ChemicalBook > CAS DataBase List > Prostaglandin E2

Prostaglandin E2

Product Name
Prostaglandin E2
CAS No.
363-24-6
Chemical Name
Prostaglandin E2
Synonyms
PROSTAGLANDIN;DINOPROSTONE;PGE2;dinoproston;Propess;Cervidil;Prepidil;Dinoprostol;Prostaglandin E2 (PGE2);l-pge2
CBNumber
CB8461799
Molecular Formula
C20H32O5
Formula Weight
352.47
MOL File
363-24-6.mol
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Prostaglandin E2 Property

Melting point:
66-68 °C
alpha 
-85.5 º (c=1, C2H5OH)
Boiling point:
406.07°C (rough estimate)
Density 
1.0601 (rough estimate)
refractive index 
1.6120 (estimate)
storage temp. 
-20°C
solubility 
ethanol: 1 mg/mL
form 
powder
pka
pKa 4.77± 0.09(H2O,t=25±0.1,I=0.1(NaCl)) (Uncertain)
color 
Clear yellow to amber
Water Solubility 
insoluble
Merck 
14,7877
BRN 
4709356
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
InChIKey
XEYBRNLFEZDVAW-ARSRFYASSA-N
CAS DataBase Reference
363-24-6(CAS DataBase Reference)
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Safety

Hazard Codes 
T
Risk Statements 
60-22-61
Safety Statements 
53-22-26-36/37/39-45
WGK Germany 
3
RTECS 
UK8000000
F 
8-10
HS Code 
29375000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
538904
Product name
Prostaglandin E?
Packaging
1mg
Price
$214
Updated
2024/03/01
Sigma-Aldrich
Product number
1213103
Product name
Dinoprostone
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
125mg
Price
$4250
Updated
2024/03/01
Sigma-Aldrich
Product number
BP902
Product name
Dinoprostone
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
100MG
Price
$142
Updated
2022/05/15
TCI Chemical
Product number
P1884
Product name
Prostaglandin E2
Purity
>98.0%(HPLC)
Packaging
1mg
Price
$75
Updated
2024/03/01
TCI Chemical
Product number
P1884
Product name
Prostaglandin E2
Purity
>98.0%(HPLC)
Packaging
10mg
Price
$445
Updated
2024/03/01
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Prostaglandin E2 Chemical Properties,Usage,Production

Description

Prostaglandin E2 (363-24-6; PGE2) is an endogenous prostaglandin derived from the action of cyclooxygenase on arachidonic acid. PGE2 has diverse biological actions in the areas of inflammation, cancer, immune modulation, fertility, smooth muscle relaxation and hematopoietic stem cell homeostasis. Prostaglandin E2 acts through four distinct receptors: EP1, EP2, EP3, EP4.

Chemical Properties

White to pale yellowish-cream powder. Melting point 64-66°C, specific rotation -61°(26°C, c=1, THF). Easily hydrolyzed at pH<4 or pH>8. Soluble in chloroform, ethyl acetate, methanol, absolute ethanol and other organic solvents, slightly soluble in water.

Originator

Prostin E2,Upjohn,UK,1972

Uses

For use in cell culture applications for the study of prostaglandin regulated cell signaling and gene regulation.

Uses

The most common and most biologically potent of mammalian prostaglandins. Isolated from sheep prostate. Oxytocic; abortifacient.

Definition

ChEBI: Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostagland ns.

Manufacturing Process

Hexamethyldisilazane (1 ml) and trimethylchlorosilane (0.2 ml) are added with stirring to a solution of PGA2 (250 mg) in 4 ml of tetrahydrofuran at 0°C under nitrogen. This mixture is maintained at 5°C for 15 hours. The mixture is then evaporated under reduced pressure. Toluene is added and evaporated twice. Then the residue is dissolved in 6 ml of methanol, and the solution is cooled to -20°C. Hydrogen peroxide (0.45 ml; 30% aqueous) is added. Then, 1N sodium hydroxide solution (0.9 ml) is added dropwise with stirring at - 20°C. After 2 hours at -20°C, an additional 0.3 ml of the sodium hydroxide solution is added with stirring at -20°C. After another hour in the range -10°C to -20°C, an additional 0.1 ml of the sodium hydroxide solution is added. Then, 1.5 ml of 1 N hydrochloric acid is added, and the mixture is evaporated under reduced pressure. The residue is extracted with ethyl acetate, and the extract is washed successively with 1 N hydrochloric acid and
ine, dried with anhydrous sodium sulfate and evaporated. The residue is dissolved in 5 ml of diethyl ether. To this solution is added 0.5 ml of methanol and 0.1 ml of water. Amalgamated aluminum made from 0.5 g of aluminum metal is then added in small portions during 3 hours at 25°C. Then, ethyl acetate and 3 N hydrochloric acid are added, and the ethyl acetate layer is separated and washed successively with 1 N hydrochloric acid and
ine, dried with anhydrous sodium sulfate, and evaporated. The residue is chromatographed on 50 g of acid-washed silica gel, eluting first with 400 ml of a gradient of 50- 100% ethyl acetate in Skellysolve B, and then with 100 ml of 5% methanol in ethyl acetate, collecting 25 ml fractions. Fractions 9 and 10 are combined and evaporated to give 18 mg of 11β-PGE2. Fractions 17-25 are combined and evaporated to give 39 mg of PGE2.

