LBF20107PG03

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Upper classes: LB LBF



Prostaglandin F1α
LBF20107PG03.png
Structural Information
Systematic Name 7- [ (3R,5S) -Dihydroxy-2R- (3S-hydroxy-trans-1-octenyl) -cyclopentan-1R -yl] -heptanoic acid
Common Name
  • Prostaglandin F1α
  • (8R,9S,11R,13E,15S) -9,11,15-Trihydroxyprost-13-enoic acid
Symbol PGF1α
Formula C20H36O5
Exact Mass 356.256274262
Average Mass 356.49684
SMILES C(CC[C@@H](O)C=C[C@H]([C@H]1CCCCCCC(O)=O)[C@@H](C[C@@H]1O)O)CC
Physicochemical Information
Melting Point 102-103°C
Boiling Point
Density
Optical Rotation [ α ]X25
D
   =+30°(ETHANOL) Pike_JE et al.
Refractive Index
Solubility DIETHYL ETHER, ETHYL ACETATE, METHANOL , ETHANOL Pike_JE et al. BergstromSet al.
Source Prostaglandin F1 alpha is contained in human seminal plasma in an amount of 3.6 microgram/ml Bergstrom_S , and is detected in ovine seminal plasma and seminal vesicle, human amniotic fluid, umbilical cord, placental vessels and decidua, frog spinal cord and intestine, and rat adrenal Horton_EW .
Chemical Synthesis Miyano_M et al.
LBF20107PG03FT0001.gif
Metabolism
Biological Activity In terms of contraction of gastrointestinal smooth muscles, prostaglandin F1 alpha was repoprted to be about 10 times less active than prostaglandin F2 alpha Horton_EW . Reference Bergstrom_S et al. contains a table for comparison of biological activities of various prostaglandins including F1 alpha .
Genetic Information
Note
Spectral Information
Mass Spectra m/e 356(M+), 338, 320 Ramwell_PW et al.
UV Spectra
IR Spectra d,l-PGF1 α  ; KBr : ν 3330, 1716, 967 cm-1 MiyanoMet al.
NMR Spectra 1H-NMR(ACETONE-d6, TMS) : δ 5.50(2H, 13-,14-CH), 3.75-4.3(m, 3H), 0.88(t, 3H) Ramwell_PW et al.1H-NMR(CD3OD, TMS, 300MHz): δ 4.10(1H, 9-CH), 3.81(1H, 11-CH), 2.36(1H, 10 β -CH), 1.57(1H, 10 α -CH) De_ClercqPet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20107PG03 See above. Bergstrom_S 1967
n.a. LBF20107PG03 See above. Bergstrom_S et al. 1968
n.a. LBF20107PG03 See above. Bergstrom_S et al. 1960
n.a. LBF20107PG03 See above. De_Clercq_P et al. 1977
n.a. LBF20107PG03 See above. Horton_EW 1965
n.a. LBF20107PG03 See above. Horton_EW 1969
n.a. LBF20107PG03 See above. Miyano_M et al. 1972
n.a. LBF20107PG03 See above. Pike_JE et al. 1969
n.a. LBF20107PG03 See above. Ramwell_PW et al. 1971


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