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V9130

Sigma-Aldrich

N-Vanillylnonanamide

≥97%, powder

Sinónimos:

Capsaicin synthetic, N-(4-Hydroxy-3-methoxybenzyl)nonanamide, N-Vanillylpelargonamide, Nonanoic acid vanillylamide, Nonylvanylamide, Pelargonic acid vanillylamide, Pseudocapsaicin

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About This Item

Fórmula empírica (notación de Hill):
C17H27NO3
Número de CAS:
2444-46-4
Peso molecular:
293.40
Beilstein/REAXYS Number:
2144300
EC Number:
219-484-1
MDL number:
MFCD00017286
UNSPSC Code:
12352200
PubChem Substance ID:
24278775
NACRES:
NA.77

assay

≥97%

form

powder

color

white to off-white

solubility

methanol: 100 mg/mL, clear to slightly hazy, colorless to deep brown-yellow

storage temp.

2-8°C

SMILES string

CCCCCCCCC(=O)NCc1ccc(O)c(OC)c1

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)

InChI key

RGOVYLWUIBMPGK-UHFFFAOYSA-N

Gene Information

rat ... Trpv1(83810) , Trpv4(66026)

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General description

N-Vanillylnonanamide has antifouling properties. It acts as an nicotinamide adenine dinucleotide phosphate (NADPH) inhibitor.

Application

N-Vanillylnonanamide has been used for the preparation of spicules. It has also been used to reduce the firing of most extrinsic sensory axons.

Other Notes

Synthetic analogue of capsaicin with similar bioactivity.

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificados de análisis (COA)

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Federica Villa et al.
Biotechnology letters, 31(9), 1407-1413 (2009-06-03)
The potential on N-vanillylnonanamide (NVN) in preventing the attachment of Pseudomonas stutzeri and a Bacillus cereus-group strain was investigated. NVN up to 852 microM was not toxic, nor was it an energy source for either organism. Microbial attachment assays were
R W Foster et al.
Pain, 25(2), 269-278 (1986-05-01)
The chemical irritants o-chlorobenzylidene malononitrile (CS), n-nonanoylvanillylamine (VAN) and dibenzoxazepine (CR) and several of its derivatives have been assayed using the human blister base. The relative potencies found by this method, CR greater than VAN greater than CS, conflicted with
S M Gardiner et al.
The American journal of physiology, 257(6 Pt 2), R1429-R1435 (1989-12-01)
The vasopressin-mediated recovery of arterial pressure observed in adult rats following pharmacological blockade of the sympathetic nervous and renin-angiotensin systems is reduced by neonatal capsaicin treatment. We now demonstrate a similar but reversible effect following treatment of adult Wistar or
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