(5Z,7S,8E,10Z,13Z,15E,17S,19Z)-7,17-dihydroxydocosa-5,8,10,13,15,19-hexaenoic acid

Base Information

• Chemical Name: (5Z,7S,8E,10Z,13Z,15E,17S,19Z)-7,17-dihydroxydocosa-5,8,10,13,15,19-hexaenoic acid
• CAS No.: 578008-43-2
• Molecular Formula: C22H32O4
• Molecular Weight: 360.49
• Mol file: 578008-43-2.mol

Synonyms:

Chemical Property of (5Z,7S,8E,10Z,13Z,15E,17S,19Z)-7,17-dihydroxydocosa-5,8,10,13,15,19-hexaenoic acid

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

7(S),17(S)-ResolvinD5 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Resolvins are a family of potent lipid mediators derived from both eicosapentaenoic acid (EPA; ) and docosahexaenoic acid (DHA; ). In addition to being anti-inflammatory, resolvins promote the resolution of the inflammatory response back to a non-inflamed state. Resolvins are a family of potent lipid mediators derived from both eicosapentaenoic acid (EPA; ) and docosahexaenoic acid (DHA; ). In addition to being anti-inflammatory, resolvins promote the resolution of the inflammatory response back to a non-inflamed state. Resolvin D5 (RvD5) is a DHA-derived resolvin generated by a double dioxygenation mechanism. RvD5 has been identified in media from ionophore-stimulated trout brain cells, in human synovial fluid from patients with rheumatoid arthritis, and in exudates of bacterial infections in mice. RvD5 stimulates the phagocytosis of E. coli by human macrophages, and RvD5 methyl ester enhances bacterial killing in mice inoculated with E. coli. Analytical and biological comparisons of synthetic RvD5 with endogenously derived RvD5 have confirmed its identity as matching the natural product.
• Uses: 7(S),17(S)-Resolvin D5 is a docosahexaenoic acid (D494500), which is a ω-3 fatty acid that is found in the brain, synapses, and retina. It also exhibits anti-inflammatory activity.

Technology Process of (5Z,7S,8E,10Z,13Z,15E,17S,19Z)-7,17-dihydroxydocosa-5,8,10,13,15,19-hexaenoic acid

There total 52 articles about (5Z,7S,8E,10Z,13Z,15E,17S,19Z)-7,17-dihydroxydocosa-5,8,10,13,15,19-hexaenoic acid 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: 75.0%

C37H42O6 (853929-65-4) → 7(S),17(S)-resolvin D5 (578008-43-2)

Guidance literature:

With Candida rugosa (EC 3.1.1.3, type VII) lipase; sodium chloride; calcium chloride; In tetrahydrofuran; water;

DOI:10.1016/j.tetlet.2005.03.175

Reference yield: 45.0%

methyl (4Z,7S,8E,10Z,13Z,15E,17S,19Z)-7,17-dihydroxydocosa-4,8,10,13,15,19-hexaenoate → 7(S),17(S)-resolvin D5 (578008-43-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 1.5h;

DOI:10.1021/acs.joc.6b02870

Reference yield:

docosahexaenoic acid (6217-54-5) → (±)-(4Z,7Z,10Z,13Z,15E,19Z)-17-hydroxydocosa-4,7,10,13,15,19-hexaenoic acid (90780-52-2) + 7,17-dihydroxy DHA (887752-07-0,578008-43-2) + 10,17-dihydroxy DHA (887752-08-1)

Guidance literature:

docosahexaenoic acid; With water; 15-lipoxygenase; at 4 ℃; for 0.5h; pH=9.0; Enzymatic reaction; Aqueous sodium borate buffer;

With sodium tetrahydroborate; In water;

upstream raw materials:

C₃₇H₄₂O₆

(S)-1-Benzyloxy-hept-4-yn-2-ol

Benzoic acid (Z)-(S)-1-hydroxymethyl-hex-3-enyl ester

Benzoic acid (Z)-(S)-1-formyl-6-methoxycarbonyl-hex-3-enyl ester