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D8440

Sigma-Aldrich

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:
87893-55-8
Molecular Weight:
316.43
EC Number:
201-185-2
MDL number:
MFCD00065806
UNSPSC Code:
12352211
PubChem Substance ID:
329798863
NACRES:
NA.77

Quality Level

200

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).

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

Hazard Classifications

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

target_organs

Central nervous system

supp_hazards

EUH066

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

15.8 °F - closed cup

flash_point_c

-9 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
15-Deoxy-$\Delta$ (12, 14)-prostaglandin J2 induces vascular endothelial cell apoptosis through the sequential activation of MAPKS and p53
Ho TC, et al.
Test, 283(44), 30273-30288 (2008)
Presence of Vasculature Results in Faster Insulin Response in Adipocytes in Novel in vitro Vascularized Adipose Tissue Model1
Huttala O, et al.
ALTEX, 277(12), 10459-10466 (2019)
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
15-Deoxy-Delta 12, 14-prostaglandin J2 inhibits multiple steps in the NF-kappa$B signaling pathway
Straus DS, et al.
Proceedings of the National Academy of Sciences, 97(9), 4844-4849 (2000)
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