brand name

Cervidil (Controlled Therapeutics); Prepidil (Pharmacia & Upjohn); Prostin E2 (Pharmacia & Upjohn);Minprostin;Prostaglandin;Prostarmon e;Prostin vr pediatric.

Therapeutic Function

Oxytocic, Abortifacient

World Health Organization (WHO)

Dinoprostone, prostaglandin E2, was introduced into medicine in 1971 and is primarily used for cervical ripening during the induction of labour. It is available in various formulations for oral, parenteral and vaginal administration. Tablets, ampoules and vaginal dosage forms (tablets, pessaries, gel) remain registered in many countries.

General Description

PGE2 Dinoprostone (Prostin E2;Cervidil) is a naturally occurring prostaglandin that is administeredin a single dose of 10 mg by controlled-release(0.3 mg/hr) vaginal insert to induce cervical ripening. Use ofthis agent will potentiate the effects of oxytocin.

Biological Activity

Endogenous prostaglandin and primary product of arachidonic acid/cyclooxygenase pathway. Binds with high affinity to EP 1 , EP 2 , EP 3 and EP 4 receptors (K d values range between ~ 1-10 nM). Influences a wide range of processes including inflammation, smooth muscle relaxation, fertility and gastric mucosal integrity. Regulates vertebrate hematopoietic stem cell (HSC) homeostasis.

Biochem/physiol Actions

Most biologically active prostaglandin. PGE2 induces cervical ripening and parturition; mediates bradykinin-induced vasodilation; regulates adenylyl cyclase. Tumor cells that over-express cyclooxygenase 2 display increased invasiveness, angiogenesis, and resistance to apoptosis that may be due to the PGE2-induced expression of angiogenic factors and stabilization of the anti-apoptotic protein, survivin.The effect of PGE2 on the immune system is mixed. It inhibits T cell activation in vitro, suggesting it is an immunosuppressant. However, in vivo, it appears to effect expansion of the Th17 subset and differentiation of the Th1 subset of T helper cells, marking it as an immunoactivator.

Safety Profile

Poison by subcutaneous and intravenous routes. Moderately toxic by ingestion and intraperitoneal routes. An experimental teratogen. Human reproductive effects by intravenous, intraplacental, and intravaginal routes: changes in the uterus, cervix and vagina; termination of pregnancy; and changes in ferthty. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

in vitro

pge2 can stimulate the gastric nonparietal secretion [3] and has been shown to regulate the function of many cell types including dendritic cells, macrophages, t and b lymphocytes leading to both pro- and anti-inflammatory effects [2].

in vivo

pge2 regulates many physiological systems including the gastrointestinal and immune systems. in the gastrointestinal tract, pge2 plays a protective role in maintaining the integrity of the gastric mucosa. pge2 has also been shown to play a role in the maintenance of blood pressure, particularly in the setting of salt overload [2].

storage

-20°C

References

1) Healy (1990) Progesterone receptor antagonist and prostaglandins in human fertility regulation: a clinical review; Reprod. Fertil. Dev. 2 477
2) Greenhough et al. (2009) The COX-2/PGE2 pathway: key roles in the hallmarks of cancer and adaptation to the tumour microenvironment; Carcinogenesis, 30 377
3) Kalinski (2012) Regulation of Immune Responses by Prostaglandin E2; J. Immunol., 188 21
4) North et al. (2007) Prostaglandin E2 regulates vertebrate haematopoietic stem cell homeostasis; Nature, 447 1007
5) Hoggatt et al. (2013) Differential stem- and progenitor-cell trafficking by prostaglandin E2; Nature, 495 365
6) Coleman et al. (1994) Classification of prostanoid receptors: Properties, distribution and structure of the receptors and their subtypes; Pharmacol. Rev. 46 205

Prostaglandin E2 Preparation Products And Raw materials

Raw materials

Phosphate Buffer solution Citric acid monohydrate Glutathione Hydrogen Arachidonic acid Potassium chloride

Preparation Products

Prostaglandin E1
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View Lastest Price from Prostaglandin E2 manufacturers

