Spilanthol

Base Information

• Chemical Name: Spilanthol
• CAS No.: 25394-57-4
• Deprecated CAS: 504-47-2
• Molecular Formula: C₁₄H₂₃NO
• Molecular Weight: 221.343
• UNII: 4W9L3S4856
• DSSTox Substance ID: DTXSID90893963
• Wikipedia: Spilanthol
• Wikidata: Q7577248
• Metabolomics Workbench ID: 127839
• ChEMBL ID: CHEMBL2287714
• Mol file: 25394-57-4.mol

Synonyms:(2E,6Z,8E)-N-isobutyl-2,6,8-decatrienamid;affinin;N-isobutyl-2E-decenamide;spilanthol

Chemical Property of Spilanthol

Chemical Property:

• Vapor Pressure: 4.02E-06mmHg at 25°C
• Melting Point: 26 °C
• Refractive Index: nD25 1.5134
• Boiling Point: 384.7°C at 760 mmHg
• PKA: 15.07±0.46(Predicted)
• Flash Point: 234°C
• PSA: 29.10000
• Density: 0.896g/cm³
• LogP: 3.61820
• Storage Temp.: Amber Vial, -86°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 7
• Exact Mass: 221.177964357
• Heavy Atom Count: 16
• Complexity: 262

Purity/Quality:

98%,99%, ^*data from raw suppliers

SpilantholAmixtureof(2E,6Z,8E)>80%;(2E,6E,8E);and(2E,6Z,8Z) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC=CCCC=CC(=O)NCC(C)C
• Isomeric SMILES: C/C=C/C=C\CC/C=C/C(=O)NCC(C)C
• Uses: Spilanthol is a fatty acid amide isolated from Acmella oleracea. Spilanthol extract has been discovered to aid in saliva stimulation (sialogogue) for people suffering from dry mouth (xerostomia).

Technology Process of Spilanthol

There total 24 articles about Spilanthol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

(2E,6Z,8E)-9-Bromo-nona-2,6,8-trienoic acid isobutyl-amide + methylzinc chloride (5158-46-3) → spilanthol (504-48-3,76361-77-8,25394-57-4)

Guidance literature:

palladium diacetate; In tetrahydrofuran;

DOI:10.1021/jo980440x

Reference yield: 61.0%

(Z,E)-4,6-octadienal (95404-20-9) + isobutyl triphenylphosphonium acetamide (62826-50-0) → spilanthol (504-48-3,76361-77-8,25394-57-4)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃; for 0.166667h;

DOI:10.1016/S0040-4039(01)81556-2

Reference yield: 18.0%

(Z,E)-4,6-octadienal (95404-20-9) + [2-[(2-methylpropyl)amino]-2-oxoethyl]triphenylphosphonium bromide (110890-35-2) → spilanthol (504-48-3,76361-77-8,25394-57-4) + N-isobutyl-3,6,8-decatrienoylamide (110890-36-3)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃; for 0.166667h; Yield given;

DOI:10.1016/S0040-4020(01)90007-9

upstream raw materials:

(2E,8E)-N-isobutyldeca-2,8-dien-6-ynamide

(Z,E)-4,6-octadienal

isobutyl triphenylphosphonium acetamide

[2-[(2-methylpropyl)amino]-2-oxoethyl]triphenylphosphonium bromide

Refernces

• 1、 Alonso, Isabella G.,Yamane, Lais T.,de Freitas-Blanco, Ver?nica S.,Novaes, Luiz F.T.,Franz-Montan, Michelle,de Paula, Eneida,Rodrigues, Marili V.N.,Rodrigues, Rodney A.F.,Pastre, Julio C.. "A new approach for the total synthesis of spilanthol and analogue with improved anesthetic activity". . p. 5192 - 5199. Retrieved 2018/07/06.
• 2、 Ikeda, Yoshihiko,Ukai, Junzo,Ikeda, Nobuo,Yamamoto, Hisashi. "Stereoselective Synthesis of 1,4-Disubstituted 1,3-Diene from Aldehyde Using Organotitanium Reagent". . p. 731 - 742. Retrieved 2007/10/02.