87893-55-8

Basic information

• Product Name: 15D-PGJ2
• Synonyms: 15-deoxy-Δ12,14-Prostaglandin J2 Lipid Maps MS Standard;11-Oxoprosta-(5Z,9,12E,14E)-tetraen-1-oic acid;15-Deoxy-Δ12,14-PGJ2;15-deoxy-Δ12,14-Prostaglandin J2 solution;15d-PGJ?;15D-PGJ2;15-DEOXY-DELTA12,14-PROSTAGLANGIN J2;15-DEOXY-DELTA12,DELTA14-PROSTAGLANDIN J2
• CAS NO: 87893-55-8
• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.43
• EINECS: 201-185-2
• Mol File: 87893-55-8.mol

Chemical Properties

• Boiling Point: 495.8 °C at 760 mmHg
• Flash Point: -9℃
• Appearance: /methyl acetate solution
• Density: 1.066 g/cm³
• Vapor Pressure: 3.5E-11mmHg at 25°C
• Refractive Index: 1.557
• Storage Temp.: −20°C
• CAS DataBase Reference: 15D-PGJ2(CAS DataBase Reference)
• NIST Chemistry Reference: 15D-PGJ2(87893-55-8)
• EPA Substance Registry System: 15D-PGJ2(87893-55-8)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/38-66-67-36
• Safety Statements: 16-26-29-33-36/37/39
• RIDADR: UN 1231 3/PG 2
• WGK Germany: 1
• Hazardous Substances Data: 87893-55-8(Hazardous Substances Data)

Usage

Uses

Used in Research Applications:
15D-PGJ2 is used as a research tool to study its effects on lipid accumulation, cell viability, mitochondrial activity, and the amount of vasculature in vascularized adipose tissue models. This helps researchers understand the underlying mechanisms of PPARγ activation and its implications in various biological processes.
Used in Pharmaceutical Industry:
15D-PGJ2 is used as a PPARγ agonist in the development of drugs targeting metabolic disorders, such as diabetes and obesity. By activating the PPARγ pathway, it can potentially improve insulin sensitivity and regulate lipid metabolism, offering therapeutic benefits for patients with these conditions.
Used in Regenerative Medicine:
15D-PGJ2 is used as a supplement in culture medium for induced neural stem/progenitor cells (NSPCs) differentiation. Its role in promoting the differentiation of NSPCs into mature neurons highlights its potential application in regenerative medicine and the treatment of neurodegenerative diseases.
Used in Intestinal Health Applications:
15D-PGJ2 is used to activate the intestinal fatty acid binding protein (I-FABP)-PPARγ pathway, which plays a crucial role in maintaining intestinal health and regulating lipid metabolism. This application can contribute to the development of therapeutic strategies for gastrointestinal disorders and related health issues.

Biological Activity

Selective PPAR γ agonist that induces adipocyte differentiation in C3H10Y1/2 fibroblasts (EC 50 = 7 μ M).

Biochem/physiol Actions

15-Deoxy-Δ12,14-prostaglandin J2 (15d-PGJ2) regulates inflammatory response in vivo. 15d-PGJ2 also elicits PPARγ-independent inhibition of nuclear factor (NF)-κB dependent transcription. It acts as an anti-angiogenic factor and triggers endothelial cell apoptosis.

InChI:InChI=1/C20H28O3/c1-2-3-4-5-6-10-13-18-17(15-16-19(18)21)12-9-7-8-11-14-20(22)23/h6-7,9-10,13,15-17H,2-5,8,11-12,14H2,1H3,(H,22,23)/b9-7-,10-6+,18-13+/t17-/m0/s1

Upstream product

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• 660430-04-6 methyl 2-((1S,4S)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-en-1-yl)acetate 
• 426226-00-8 dimethyl 2-((1R,4S)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-en-1-yl)malonate 
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• 869801-10-5 (1S,4R,2'Z)-4-[7'-(4-methoxybenzyloxy)-2'-heptenyl]-2-cyclopenten-1-ol 
• 869801-19-4 (S,E)-4-((Z)-7-hydroxyhept-2-en-1-yl)-5-((E)-oct-2-en-1-ylidene)cyclopent-2-enone 
• 676236-00-3 (1S,4R,2'Z)-1-[(tert-butyldimethylsilyl)oxy]-4-[7'-(4-methoxybenzyloxy)-2'-heptenyl]-2-cyclopentene 
• 869801-12-7 (S,E)-4-((Z)-7-((4-methoxybenzyl)oxy)hept-2-en-1-yl)-5-((E)-oct-2-en-1-ylidene)cyclopent-2-enone 
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• 131375-63-8 5-(4-methoxybenzyloxy)-1-pentanol 
• 1253966-22-1 C₂₁H₃₀O₃ 

