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Prostaglandin F2a
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Name

Prostaglandin F2a

 EINECS N/A
CAS No. 551-11-1 Density 1.153 g/cm3
PSA 97.99000 LogP 3.04290
Solubility N/A Melting Point 25-35°
Formula C20H34O5 Boiling Point 531 °C at 760 mmHg
Molecular Weight 354.487 Flash Point 289 °C
Transport Information N/A Appearance White to off-white crystalline solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 551-11-1 (Prostaglandin F2a) Hazard Symbols N/A
Synonyms

(+)-ProstaglandinF2a;7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acid;9a,11a,15(S)-Trihydroxy-5-cis-13-trans-prostadienoic acid;9a,11a-PGF2;9a,11a-PGF2a;Amoglandin;Cyclosin;Cyclosin (pharmaceutical);Dinifertin;Dinoprost;Enzaprost;Enzaprost F;Glandin N;PGF2a;Panacelan;Prostaglandin F2;Prostaglandin F2a;Prostamate;Prostarmon F;Prostin F 2 alpha;Protamodin;U 14583;

Article Data 72

Prostaglandin F2a Synthetic route

(Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((S,E)-3-(tert-butyldimethylsilyloxy)oct-1-enyl)-5-(triethylsilyloxy)cyclopentyl)hept-5-enoic acid

551-11-1

dinoprost

Conditions
ConditionsYield
With hydrogenchloride In water; acetone at 20℃; for 0.333333h; Inert atmosphere;99%
55022-57-6

methyl (5Z)-7-{(1R,2R,3R,5R)-5-acetoxy-3-hydroxy-2-[(1E,3S)-3-hydroxy-1-octenyl]cyclopentyl}-5-heptenoate

551-11-1

dinoprost

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; methanol Ambient temperature;95%
With sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 2h;
33854-16-9

(+)-prostaglandin F2α

551-11-1

dinoprost

Conditions
ConditionsYield
With water In tert-butyl methyl ether at 35℃; for 18h; Enzymatic reaction;90%
base hydrolysis; Yield given;
1239683-12-5

(Z)-7-((1R,2R,3R,5S)-3-[(tert-butyldimethylsilanyl)oxy]-2-{(S,E)-3-[(tert-butyldimethylsilanyl)oxy]oct-1-en-1-yl}-5-hydroxycyclopentyl)hept-5-enoic acid

551-11-1

dinoprost

Conditions
ConditionsYield
With hydrogen fluoride; water In acetonitrile at 20℃; for 7h; stereoselective reaction;90%
With hydrogenchloride In tetrahydrofuran; water at -78 - 20℃; for 6h;89%
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 6h; Inert atmosphere;89%
145313-85-5

(Z)-7-[(1R,2R,3R,5S)-3-Benzyloxy-2-((E)-(S)-3-benzyloxy-oct-1-enyl)-5-hydroxy-cyclopentyl]-hept-5-enoic acid

551-11-1

dinoprost

Conditions
ConditionsYield
With ammonia; sodium75%
1577-22-6

5-hexenoic acid

C16H28O3

551-11-1

dinoprost

Conditions
ConditionsYield
With (Z)-2-Butene; C37H40Cl2N2ORuS2 In tetrahydrofuran at 22℃; under 7 Torr; Pressure; Inert atmosphere; Glovebox; Sealed tube;75%
51388-75-1, 59829-49-1, 59829-50-4, 59829-51-5, 59829-52-6, 85550-76-1, 85550-82-9, 136235-23-9, 136235-24-0

(3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol

17814-85-6

(4-carboxybutyl)triphenylphosphonium bromide

551-11-1

dinoprost

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 20℃; Wittig Olefination;55%
Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.666667h; Wittig Olefination; Schlenk technique; Inert atmosphere;
Stage #2: (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol In tetrahydrofuran at 20℃; for 1h; Wittig Olefination; Schlenk technique; Inert atmosphere;		152 mg
Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.666667h; Inert atmosphere;
Stage #2: (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;		152 mg
Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.666667h; Wittig Olefination; Schlenk technique; Inert atmosphere;
Stage #2: (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol In tetrahydrofuran at 0 - 20℃; for 1.5h; Wittig Olefination; Schlenk technique; Inert atmosphere;		24.8 mg
Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.666667h; Inert atmosphere;
Stage #2: (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;		70 mg
51388-75-1, 59829-49-1, 59829-50-4, 59829-51-5, 59829-52-6, 85550-76-1, 85550-82-9, 136235-23-9, 136235-24-0

