15-Deoxy-Δ-12,14-prostaglandin J2 (15d-PGJ2) is a novel and potent cyclopentenone prostaglandin and metabolite of PGD2, acting as a selective PPARγ (EC50 of 2 µM) and a covalent PPARδ agonist that promotes efficient differentiation of C3H10T1/2 fibroblasts to adipocytes with an EC50 of 7 μM.
Physicochemical Properties
| Molecular Formula | C₂₀H₂₈O₃ |
| Molecular Weight | 316.43 |
| Exact Mass | 316.203 |
| CAS # | 87893-55-8 |
| Related CAS # | 15-Deoxy-Δ-12,14-prostaglandin J2-d4;1542166-82-4 |
| PubChem CID | 5311211 |
| Appearance | Colorless to light yellow liquid |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 495.8±34.0 °C at 760 mmHg |
| Flash Point | 267.8±22.2 °C |
| Vapour Pressure | 0.0±2.7 mmHg at 25°C |
| Index of Refraction | 1.558 |
| LogP | 5.1 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 11 |
| Heavy Atom Count | 23 |
| Complexity | 495 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | C(=C1/C(=O)C=C[C@@H]/1C/C=C\CCCC(=O)O)\C=C\CCCCC |
| InChi Key | VHRUMKCAEVRUBK-GODQJPCRSA-N |
| InChi Code | 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 |
| Chemical Name | (Z)-7-[(1S,5E)-5-[(E)-oct-2-enylidene]-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid |
| Synonyms | 15DeoxyΔ12,14prostaglandin J2 15 Deoxy Δ 12,14 prostaglandin J2 |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | In the cyclopentenone ring of 15-Deoxy-Δ-12,14-prostaglandin J2 (15d-PGJ2), there is an electrophilic α,β-unsaturated ketone (enone). 15-Deoxy-Δ-12,14-prostaglandin J2 is a cyPG that can cause inflammation, bursting, and cellular ischemia. Through the receptor ligand binding domain and its internal cyclic enone at the C9 position, 15-deoxy-Δ-12,14-prostaglandin J2 is activated in a dose-dependent manner. Cys249 forms covalent adducts with other residues to initiate PPARδ's polymerization activity [1]. |
| References |
[1]. Identification and Molecular Characterization of Peroxisome Proliferator-Activated Receptor δ as a Novel Target for Covalent Modification by 15-Deoxy-Δ12,14-prostaglandin J2. CS Chem Biol. 2018 Dec 21;13(12):3269-3278. [2]. A prostaglandin J2 metabolite binds peroxisome proliferator-activated receptor gamma and promotes adipocyte differentiation. Cell. 1995 Dec 1;83(5):813-9. |
| Additional Infomation |
15-deoxy-Delta(12,14)-prostaglandin J2 is a prostaglandin J derivative comprising prostaglandin J2 lacking the 15-hydroxy group and having C=C double bonds at the 12- and 14-positions. It has a role as a metabolite, an electrophilic reagent and an insulin-sensitizing drug. It is functionally related to a prostaglandin J2. It is a conjugate acid of a 15-deoxy-Delta(12,14)-prostaglandin J2(1-). See also: 15-Deoxy-Delta12,14-PGJ2 (annotation moved to). |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.1603 mL | 15.8013 mL | 31.6026 mL | |
| 5 mM | 0.6321 mL | 3.1603 mL | 6.3205 mL | |
| 10 mM | 0.3160 mL | 1.5801 mL | 3.1603 mL |