An endocannabinoid metabolite
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15-deoxy-Δ12,14-Prostaglandin J2-2-glyceryl ester

Item No. 10010132

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
11-oxo-prosta-5Z,9,12E,14E-tetraen-1-oic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester
CAS Number
1947405-90-4
Synonyms
  • 15-deoxy-Δ12,14-PGJ2-2-glyceryl ester
Molecular Formula
C23H34O5
Formula Weight
390.5
Purity
≥98% (isomer mixture)
Formulation
A 1 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 0.3 mg/ml
λmax
229, 306 nm
SMILES
O=C1C=C[C@H](C/C=C\CCCC(OC(CO)CO)=O)/C1=C\C=C\CCCCC
InChi Code
InChI=1S/C23H34O5/c1-2-3-4-5-6-10-13-21-19(15-16-22(21)26)12-9-7-8-11-14-23(27)28-20(17-24)18-25/h6-7,9-10,13,15-16,19-20,24-25H,2-5,8,11-12,14,17-18H2,1H3/b9-7-,10-6+,21-13+/t19-/m0/s1
InChi Key
JGKIBUMNHSZUSL-SLDNAQRASA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    Product Description

    15-deoxy-Δ12,14-Prostaglandin J2-2-glyceryl ester (15-deoxy-Δ12,14-PGJ2-2-glyceryl ester) is formed from PGD2 by the elimination of two molecules of water. It binds selectively to PPARγ with an EC50 value of 2 µM in a murine chimera system.1,2 15-deoxy-Δ12,14-PGJ2-2-glyceryl ester is more potent than PGD2, Δ12-PGJ2, and PGJ2 in stimulating lipogenesis in C3H10T1/2 cells. The EC50 value for induction of adipocyte differentiation in cultured fibroblasts is 7 µM.1 PG glycerol esters are generated by the action of cyclooxygenase-2 on the endocannabinoid 2-arachidonyl glycerol.3 The biosynthesis of PGH, PGD, PGE, PGF, and TXA-2-glyceryl ester compounds have all been documented. While the stability and metabolism of these PG products has been investigated,4 little is known about their intrinsic biological activity.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kliewer, S.A., Lenhard, J.M., Willson, T.M., et al. A prostaglandin J2 metabolite binds peroxisome proliferator-activated receptor γ and promotes adipocyte differentiation. Cell 83(5), 813-819 (1995).

    2. Forman, B.M., Tontonoz, P., Chen, J., et al. 15-Deoxy-Δ12,14-prostaglandin J2 is a ligand for the adipocyte determination factor PPARγ. Cell 83(5), 803-812 (1995).

    3. Kozak, K.R., Crews, B.C., Morrow, J.D., et al. Metabolism of the endocannabinoids, 2-arachidonylgycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides. The Journal of Biological Chemisty 277(47), 44877-44885 (2002).

    4. Kozak, K.R., Crews, B.C., Ray, J.L., et al. Metabolism of prostaglandin glycerol esters and prostaglandin ethanolamides in vitro and in vivo. The Journal of Biological Chemisty 276(40), 36993-36998 (2001).