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General Material Information

Preferred name capscaisin
Trivial Name Nonivamide
Short Description nonanoyl 4-hydroxy-3-methoxybenzylamide
Formula C17 H27 N O3
CAS Number 2444-46-4
Deleted CAS Number 497080-86-1
FEMA Number 2787
Flavis Number 16.006
ECHA Number 219-484-1
FDA UNII S846B891OR
Nikkaji Number J7.575B
Beilstein Number 2144300
MDL MFCD00017286
COE Number 590
xLogP3-AA 4.20 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 1599 nonanoyl 4-hydroxy-3-methoxybenzylamide
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 2444-46-4 ; NONANOYL 4-HYDROXY-3-METHOXYBENZYLAMIDE
Synonyms
  • pseudo capsaicin
  • capsaicin synthetic
  • capscaisin 10% vegetable oil
  • N-[(4-hydroxy-3-methoxy-phenyl)methyl]nonanamide
  • N-4-hydroxy-3-methoxybenzyl nonanamide
  • N-(4-hydroxy-3-methoxybenzyl)nonanamide
  • N-((4-hydroxy-3-methoxyphenyl)methyl) nonanamide
  • N-(( hydroxy-3-methoxyphenyl)methyl)4-nonanamide
  • N-((4-hydroxy-3-methoxyphenyl)methyl)nonanamide
  • N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide
  • hydroxymethoxybenzyl pelargonamide
  • 8-methyl-N-vanillyl-trans-b-nonenamide
  • nonanamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-
  • nonanamide, N-[ (4-hydroxy-3-methoxyphenyl)methyl]-
  • nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-
  • nonanamide, N-vanillyl-
  • nonanoic acid 4-hydroxy-3-methoxy-benzylamide
  • nonanoic acid vanillylamide
  • nonanoyl 4-hydroxy-3-methoxy benzylamide
  • nonanoyl 4-hydroxy-3-methoxybenzyl amide
  • nonanoyl 4-hydroxy-3-methoxybenzylamide
  • N- nonanoyl vanillyl amide
  • N- nonanoyl vanillylamide congealed liquid
  • N- nonanoyl vanillylamide powder
  • nonivamide
  • nonivamide (non-kosher)
  • nonivamide 10 wt% solution in benzyl alcohol
  • nonoyl vanillylamide
  • nonylic acid vanillylamide
  • nonylvanylamide
  • pelargonic acid vanillyl amide
  • pelargonic acid vanillylamide
  • pelargonic acid, vanillylamide
  • pelargonyl vanillilamide
  • pelargonyl vanillyl amide
  • pelargonyl vanillylamide
  • vanillyl pelargonic amide
  • vanillyl-N-nonyl amide
  • vanillyl-N-nonylamide
  • N- vanillylnonamide
  • N- vanillylnonanamide
  • N- vanillylnonanoamide
  • N- vanillylpelargonamide
  • N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide
  • N-Vanillylnonanamide
  • N-Vanillylpelargonamide
  • Vanillyl n-nonylamide
  • N-Vanillylnonamide
  • Nonylic vanillylamide
  • AH 23491X
  • Pseudocapsaicin
  • N-(4-Hydroxy-3-methoxybenzyl)nonamide
  • Nonanoylvanillyl amide
  • 8-Nordihydrocapsaicin
  • NSC 172795

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:2444-46-4
Pubchem (cid):2998
Pubchem (sid):134981769
Publications by Info
aliphatic and aromatic amines and amides
Publications by PubMed
The capsaicin analog nonivamide decreases total energy intake from a standardized breakfast and enhances plasma serotonin levels in moderately overweight men after administered in an oral glucose tolerance test: A randomized, crossover trial.
Oil-in-Oil-Emulsions with Enhanced Substantivity for the Treatment of Chronic Skin Diseases.
Evaluation of changes in the haemoglobin of skin and muscle tissue of the calf, as induced by topical application of a nonivamide/nicoboxil cream.
In vitro studies on release and skin permeation of nonivamide from novel oil-in-oil-emulsions.
Nonivamide, a capsaicin analog, increases dopamine and serotonin release in SH-SY5Y cells via a TRPV1-independent pathway.
In vitro skin permeation and penetration of nonivamide from novel film-forming emulsions.
[A novel method for the identification of illegal cooking oil (1): detection of three capsaicinoids with liquid chromatography-mass spectrometry].
Toxic effects of environment-friendly antifoulant nonivamide on Phaeodactylum tricornutum.
