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| CAS No.: | 2444-46-4 |
|---|---|
| Name: | Nonivamide |
| Article Data: | 29 |
| Molecular Structure: | |
|
|
|
| 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: |
 T, Xi
|
| 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 |
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| 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% |
3-methoxy-4-(triisopropylsilyloxy)-N-(nonanoyl)benzylamine
Nonivamide
| Conditions | Yield |
|---|---|
| With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; | 84% |
| With tetrabutyl ammonium fluoride In tetrahydrofuran | 81% |
| Conditions | Yield |
|---|---|
| With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Temperature; | 81.1% |
N-(4-benzyloxy-3-methoxy-benzyl)-nonanamide
Nonivamide
| Conditions | Yield |
|---|---|
| With palladium on activated charcoal; ethanol Hydrogenation; |
| Conditions | Yield |
|---|---|
| With hydrogenchloride |
3-methoxy-4-(triisopropylsilyloxy)benzonitrile
Nonivamide
| Conditions | Yield |
|---|---|
| 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 |
3-methoxy-4-(triisopropylsilyloxy)-benzylamine
Nonivamide
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 4-DMAP; pyridine / CH2Cl2 / 0 - 20 °C 2: 81 percent / TBAF / tetrahydrofuran View Scheme |
| Conditions | Yield |
|---|---|
| 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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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
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.
| 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. |
Hazard Codes Nonivamide (CAS NO.2444-46-4): 
T,
Xi
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
