Prostaglandin f1alpha

Base Information

• Chemical Name: Prostaglandin f1alpha
• CAS No.: 745-62-0
• Molecular Formula: C₂₀H₃₆O₅
• Molecular Weight: 356.503
• UNII: WJ72O6860W
• ChEMBL ID: CHEMBL1325783
• DSSTox Substance ID: DTXSID901339475
• Metabolomics Workbench ID: 2479
• Nikkaji Number: J14.832F
• Pharos Ligand ID: GCD9ZWS3GCYS
• Wikidata: Q27088352
• Mol file: 745-62-0.mol

Synonyms:PGF1;PGF1 alpha;PGF1alpha;prostaglandin F1;prostaglandin F1, (8beta,9alpha,11alpha,13E,15S)-isomer;prostaglandin F1, (9alpha,11alpha,13E,15R)-isomer;prostaglandin F1, (9alpha,11alpha,13E,15S)-(+-)-isomer;prostaglandin F1, (9alpha,11beta,13E,15S)-isomer;prostaglandin F1alpha

Chemical Property of Prostaglandin f1alpha

Chemical Property:

• Vapor Pressure: 2.75E-13mmHg at 25°C
• Melting Point: 102.5°C
• Refractive Index: 1.6120 (estimate)
• Boiling Point: 526.5 °C at 760 mmHg
• Flash Point: 286.3 °C
• PSA: 97.99000
• Density: 1.136 g/cm³
• LogP: 3.26690
• Storage Temp.: −20°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 13
• Exact Mass: 356.25627424
• Heavy Atom Count: 25
• Complexity: 396

Purity/Quality:

98%,99%, ^*data from raw suppliers

PGF1alpha(ProstaglandinF1alpha) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(CC(C1CCCCCCC(=O)O)O)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1CCCCCCC(=O)O)O)O)O
• Description: Prostaglandin F1α (PGF1α) is the putative metabolite of dihomo-γ-linolenic acid (DGLA) via the cyclooxygenase (COX) pathway. Both PGF1α and PGF2α (Item Nos. 16010 | 10007221) have been shown to act as priming pheromones for male Atlantic salmon with a threshold concentration of 10?11 M. PGF1α binds to the ovine corpus luteum FP receptor at only 8% of the relative potency of PGF2α. It is only half as active as PGF2α in inducing human respiratory smooth muscle contractions in vitro. Prostaglandin F1α (PGF1α) is the putative metabolite of dihomo-γ-linolenic acid (DGLA) via the cyclooxygenase (COX) pathway. Both PGF1α and PGF2α (Item Nos. 16010 | 10007221) have been shown to act as priming pheromones for male Atlantic salmon with a threshold concentration of 10?11 M. PGF1α binds to the ovine corpus luteum FP receptor at only 8% of the relative potency of PGF2α. It is only half as active as PGF2α in inducing human respiratory smooth muscle contractions in vitro. PGF1α MaxSpec? standard is a quantitative grade standard of PGF1α that has been prepared specifically for mass spectrometry and related applications where quantitative reproducibility is required. The solution has been prepared gravimetrically and is supplied in a deactivated glass ampule sealed under argon. The concentration was verified by comparison to an independently prepared calibration standard. This PGF1α MaxSpec? standard is guaranteed to meet identity, purity, stability, and concentration specifications and is provided with a batch-specific certificate of analysis. Ongoing stability testing is performed to ensure the concentration remains accurate throughout the shelf life of the product. Note: The amount of solution added to the vial is in excess of the listed amount. Therefore, it is necessary to accurately measure volumes for preparation of calibration standards. Follow recommended storage and handling conditions to maintain product quality.
• Uses: Prostaglandin F1α (PGF1α) is the putative metabolite of dihomo-γ-linolenic acid (DGLA) via the cyclooxygenase (COX) pathway. Both PGF1α and PGF2α have been shown to act as priming pheromones for male Atlantic salmon with a threshold concentration of 10?11 M. PGF1α binds to the ovine corpus luteum FP receptor at only 8% of the relative potency of PGF2α. It is only half as active as PGF2α in inducing human respiratory smooth muscle contractions in vitro. PGF1alpha (Prostaglandin F1alpha) is a smooth muscle relaxant and a stable metabolite of prostacyclin (PGI2).

