171030-11-8

Basic information

• Product Name: (5S,6R,15R)-5,6,15-TRIHYDROXY-7,9,13-TRANS-11-CIS-EICOSATETRAENOIC ACID
• Synonyms: 15(R)-LXA4;(5S,6R,15R)-5,6,15-TRIHYDROXY-7,9,13-TRANS-11-CIS-EICOSATETRAENOIC ACID;ASPIRIN-TRIGGERED LXA4;LXA4-15-EPI;LIPOXIN A4, 15-EPI;5(S),6(R),15(R)-Lipoxin A4;15(R)-Lipoxin A4;IXAQOQZEOGMIQS-JEWNPAEBSA-N
• CAS NO: 171030-11-8
• Molecular Formula: C20H32O5
• Molecular Weight: 352.46508
• Mol File: 171030-11-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 589.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.096±0.06 g/cm3(Predicted)
• Storage Temp.: = -70C
• PKA: 4.67±0.10(Predicted)
• CAS DataBase Reference: (5S,6R,15R)-5,6,15-TRIHYDROXY-7,9,13-TRANS-11-CIS-EICOSATETRAENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (5S,6R,15R)-5,6,15-TRIHYDROXY-7,9,13-TRANS-11-CIS-EICOSATETRAENOIC ACID(171030-11-8)
• EPA Substance Registry System: (5S,6R,15R)-5,6,15-TRIHYDROXY-7,9,13-TRANS-11-CIS-EICOSATETRAENOIC ACID(171030-11-8)

Safety Data

• Hazardous Substances Data: 171030-11-8(Hazardous Substances Data)

Usage

Description

(5S,6R,15R)-5,6,15-TRIHYDROXY-7,9,13-TRANS-11-CIS-EICOSATETRAENOIC ACID, also known as Lipoxin A4, 15-epi, is a bioactive molecule that belongs to the eicosanoid family. It is a lipid mediator derived from arachidonic acid through the action of lipoxygenase enzymes. (5S,6R,15R)-5,6,15-TRIHYDROXY-7,9,13-TRANS-11-CIS-EICOSATETRAENOIC ACID exhibits unique stereochemistry and possesses potent anti-inflammatory and pro-resolving properties. Its structure and bioactivity make it a promising candidate for therapeutic applications in various inflammatory and immune-related disorders.

Uses

Used in Pharmaceutical Industry:
(5S,6R,15R)-5,6,15-TRIHYDROXY-7,9,13-TRANS-11-CIS-EICOSATETRAENOIC ACID is used as an anti-inflammatory agent for its ability to block the release of pro-inflammatory cytokines, such as IL-8. This makes it a potential therapeutic agent for treating inflammatory conditions, such as arthritis, asthma, and inflammatory bowel disease.
Used in Immunomodulation:
(5S,6R,15R)-5,6,15-TRIHYDROXY-7,9,13-TRANS-11-CIS-EICOSATETRAENOIC ACID is used as an immunomodulatory agent for its ability to promote the resolution of inflammation and enhance tissue repair. Its pro-resolving properties make it a promising candidate for the treatment of chronic inflammatory and autoimmune diseases, such as lupus, multiple sclerosis, and rheumatoid arthritis.
Used in Drug Development:
(5S,6R,15R)-5,6,15-TRIHYDROXY-7,9,13-TRANS-11-CIS-EICOSATETRAENOIC ACID is used as a lead compound in drug development for its unique stereochemistry and bioactivity. Researchers are exploring its potential as a template for the design and synthesis of novel analogs with improved pharmacological properties, such as enhanced stability, bioavailability, and target selectivity.
Used in Cosmetic Industry:
(5S,6R,15R)-5,6,15-TRIHYDROXY-7,9,13-TRANS-11-CIS-EICOSATETRAENOIC ACID is used as an anti-aging and skin health ingredient in cosmetic formulations. Its anti-inflammatory and pro-resolving properties can help reduce skin inflammation, promote skin repair, and improve skin appearance by reducing wrinkles and fine lines.

Upstream product

• 94235-57-1 (5S,6R,15S)-(7E,9E,11Z,13E)-5,6-O-carbonyl lipoxin A₄ ethyl ester 
• 94235-42-4 epi-lipoxin A₄ 
• 94235-41-3 4-[(2S,3S)-3-((1E,3E,5Z,7E)-(S)-9-Hydroxy-tetradeca-1,3,5,7-tetraenyl)-oxiranyl]-butyric acid ethyl ester 
• 94235-50-4 (7E,9E,11Z,13E)-(5S,6R,15S)-15-Hydroperoxy-5,6-dihydroxy-icosa-7,9,11,13-tetraenoic acid 
• 97643-35-1 lipoxin A methyl ester 
• 78606-80-1 5(S), 6(R), 7-trihydroxyheptanoic acid methyl ester 
• 76745-15-8 4-((4S,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyric acid methyl ester 
• 102354-82-5 methyl 4-(5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl)butanoate 
• 193410-68-3 (S)-3(E)-decen-1-yn-5-ol 
• 201672-53-9 [(S)-((E)-1-But-1-en-3-ynyl)-hexyloxy]-tert-butyl-dimethyl-silane 
• 201672-48-2 (5S,6R)-7-(2,2-Dimethyl-propionyloxy)-5,6-dihydroxy-heptanoic acid methyl ester 
• 201672-44-8 4-[(4S,5R)-5-((1E,3E)-4-Bromo-buta-1,3-dienyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-butyric acid methyl ester 
• 201672-49-3 4-[(4S,5R)-5-(2,2-Dimethyl-propionyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-butyric acid methyl ester 
• 201672-50-6 4-{(4S,5R)-5-[(1E,3E,7E)-(S)-9-(tert-Butyl-dimethyl-silanyloxy)-tetradeca-1,3,7-trien-5-ynyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester 

Relevant articles and documents

Total synthesis of aspirin-triggered 15-epi-lipoxin A4

The total synthesis of aspirin-triggered 15-epi-LXA4 has been achieved using a chiral pool strategy for the C1-C12 fragment starting from 2-deoxy-D-ribose. Sharpless catalytic AE generated the C15 chiral center with >98% ee. The stereospecific (Z)-reduction of the conjugated trienyne to the tetraene was achieved with Zn(Cu/Ag) in aq. CH3OH at rt.

COMPOSITIONS AND METHODS RELATING TO SALTS OF SPECIALIZED PRO-RESOLVING MEDIATORS OF INFLAMMATION

The present invention relates to compounds of Formulas I-IV, which are salts of special lipid mediators of inflammation, compositions containing same, and methods of using same in the treatment of various diseases and disorders characterized by chronic or excessive inflammation, or both.

SYNTHESIS OF 5S-HYDROXY-14,15 LTA4 A BIOGENIC PRECURSOR TO THE LIPOXINS

A synthesis of 5S-hydroxy-14,15-LTA4 10 an intermediate in the biosynthesis of the lipoxins is described.