97643-35-1

Basic information

• Product Name: 5(S),6(R),15(S)-TRIHETE METHYL ESTER
• Synonyms: 5(S),6(R)-LIPOXIN A4 METHYL ESTER;5(S),6(R),15(S)-TRIHETE METHYL ESTER;5S,6R,15S-TRIHYDROXY-7E,9E,11Z,13E-EICOSATETRAENOIC ACID, METHYL ESTER;Lipoxin A4 Methyl Ester Solution
• CAS NO: 97643-35-1
• Molecular Formula: C₂₁H₃₄O₅
• Molecular Weight: 366.49
• Mol File: 97643-35-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 540.2±50.0 °C(Predicted)
• Flash Point: 10℃ (tag closed test)
• Appearance: /
• Density: 1.056±0.06 g/cm3(Predicted)
• PKA: 13.38±0.20(Predicted)
• CAS DataBase Reference: 5(S),6(R),15(S)-TRIHETE METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 5(S),6(R),15(S)-TRIHETE METHYL ESTER(97643-35-1)
• EPA Substance Registry System: 5(S),6(R),15(S)-TRIHETE METHYL ESTER(97643-35-1)

Safety Data

• Hazardous Substances Data: 97643-35-1(Hazardous Substances Data)

Usage

Description

5(S),6(R),15(S)-TRIHETE METHYL ESTER, also known as Lipoxin A4 methyl ester (LXA4 methyl ester), is a lipid-soluble prodrug formulation of the transcellular metabolite LXA4. LXA4 is a trihydroxy fatty acid containing a conjugated tetraene, produced by the metabolism of 15-HETE or 15-HpETE with human leukocytes. It is equipotent to leukotriene B4 (LTB4) in inducing superoxide generation in human neutrophils at 0.1 μM and is associated with several biological functions, including leukocyte activation, chemotaxis effects, natural killer cell inhibition, and monocyte migration and adhesion.

Uses

Used in Pharmaceutical Industry:
5(S),6(R),15(S)-TRIHETE METHYL ESTER is used as a prodrug formulation for enhancing the lipid solubility and bioavailability of LXA4, allowing for better absorption and distribution in the body. This leads to improved therapeutic outcomes in various inflammatory and immune-related conditions.
Used in Inflammatory Disease Treatment:
5(S),6(R),15(S)-TRIHETE METHYL ESTER is used as an anti-inflammatory agent for the treatment of various inflammatory diseases. Its ability to modulate leukocyte activation, chemotaxis, and other immune functions helps in reducing inflammation and promoting tissue repair.
Used in Immune Regulation:
5(S),6(R),15(S)-TRIHETE METHYL ESTER is used as an immune modulator to regulate the immune response in various conditions. Its effects on natural killer cell inhibition and monocyte migration and adhesion contribute to the fine-tuning of the immune system and prevention of excessive immune reactions.
Used in Drug Delivery Systems:
5(S),6(R),15(S)-TRIHETE METHYL ESTER can be incorporated into drug delivery systems to improve the targeting and efficacy of LXA4 in specific tissues and cells. This can lead to better treatment outcomes and reduced side effects in various therapeutic applications.

Upstream product

• 97643-30-6 (S)-5-{(2S,3S)-3-[(1Z,4Z,6E)-(S)-8-(tert-Butyl-dimethyl-silanyloxy)-trideca-1,4,6-trienyl]-oxiranyl}-5-hydroxy-pentanoic acid methyl ester 
• 97579-44-7 5-{3-[(1Z,4Z,6E)-(S)-8-(tert-Butyl-dimethyl-silanyloxy)-trideca-1,4,6-trienyl]-oxiranyl}-5-hydroxy-pentanoic acid methyl ester 
• 97579-42-5 (6E,8Z,11Z,13E)-(S)-15-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-icosa-6,8,11,13-tetraenoic acid methyl ester 
• 97643-28-2 (5Z,8Z,11Z,13E)-(S)-15-(tert-Butyl-dimethyl-silanyloxy)-icosa-5,8,11,13-tetraenoic acid methyl ester 
• 97579-38-9 (5Z,8Z,11Z,13E)-(S)-15-(tert-Butyl-dimethyl-silanyloxy)-icosa-5,8,11,13-tetraenoic acid 
• 70946-44-0 (5Z,8Z,11Z,13E,15S)-15-hydroxy-5,8,11,13-eicosatetraenoic acid methyl ester 
• 97579-45-8 (7E,9E,11Z,13E)-(5R,6R,15R)-15-(tert-Butyl-dimethyl-silanyloxy)-5,6-bis-trimethylsilanyloxy-icosa-7,9,11,13-tetraenoic acid methyl ester 
• 97579-43-6 (6E,8Z,11Z,13E)-(5S,15S)-15-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-icosa-6,8,11,13-tetraenoic acid methyl ester 
• 97579-41-4 (S)-6-[(1E,3Z,6Z,8E)-(S)-10-(tert-Butyl-dimethyl-silanyloxy)-pentadeca-1,3,6,8-tetraenyl]-tetrahydro-pyran-2-one 
• 127251-13-2 (S)-6-((1E,3Z,6Z,8E)-(S)-10-Hydroxy-pentadeca-1,3,6,8-tetraenyl)-tetrahydro-pyran-2-one 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 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 
• 201672-49-3 4-[(4S,5R)-5-(2,2-Dimethyl-propionyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-butyric 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 

Downstream Products

• 89663-86-5 lipoxin A₄ 
• 94292-80-5 6S-Lipoxin A₄ 
• 94292-86-1 lipoxin A4 

Relevant articles and documents

Stereoselective total synthesis of 5(S), 6(R), 15(S)-trihydroxy-7(E), 9(E), 11(Z), 13(E)-eicosatetraenoic acid (Lipoxin A)

A stereoselective synthesis of the title compound from D-xylose using zinc mediated deoxygenation of 4-hydroxy-2-butenoic acid moiety and base induced double elimination of 4,5-epoxy allyl chloride as key steps is described.

SIMPLE SYNTHESIS AND ASSIGNMENT OF STEREOCHEMISTRY OF LIPOXIN A

A synthesis of lipoxin A, a recently descovered biologically active eicosanoid, and the assignment of stereoformula 1 is reported herein.