Technology Process of Prostaglandin f1alpha

There total 38 articles about Prostaglandin f1alpha which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

2β-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-3α-(6-carboxyhexyl)-1α,4α-dihydroxycyclopentanone (71120-99-5,71121-00-1,72120-47-9) → (+/-)-prostaglandin F1α (745-62-0,3613-66-9,10164-73-5,17066-90-9,20348-60-1,21562-54-9,26771-95-9,26771-96-0,34388-84-6,34388-86-8,34388-87-9,34388-89-1,34402-61-4,34437-28-0,37785-86-7,37818-61-4,42048-97-5,42587-03-1,42607-55-6,42607-56-7,54422-22-9,54422-23-0,55528-78-4,57759-92-9,57759-93-0,61375-87-9,61557-40-2,62860-86-0,62960-89-8)

Guidance literature:

With hydrogen fluoride; In water; acetonitrile; for 1h; Ambient temperature;

DOI:10.1021/jo00231a014

Reference yield:

trans-4-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-2,3-epoxycyclopentanone (78823-20-8) → (+/-)-prostaglandin F1α (745-62-0,3613-66-9,10164-73-5,17066-90-9,20348-60-1,21562-54-9,26771-95-9,26771-96-0,34388-84-6,34388-86-8,34388-87-9,34388-89-1,34402-61-4,34437-28-0,37785-86-7,37818-61-4,42048-97-5,42587-03-1,42607-55-6,42607-56-7,54422-22-9,54422-23-0,55528-78-4,57759-92-9,57759-93-0,61375-87-9,61557-40-2,62860-86-0,62960-89-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to r.t., 6 h

2: 1.) CuCN / 1.) diethyl ether, -40 deg C, 1.5 h, 2.) ether, from -78 deg C to -10 deg C, overnight

3: KF, pH 7 phosphate buffer / ethanol / 3 h / Ambient temperature

4: 84 percent / L-selectride / tetrahydrofuran / 6 h / Ambient temperature

5: 75 percent / O₂ / PtO₂ / acetone; H₂O / 4 h / 40 °C

6: 90 percent / 47-52percent aq. HF / acetonitrile; H₂O / 1 h / Ambient temperature

With potassium fluoride; pH 7 phosphate buffer; hydrogen fluoride; oxygen; L-Selectride; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; ethanol; water; acetone; acetonitrile;

DOI:10.1021/jo00231a014

Reference yield:

trans-4,5-epoxy-3-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-1-<(triethylsilyl)oxy>cyclopentene (93566-56-4,93711-56-9,110548-21-5) → (+/-)-prostaglandin F1α (745-62-0,3613-66-9,10164-73-5,17066-90-9,20348-60-1,21562-54-9,26771-95-9,26771-96-0,34388-84-6,34388-86-8,34388-87-9,34388-89-1,34402-61-4,34437-28-0,37785-86-7,37818-61-4,42048-97-5,42587-03-1,42607-55-6,42607-56-7,54422-22-9,54422-23-0,55528-78-4,57759-92-9,57759-93-0,61375-87-9,61557-40-2,62860-86-0,62960-89-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) CuCN / 1.) diethyl ether, -40 deg C, 1.5 h, 2.) ether, from -78 deg C to -10 deg C, overnight

2: KF, pH 7 phosphate buffer / ethanol / 3 h / Ambient temperature

3: 84 percent / L-selectride / tetrahydrofuran / 6 h / Ambient temperature

4: 75 percent / O₂ / PtO₂ / acetone; H₂O / 4 h / 40 °C

5: 90 percent / 47-52percent aq. HF / acetonitrile; H₂O / 1 h / Ambient temperature

With potassium fluoride; pH 7 phosphate buffer; hydrogen fluoride; oxygen; L-Selectride; platinum(IV) oxide; In tetrahydrofuran; ethanol; water; acetone; acetonitrile;

DOI:10.1021/jo00231a014

upstream raw materials:

7-{(1S,2S,3S,5R)-2-[(E)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-3,5-dihydroxy-cyclopentyl}-heptanoic acid

(1R,3S,4S,5S)-4-[(E)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-(7-hydroxy-heptyl)-cyclopentane-1,3-diol

3β-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-2α-(7-hydroxyheptyl)-4α-hydroxycyclopentanone

2β-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-3α-(6-carboxyhexyl)-1α,4α-dihydroxycyclopentanone

Downstream raw materials:

Prostaglandin F(1α)-p-phenylphenacylester

7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-heptanoic acid biphenyl-4-yloxycarbonylmethyl ester

Prostaglandin F(1α)-p-phenylbenzylester

7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-heptanoic acid 2-(2,5-dimethoxy-phenyl)-2-oxo-ethyl ester

Refernces

• 1、 Marino, Joseph P.,Pradilla, Roberto Fernandez de la,Laborde, Edgardo. "Stereocontrolled Synthesis of Prostaglandins from Cyclopentadiene Monoepoxide". . p. 5279 - 5280. Retrieved 2007/10/02.
• 2、 Corey,Andersen,Carlson,Paust,Vedejs,Vlattas,Winter. "Total synthesis of prostaglandins. Synthesis of the pure dl-E1, -F1-alpha-F1-beta, -A1, and -B1 hormones.". . p. 3245 - 3247. Retrieved 2007/10/12.