16,16-Dimethyl prostaglandin E2

Names

[ Name ]:
16,16-Dimethyl prostaglandin E2

[Synonym ]:
(5Z,11α,13E,15R)-11,15-Dihydroxy-16,16-dimethyl-9-oxoprosta-5,13-dien-1-oic acid
Prosta-5,13-dien-1-oic acid, 11,15-dihydroxy-16,16-dimethyl-9-oxo-, (5Z,11α,13E,15R)-
16,16-Dimethyl Prostaglandin E2,(5Z,11α,13E,15R)-11,15-Dihydroxy-16,16-dimethyl-9-oxo-prosta-5,13-dien-1oicacid

Biological Activity

[Description]:

16,16-Dimethyl prostaglandin E2 (16,16-dimethyl PGE2) is an orally active vertebrate Hematopoietic stem cells (HSCs) homeostasis critical regulator. 16,16-Dimethyl prostaglandin E2 can act through EP2/EP4 and has an interaction with the Wnt pathway[1][2].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Prostaglandin Receptor

Research Areas >> Inflammation/Immunology

[Target]

EP2

EP4

[In Vivo]

16,16-Dimethyl prostaglandin E2 (16,16-dimethyl PGE2; 10 µg/kg; i.p.; every 12 hours; for 8 days) rescues the exacerbated DSS colitis phenotype of Tpl2IMF-KO mice and restores epithelial proliferation and structure[2]. Animal Model: Tpl2IMF-KO mice[2] Dosage: 10 µg/kg Administration: IP; every 12 hours; for 8 days Result: Rescued the exacerbated DSS colitis phenotype and restores epithelial proliferation and structure.

[References]

[1]. Hagedorn EJ, et al. Getting more for your marrow: boosting hematopoietic stem cell numbers with PGE2. xp Cell Res. 2014 Dec 10;329(2):220-6.

[2]. Roulis M, et al. Intestinal myofibroblast-specific Tpl2-Cox-2-PGE2 pathway links innate sensing to epithelial homeostasis. Proc Natl Acad Sci U S A. 2014 Oct 28;111(43):E4658-67.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
541.3±50.0 °C at 760 mmHg

[ Melting Point ]:
-85.6ºC

[ Molecular Formula ]:
C₂₂H₃₆O₅

[ Molecular Weight ]:
380.518

[ Flash Point ]:
295.2±26.6 °C

[ Exact Mass ]:
380.256287

[ PSA ]:
94.83000

[ LogP ]:
2.57

[ Vapour Pressure ]:
0.0±3.3 mmHg at 25°C

[ Index of Refraction ]:
1.551

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UK7894000

CHEMICAL NAME :: Prosta-5,13-dien-1-oic acid, 11,15-dihydroxy-16,16-dimethyl-9-oxo-, (5Z,11-alpha,13E,15R)-

CAS REGISTRY NUMBER :: 39746-25-3

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C22-H36-O5

MOLECULAR WEIGHT :: 380.58

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 4 ug/kg

SEX/DURATION :: female 34 week(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: PRGLBA Prostaglandins. (Geron-X, Inc., P.O. Box 1108, Los Altos, CA 94022) V.1- 1972- Volume(issue)/page/year: 6,349,1974

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravaginal

DOSE :: 64 ug/kg

SEX/DURATION :: female 6 week(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 16,167,1977

Safety Information

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H319-H336

[ Supplemental HS ]:
Repeated exposure may cause skin dryness or cracking.

[ Precautionary Statements ]:
P210-P280-P304 + P340 + P312-P305 + P351 + P338-P337 + P313-P403 + P235

[ Personal Protective Equipment ]:
Eyeshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
F,Xn,Xi

[ Risk Phrases ]:
11-20/21/22-36/37/38-67-66-36

[ Safety Phrases ]:
16-26-36

[ RIDADR ]:
UN 1231 3/PG 2

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

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Several clinical trials are exploring therapeutic effect of human CD34(+) cells in ischemic diseases, including myocardial infarction. Unfortunately, most of the cells die few days after delivery. Her...

Prostaglandin E2--mediated relaxation of the ductus arteriosus: effects of gestational age on g protein-coupled receptor expression, signaling, and vasomotor control.

Circulation 110(16) , 2326-32, (2004)

In the preterm newborn, a patent ductus arteriosus is in large part a result of the increased sensitivity of the immature ductus to prostaglandin E2 (PGE2). PGE2 acts through 3 G protein-coupled recep...

Prostanoids regulate angiogenesis acting primarily on IP and EP4 receptors.

Microvasc. Res. 101 , 127-34, (2015)

Angiogenesis is regulated by numerous activators and inhibitors, including prostanoids. Although many studies have identified their roles in inflammation, regulatory functions of prostanoids in angiog...