Grundinformationen
- Standard-SMILES
CCCCCCCCC(=O)NCc1ccc(O)c(OC)c1- InChIKey
RGOVYLWUIBMPGK-UHFFFAOYSA-N- Summenformel
- C17H27NO3
- Durchschnittliche Molmasse
- 293,4 g/mol
- Monoisotopische Masse
- 293,19909372
Namen und Bezeichner
- Bevorzugter Name
- Nonivamide
- IUPAC
- N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide
- Lokaler Name
- Nonivamid
- Englischer Name
- Nonivamide
- Summenformel
- C17H27NO3
- Molmasse
- 293.4
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
2444-46-4- PubChem CID
- 2998
- DTXSID
DTXSID1034769- ChEMBL
CHEMBL75124- ChEBI
CHEBI:46936- UNII
- S846B891OR
- EC Number
- 219-484-1
- Nikkaji
- J7.575B
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,2
- Polarare Oberfläche (TPSA)
- 58,6 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 10
- Schwere Atome
- 21
- Formalladung
- 0
- Komplexität
- 283
Experimentelle und physikochemische Eigenschaften
Solubility
Soluble in water (slightly)
slightly
Slightly soluble in water
Soluble (in ethanol)
Melting Point
57
124.00 to 128.00 °C. @ 760.00 mm Hg
Physical Description
Powder with a stinging odor; [Sigma-Aldrich MSDS]
Solid
White powder or crystals; odourless
Physikochemische Eigenschaften
- Schmelzpunkt
- 54 °C · 54°C
- Siedepunkt
- 200 · 200-210 °C(Press: 0.05 Torr)
- Dichte
- 1 · 1,1 g/cm3
- FEMA
- 2787 · 2787 | NONANOYL 4-HYDROXY-3-METHOXYBENZYLAMIDE
- Flammpunkt
- 190 °C · 190°C
- storage temp.
- 2 · Sealed in dry,2-8°C
- Löslichkeit
- 100 mg/mL, · methanol: 100 mg/mL, clear to slightly hazy
- Aggregatzustand
- powder
- pka
- 9.76 · 9.76±0.20(Predicted)
- Farbe
- white to off-white
- Geruch (Odor)
- bland odorless
- Geruchsart
- bland
- JECFA Number
- 1599 · 1599
- BRN
- 2144300 · 2144300
- Stabilität
- Stable. Incompatible with strong oxidizing agents.
- Major Application
- cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care
- Kosmetik-Inhaltsstoffe Funktionen
- FRAGRANCE
- 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)
- InChIKey
- RGOVYLWUIBMPGK-UHFFFAOYSA-N
- SMILES
- CCCCCCCCC(=O)NCc1ccc(O)c(OC)c1
- LogP
- 3.43 · 3.43
- CAS Datenbank
- 2444 · 2444-46-4(CAS DataBase Reference)
- EPA chemische Informationen
- Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]- (2444-46-4)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 0.3% (5 of 1513) of reports.
Danger
H301 (85.7%): Toxic if swallowed [Danger Acute toxicity, oral];H315 (99.6%): Causes skin irritation [Warning Skin corrosion/irritation];H317 (89.2%): May cause an allergic skin reaction [Warning Sensitization, Skin];H318 (85.7%): Causes serious eye damage [Danger Serious eye damage/eye irritation];H319 (14%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H334 (85.7%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory];H335 (14.1%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1513 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 5 of 1513 reports by companies.;There are 16 notifications provided by 1508 of 1513 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Gefahrenhinweise
Regulatory Information
Chemical: Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Nonivamide: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Effects sensory neurons; [ChemIDplus] Causes lung inflammation in acute inhalation studies of mice; [RTECS] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; May cause skin sensitization; [Sigma-Aldrich MSDS] Search for (2444-46-4[EC/RN Number]) AND (sensitizer OR sensitization OR dermatitis OR allergic): no results; [PubMed]
Regulatorische Informationen
Regulatory Information
Chemical: Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Nonivamide: Does not have an individual approval but may be used under an appropriate group standard
Sicherheitsdaten
- F
- 19
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 3462 6.1/PG 2
- hs_code
- 29242990
- RTECS-Nr.
