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2444-46-4

Basic Information
CAS No.: 2444-46-4
Name: Nonivamide
Article Data: 29
Cas Database
Molecular Structure:
Molecular Structure of 2444-46-4 (Nonivamide)
Formula: C17H27NO3
Molecular Weight: 293.406
Synonyms: Nonanamide,N-vanillyl- (6CI,7CI,8CI);AH 23491X;N-Vanillylnonamide;NSC 172795;Nonanoylvanillyl amide;Vanillyl pelargonic amide;
EINECS: 219-484-1
Density: 1.037 g/cm3
Melting Point: 54 °C
Boiling Point: 492.7 °C at 760 mmHg
Flash Point: 251.8 °C
Solubility: methanol: 100 mg/mL, clear to slightly hazy
Appearance: solid
Hazard Symbols: ToxicT,IrritantXi
Risk Codes: 25-36/37/38
Safety: 26-45-37/39
Transport Information: UN 3462 6.1/PG 2
PSA: 58.56000
LogP: 4.15850
Synthetic route
1196-92-5

Vanillylamin

112-05-0

nonanoic acid

2444-46-4

Nonivamide

Conditions
ConditionsYield
With 2-((N,N-diisopropylamino)methyl)-4-cyanophenylboronic acid In fluorobenzene at 85℃; for 3.5h; Reagent/catalyst; Solvent; Temperature; Molecular sieve; Green chemistry;99%
With SiO2-H3BO3 In toluene for 7h; Reflux;91%
With boric acid In toluene at 130℃; for 8h; Concentration; Temperature;87.4%
764-85-2

Nonanoyl chloride

1196-92-5

Vanillylamin

2444-46-4

Nonivamide

Conditions
ConditionsYield
Stage #1: Vanillylamin With sodium hydrogencarbonate In chloroform; water at 20℃; for 0.75h;
Stage #2: Nonanoyl chloride In chloroform; water at 20 - 40℃; for 1h;
94%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;88.6%
In diethyl ether; N,N-dimethyl-formamide Ambient temperature;59%
With diethyl ether
With triethylamine
764-85-2

Nonanoyl chloride

7149-10-2

vanillylamine hydrochloride

2444-46-4

Nonivamide

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane; water at 20 - 42℃; for 2.5h; Temperature;91.5%
Stage #1: vanillylamine hydrochloride With sodium hydroxide In water; N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Cooling with ice;
Stage #2: Nonanoyl chloride In tetrahydrofuran; water; N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere; Cooling with ice;
60.51%
871570-36-4

3-methoxy-4-(triisopropylsilyloxy)-N-(nonanoyl)benzylamine

2444-46-4

Nonivamide

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;84%
With tetrabutyl ammonium fluoride In tetrahydrofuran81%
112-05-0

nonanoic acid

7149-10-2

vanillylamine hydrochloride

2444-46-4

Nonivamide

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Temperature;81.1%
102811-97-2

N-(4-benzyloxy-3-methoxy-benzyl)-nonanamide

2444-46-4

Nonivamide

Conditions
ConditionsYield
With palladium on activated charcoal; ethanol Hydrogenation;
90-05-1

2-methoxy-phenol

N-hydroxymethyl-nonamide

N-hydroxymethyl-nonamide

2444-46-4

Nonivamide

Conditions
ConditionsYield
With hydrogenchloride
222622-85-7

3-methoxy-4-(triisopropylsilyloxy)benzonitrile

2444-46-4

Nonivamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: LiAlH4 / tetrahydrofuran / 20 °C
2: 4-DMAP; pyridine / CH2Cl2 / 0 - 20 °C
3: 81 percent / TBAF / tetrahydrofuran
View Scheme
222620-67-9

3-methoxy-4-(triisopropylsilyloxy)-benzylamine

2444-46-4

Nonivamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 4-DMAP; pyridine / CH2Cl2 / 0 - 20 °C
2: 81 percent / TBAF / tetrahydrofuran
View Scheme
4421-08-3

3-methoxy-4-hydroxybenzonitrile

2444-46-4

Nonivamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 91 percent / imidazole / dimethylformamide / 20 °C
2: LiAlH4 / tetrahydrofuran / 20 °C
3: 4-DMAP; pyridine / CH2Cl2 / 0 - 20 °C
4: 81 percent / TBAF / tetrahydrofuran
View Scheme
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Chemistry

IUPAC Name:N-[(4-Hydroxy-3-methoxyphenyl)methyl]nonanamide
Molecular Formula:C17H27NO3
Molecular Weight:293.401180 g/mol
Appearance:white to off-white powder
Melting Point:54°C
Boiling Point:492.7 °C at 760 mmHg
Flash Point:190°C
Density:1,1 g/cm3 
Storage temp.:2-8°C
Methanol solubility:100 mg/mL, clear to slightly hazy
FEMA:2787
EINECS:219-484-1
Synonyms of Nonivamide (CAS NO.2444-46-4): N-((4-hydroxy-3-methoxyphenyl)methyl)-nonanamid ; N-[(4-hydroxy-3-methoxyphenyl)methyl]-nonanamid;Nonanoylvanilylamide ; Nonylicacidvanillylamide(nonivamide) ; Vanillyl-n-nonylamide ; Pseudocapsaicin ; Synthetic capsaicin ; Pelargonyl vanillylamide
Categories of Nonivamide(2444-46-4): INORGANIC & ORGANIC CHEMICALS ; Anilines, Aromatic Amines and Nitro Compounds

Uses

 Nonivamide (CAS NO.2444-46-4) is used as a food additive to add pungency to seasonings, flavorings, and spice blends. 
It  is also used in confectionary industry to create hot sensation, and in the pharmaceutical industry in some formulations.
As a potent lachrymatory agent, Nonivamide (CAS NO.2444-46-4) is used as the active ingredient of some oleoresin capsicum-based riot control agents.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 8mg/kg (8mg/kg)   Journal of Medicinal Chemistry. Vol. 36, Pg. 2595, 1993.

Safety Profile

Hazard Codes Nonivamide (CAS NO.2444-46-4): ToxicT,IrritantXi
Risk Statements: 25-36/37/38 
R25: Toxic if swallowed. 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-45-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S37/39: Wear suitable gloves and eye/face protection.
RIDADR: UN 3462 6.1/PG 2
WGK Germany: 3
RTECS: RA5998000
F: 19