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CAS No.: | 745-65-3 |
---|---|
Name: | Prostaglandin E1 |
Article Data: | 30 |
Molecular Structure: | |
Formula: | C20H34O5 |
Molecular Weight: | 354.487 |
Synonyms: | Cyclopentaneheptanoicacid, 3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-, (-)- (8CI);Cyclopentaneheptanoicacid, 3a-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-(7CI);(-)-Prostaglandin E1;11a,15(S)-Dihydroxy-9-oxo-13-trans-prostenoic acid;11a,15a-Dihydroxy-9-oxo-13-trans-prostenoic acid;Alprox TD;Caveject;Caverject;Eglandin;Liple;Lipoprost;Liprostin;Minprog;NSC 165559;ONO 1608;Palux;Prostandin 500;Prostin VR Pediatric;Prostivas;SEPA-PGE1;SEPA-alprostadil;Topiglan;Vasaprostan;l-PGE1;l-Prostaglandin E1;Prostaglandin E1; |
EINECS: | 212-017-2 |
Density: | 1.131 g/cm3 |
Melting Point: | 115-116 °C |
Boiling Point: | 529.3 °C at 760 mmHg |
Flash Point: | 288 °C |
Solubility: | insoluble in water |
Appearance: | Crystalline solid |
Hazard Symbols: | Xn, Xi |
Risk Codes: | 22-36/37/38 |
Safety: | 36-26 |
Transport Information: | UN 2811 6.1/PG 3 |
PSA: | 94.83000 |
LogP: | 3.47510 |
C32H64O5Si2
ALPROSTADIL
Conditions | Yield |
---|---|
With hydrogen fluoride; water In acetonitrile at 20℃; for 6h; stereoselective reaction; | 90% |
Conditions | Yield |
---|---|
With porcine pancreatic lipase; sodium chloride; calcium chloride In tetrahydrofuran; water for 0.5h; Hydrolysis; Enzymatic reaction; pH 7.1; | 89% |
With pig liver esterase In water for 4h; Ambient temperature; | 86% |
With porcine liver esterase; phosphate buffer solution In acetone for 4h; Ambient temperature; | 86% |
With phosphate buffer Baker's yeast, pH 7.0; | 72% |
(microbiological transformation); |
7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid
ALPROSTADIL
Conditions | Yield |
---|---|
With hydrogen fluoride In acetonitrile Yield given; |
(8R,11R,12R,15S)-11,15-Bis-(2-trimethylsilylethoxymethoxy)-9-oxo-prost-13-en-1-oic acid 2-trimethylsilylethoxymethyl ester
ALPROSTADIL
Conditions | Yield |
---|---|
With nitromethane; n-butanethiol; magnesium bromide In diethyl ether at 20℃; for 1h; |
(S)-E-3-(2-trimethylsilylethoxymethoxy)-1-tributylstannyl-1-octene
ALPROSTADIL
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: 2-thienyl(cyano)copper lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.3: 67 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.1: magnesium bromide; nitromethane; n-butanethiol / diethyl ether / 1 h / 20 °C View Scheme |
2-trimethylsilylethoxymethyl-(R)-3-(2-trimethylsilylethoxymethoxy)-5-oxo-1-cyclopentene-1-heptenoate
ALPROSTADIL
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: 2-thienyl(cyano)copper lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.3: 67 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.1: magnesium bromide; nitromethane; n-butanethiol / diethyl ether / 1 h / 20 °C View Scheme |
7-(3R-hydroxy-5-oxo-cyclopent-1-enyl)heptanoic acid
ALPROSTADIL
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 31 percent / 4-(dimethylamino)pyridine; lithium carbonate / dimethylformamide / 20 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: 2-thienyl(cyano)copper lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.3: 67 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 3.1: magnesium bromide; nitromethane; n-butanethiol / diethyl ether / 1 h / 20 °C View Scheme |
(E)-1-iodo-1-octen-3-one
ALPROSTADIL
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 95 percent / n-butylboronic complex of diphenyl D-prolinol; catecholborane / toluene / 36 h / -78 °C 2.1: 97 percent / Et3N; imidazole / dimethylformamide / 20 °C 3.1: n-BuLi; CuCN; MeLi / diethyl ether / 3.08 h / -78 - 0 °C 3.2: diethyl ether; hexane / 0.33 h / -78 °C 4.1: pyridinium p-toluenesulfonate / acetone; H2O / 4 h / 20 °C 5.1: 89 percent / porcine pancreatic lipase; NaCl; CaCl2 / H2O; tetrahydrofuran / 0.5 h / Enzymatic reaction; pH 7.1 View Scheme |
1. Introduction of Prostaglandin E1
Prostaglandin E1 is one kind of white powder. The IUPAC Name of this chemical is 7-[(1R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid. Besides, Prostaglandin E1 belogns to Miscellaneous Biochemicals; Prostaglandins; Prostaglandin; Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals; Prostanoid receptor and related. In addition, Prostaglandin E1 is reported soluble in ethanol at >100 mg/ml. It is insoluble in water.
