| Identification | More | [Name]
Nonivamide | [CAS]
2444-46-4 | [Synonyms]
8-METHYL-N-VANILLYLNONANAMIDE
8-METHYL-N-VANILLYLNONENAMIDE
CAPSAICIN
CAPSAICIN, DIHYDRO-
CAPSAICINE SYNTHETIC
CAPSAICIN (SYNTHETIC)
CAPSAICIN SYNTHETIC ANALOG
DIHYDROCAPSAICIN
N-(4-HYDROXY-3-METHOXYBENZYL)NONANAMIDE
N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL NONANAMIDE
N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-NONANAMIDE
N-NONYLVANYLAMIDE
NONANOIC ACID VANILLYLAMIDE
NONANYL VANILLYLAMIDE
NONIVAMIDE
NONYLIC VANILLYLAMIDE
NONYLVANYLAMIDE
N-PELARGONIC ACID VANILLYLAMIDE
N-PELARGONYLVANILLYLAMIDE
N-VANILLYLNONAMIDE | [EINECS(EC#)]
219-484-1 | [Molecular Formula]
C17H27NO3 | [MDL Number]
MFCD00017286 | [Molecular Weight]
293.4 | [MOL File]
2444-46-4.mol |
| Chemical Properties | Back Directory | [Appearance]
solid | [Melting point ]
54°C | [Boiling point ]
200-210 °C(Press: 0.05 Torr) | [density ]
1,1 g/cm3 | [FEMA ]
2787 | [Fp ]
190°C | [storage temp. ]
2-8°C
| [solubility ]
methanol: 100 mg/mL, clear to slightly hazy
| [form ]
powder
| [pka]
9.76±0.20(Predicted) | [color ]
white to off-white
| [Odor]
bland odorless | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [Odor Type]
bland | [JECFA Number]
1599 | [BRN ]
2144300 | [Major Application]
cleaning products
cosmetics
flavors and fragrances
food and beverages
personal care | [Cosmetics Ingredients Functions]
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 | [CAS DataBase Reference]
2444-46-4(CAS DataBase Reference) | [EPA Substance Registry System]
2444-46-4(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
  
GHS05,GHS07,GHS08 | [Signal word ]
Danger | [Hazard statements ]
H315-H317-H318-H334-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
T,Xi | [Risk Statements ]
R25:Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
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 label where possible) .
S37/39:Wear suitable gloves and eye/face protection . | [RIDADR ]
UN 3462 6.1/PG 2
| [WGK Germany ]
3
| [RTECS ]
RA5998000
| [F ]
19 | [TSCA ]
TSCA listed | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29242990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Dam. 1
Resp. Sens. 1
Skin Irrit. 2
Skin Sens. 1
STOT SE 3 | [Toxicity]
mouse,LD50,intraperitoneal,8mg/kg (8mg/kg),Journal of Medicinal Chemistry. Vol. 36, Pg. 2595, 1993. |
| Questions And Answer | Back Directory | [Description]
Nonivamide is also called pelargonic acid vanillylamide or PAVA. It is a capsaicinoid. Nonivamide, isolated from peppers, is a naturally occurring analog of capsaicin (sc-3577). Similar to capsaicin, nonivamide can activate the TRPV1 receptor, thus, stimulate the firing rate of dopaminergic neurons in the ventral tegmental area of the brain and to increase the expression of the serotonin receptor gene HTR2A. Nonivamide is with lower TRPV1 binding affinity, thus, a reduced pungency (9 200 000 scoville heat units) compared to capsaicin (16 000 000 scoville heat units).
Nonivamide is used in the food production to add a hot sensation to flavoring agents and spice mixtures. It is also used in the sweets and confectionary industries to add hot sensation into products. In pharmaceutical industries, nonivamide is used as a cheaper alternative for capsaicin. Warming or heating ointment of nonivamide is used for temporary relief of pain from conditions such as rheumatism, arthritis, lumbao, muscular aches, sprains and strains, sporting injuries and other conditions where local warmth is beneficial. Finalgon is one of the common product utilizing nonivamide for this purpose. Nonivamide is also used as an incapacitant spray, affecting the assailed person’s eyes, causing intense pain and swelling.
| [References]
[1] https://www.scbt.com/scbt/product/nonivamide-2444-46-4
[2] https://pubchem.ncbi.nlm.nih.gov/compound/N-Vanillylnonanamide#section=Clinical-Trials
[3] https://cot.food.gov.uk/sites/default/files/cot/cotsection.pdf
|
| Hazard Information | Back Directory | [Chemical Properties]
n-Nonanyl-4-hydroxy-3-methoxybenzyl-amide is an odorless compound, but has a pungent, burning taste | [Chemical Properties]
solid | [Uses]
analgesic (topical), depletes Substance P | [Uses]
N-Vanillylnonanamide is a synthetic analogue of Capsaicin (175680) with similar bioactivity. | [Definition]
ChEBI: 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. | [Preparation]
From nonanyl chloride and vanillylamine. | [Synthesis]
The general procedure for the synthesis of N-(4-hydroxy-3-methoxybenzyl)nonanamide from nonanoyl chloride and 4-(aminomethyl)-2-methoxyphenol was as follows: first, the hydrochloride or hydrobromide of 4-(aminomethyl)-2-methoxyphenol (1 mmol) was dissolved in anhydrous N,N-dimethylformamide (DMF) (2 mL). Subsequently, N,N-diisopropylethylamine (DIPEA) (2 mmol) was added to neutralize the salt and release the free amine. After stirring the reaction mixture for 10 minutes at room temperature, nonanoyl chloride (1 mmol) was slowly added. The reaction continued to be stirred at room temperature for 6 to 24 hours. Upon completion of the reaction, water (40 mL) was added to the reaction mixture to quench the reaction. The mixture was transferred to a partition funnel and extracted with dichloromethane (CH2Cl2) (3 x 6 mL). The organic phases were combined and concentrated under reduced pressure to obtain the crude product. Finally, the crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate, 2:1 v/v) or preparative high-performance liquid chromatography (HPLC) (according to the analytical scheme described above) to afford the target compound N-(4-hydroxy-3-methoxybenzyl)nonanamide. |
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| Company Name: |
Henan yingchuang Gold
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| Telephone: |
16650708709 |
| Website: |
www.hnyingchuang.com/ |
| Company Name: |
Kono Chem Co., Ltd Gold
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| Telephone: |
029-86107037-8014 18292830413 |
| Website: |
http://www.konochemical.com |
| Company Name: |
BOYAN PHARMA Gold
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| Telephone: |
18566078841 18566078841 |
| Website: |
boyanpharma.com/index.php?c=category&id=9 |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
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