Hebei Lingding Biotechnology Co., Ltd.
Product
Prostaglandin E2 363-24-6
Price
US $100.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
1 T
Release date
2024-12-13
Hebei Lingding Biotechnology Co., Ltd.
Product
Prostaglandin E2 363-24-6
Price
US $100.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
1 T
Release date
2024-12-13
Hangzhou Hyper Chemicals Limited
Product
Dinoprostone 363-24-6
Price
US $350.00-250.00/Gram
Min. Order
1Gram
Purity
USP
Supply Ability
1kg
Release date
2024-03-27

363-24-6, Prostaglandin E2 Related Search:

Glycine Folic acid 6-Methyl-5-hepten-2-one Prostaglandin E1 Cyclopentanecarbaldehyde Dienogestrel CHLOROPHOSPHONAZO III Hydroxy silicone oil Ethyl 2-(Chlorosulfonyl)acetate CYCLOPENTYLMAGNESIUM CHLORIDE Arachidonic acid TERT-AMYL METHYL ETHER PROSTAGLANDIN B1 PROSTAGLANDIN A2 PROSTAGLANDIN H2 Prostaglandin E1 Impurity 4 8-ISO PROSTAGLANDIN E1 2-Chlorophenyl cyclopentyl ketone

  • DINOPROSTONE
  • 7-(3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-5-heptenoicaci
  • dinoproston
  • l-5-heptenoicaci
  • l-7-(3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-5-heptenoicacid
  • l-pge2
  • l-prostaglandine2
  • prostin
  • prostine2
  • 7-[3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]-5-heptenoic acid
  • (5Z,11A,13E,15S)-11,15-DIHYDROXY-9-OXO-PROSTA-5,13-DIEN-1OIC ACID
  • [5Z,11ALPHA,13E,15S]-11,15-DIHYDROXY-9-OXOPROSTA-5,13-DIEN-1-OIC ACID
  • [5Z,11ALPHA,13E,15S]-11,15-DIHYDROXY-9-OXOPROSTA-5,13-DIENOIC ACID
  • PROSTAGLANDIN
  • PROSTAGLANDIN E2
  • PROSTAGLANDINS E2
  • PGE2
  • (15s)-prostaglandine2
  • (5z,11-alpha,13e,15s)-11,15-dihydroxy-9-oxo-prosta-13-dien-1-oicacid
  • 11,15-dihydroxy-9-oxo-,(5z,11-alpha,13e,15s)-prosta-13-dien-1-oicacid
  • PROSTAGLANDIN E2 CELL CULTURE TESTED
  • PROSTAGLANDIN E2 GAMMA-IRRADIATED*CELL C ULTURE TEST
  • PROSTAGLANDIN,PGE2
  • Dinoprostol
  • 9-OXO-11ALPHA,15S-DIHYDROXY-PROSTA-5Z,13E-DIEN-1-OIC ACID
  • 7-(3-HydroxyProsta-5,13-dien-1-oic acid, (5Z,11-alpha,13E,15S)-11,15-dihydroxy-9-oxo-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-5-heptenoic acid
  • [5Z,11R,13E,15S,(-)]-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
  • Prostaglandin E2,98%
  • [5Z,11ALPHA,13E,15S]-11,15-DIHYDROXY-9-OXOPROS
  • Prostaglandin E2,(5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid, PGE2
  • Dinoprostone (50 mg) (COLD SHIPMENT REQUIRED)
  • cGMP Dinoprostone
  • Prostaglandin E2 Lipid Maps MS Standard
  • (5Z,11α,13E,15S)-
  • CervidilProstaglandin E2
  • (5z,11α,13e,15s)-11,15-dihydroxy-9-oxoprosta-5,13-dienoic acid
  • (E)-7-[(1S,2S,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxo-cyclopentyl]hept-5-enoic acid
  • 11α,15α-Dihydroxy-9-ketoprosta-5,13-dienoic acid
  • 11α,15α-Dihydroxy-9-oxo-5-cis,13-trans-prostadienoic acid
  • 5-Heptenoic acid, 7-[3a-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]- (7CI)
  • Cervidil
  • Cerviprost
  • Enzaprost E
  • Minprositin E2
  • Minprostin E2
  • NSC 165560
  • NSC 196514
  • Prepidil
  • Propess
  • Prostarmon E
  • Prostenon
  • Prostenone
  • Prostin (prostaglandin)
  • U 12062
  • PGE2, (5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid
  • Dinoprostone, PGE2, (5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid
  • (5Z，11α，13E，15S)-11，15-dihydroxy-9-oxoprosta-5，13-dien-1-oic acid
  • Dinoprostone PGE2