660430-03-5

Usage

Uses

Used in Pharmaceutical Industry:
4,7,11,13,15,19-Docosahexaenoic acid, 10,17-dihydroxy-, (4Z,7Z,11E,13E,15Z,17S,19Z)is used as an anti-inflammatory agent for its potent anti-inflammatory properties. It increases phagocytosis of apoptotic polymorphonuclear leukocytes (PMNs) by macrophages in a non-phlogistic manner, promoting the resolution of inflammation.
Used in Immunology Research:
In the field of immunology, 4,7,11,13,15,19-Docosahexaenoic acid, 10,17-dihydroxy-, (4Z,7Z,11E,13E,15Z,17S,19Z)is used as a research tool to study the mechanisms of inflammation resolution and the role of specialized pro-resolving mediators in the immune system.
Used in Inflammation Treatment:
4,7,11,13,15,19-Docosahexaenoic acid, 10,17-dihydroxy-, (4Z,7Z,11E,13E,15Z,17S,19Z)is used as a therapeutic agent for treating various inflammatory conditions. It has been shown to decrease PMN infiltration in a zymosan-induced mouse model of inflammation and inhibit increases in neutrophil counts in bronchoalveolar fluid (BALF) and lung myeloperoxidase activity in a mouse model of pulmonary injury and inflammation induced by intratracheal LPS instillation.
Used in Drug Delivery Systems:
Similar to gallotannin, novel drug delivery systems could be developed to enhance the applications and efficacy of 4,7,11,13,15,19-Docosahexaenoic acid, 10,17-dihydroxy-, (4Z,7Z,11E,13E,15Z,17S,19Z)against inflammatory conditions. Various organic and metallic nanoparticles could be employed as carriers for 4,7,11,13,15,19-Docosahexaenoic acid, 10,17-dihydroxy-, (4Z,7Z,11E,13E,15Z,17S,19Z)-, aiming to improve its delivery, bioavailability, and therapeutic outcomes.

Upstream product

• 1311298-08-4 C₂₈H₃₇IO₂Si 
• 1311298-09-5 C₂₉H₃₇IO₃Si 
• 1311297-97-8 C₁₃H₁₉IO₃ 
• 120891-49-8 C₁₃H₂₄O₂Si 
• 127268-90-0 C₁₅H₂₈O₂Si 
• 1311298-12-0 C₈H₁₁BrO 
• 1311298-13-1 C₁₄H₂₅BrOSi 
• 1311298-14-2 C₁₉H₃₄OSi₂ 
• 1311298-15-3 C₁₉H₃₆OSi₂ 
• 1311298-16-4 tert-butyl[((S,3Z,7Z)-deca-3,7-dien-1-yn-5-yl)oxy]dimethylsilane 
• 1311297-96-7 C₂₆H₅₁BOSi 
• 934005-36-4 methyl (4Z,7Z,10R,11E,13E,15Z,17S,19Z)-10,17-dihydroxydocosa-4,7,11,13,15,19-hexaenoate 
• 192438-81-6 (E)-1-Trimethylsilanyl-hex-1-en-5-yn-3-ol 
• 42824-16-8 pyridine-SO₃ complex 

Relevant academic research and scientific papers

Synthesis of the 16S,17S-Epoxyprotectin Intermediate in the Biosynthesis of Protectins by Human Macrophages

The n-3 polyunsaturated fatty acids act as substrates during the resolution phase of acute inflammation for the biosynthesis of specialized pro-resolving lipid mediators. One premier example is the C22-dihydroxy-polyunsaturated fatty acid protectin D1 (1). The human 15-lipoxygenase type I, via stereoselective processes and with docosahexaenoic acid as the substrate, enables the formation of this specialized pro-resolving lipid mediator. Herein, based on results from LC/MS-MS metabololipidomics, support is presented for the apprehended biosynthesis of 1 in human macrophages occurring via the intermediate 16S,17S-epoxyprotectin (5). Stereochemically pure 5 was obtained using the Katsuki-Sharpless epoxidation protocol, establishing the chirality at the C16 and C17 atoms, one Z-selective reduction, and E- and Z-stereoselective Wittig reactions. In addition, information on the nonenzymatic aqueous hydrolysis products and the half-life of 16S,17S-epoxyprotectin (5) is presented.

Total synthesis of the potent anti-inflammatory lipid mediator Protectin D1

The total synthesis of the potent anti-inflammatory lipid mediator Protectin D1 derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C10 and C17 were obtained via a chiral pool strategy from (4R)-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane and 3,4-O-isopropylidene-2-deoxy-d-ribose, respectively. Wittig reactions, Takai olefination, Pd0/CuISonogashira coupling, and Zn(Cu/Ag) reduction completed the total synthesis of Protectin D1.

Stereoselective synthesis of protectin D1: A potent anti-inflammatory and proresolving lipid mediator

A convergent stereoselective synthesis of the potent anti-inflammatory, proresolving and neuroprotective lipid mediator protectin D1 (2) has been achieved in 15% yield over eight steps. The key features were a stereocontrolled Evans-aldol reaction with Nagao's chiral auxiliary and a highly selective Lindlar reduction of internal alkyne 23, allowing the sensitive conjugated E,E,Z-triene to be introduced late in the preparation of 2. The UV and LC/MS-MS data of synthetic protectin D1 (2) matched those obtained from endogenously produced material.

Total synthesis of the antiinflammatory and proresolving protectin D1

Stereoselective total synthesis of protectin D1 was completed through construction of the Z,E,E-triene structure by using the Suzuki coupling between the vinyl borane (C13-C22) and the vinyl iodide (C1-C12). The Z-enyne, the acetylene precursor of the vinyl borane was synthesized from optically active γ-TMS allylic alcohol in a straightforward way. On the other hand, the vinyl iodide was prepared by using Wittig reaction between the C8-C12 aldehyde possessing the requisite iodo-olefin moiety and the C1-C7 phosphonium iodide.