D8440
15-Deoxy-Δ12,14-prostaglandin J2
≥95% (HPLC), 1 mg/mL in methyl acetate
Synonym(s):
11-Oxoprosta-(5Z,9,12E,14E)-tetraen-1-oic acid, 15-Deoxy-Δ12,14-PGJ2
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About This Item
Empirical Formula (Hill Notation):
C20H28O3
CAS Number:
Molecular Weight:
316.43
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352211
EC Number:
201-185-2
MDL number:
Quality Level
assay
≥95% (HPLC)
form
liquid
concentration
1 mg/mL in methyl acetate
shipped in
wet ice
storage temp.
−20°C
SMILES string
CCCCC\C=C\C=C1/[C@@H](C\C=C/CCCC(O)=O)C=CC1=O
InChI
1S/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
InChI key
VHRUMKCAEVRUBK-GODQJPCRSA-N
General description
15-Deoxy-Δ12,14-prostaglandin J2 (15d-PGJ2) is a prostaglandin J2 (PGJ2) metabolite and a naturally occurring derivative of prostaglandin D2. It is produced during inflammatory processes.
Application
15-Deoxy-Δ12,14-prostaglandin J2 has been used:
- to study its effect on lipid accumulation, viability/mitochondrial activity, and amount of vasculature in vascularized adipose tissue model
- as a peroxisome proliferator-activated receptor (PPARγ) agonist to activate intestinal fatty acid binding protein (I-FABP)-PPARγ pathway
- as a supplement in culture medium for induced neural stem/progenitor cells (NSPCs) differentiation
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.
Selective agonist to PPARγ (peroxisome proliferator-activated receptors). Inhibits the proliferation of cancer cell lines that express PPARγ and cyclooxygenase-2 (COX-2).
Disclaimer
Supply conditions do not apply to the regions and states of Brazil: North, Northeast, Mato Grosso do Sul, Mato Grosso, and Rio Grande do Sul.
signalword
Danger
hcodes
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3
target_organs
Central nervous system
supp_hazards
Storage Class
3 - Flammable liquids
wgk
WGK 2
flash_point_f
15.8 °F - closed cup
flash_point_c
-9 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves
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Gabriela Magenta et al.
BMC cancer, 8, 47-47 (2008-02-12)
Activation of peroxisome proliferator-activated receptors gamma (PPARgamma) induces diverse effects on cancer cells. The thiazolidinediones (TZDs), such as troglitazone and ciglitazone, are PPARgamma agonists exhibiting antitumor activities; however, the underlying mechanism remains inconclusive. Rosiglitazone (RGZ), a synthetic ligand of PPARgamma
Min Zhao et al.
Oncotarget, 7(40), 64690-64701 (2016-09-08)
Accumulating evidence suggests that loss of the renal tubular epithelial phenotype plays an important role in the pathogenesis of renal tubulointerstitial fibrosis. Systemic activation of peroxisome proliferator-activated receptor γ (PPAR-γ) has been shown to be protective against renal fibrosis, although
M2 microglia promotes neurogenesis and oligodendrogenesis from neural stem/progenitor cells via the PPAR gamma signaling pathway
Yuan J, et al.
Oncotarget, 8(12), 19855-19855 (2017)