2. Properties of Prostaglandin E1
Physical properties about Prostaglandin E1 are:
(1)Melting Point: 115-116 °C; (2)Boiling point: 529.3 °C at 760 mmHg; (3)Storage Temperature: -20°C; (4)Flash Point: 288 °C; (5)Density: 1.131 g/cm3; (6)Surface Tension: 52.3 dyne/cm; (7)Enthalpy of Vaporization: 92.52 kJ/mol; (8)Vapour Pressure: 2.06E-13 mmHg at 25°C; (9)XLogP3-AA: 3.2; (10)H-Bond Donor: 3; (11)H-Bond Acceptor: 5; (12)Rotatable Bond Count: 13; (13)Tautomer Count: 3; (14)Exact Mass: 354.240624; (15)MonoIsotopic Mass: 354.240624; (16)Topological Polar Surface Area: 94.8; (17)Heavy Atom Count: 25; (18)Formal Charge: 0; (19)Complexity: 432; (20)Isotope Atom Count: 0; (21)Defined Atom Stereocenter Count: 0; (22)Undefined Atom Stereocenter Count: 4; (23)Defined Bond Stereocenter Count: 0; (24)Undefined Bond Stereocenter Count: 1; (25)Covalently-Bonded Unit Count: 1; (26)Feature 3D Acceptor Count: 5; (27)Feature 3D Donor Count: 2; (28)Feature 3D Anion Count: 1; (29)Feature 3D Hydrophobe Count: 4; (30)Feature 3D Ring Count: 1; (31)Effective Rotor Count: 13.8; (32)Conformer Sampling RMSD: 1.6; (33)CID Conformer Count: 88.
3. Structure Descriptors of Prostaglandin E1
(1)Canonical SMILES: CCCCCC(C=CC1C(CC(=O)C1CCCCCCC(=O)O)O)O
(2)Isomeric SMILES: CCCCC[C@@H](/C=C/C1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)O)O)O
(3)InChI: InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17?,19+/m0/s1
(4)InChIKey: GMVPRGQOIOIIMI-ZWLIRFKBSA-N
4. Toxicity information of Prostaglandin E1
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 19800ug/kg (19.8mg/kg) | Drugs in Japan Vol. 6, Pg. 47, 1982. | |
mouse | LD50 | intravenous | 21mg/kg (21mg/kg) | Drugs in Japan Vol. 6, Pg. 47, 1982. | |
mouse | LD50 | oral | 186mg/kg (186mg/kg) | Drugs in Japan Vol. 6, Pg. 47, 1982. | |
mouse | LD50 | subcutaneous | 26400ug/kg (26.4mg/kg) | Drugs in Japan Vol. 6, Pg. 47, 1982. | |
rat | LD50 | intraarterial | 21mg/kg (21mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 25, Pg. 499, 1983. |
rat | LD50 | intraperitoneal | 24900ug/kg (24.9mg/kg) | Drugs in Japan Vol. 6, Pg. 47, 1982. | |
rat | LD50 | intravenous | 19200ug/kg (19.2mg/kg) | Drugs in Japan Vol. 6, Pg. 47, 1982. | |
rat | LD50 | oral | 228mg/kg (228mg/kg) | Drugs in Japan Vol. 6, Pg. 47, 1982. | |
rat | LD50 | subcutaneous | 18600ug/kg (18.6mg/kg) | Drugs in Japan Vol. 6, Pg. 47, 1982. |