Relevant articles and documents

Concise and enantioselective total synthesis of 15-deoxy-Δ 12,14-prostaglandin J2

The concise and enantioselective synthesis of 15-deoxy-Δ 12,14-prostaglandin J2 (15d-PGJ2) has been accomplished in 11 steps from a known alcohol. The key step of the synthesis involves an asymmetric Rh-catalyzed cycloisomerization of ene-ynone, followed by an olefin isomerization.

Concise Syntheses of ?"12-Prostaglandin J Natural Products via Stereoretentive Metathesis

δ12-Prostaglandin J family is recently discovered and has potent anticancer activity. Concise syntheses of four δ12-prostaglandin J natural products (7-8 steps in the longest linear sequences) are reported, enabled by convergent stereoretentive cross-metathesis. Exceptional control of alkene geometry was achieved through stereoretention.

Total Synthesis of Prostaglandin 15d-PGJ2 and Investigation of its Effect on the Secretion of IL-6 and IL-12

An efficient synthesis of 15-deoxy-Δ12,14-prostaglandin J2 (15d-PGJ2, 1) is reported. The route described allows for diversification of the parent structure to prepare seven analogues of 1 in which the positioning of electrophilic sites is varied. These analogues were tested in SAR studies for their ability to reduce the secretion of proinflammatory cytokines. It was shown that the endocyclic enone is crucial for the bioactivity investigated and that the conjugated ω-side chain serves in a reinforcing manner.

Highly efficient total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and their analogues

Palladium-catalyzed reaction of TBS ether of 4-cyclopentene-1,3-diol monoacetate (>95% ee) with an anion derived from methyl malonate and a base such as t-BuOK and LDA proceeded highly efficiently and reproducibly. The product obtained in >90% isolated yield was transformed in five steps into the key cyclopentenone possessing the α-chain at the γ position. Aldol reaction of this enone with the ω-chain aldehyde afforded the aldol adduct, and exposure of the derived mesylate to Al2O3 furnished the cross-conjugated dienone of the full structure. Finally, functional group manipulation furnished Δ12-PGJ2 efficiently. Similarly, 15-deoxy-Δ12,14-PGJ2, 5,6-acetylene analogues, and a 5,6-dihydro analogue were synthesized.

METHOD FOR PRODUCING PROSTAGLANDIN DERIVATIVE, PROSTAGLANDIN DERIVATIVE, INTERMEDIATE COMPOUND THEREFOR AND METHOD FOR PRODUCING THE SAME

PROBLEM TO BE SOLVED: To provide a method for producing a prostaglandin derivative, the prostaglandin derivative and an intermediate compound therefor, especially a method for producing a δ-12-prostaglandin J2 derivative using a new method for chemical synthesis through the intermediate compound. SOLUTION: The method for production is a method for producing the prostaglandin derivative using (1R,3R)-4-cyclopentene-1,3-diol 3-acetate (carboxylate) as a starting material. The method is composed of (A) an α-side chain introduction step of providing a malonic acid ester addition compound at the 3-position of the (1R,3R)-4-cyclopentene-1,3-diol, (B) an α-side chain extension step of affording a (1R,3R)-4-cyclopenten-1-one compound having the α-side chain of the prostaglandin derivative at the 3-position and (C) a prostaglandin derivative synthesizing step of conversion into the prostaglandin derivative.

Total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and related compounds

A key cyclopentenone possessing the α-chain was synthesized from TBS ether of 4-cyclopentene-1,3-diol monoacetate, and submitted to aldol reaction at the α′-position with the ω-chain aldehydes followed by dehydration to produce the title compounds. In a similar manner, 5-dehydro compounds (acetylene analogues) were synthesized successfully. In addition, palladium-catalyzed reaction of 4-cyclopentene-1,3-diol monoacetate with methyl malonate, the first step of the synthesis, was improved to afford the product in high yield by using t-BuOK or LDA in place of NaH.