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V9130

Sigma-Aldrich

N-Vanillylnonanamide

≥97%, powder

Synonym(s):

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

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

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sphingolipids in Disease (2013)
Berrin Ozçelik et al.
Pharmaceutical biology, 49(4), 396-402 (2011-03-12)
Some natural products consisting of the alkaloids yohimbine and vincamine (indole-type), scopolamine and atropine (tropane-type), colchicine (tropolone-type), allantoin (imidazolidine-type), trigonelline (pyridine-type) as well as octopamine, synephrine, and capsaicin (exocyclic amine-type); the flavonoid derivatives quercetin, apigenin, genistein, naringin, silymarin, and silibinin;
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)
G B Kasting et al.
Journal of pharmaceutical sciences, 86(1), 142-146 (1997-01-01)
The percutaneous absorption of three highly lipophilic analogs of capsaicin--vanillylnonanamide (VN), olvanil, and NE-21610--was measured in vivo in the CD:VAF rat, and in vitro through excised CD: VAF and SkH:Fz rat skin and human cadaver skin. Absorption and skin metabolism
R Ando et al.
Nihon yakurigaku zasshi. Folia pharmacologica Japonica, 91(1), 55-59 (1988-01-01)
Effects of cysteamine (2-mercaptoethylamine) on vocalization responses, a parameter of nociceptive response, was studied in conscious guinea pigs. Intra-arterial injection of bradykinin (3 micrograms), acetylcholine (300 micrograms), capsaicin (3 micrograms) and vanillyl n-nonoylamide (3 micrograms, VNA) induced severe vocalization responses.
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