2,4-Dodecadienamide, N-(2-methylpropyl)-, (2E,4E)-

Base Information

• Chemical Name: 2,4-Dodecadienamide, N-(2-methylpropyl)-, (2E,4E)-
• CAS No.: 24738-51-0
• Molecular Formula: C₁₆H₂₉NO
• Molecular Weight: 251.412
• UNII: 5F4WO3BVS9
• DSSTox Substance ID: DTXSID801346924
• Nikkaji Number: J510.103D,J593.559H
• Wikidata: Q27138440
• Pharos Ligand ID: 5CTUH3U2U5ML
• Metabolomics Workbench ID: 133930
• ChEMBL ID: CHEMBL426912
• Mol file: 24738-51-0.mol

Synonyms:24738-51-0;2,4-Dodecadienamide, N-(2-methylpropyl)-, (2E,4E)-;dodeca-2E,4E-dienoic acid isobutylamide;(2E,4E)-N-(2-methylpropyl)dodeca-2,4-dienamide;N-isobutyl-(2E,4E)-dodecadienamide;N-Isobutyldodeca-trans-2,4-dienamide;UNII-5F4WO3BVS9;5F4WO3BVS9;(2e,4e)-n-isobutyldodeca-2,4-dienamide;CHEMBL426912;CHEBI:70101;Dodecatetraenoic acid isobutylamide, (2E,4E)-;N-Isobutyl-(2E,4E)-dodeca-2,4-dienamide;(2E,4E)-dodecatetraenoic acid isobutylamide;DODECA-2(E),4(E)-DIENOIC ACID ISOBUTYLAMIDE(P);Kalecide;D0EC6B;SCHEMBL2262688;BBRMJCAPNGJKEM-AQASXUMVSA-N;DTXSID801346924;2,4-Dodecadienoic acid isobutylamide;BDBM50212599;2,4-(E,E)-Dodecadienoylisobutylamide;AKOS040735216;(E,E)-N-Isobutyl-2,4-dodecadienamide;N-(2-Methylpropyl)-2,4-dodecadienamide;(2E,4E)-N-Isobutyl-2,4-dodecadienamide;N-Isobutyl-(2E,4E-dodeca-2,4-dienamide;2,4-Dodecadienamide, N-isobutyl-, (E,E)-;(2E,4E)-N-(2-Methylpropyl)-2,4-dodecadienamide;2,4-Dodecadienamide, N-(2-methylpropyl)-, (E,E)-;Q27138440

Chemical Property of 2,4-Dodecadienamide, N-(2-methylpropyl)-, (2E,4E)-

Chemical Property:

• Vapor Pressure: 1.65E-06mmHg at 25°C
• Boiling Point: 396.9°Cat760mmHg
• Flash Point: 244.2°C
• PSA: 32.59000
• Density: 0.878g/cm³
• LogP: 5.07180
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to 25 mg/ml) on in Ethanol (up to 25 mg/ml)
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 10
• Exact Mass: 251.224914549
• Heavy Atom Count: 18
• Complexity: 254

Purity/Quality:

98% ^*data from raw suppliers

Kalecide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCC=CC=CC(=O)NCC(C)C
• Isomeric SMILES: CCCCCCC/C=C/C=C/C(=O)NCC(C)C
• Description: Dienamide A2 (24738-51-0) is an analog of the natural amides occurring in Echinacea which represent a new class of cannabinomimetic compounds. This class of compounds modulates TNFα mRNA expression in human monocytes/macrophages via the CB2 receptor.1?Dienamide A2 binds to cannabinoid receptors with greater affinity than endogenous cannabinoids (Ki= ~60 and >1500 nM for CB2 and CB1 respectively)2. It elevates intracellular Ca2+ levels in CB2-positive? but not in CB2-negative cells and this effect was blocked by SR144528.2??It significantly inhibits LPS-induced TNFα and IL-1β expression in a CB2-independent manner.2
• Uses: Kalecide is a natural pesticide of Echinacea angustifolia, Echinacea atrorubens and Piper sarmentosum.

Technology Process of 2,4-Dodecadienamide, N-(2-methylpropyl)-, (2E,4E)-

There total 17 articles about 2,4-Dodecadienamide, N-(2-methylpropyl)-, (2E,4E)- 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: 66.0%

(E)-2-decenal (3913-81-3) + 2-N-iso-butyl-2-oxoethyl phosphonium chloride (18498-20-9) → (2E,4E)-N-isobutyldodeca-2,4-dienamide (24738-51-0) + dodeca-2Z,4E-dienoic acid isobutylamide

Guidance literature:

2-N-iso-butyl-2-oxoethyl phosphonium chloride; With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 0.5h;

(E)-2-decenal; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1021/jo200289f

Reference yield: 61.0%

(E)-2-decenal (3913-81-3) + [2-[(2-methylpropyl)amino]-2-oxoethyl]triphenylphosphonium bromide (110890-35-2) → (2E,4E)-N-isobutyldodeca-2,4-dienamide (24738-51-0)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; diethyl ether; for 2h;

DOI:10.3390/10101242

Reference yield: 51.0%

isobutylamine (78-81-9) + (2E,4E)-dodeca-2,4-dien-1-ol (18485-38-6) → (2E,4E)-N-isobutyldodeca-2,4-dienamide (24738-51-0)

Guidance literature:

With manganese(IV) oxide; sodium cyanide; In hexane; at 0 ℃; for 5h;

DOI:10.1055/s-2003-39163

upstream raw materials:

2,4-dodecadienoic acid

isobutylamine

(2E,4E)-dodeca-2,4-dienoyl chloride

(2E,4E)-dodeca-2,4-dien-1-ol