Nonivamide CAS 2444-46-4
Introduction：Basic information about Nonivamide CAS 2444-46-4, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Nonivamide Basic informationDescription References
| Product Name: | Nonivamide |
| Synonyms: | Nonivamide(Synthetic Capsaicin);N-((Hydroxy-3-methoxyphenyl)methyl)4-nonanamide;N-Nonanoyl vanillylamide;Nonanamide, N-((4-hydroxy-3-methoxyphenyl)meth;SYNTHETIC CAPSAICIN;PELARGONYL VANILLYLAMIDE;PELARGONIC ACID VANILLYLAMIDE;N-PELARGONIC ACID VANILLYLAMIDE |
| CAS: | 2444-46-4 |
| MF: | C17H27NO3 |
| MW: | 293.4 |
| EINECS: | 219-484-1 |
| Product Categories: | Anilines, Aromatic Amines and Nitro Compounds;INORGANIC & ORGANIC CHEMICALS;Inhibitors;Herb extract;Plant extract;API;2444-46-4 |
| Mol File: | 2444-46-4.mol |
Nonivamide Chemical Properties
| Melting point | 54°C |
| Boiling point | 200-210 °C(Press: 0.05 Torr) |
| density | 1,1 g/cm3 |
| FEMA | 2787 | NONANOYL 4-HYDROXY-3-METHOXYBENZYLAMIDE |
| Fp | 190°C |
| storage temp. | Sealed in dry,2-8°C |
| solubility | methanol: 100 mg/mL, clear to slightly hazy |
| pka | 9.76±0.20(Predicted) |
| form | powder |
| color | white to off-white |
| Odor | bland odorless |
| Odor Type | bland |
| JECFA Number | 1599 |
| BRN | 2144300 |
| Stability: | Stable. Incompatible with strong oxidizing agents. |
| 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 | Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]- (2444-46-4) |
Safety Information
| Hazard Codes | T,Xi |
| Risk Statements | 25-36/37/38-43 |
| Safety Statements | 26-45-37/39-36/37 |
| 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. |
| 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 |
| Description | Nonanoyl-4-hydroxy-3-methoxybenzylamide is odorless with a pungent, burning taste. Synthesized from nonanyl chloride and vanillylamine. |
| 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 | 764-85-2 1196-92-5 2444-46-4 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. |
| references | 1. m. j. caterina, m. a. schumacher, m. tominaga, t. a. rosen, j. d. levine and d. julius, nature 1997, 389, 816-824. 2. y. g. gil and m. k. kang, life sci 2008, 82, 997-1003. 3. y. s. lee, d. h. nam and j. a. kim, cancer lett 2000, 161, 121-130. 4. h. c. chang, s. t. chen, s. y. chien, s. j. kuo, h. t. tsai and d. r. chen, hum exp toxicol 2011, 30, 1657-1665. 5. k. c. brown, t. r. witte, w. e. hardman, h. luo, y. c. chen, a. b. carpenter, j. k. lau and p. dasgupta, plos one 2010, 5, e10243.> |
Nonivamide Preparation Products And Raw materials
| Raw materials | L-Phenylalanine-->L-Valine-->Nonanoic acid-->NONANOYL CHLORIDE-->vanillylamin-->4-Hydroxy-3-methoxybenzylamine hydrochloride-->N,N-Dimethylformamide-->N,N-Diisopropylethylamine |
| Preparation Products | CAPSANTHIN |