Reactive intermediates produced from the metabolism of the vanilloid ring of capsaicinoids by p450 enzymes.
Comparison of the effects of pelargonic acid vanillylamide and capsaicin on human vanilloid receptors.
New film forming emulsions containing Eudragit® NE and/or RS 30D for sustained dermal delivery of nonivamide.
Determination and pharmacokinetics of [6]-gingerol in mouse plasma by liquid chromatography-tandem mass spectrometry.
Novel penetration enhancers for skin applications: a review.
Contributions of TRPV1, endovanilloids, and endoplasmic reticulum stress in lung cell death in vitro and lung injury.
Structure-activity relationship of capsaicin analogs and transient receptor potential vanilloid 1-mediated human lung epithelial cell toxicity.
Molecular dynamics at ambient and elevated pressure of the amorphous pharmaceutical: nonivamide (pelargonic acid vanillylamide).
Synthesis, photolysis studies and in vitro photorelease of caged TRPV1 agonists and antagonists.
Protective effect and relation structure-activity of nonivamide and iododerivatives in several models of lipid oxidation.
A comparison of pretreatment with a topical combination of nonivamide and nicoboxil and surgical delay in a random pattern skin flap model.
Neuroprotective effects of glyceryl nonivamide against microglia-like cells and 6-hydroxydopamine-induced neurotoxicity in SH-SY5Y human dopaminergic neuroblastoma cells.
Transdermal delivery of capsaicin derivative-sodium nonivamide acetate using microemulsions as vehicles.
Evaluation of ketoprofen formulations via penetration rate and irritation in vivo study.
Transient receptor potential vanilloid 1 agonists cause endoplasmic reticulum stress and cell death in human lung cells.
Effect of topical application of capsaicin and its related compounds on dermal insulin-like growth factor-I levels in mice and on facial skin elasticity in humans.
Analysis of eight capsaicinoids in peppers and pepper-containing foods by high-performance liquid chromatography and liquid chromatography-mass spectrometry.
Assessment of pepper spray product potency in Asian and Caucasian forearm skin using transepidermal water loss, skin temperature and reflectance colorimetry.
Electrically-assisted skin permeation of two synthetic capsaicin derivatives, sodium nonivamide acetate and sodium nonivamide propionate, via rate-controlling polyethylene membranes.
TRPV1 antagonists elevate cell surface populations of receptor protein and exacerbate TRPV1-mediated toxicities in human lung epithelial cells.
The taming of capsaicin. Reversal of the vanilloid activity of N-acylvanillamines by aromatic iodination.
Local heating of human skin by millimeter waves: effect of blood flow.
Metabolism of capsaicin by cytochrome P450 produces novel dehydrogenated metabolites and decreases cytotoxicity to lung and liver cells.
Improved dorsal random-pattern skin flap survival in rats with a topically applied combination of nonivamide and nicoboxil.
Effect of arvanil (N-arachidonoyl-vanillyl-amine), a nonpungent anandamide-capsaicin hybrid, on ion currents in NG108-15 neuronal cells.
Determination of capsaicin, nonivamide, and dihydrocapsaicin in blood and tissue by liquid chromatography-tandem mass spectrometry.
In vitro topical application and in vivo pharmacodynamic evaluation of nonivamide hydrogels using Wistar rat as an animal model.
Transdermal iontophoresis of sodium nonivamide acetate. V. Combined effect of physical enhancement methods.
Prevention of cerebral vasospasm by a capsaicin derivative, glyceryl nonivamide, in an experimental model of subarachnoid hemorrhage.
In vitro and in vivo evaluations of topically applied capsaicin and nonivamide from hydrogels.
Evaluation of percutaneous absorption and skin irritation of ketoprofen through rat skin: in vitro and in vivo study.
Quantitative analysis of capsaicinoids in fresh peppers, oleoresin capsicum and pepper spray products.
Determination of capsaicin, dihydrocapsaicin, and nonivamide in self-defense weapons by liquid chromatography-mass spectrometry and liquid chromatography-tandem mass spectrometry.
Capsaicin and nonivamide as novel skin permeation enhancers for indomethacin.
The transepidermal oxygen flux from the environment is in balance with the capillary oxygen supply.
Nitrated nonivamide displaying a drawback of proton's role in capsaicin-associated sensory and neuronal activities.
The effect of the base on the kinetics of action of the capsaicinoid nonivamide: evaluation with a hyperemic test.
Transdermal delivery of sodium nonivamide propionate by iontophoresis.
Selective block by glyceryl nonivamide of inwardly rectifying K+ current in rat anterior pituitary GH3 cells.
