CAS 745-62-0 PGF1alpha (HCID 5280939)

Names & identifiers

Preferred name: PGF1alpha
IUPAC: 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]heptanoic acid
English name: PROSTAGLANDIN F1ALPHA
Molecular formula: C20H36O5
Molecular weight: 356.5

Names & synonyms

Prostaglandin f1alpha745-62-0Prostaglandin F1PGF1alphaPGF 1-alphaProstaglandin f1-alphaPGF1WJ72O6860W9S,11R,15S-trihydroxy-13E-prostaenoic acid7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]heptanoic acidCHEBI:28852Cyclopentaneheptanoic acid, 3,5-dihydroxy-2-(3-hydroxy-1-octenyl)-

Show more names

PGF1αPGF1αC06475protaglandinf1prostaglandinf1Prostaglandin F1α

Prost-13-en-1-oic acid, 9,11,15-trihydroxy-, (9-alpha,11-alpha,13E,15S)(13E,15S)-9alpha,11alpha-9,11,15-Trihydroxyprost-13-en-1-oic acidPGF1 alpha7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]heptanoic acid7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((E,3S)-3-hydroxyoct-1-enyl)cyclopentyl)heptanoic acid7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((1E,3S)-3-hydroxyoct-1-en-1-yl)cyclopentyl)heptanoic acidRefChem:928952prostaglandin F1a

Database identifiers

CAS: 745-62-0
PubChem CID: 5280939
DTXSID: DTXSID901339475
ChEMBL: CHEMBL1325783
ChEBI: CHEBI:28852
UNII: WJ72O6860W
Nikkaji: J14.832F

Properties

Computed structural properties

XLogP: 3.5
Topological polar surface area: 98 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 5
Rotatable bonds: 13
Heavy atoms: 25
Formal charge: 0
Complexity: 396

Physicochemical properties

Melting point: 102.5 °C · 102.5°C
Boiling point: 409.31 °C · 409.31°C (rough estimate)
alpha: 24 ° · +24°(D/24℃)(c=0.87,THF)
Density: 1.0321 · 1.0321 (rough estimate)
refractive index: 1.612 · 1.6120 (estimate)
storage temp.: -20 °C · -20°C
solubility: 50 mg/ml; · DMF: 50 mg/ml; DMSO: 50 mg/ml; Ethanol: 50 mg/ml; PBS pH 7.2: 2 mg/ml
form: A crystalline solid
pka: 4.78 · 4.78±0.10(Predicted)
color: White to off-white
BRN: 2704846 · 2704846
InChI: 1S/C20H36O5/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/h12-13,15-19,21-23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,18-,19+/m0/s1
InChIKey: DZUXGQBLFALXCR-CDIPTNKSSA-N
SMILES: O[C@@H]1[C@H](CCCCCCC(O)=O)[C@@H](/C=C/[C@H](CCCCC)O)[C@H](O)C1
FDA UNII: 72 O6860W · WJ72O6860W
UNSPSC Code: 12352211 · 12352211
NACRES: 25 · NA.25
Safety Statements: 22 · 22-24/25
WGK Germany: 3 · 3
RTECS: 4569700 · GY4569700
F: 8 · 8-10
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Safety data

F: 8-10
wgk: 3
rtecs: GY4569700
safety_code: 22-24/25
Storage Class: 11 - Combustible Solids

Chemistry & industry

Applications · 5 items

DescriptionProstaglandin 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.

DescriptionProstaglandin 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.

UsesPGF1alpha (Prostaglandin F1alpha) is a smooth muscle relaxant and a stable metabolite of prostacyclin (PGI2).

UsesProstaglandin 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 1011 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.

General DescriptionProstaglandins (PGs) contain prostanoic acid. They are divided as PGA, PGB, PGC, PGD, PGE and PGF groups. They all contain a five-member ring structure differing in their functions. PGF is known to be more soluble in phosphate buffer. PGF1α is a serum eicosanoid.