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

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

• 6372-02-7 (E)-3-iodoacrylic acid 
• 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 
• 124-38-9 carbon dioxide 
• 74-86-2 acetylene 
• 513-35-9 2-methyl-but-2-ene 
• 3913-81-3 (E)-2-decenal 
• 55976-13-1 (E)-undeca-1,4-diene 
• 24738-46-3 methyl (E,E)-dodeca-2,4-dienoate 

Downstream Products

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

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differences were observed between analogues in which either of the two methoxy substituents in the head group had been replaced by the same bulkier alkoxy group.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.

Concise Chemoenzymatic Total Synthesis and Identification of Cellular Targets of Cepafungin I

Amatuni et al. established a concise chemoenzymatic synthesis of cepafungin I. The route enabled access to a chemoproteomic probe, revealing high selectivity for proteasome subunits β5/2. Potent inhibition was associated with the macrocyclic hydroxyl group and lipid tail. Cepafungin I exhibited similar mode of action with the clinical drug bortezomib. The natural product cepafungin I was recently reported to be one of the most potent covalent inhibitors of the 20S proteasome core particle through a series of in vitro activity assays. Here, we report a short chemoenzymatic total synthesis of cepafungin I featuring the use of a regioselective enzymatic oxidation to prepare a key hydroxylated amino acid building block in a scalable fashion. The strategy developed herein enabled access to a chemoproteomic probe, which in turn revealed the exceptional selectivity and potency of cepafungin I toward the β2 and β5 subunits of the proteasome. Further structure-activity relationship studies suggest the key role of the hydroxyl group in the macrocycle and the identity of the lipid tail in modulating the potency of this natural product family. This study lays the groundwork for further medicinal chemistry exploration to fully realize the anticancer potential of cepafungin I.

ALKAMIDE COMPOUNDS AND USES THEREOF

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

Inhibitor of endocannabinoid cellular reuptake

Provided is a highly potent and selective endocannabioid cellular reuptake inhibitor represented by formula (I): or a pharmaceutically acceptable solvate or co-crystal thereof as well as to a formulation comprising this inhibitor, and to methods of treatment in which this inhibitor is used.

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.

Synthesis and biological evaluation of a series of fatty acid amides from Echinacea

Abstract Alkylamides are lipophilic constituents of Echinacea and possess numerous biological activities. Although significant effort has been focused on the study of crude Echinacea extracts, very little is known regarding the activities of the individual constituents that make up these herbal treatments. Herein we explore the SAR of simple alkylamides found in Echinacea extracts with respect to their ability to decrease the production of the pro-inflammatory mediator TNF-α. Our results have revealed the key structural requirements for activity and provide lead compounds for further investigation of these poorly understood molecules.

DODECA-2E,4E-DIENE AMIDES AND THEIR USE AS MEDICAMENTS AND COSMETICS

The present invention relates to a novel class of compounds, namely dodeca-2E, 4E-diem amides and their use a medicament, preferably as a dermatologic agent, and as a cosmetic:. These novel compounds are particularly useful in treating and/or preventing inflammation, irritation, itching, pruritus, pain, oedema and/or pro-allergic or allergic conditions in a patient. Usually they are topically applied to the skin or mucosa in the form of a pharmaceutical or cosmetic composition comprising the compound and a pharmaceutically and/or cosmetically acceptable carrier.

NOVEL 1,3-BENZOXAZOL-2(3H)-ONES AND THEIR USE AS MEDICAMENTS AND COSMETICS

The present invention relates to a novel class of 1,3-benzoxazol-2(3H) -ones of formula (1) and their use as a medicament, preferably as a dermatologic agent, and as a cosmetic. These novel compounds are particularly useful in treating and/or preventing inflammation, irritation, itching, pruritus, pain, oedema and/or pro-allergic or allergic conditions in a patient. Usually they are topically applied to the skin or mucosa in the form of a pharmaceutical or cosmetic composition comprising the compound and a pharmaceutically and/or cosmetically acceptable carrier.

The natural product hybrid of Syringolin A and Glidobactin A synergizes proteasome inhibition potency with subsite selectivity

The preparation of a Syringolin A/Glidobactin A hybrid (SylA-GlbA) consisting of a SylA macrocycle connected to the GlbA side chain and its potent proteasome targeting of all three proteasomal subsites is reported. The influence of the syrbactin macrocycle moiety on subsite selectivity is demonstrated.

A synthetic approach to natural dienamides of insecticidal interest

An efficient synthesis of dienamides of insecticidal interest has been stereoselectively achieved featuring a Stille cross-coupling reaction as the key step.