A possible role of nitric oxide formation in the vasodilatation of rabbit ear artery induced by a topically applied Capsaicin analogue.
The responses of rat trigeminal ganglion neurons to capsaicin and two nonpungent vanilloid receptor agonists, olvanil and glyceryl nonamide.
Glyceryl nonivamide: a capsaicin derivative with cardiac calcitonin gene-related peptide releasing, K+ channel opening and vasorelaxant properties.
Glyceryl nonivamide, a nonpungent analogue of capsaicin, enhances substance P release and renal function in rats.
Development and evaluation of transdermal patches of nonivamide and sodium nonivamide acetate.
Capsinolol: the first beta-adrenoceptor blocker with an associated calcitonin gene-related peptide releasing activity in the heart.
Multiple sensory and functional effects of non-phenolic aminodimethylene nonivamide: an approach to capsaicin antagonist.
Sodium nonivamide acetate: a non-pungently antinociceptive capsaicin derivative with unusual anti-inflammatory properties.
In vitro effect of penetration enhancers on sodium nonivamide acetate in rat skin.
Metabolism of capsaicinoids: evidence for aliphatic hydroxylation and its pharmacological implications.
Autonomic and sensory cardiovascular activities of nonivamide: intrathecal administration of clonidine.
Desensitizing mechanism of capsaicin and nonanoyl vanillylamide on the vascular nociceptive response in the guinea pig.
Capsaicin: identification, nomenclature, and pharmacotherapy.
Cardiovascular interactions of nonivamide, glyceryl nonivamide, capsaicin analogues, and substance P antagonist in rats.
Cardiovascular effects of nonivamide succinate.
[The effect of nonanoyl vanillylamide on the chemically-induced nociception].
Studies on the hypothermic response of capsaicin and its analogue in mice.
Comparison of nonivamide and capsaicin with regard to their pharmacokinetics and effects on sensory neurons.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):D08282
HMDB (The Human Metabolome Database):HMDB29846
FooDB:FDB001066
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 293.40679931641
Specific gravity @ 20 °C
Pounds per Gallon
Melting Point 124 to 128°C @ 760 mm Hg
Boiling Point 492 to 493°C @ 760 mm Hg
Acid Value 1 max KOH/g
Flash Point TCC Value 251.8 °C TCC
logP (o/w) 3.202 est
Shelf life 12 months (or longer if stored properly.)
Storage notes Refrigerate in tightly sealed containers.
Solubility
alcohol Yes
dipropylene glycol Yes
water, slightly Yes
water, 7.716 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Flavor Type: Pungent
pungent, spicy
General comment Pungent burning

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
T - Toxic.
R 25 - Toxic if swallowed.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
S 23 - Do not breath vapour.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50 8 mg/kg
Journal of Medicinal Chemistry. Vol. 36, Pg. 2595, 1993.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavoring agents
Recommendation for capscaisin usage levels up to:
not for fragrance use.
Maximised Survey-derived Daily Intakes (MSDI-EU): 6.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 0.07 (μg/capita/day)
Threshold of Concern:90 (μg/person/day)
Structure Class: III
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: -10.00000
beverages(nonalcoholic): --
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: -10.00000
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: --
fruit ices: --
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -10.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): --
Fats and oils, and fat emulsions (type water-in-oil) (02.0): --
Edible ices, including sherbet and sorbet (03.0): --
Processed fruit (04.1): --
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): 10.00000300.00000
Confectionery (05.0): --
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): --
Bakery wares (07.0): --
Meat and meat products, including poultry and game (08.0): --
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): --
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): --
Foodstuffs intended for particular nutritional uses (13.0): --
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): --
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): --
Ready-to-eat savouries (15.0): --
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 86, (FGE.86)[1] - Consideration of aliphatic and aromatic amines and amides evaluated by JECFA (65th meeting) - Scientific Opinion of the Panel on Food Additives - Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 40: An aromatic derivative of 2-hydroxy-propionamide. Chemical group 16
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 86, Revision 1 (FGE.86Rev1): Consideration of aliphatic and aromatic amines and amides evaluated by JECFA (65th meeting)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 86, Revision 2 (FGE.86Rev2): Consideration of aliphatic and arylalkyl amines and amides evaluated by JECFA (65th meeting)
View page or View pdf

EPI System: View
ClinicalTrials.gov:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):2444-46-4
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :2998
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 2811
WGK Germany:3
N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide
Chemidplus:0002444464
RTECS:RA5955000 for cas# 2444-46-4