methyl (11alpha,13E,16S)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate
Misoprostol
CAS: 59122-46-2;62015-39-8
Molecular Formula: C22H38O5
methyl (11alpha,13E,16S)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate - Names and Identifiers
| Name | Misoprostol |
| Synonyms | Misogon SC 2933 Misoprostol Misoprostil DL-MISOPROSTOL Misoprostol API (±)-15-Deoxy-(16RS)-16-hydroxy-16-methyl-PGE1 Methyl Ester methyl (11alpha,13E)-11-hydroxy-16,16-dimethyl-9-oxoprost-13-en-1-oate methyl (11alpha,13E,16S)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate (11a,13E)-(±)-11,16-Dihydroxy-16-methyl-9-oxoprost-13-en-1-oic Acid Methyl Ester Prost-13-en-1-oic acid, 11,16-dihydroxy-16-methyl-9-oxo-, methyl ester, (11a,13E)- (9CI) (11alpha,13E)-(+)-11alpha,16-Dihydroxy-16-methyl-9-oxoprost-13E-en-1-oic acid methyl ester (±)-Methyl-(1R,2R,3R)-3-hydroxy-2-[(E)-(4RS)-4-hydroxy-4-methyl-1-octenyl]-5-oxocyclopentaneheptanoate (+-)-Methyl (1R,2R,3R)-3-hydroxy-2-((E)-(4RS)-4-hydroxy-4-methyl-1-octenyl)-5-oxocyclopentaneheptanoate |
| CAS | 59122-46-2 62015-39-8 |
| EINECS | 664-288-5 |
| InChI | InChI=1/C23H40O4/c1-5-6-15-23(2,3)16-11-13-19-18(20(24)17-21(19)25)12-9-7-8-10-14-22(26)27-4/h11,13,18-19,21,25H,5-10,12,14-17H2,1-4H3/b13-11+/t18-,19-,21-/m1/s1 |
methyl (11alpha,13E,16S)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate - Physico-chemical Properties
| Molecular Formula | C22H38O5 |
| Molar Mass | 382.54 |
| Density | 1.0323 (rough estimate) |
| Melting Point | 261-263°C |
| Boling Point | 429.67°C (rough estimate) |
| Flash Point | 145.405°C |
| Solubility | Practically insoluble in water, soluble in ethanol (96 per cent), sparingly soluble in acetonitrile. |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | neat |
| pKa | 13.92±0.60(Predicted) |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| Refractive Index | 1.6120 (estimate) |
| MDL | MFCD00274550 |
| Physical and Chemical Properties | Light yellow viscous liquid. And ethanol, ether or chloroform miscible, very difficult to dissolve in water or hexane. Very unstable at room temperature, thermal differential isomerization to the 8-isomer occurs. Also extremely sensitive to pH, the hydroxyl group at 11 α is removed in acidic and alkaline conditions, converted to type a prostaglandins, and isomerized to type B prostaglandins. But in the hydroxypropyl methyl cellulose dispersion system is relatively stable, can be stored at room temperature. Acute toxicity LD50 rats, mice (mg/kg):40~62,70~160 intraperitoneal injection; 81~100,27~138 oral. |
methyl (11alpha,13E,16S)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate - Risk and Safety
| Hazard Symbols | T - Toxic |
| Risk Codes | R45 - May cause cancer R60 - May impair fertility R61 - May cause harm to the unborn child R25 - Toxic if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S53 - Avoid exposure - obtain special instructions before use. S22 - Do not breathe dust. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| UN IDs | UN 2810 6.1/PG 3 |
| WGK Germany | 2 |
| RTECS | UK8390000 |
| HS Code | 2937500000 |
| Toxicity | LD50 in rats, mice (mg/kg): 40-62, 70-160 i.p.; 81-100, 27-138 orally (Kotsonis) |
methyl (11alpha,13E,16S)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate - Nature
Open Data Verified Data
light yellow viscous liquid. And ethanol, ether or chloroform miscible, very difficult to dissolve in water or hexane. Very unstable at room temperature. Also extremely sensitive to pH, the hydroxyl group at the lla position is removed in acidity and alkalinity, converted to type a prostaglandins, and isomerized to type B prostaglandins. But in the hydroxypropyl methyl cellulose dispersion system is relatively stable, can be stored at room temperature.
Last Update：2024-01-02 23:10:35
methyl (11alpha,13E,16S)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate - Preparation Method
Open Data Verified Data
with azelaic acid as raw material, and two imidazole sulfoxide reaction, product and malonic acid monomethyl Ester reaction, and then acidification decarboxylation to produce 2 A [8 (methoxycarbonyl) octanoyl] acetic acid methyl ester, then it is hydrolyzed and decarboxylated to produce 8-oxodecanoic acid, and dimethyl oxalate is cyclized to form cyclopentanone, and one of the carbonyl groups is selectively hydrogenated to a hydroxyl group, after reaction with acetone acetal, 4-hydroxy-2-(methyl heptanoate -7-yl) 2, 3-cyclopentenone is reduced, and finally misoprostol is obtained by reaction with organic aluminum.
Last Update：2022-01-01 09:23:49
methyl (11alpha,13E,16S)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate - Use
Open Data Verified Data
The first chemically synthesized prostaglandin Ei antiulcer drug. Has a strong inhibitory effect on gastric acid secretion and prevent ulcer formation. Mainly used for gastric and duodenal ulcer, the prevention of gastrointestinal ulcers caused by the use of non-steroidal anti-inflammatory drugs.
Last Update：2022-01-01 09:23:50
methyl (11alpha,13E,16S)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate - Safety
Open Data Verified Data
rat, mouse LD50( mglkg):40-62, 70-160 intraperitoneal injection; 81-100.27-138 by mouth.
Last Update：2022-01-01 09:23:50
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View History
methyl (11alpha,13E,16S)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate
3-BROMO-4(H)-THIENO[3,2-B]PYRROLE-5-CARBOXYLICACID
1,3,8-Triazaspiro[4.5]decan-4-one, 3-methyl-8-[4-oxo-4-(2-thienyl)butyl]-
Phosphorus(1+), (N-bromomethanaminato)tris(N-ethylethanaminato)-, bromide, (T-4)- (9CI)
10220-90-3
1-(2-IODO-BENZYL)-PIPERIDINE-4-CARBOXYLIC ACID
Methyl2-(2-((3-chloro-5-(trifluoromethyl)-2-pyridinyl)sulfanyl)acetyl)-6-oxohexahydro-4-pyridazinecarboxylate
(Fluorosulfonyl)(trifluoromethanesulfonyl)imide
(2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester
DL-2,4,5-Trifluoro-Phe-OH
3-BROMO-4(H)-THIENO[3,2-B]PYRROLE-5-CARBOXYLICACID
1,3,8-Triazaspiro[4.5]decan-4-one, 3-methyl-8-[4-oxo-4-(2-thienyl)butyl]-
Phosphorus(1+), (N-bromomethanaminato)tris(N-ethylethanaminato)-, bromide, (T-4)- (9CI)
10220-90-3
1-(2-IODO-BENZYL)-PIPERIDINE-4-CARBOXYLIC ACID
Methyl2-(2-((3-chloro-5-(trifluoromethyl)-2-pyridinyl)sulfanyl)acetyl)-6-oxohexahydro-4-pyridazinecarboxylate
(Fluorosulfonyl)(trifluoromethanesulfonyl)imide
(2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester
DL-2,4,5-Trifluoro-Phe-OH