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D8440

Sigma-Aldrich

15-Deoxy-Δ12,14-prostaglandin J2

≥95% (HPLC), 1 mg/mL in methyl acetate

Synonym(e):

11-Oxoprosta-(5Z,9,12E,14E)-tetraen-1-oic acid, 15-Deoxy-Δ12,14-PGJ2

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About This Item

Empirische Formel (Hill-System):
C20H28O3
CAS-Nummer:
87893-55-8
Molekulargewicht:
316.43
EG-Nummer:
201-185-2
MDL-Nummer:
MFCD00065806
UNSPSC-Code:
12352211
PubChem Substanz-ID:
329798863
NACRES:
NA.77

Qualitätsniveau

200

Assay

≥95% (HPLC)

Form

liquid

Konzentration

1 mg/mL in methyl acetate

Versandbedingung

wet ice

Lagertemp.

−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

InChIKey

VHRUMKCAEVRUBK-GODQJPCRSA-N

Allgemeine Beschreibung

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.

Anwendung

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. Wirkung

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).

Piktogramme

FlameExclamation mark
GHS02,GHS07

Signalwort

Danger

Gefahreneinstufungen

Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

Zielorgane

Central nervous system

Zusätzliche Gefahrenhinweise

EUH066

Lagerklassenschlüssel

3 - Flammable liquids

WGK

WGK 2

Flammpunkt (°F)

15.8 °F - closed cup

Flammpunkt (°C)

-9 °C - closed cup

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves

Analysenzertifikate (COA)

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J M Launay et al.
Translational psychiatry, 1, e56-e56 (2011-01-01)
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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
Mojgan Masoodi et al.
Rapid communications in mass spectrometry : RCM, 20(20), 3023-3029 (2006-09-21)
Prostanoids are potent mediators of many physiological and pathophysiological processes. Of the many analytical methodologies used for their qualitative and quantitative analysis, electrospray tandem mass spectrometry coupled to liquid chromatography (LC/ESI-MS/MS) offers a rapid, sensitive and versatile system applicable to
Gas chromatographic-mass spectrometric measurement of 15-deoxy-delta(12,14)-prostaglandin J(2), the peroxisome proliferator-activated receptor gamma ligand, in urine.
C Thévenon et al.
Clinical chemistry, 47(4), 768-770 (2001-03-29)
Helder Veras Ribeiro Filho et al.
Molecular and cellular endocrinology, 484, 1-14 (2019-02-01)
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