24738-48-5

Basic information

• Product Name: DODECA-2(E),4(E)-DIENOIC ACID(SG)
• Synonyms: DODECA-2(E),4(E)-DIENOIC ACID(SG)
• CAS NO: 24738-48-5
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.286
• Mol File: 24738-48-5.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• CAS DataBase Reference: DODECA-2(E),4(E)-DIENOIC ACID(SG)(CAS DataBase Reference)
• NIST Chemistry Reference: DODECA-2(E),4(E)-DIENOIC ACID(SG)(24738-48-5)
• EPA Substance Registry System: DODECA-2(E),4(E)-DIENOIC ACID(SG)(24738-48-5)

Safety Data

• Hazardous Substances Data: 24738-48-5(Hazardous Substances Data)

Upstream product

• 24738-46-3 methyl (E,E)-dodeca-2,4-dienoate 
• 6372-02-7 (E)-3-iodoacrylic acid 
• 55976-13-1 (E)-undeca-1,4-diene 
• 124-38-9 carbon dioxide 
• 3913-81-3 (E)-2-decenal 
• 124-13-0 Octanal 
• 39924-20-4 (2E,4E)-dodecadien-2,4-oic acid ethyl ester 
• 18485-38-6 (2E,4E)-dodeca-2,4-dien-1-ol 
• 21662-16-8 trans,trans-2,4-dodecadienal 
• 513-35-9 2-methyl-but-2-ene 
• 74-86-2 acetylene 

Downstream Products

• 24738-53-2 dodeca-2E,4E-dienoic acid 4-hydroxy-2-phenylethylamide 
• 24738-51-0 (2E,4E)-N-isobutyldodeca-2,4-dienamide 
• 2108100-73-6 (2E,4E)-N-[2-(3,4-dimethoxyphenyl)ethyl]dodeca-2,4-dienamide 
• 108351-50-4 glidobactin A 

Relevant articles and documents

Synthesis and Biological Evaluation of Endocannabinoid Uptake Inhibitors Derived from WOBE437

WOBE437 ((2E,4E)-N-(3,4-dimethoxyphenethyl)dodeca-2,4-dienamide, 1) is a natural product-derived, highly potent inhibitor of endocannabinoid reuptake. In this study, we synthesized almost 80 analogues of 1 with different types of modifications in the dodecadienoyl domain as well as the dimethoxyphenylethyl head group, and we investigated their effects on anandamide uptake into U937 cells. Intriguingly, none of these analogues was a more potent inhibitor of anandamide uptake than WOBE437 (1). At the same time, a number of WOBE437 variants exhibited potencies in the sub-100 nM range, with high selectivity over inhibition of the endocannabinoid-degrading enzyme fatty acid amide hydrolase; two compounds were virtually equipotent with 1. Interestingly, profound activity differences were observed between analogues in which either of the two methoxy substituents in the head group had been replaced by the same bulkier alkoxy group. Some of the compounds described here could be interesting departure points for the development of potent endocannabinoid uptake inhibitors with more drug-like properties.

ALKAMIDE COMPOUNDS AND USES THEREOF

The present disclosure relates to alkamide compounds and compositions for treating allergic diseases, pain, or itch.

An unprecedented medium-chain diunsaturated n-acylhomoserine lactone from marine roseobacter group bacteria

N-acylhomoserine lactones (AHLs), bacterial signaling compounds involved in quorum-sensing, are a structurally diverse group of compounds. We describe here the identification, synthesis, occurrence and biological activity of a new AHL, N-((2E,5Z)-2,5-dodecadienoyl)homoserine lactone (11) and its isomer N-((3E,5Z)-3,5-dodecadienoyl)homoserine lactone (13), occurring in several Roseobacter group bacteria (Rhodobacteraceae). The analysis of 26 strains revealed the presence of 11 and 13 in six of them originating from the surface of the macroalgae Fucus spiralis or sediments from the North Sea. In addition, 18 other AHLs were detected in 12 strains. Compound identification was performed by GC/MS. Mass spectral analysis revealed a diunsaturated C12 homoserine lactone as structural element of the new AHL. Synthesis of three likely candidate compounds, 11, 13 and N-((2E,4E)-2,4-dodecadienoyl)homoserine lactone (5), revealed the former to be the natural AHLs. Bioactivity test with quorum-sensing reporter strains showed high activity of all three compounds. Therefore, the configuration and stereochemistry of the double bonds in the acyl chain seemed to be unimportant for the activity, although the chains have largely different shapes, solely the chain length determining activity. In combination with previous results with other Roseobacter group bacteria, we could show that there is wide variance between AHL composition within the strains. Furthermore, no association of certain AHLs with different habitats like macroalgal surfaces or sediment could be detected.