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16,16-DIMETHYL PROSTAGLANDIN E2, also known as 16,16-dimethyl PGE2, is a synthetic prostaglandin analog with unique properties. It functions as a competitive inhibitor of 15-hydroxy PGDH, an enzyme involved in prostaglandin metabolism, without being a substrate for the enzyme itself. This characteristic grants 16,16-dimethyl PGE2 a longer half-life in vivo. Acting as an agonist on most EP receptor subtypes, it has been utilized in various experimental applications, including cervical ripening, uterine contraction, and gastric mucosa protection. Additionally, it plays a role in maintaining the self-renewal properties of hematopoietic stem cells during in vitro expansion, with a Kd of approximately 1 nM for activating isolated EP2 receptors.

39746-25-3

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39746-25-3 Usage

Uses

Used in Pharmaceutical Applications:
16,16-DIMETHYL PROSTAGLANDIN E2 is used as a pharmaceutical agent for inducing cervical ripening, facilitating uterine contraction, and preventing gastric ulceration in rats and dogs. Its agonistic action on EP receptor subtypes contributes to these therapeutic effects.
Used in Research and Development:
In the field of research, 16,16-DIMETHYL PROSTAGLANDIN E2 is used as a tool to study the effects of prostaglandins on various biological processes. Its ability to activate EP2 receptors with high affinity makes it a valuable compound for investigating the roles of these receptors in cellular signaling and function.
Used in Stem Cell Biology:
16,16-DIMETHYL PROSTAGLANDIN E2 is used as a stem cell preservation agent to maintain the self-renewal properties of hematopoietic stem cells during their expansion in culture. This application aids in the development of stem cell therapies and regenerative medicine by ensuring the preservation of stem cell potency and functionality.
Used in Drug Metabolism Studies:
Due to its resistance to metabolism by 15-hydroxy PGDH, 16,16-DIMETHYL PROSTAGLANDIN E2 is used in the study of prostaglandin metabolism and the role of 15-hydroxy PGDH in the process. This knowledge can be applied to develop new drugs with improved metabolic stability and efficacy.

in vitro

dmpge2 was reported to cause an increase in runx11/cmyb1 hscs, while hscs were inhibited by indomethacin treatment in 90% of embryos. moreover, dmpge2 had minimal effects on the vasculature, while indomethacin altered the intersomitic vessels slightly. imaged by confocal microscopy, red-labelled hscs and endothelium embryos showed significantly increased hscs following dmpge2 exposure [1].

in vivo

in a heterotopic model of rat allograft rejection, dmpge2 could delay the rejection onset, but all animals developed severe rejection and died subsequently. treatment of animals with low-dose csa in combination with dmpge2 led to a delay in the onset as well as a reduction in the intensity of allograft rejection. in addition, a statistical relationship between procoagulant activity levels and the time of onset of rejection was observed [1].

references

[1] north te,goessling w,walkley cr,lengerke c,kopani kr,lord am,weber gj,bowman tv,jang ih,grosser t,fitzgerald ga,daley gq,orkin sh,zon li. prostaglandin e2 regulates vertebrate haematopoietic stem cell homeostasis. nature.2007 jun 21;447(7147):1007-11.[2] koh ih,kim pc,chung sw,waddell t,wong py,gorczynski r,levy ga,cohen z. the effects of 16, 16 dimethyl prostaglandin e2 therapy alone and in combination with low-dose cyclosporine on rat small intestinal transplantation. transplantation.1992 oct;54(4):592-8.

Check Digit Verification of cas no

The CAS Registry Mumber 39746-25-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,9,7,4 and 6 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 39746-25:
(7*3)+(6*9)+(5*7)+(4*4)+(3*6)+(2*2)+(1*5)=153
153 % 10 = 3
So 39746-25-3 is a valid CAS Registry Number.
InChI:InChI=1/C22H36O5/c1-4-5-14-22(2,3)20(25)13-12-17-16(18(23)15-19(17)24)10-8-6-7-9-11-21(26)27/h6,8,12-13,16-17,19-20,24-25H,4-5,7,9-11,14-15H2,1-3H3,(H,26,27)/b8-6+,13-12+/t16-,17?,19-,20+/m0/s1

39746-25-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 16,16-Dimethylprostaglandin E2

1.2 Other means of identification

Product number -
Other names 16,16-Dimethyl Prostaglandin E2,(5Z,11α,13E,15R)-11,15-Dihydroxy-16,16-dimethyl-9-oxo-prosta-5,13-dien-1oicacid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:39746-25-3 SDS

39746-25-3Downstream Products

39746-25-3Relevant academic research and scientific papers

Effective stereoselective total synthesis of 16,16-dimethyl prostaglandin E2

Rodriguez, Ana,Nomen, Miguel,Spur, Bernd W.,Godfroid, Jean-Jacques

, p. 279 - 282 (2007/10/03)

The first stereoselective synthesis of the specific EP1 receptor agonist, 16,16-dimethyl prostaglandin E2 1, is described. The key- intermediate 3 was obtained from the E-allyl alcohol 6 via Sharpless epoxidation followed by stereospecific transformations to the γ-iodo vinyl compound 3. Two component coupling of 2 and 3, using the dilithiocyanocuprate technology, gave the 1,4-addition product. Mild desilylation and enzymatic ester cleavage produced the optically pure prostaglandin 1 in high yield.

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