578008-43-2

Basic information

• Product Name: (5Z,7S,8E,10Z,13Z,15E,17S,19Z)-7,17-dihydroxydocosa-5,8,10,13,15,19-hexaenoic acid
• Synonyms: (5Z,7S,8E,10Z,13Z,15E,17S,19Z)-7,17-dihydroxydocosa-5,8,10,13,15,19-hexaenoic acid;Resolvin D5
• CAS NO: 578008-43-2
• Molecular Formula: C22H32O4
• Molecular Weight: 360.48708
• Mol File: 578008-43-2.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (5Z,7S,8E,10Z,13Z,15E,17S,19Z)-7,17-dihydroxydocosa-5,8,10,13,15,19-hexaenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (5Z,7S,8E,10Z,13Z,15E,17S,19Z)-7,17-dihydroxydocosa-5,8,10,13,15,19-hexaenoic acid(578008-43-2)
• EPA Substance Registry System: (5Z,7S,8E,10Z,13Z,15E,17S,19Z)-7,17-dihydroxydocosa-5,8,10,13,15,19-hexaenoic acid(578008-43-2)

Safety Data

• Hazardous Substances Data: 578008-43-2(Hazardous Substances Data)

Usage

Description

(5Z,7S,8E,10Z,13Z,15E,17S,19Z)-7,17-dihydroxydocosa-5,8,10,13,15,19-hexaenoic acid, also known as Resolvin D5 (RvD5), is a potent lipid mediator derived from docosahexaenoic acid (DHA), a type of ω-3 fatty acid. It is found in the brain, synapses, and retina and exhibits anti-inflammatory activity. Resolvin D5 is a member of the resolvin family, which promotes the resolution of the inflammatory response back to a non-inflamed state. RvD5 is generated by a double dioxygenation mechanism and has been identified in various sources, including ionophore-stimulated trout brain cells, human synovial fluid from patients with rheumatoid arthritis, and exudates of bacterial infections in mice.

Uses

Used in Pharmaceutical Applications:
Resolvin D5 is used as an anti-inflammatory agent for its ability to reduce inflammation and promote the resolution of the inflammatory response back to a non-inflamed state. It has potential applications in the treatment of various inflammatory diseases and conditions.
Used in Immunological Applications:
Resolvin D5 is used as an immunomodulatory agent due to its ability to stimulate the phagocytosis of E. coli by human macrophages and enhance bacterial killing in mice inoculated with E. coli. This suggests its potential use in boosting the immune response against bacterial infections.
Used in Neurological Applications:
As Resolvin D5 is found in the brain and synapses, it is used as a neuroprotective agent for its potential role in maintaining brain health and function.
Used in Ophthalmological Applications:
Given its presence in the retina, Resolvin D5 is used as a protective agent for maintaining retinal health and potentially treating retinal diseases.
Used in Research Applications:
Resolvin D5 is used as a research tool for studying the mechanisms of inflammation resolution and the role of ω-3 fatty acids in various biological processes.

Upstream product

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Relevant articles and documents

Total Synthesis of Resolvin D5

Resolvin D5 (RvD5) is a metabolite of docosahexanoic acid with anti-inflammatory activity that has not yet been thoroughly investigated because of its low biological availability. A synthetic route to optically active RvD5 was developed by assembling the C1-C10 aldehyde, C11-C13 phosphonium salt, and C14-C22 aldehyde building blocks. The aldehyde fragments were prepared by Sharpless asymmetric epoxidation of corresponding racemic (E)-1-TMS-1-alken-3-ols followed by reaction of the TBS ethers of the resulting epoxy alcohols with Et2AlCN and DIBAL reduction of the (E)-1-cyano-1-alken-3-ol derivatives. The C14-C22 aldehyde was connected with the C11-C13 fragment, i.e., [TBSO(CH2)3PPh3]+ Br-, by Wittig reaction. The resulting C11-C22 intermediate was converted to the phosphonium salt, which was attached to the C1-C10 aldehyde by Wittig reaction to yield the structure of RvD5.

USE OF RESOLVINS TO TREAT GASTROINTESTINAL DISEASES

The present invention is generally drawn to novel isolated therapeutic agents, termed resolvins, generated from the interaction between a dietary omega-3 polyunsaturated fatty acid (PUFA) such as eicosapentaenoic acid (EPA) or docosahexaenoic acid (DHA), oxygenases and the analgesic aspirin (ASA). Surprisingly, careful isolation of compounds generated from the combination of components in an appropriate environment provide di- and tri-hydroxy containing derivatives of EPA and DHA containing compounds having unique structural and physiological properties. The present invention therefore provides for many new useful therapeutic di- and tri-hydroxy derivatives of EPA or DHA (resolvins of the E series and D series) that diminish, prevent, or eliminate gastrointestinal conditions, for example, such as colitis. The present invention also provides methods of use, methods of preparation, and packaged pharmaceuticals for use as medicaments for the compounds disclosed throughout the specification.

First total synthesis of 7(S),17(S)-Resolvin D5, a potent anti-inflammatory docosanoid

The first total synthesis of 7(S),17(S)-Resolvin D5, a lipid mediator derived from docosahexaenoic acid, has been achieved. The chiral centers were generated via a Co-salen hydrolytic kinetic resolution of a terminal epoxide with >99% ee. Key steps include Takai olefination, Pd0/Cu I coupling and simultaneous deprotection and ester cleavage with lipase from Candida rugosa.