- RA5998000
- risk_code
- 25-36/37/38-43
- Toxizität
- mouse,LD50,intraperitoneal,8mg/kg (8mg/kg),Journal of Medicinal Chemistry. Vol. 36, Pg. 2595, 1993.
- hazard_code
- T,Xi
- safety_code
- 26-45-37/39-36/37
- hazard_class
- 6.1
- packing_group
- II
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Eye Dam. 1Resp. Sens. 1Skin Irrit. 2Skin Sens. 1STOT SE 3
Chemie und Industrie
Pharmakologische Informationen
Mechanism of Action
Nonivamide is a naturally occurring analog of [DB06774], isolated from peppers, described to produce effects similar to [DB06774]. It is an agonist of the VR1 (vanilloid/TRPV1 receptor). It serves as a transient agonist of these receptors, which are potentiated by pro-inflammatory drugs, a phenomenon that leads to thermal hyperalgesia, or increased heat sensation. Nonivamide has been shown to stimulate afferent neurons with about half the potency of [DB06774]. Agonism of the VR1 (TRPV1) (vanilloid) receptor by Nonivamide was demonstrated to induce the release of Ca2+ from the endoplasmic reticulum (ER) of human lung cells, producing ER stress and cell death [MSDS]. Nonivamide, like other capsaicinoids, acts on the vanilloid receptors located in the peripheral afferent nerve fibers, providing short-acting irritant and algesic properties. Applied dermally, these substances act by stimulating sensitive chemoreceptors of the skin and by reflex, hyperemia and a local elevation in temperature. After repetitive administration, capsaicinoids have been reported to lead to desensitization to nociceptive stimuli possibly by long-acting depletion of peptide neurotransmitters (substance P) from peripheral sensory neurons. Capsaicinoids can modulate muscle tone (in bladder, bronchus etc.). Intravenous injection of nonivamide to rats (10 μg/kg) has been found to lead to bradycardia. The cardiovascular effects are partly explained by substance P release. Nonivamide given to rats subcutaneously (1 mg/kg) was found to cause body temperature decrease, vasodilatation, and increased salivation. Capsaicinoids have shown to illicit bronchospastic effects in guinea pigs. Capsaicin and its analogs were reported to increase barbiturate sleeping time in rats by interacting with hepatic metabolizing enzymes.
Metabolism/Metabolites
Limited information is available on pharmacokinetics and metabolism of nonivamide. For the closely related [DB06774] and other capsaicinoids, gastrointestinal absorption is rapid and almost entirely complete in studies of rats (oral dose of about 10 to 15 mg/kg of combined capsaicin and dihydrocapsaicin) with about 85% of the dose being absorbed within 3 hours. Both substances undergo first-pass metabolism in the liver and partly metabolized at the site of absorption.
Verwendung und Herstellung
Uses
Used as a flavoring agent; [FDA]
Use (kg; approx.) in Germany (2009): >50;Consumption (g per capita; approx.) in Germany (2009): 0.000611;Calculated removal (%): 98.2
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Pharmaceuticals
Cosmetics -> Masking
Anwendungen
BeschreibungNonanoyl-4-hydroxy-3-methoxybenzylamide is odorless with a pungent, burning taste. Synthesized from nonanyl chloride and vanillylamine.
Verwendenanalgesic (topical), depletes Substance P
Darstellung
synthetischeFrom nonanyl chloride and vanillylamine.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: A capsaicinoid that is the carboxamide resulting from the formal condensation of the amino group of 4-hydroxy-3-methoxybenzylamine with the carboxy group of nonanoic acid. It is the active ingredient in many pepper sprays.
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