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V9130

Sigma-Aldrich

N-Vanillylnonanamide

≥97%, powder

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Synonym(s):
Capsaicin synthetic, N-(4-Hydroxy-3-methoxybenzyl)nonanamide, N-Vanillylpelargonamide, Nonanoic acid vanillylamide, Nonylvanylamide, Pelargonic acid vanillylamide, Pseudocapsaicin
Empirical Formula (Hill Notation):
C17H27NO3
CAS Number:
2444-46-4
Molecular Weight:
293.40
Beilstein:
2144300
EC Number:
219-484-1
MDL number:
MFCD00017286
UNSPSC Code:
12352200
PubChem Substance ID:
24278775
NACRES:
NA.77

Quality Level

200

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.

Signal Word

Danger

Hazard Statements

H315,H317,H318,H334,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Measurement of strains experienced by viscerofugal nerve cell bodies during mechanosensitive firing using digital image correlation
Palmer G, et al.
American Journal of Physiology. Heart and Circulatory Physiology (2016)
Sphingolipids in Disease (2013)
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
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
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