MFCD00017286
Capsaicin synthetic
Pelargonic acid vanillylamide
NONYLVANYLAMIDE
N-Pelargonylvanillylamide
N-Vanillylnonanamide
Vanillyl n-nonoylamide
nonylic acid vanillylamide
PAVA
NON-4-ENE
(1Z)-N-(4-Hydroxy-3-methoxybenzyl)nonanimidic acid
Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-
N-Vanillylpelargonamide
N-Vanillyl nonan amide
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Related Compounds: More...
nonivamide
618-92-8
Glyceryl nonivamide
147465-43-8
sodium nonivamide acetate
146690-24-6
Chemsrc provides Nonivamide(CAS#:2444-46-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Nonivamide are included as well.>> amp version: Nonivamide

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