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D8440

15-Deoxy-Δ^12,14-prostaglandin J₂

Name: 15-Deoxy-Δ<SUP>12,14</SUP>-prostaglandin J<SUB>2</SUB>
Brand: SIGMA

≥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

NACRES:

NA.77

PubChem Substance ID:

329798863

UNSPSC Code:

12352211

EC Number:

201-185-2

MDL number:

MFCD00065806

Assay:

≥95% (HPLC)

Form:

liquid

Quality level:

200

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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).

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.

pictograms

GHS02,GHS07

signalword

Danger

hcodes

H225,H319,H336

pcodes

P210 - P233 - P240 - P241 - P242 - P305 + P351 + P338

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

WGK 2

flash_point_f

15.8 °F - closed cup

flash_point_c

-9 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves

Regulatory Information

危险化学品

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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)

Nrf2-mediated induction of cytoprotective enzymes by 15-deoxy-Delta12,14-prostaglandin J2 is attenuated by alkenal/one oxidoreductase.

Xiang Yu et al.

The Journal of biological chemistry, 281(36), 26245-26252 (2006-07-22)

NADPH-dependent alkenal/one oxidoreductase (Aor) was discovered to be highly inducible in rat liver following treatment with the cancer chemopreventive agent 3H-1, 2-dithiole-3-thione. Aor was further characterized as an Nrf2-regulated antioxidative enzyme that reduces carbon-carbon double bonds in a variety of

Renal tubular epithelium-targeted peroxisome proliferator-activated receptor-γ maintains the epithelial phenotype and antagonizes renal fibrogenesis.

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)

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Global Trade Item Number

SKU	GTIN
D8440-100UG	04061838070760

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