1268720-28-0

Basic information

• Product Name: 7(R)-Maresin 1
• Synonyms: 7(R)-Maresin 1;Maresin 1;7(R)-Maresin 1 Exclusive;HLHYXXBCQOUTGK-FHCQLJOMSA-N
• CAS NO: 1268720-28-0
• Molecular Formula: C22H32O4
• Molecular Weight: 360.48708
• Mol File: 1268720-28-0.mol

Chemical Properties

• Boiling Point: 559.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.048±0.06 g/cm3(Predicted)
• PKA: 4.58±0.10(Predicted)
• CAS DataBase Reference: 7(R)-Maresin 1(CAS DataBase Reference)
• NIST Chemistry Reference: 7(R)-Maresin 1(1268720-28-0)
• EPA Substance Registry System: 7(R)-Maresin 1(1268720-28-0)

Safety Data

• Hazardous Substances Data: 1268720-28-0(Hazardous Substances Data)

Upstream product

• 168295-33-8 (2E,4E)-5-bromopenta-2,4-dienal 
• 475145-69-8 (R,4E,6E)-7-bromo-3-hydroxy-1-((S)-4-isopropyl-2-thioxothiazolidin-3-yl)hepta-4,6-dien-1-one 
• 42824-16-8 pyridine-SO₃ complex 
• 909251-70-3 (R,4E,6E)-7-bromo-3-((tert-butyldimethylsilyl)oxy)-1-((S)-4-isopropyl-2-thioxothiazolidin-3-yl)hepta-4,6-dien-1-one 
• 909251-71-4 (3R,4E,6E)-7-bromo-3-((tert-butyldimethylsilyl)oxy)hepta-4,6-dienal 
• 810668-40-7 oct-7-en-4-ynoic acid methyl ester 
• 810668-41-8 6-oxiranyl-hex-4-ynoic acid methyl ester 
• 160812-22-6 oct-7-en-4-yn-1-ol 
• 810668-39-4 oct-7-en-4-ynoic acid 
• 86795-44-0 3,4-O-isopropylidene-2-deoxy-D-ribose 
• 5390-04-5 pent-1-yn-5-ol 
• 22900-10-3 2-deoxy-D-ribose 
• 1391043-16-5 C₂₉H₄₆O₄Si 
• 1391043-17-6 C₂₃H₃₂O₄ 

Relevant articles and documents

Total synthesis of the macrophage derived anti-inflammatory lipid mediator Maresin 1

The total synthesis of Maresin 1, an endogenous macrophage pro-resolving lipid mediator derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-group at C7 was obtained via a Jacobsen hydrolytic kinetic resolution of a terminal epoxide whereas the center at C14 arises from a chiral pool strategy starting from 2-deoxy-d-ribose. Pd0/CuI Sonogashira coupling of the two key fragments and Zn(Cu/Ag) reduction completed the total synthesis of Maresin 1.

Stereoselective synthesis of maresin 1

Maresin 1 is a potent anti-inflammatory and pro-resolving lipid mediator derived from docosahexaenoic acid. The total synthesis of maresin 1 is achieved in 10 steps and in 7% overall yield. The Evans-Nagao aldol reaction between (2E,4E)-5-bromopenta-2,4-dienal and different chiral auxiliaries is investigated. The reported synthesis is efficient and highly stereoselective, affording multi-milligram quantities of this biologically interesting lipid mediator.

Total synthesis and bioactivities of two proposed structures of maresin

Maresin is a potent anti-inflammatory lipid mediator derived from docosahexaenoic acid (DHA). A highly convergent total synthesis of two proposed structures of C7-epimeric maresins from the four known fragments was achieved in 17 steps. The three key coupling reactions were the BF3-mediated alkyne attack on the epoxide, chiral titanium complex-promoted enantioselective alkyne addition to the aldehyde, and a Julia-Kocienski olefination. The two synthesized diastereomers were found to be comparably active in blocking neutrophil infiltration in the acute peritonitis model. Copyright