(3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol

39968-97-3

(4-carboxybutylene)triphenylphosphorane

551-11-1

dinoprost

Conditions
ConditionsYield
Stage #1: (4-carboxybutylene)triphenylphosphorane With potassium tert-butylate In tetrahydrofuran at 0 - 5℃; for 0.666667h; Inert atmosphere;
Stage #2: (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol In tetrahydrofuran at 20℃; for 1h;		54%
51388-75-1, 59829-49-1, 59829-50-4, 59829-51-5, 59829-52-6, 85550-76-1, 85550-82-9, 136235-23-9, 136235-24-0

(3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol

41723-91-5

4-carboxybutyliden triphenylphosphorane sodium

551-11-1

dinoprost

Conditions
ConditionsYield
53%

prostaglandin G2

A

551-11-1

dinoprost

B

35850-13-6

15-Keto PGF2a

C

15-OOH-PGF2α

Conditions
ConditionsYield
In water for 0.166667h; Gersemia fruticosa preparation, pH 8.5;A 20%
B 20%
C 20%

Prostaglandin F2a Consensus Reports

EPA Genetic Toxicology Program.

Prostaglandin F2a Specification

The Prostaglandin F2α, with the CAS registry number 551-11-1, is also known as l-Prostaglandin F2-alpha. It belongs to the product category of Prostaglandins. This chemical's molecular formula is C20H34O5 and molecular weight is 354.48096. Its IUPAC name is called (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid. This chemical's classification codes are Abortifacient Agents; Abortifacient agents, nonsteroidal; Drug / Therapeutic Agent; Hormone; Human Data; Mutation data; Oxytocic; Oxytocics; Prostaglandin; Reproductive Control Agents; Reproductive Effect.

Physical properties of Prostaglandin F2α: (1)ACD/LogP: 2.14; (2)ACD/LogD (pH 5.5): 1.33; (3)ACD/LogD (pH 7.4): -0.47; (4)ACD/BCF (pH 5.5): 3.86; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 53.76; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 5; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 15; (11)Index of Refraction: 1.569; (12)Molar Refractivity: 100.75 cm3; (13)Molar Volume: 307.3 cm3; (14)Surface Tension: 48.6 dyne/cm; (15)Density: 1.153 g/cm3; (16)Flash Point: 289 °C; (17)Enthalpy of Vaporization: 92.76 kJ/mol; (18)Boiling Point: 531 °C at 760 mmHg; (19)Vapour Pressure: 1.71E-13 mmHg at 25°C.

Preparation: In domestic mammals, it is produced by the uterus when stimulated by oxytocin, in the event that there has been no implantation during the follicular phase.

Uses of Prostaglandin F2α: Prostaglandin F2α is pharmaceutically termed Dinoprost is a naturally-occurring prostaglandin used in medicine to induce labor and as an abortifacient.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCCCCC(C=CC1C(CC(C1CC=CCCCC(=O)O)O)O)O
(2)Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
(4)InChIKey: PXGPLTODNUVGFL-YNNPMVKQSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intramuscular 152mg/kg (152mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 2, Pg. 403, 1971.
mouse LD50 intravenous 56mg/kg (56mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 2, Pg. 403, 1971.
mouse LD50 oral 1300mg/kg (1300mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 2, Pg. 403, 1971.
mouse LD50 subcutaneous 212mg/kg (212mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 2, Pg. 403, 1971.
rabbit LD50 intramuscular > 10mg/kg (10mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: CYANOSIS		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 261, 1978.
rabbit LD50 intravenous 2500ug/kg (2.5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: CYANOSIS		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 261, 1978.
rat LD50 intramuscular 112mg/kg (112mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 2, Pg. 403, 1971.
rat LD50 intravenous 106mg/kg (106mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 2, Pg. 403, 1971.
rat LD50 oral 1170mg/kg (1170mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 2, Pg. 403, 1971.
rat LD50 subcutaneous 95mg/kg (95mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 4, Pg. 193, 1973.
women TDLo intravenous 20ug/kg (0.02mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING		 Japan Medical Gazette. Vol. 10(7), Pg. 9, 1973.

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