LBF20107PG18

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Upper classes: LB LBF



6-keto Prostaglandin F_1α
LBF20107PG18.png
Structural Information
Systematic Name 7- [ (3R,5S) -Dihydroxy- 2R- (3S-hydroxy-trans-1-octenyl) cyclopentan-1R -yl ] -6-oxoheptanoic acid
Common Name
  • 6-keto Prostaglandin F_1α
  • 7- [ 3 (R) ,5 (S) -Dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) cyclopentan-1 (R) -yl ] -6-oxoheptanoic acid
Symbol 6-KETO-PGF1α
Formula C20H34O6
Exact Mass 370.23553882
Average Mass 370.48036
SMILES C(CC[C@@H](O)C=C[C@H]([C@@H](CC(=O)CCCCC(O)=O)1)[C@@H](C[C@@H]1O)O)CC
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation [ α ]21
D
   = -9.6° (C=1.04 METHANOL) TanakaTet al.
Refractive Index
Solubility DIETHYL ETHER Pace-AsciakCMETHANOL, ACETONE, ETHYL ACETATE TanakaTet al.
Source When prostaglandin I2 is produced in animal tissues, it is unstable in aqueous solution, especially at acidic pH, and readily decomposed to 6-keto-prostaglandin F1 alpha Moncada_S et al.. Therefore, 6-keto-prostaglandin F1 alpha is detected where prostaglandin I2 is produced.
Chemical Synthesis Tanaka_T et al.
LBF20107PG18FT0001.gif
Metabolism 6-Keto-prostaglandin F1 alpha is subjected to beta -oxidation, and converted to 2,3-dinor-6-keto-prostaglandin F1 alpha which appears in urine as a major metabolite Needleman_P et al..
Biological Activity Degradation of prostaglandin I2 to 6-keto-prostaglandin F1 alpha brings about the loss of biological activities. For example, the hypotensive effect of prostaglandin I2 is at least 100 times mor active than 6-keto-prostaglandin F1 alpha Moncada_S et al..
Genetic Information
Note
Spectral Information
Mass Spectra METHYL ESTER ; 366(M+-18), 348, 335, 330, 323, 319, 279, 265, 223, 196, 195, 164, 143, 121, 111, 99, 95, 71 TanakaTet al.. DIRECT EXPOSURE AMMONIA CI POSITIVE : 370, 353, 244, 163, 153, 136. NEGATIVE : 368, 351, 334, 316, 225, 219, 166, 135, 127 Cepa_SR et al.
UV Spectra
IR Spectra NEAT: ν 3400, 1715, 1245, 1045, 975, 915, 875, 845, 800, 730 cm-1 TanakaTet al.
NMR Spectra 1H-NMR(ACETONE-D6) : δ 6.1-5.4(bs, 4H), 5.5-5.2(m, 2H), 4.7-3.5(m, 3H), 2.5-1.1 (m, 22H), 0.86(t, 3H) TanakaTet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20107PG18 See above. Cepa_SR et al. 1984
n.a. LBF20107PG18 See above. Moncada_S et al. 1978
n.a. LBF20107PG18 See above. Needleman_P et al. 1986
n.a. LBF20107PG18 See above. Pace-Asciak_C 1976
n.a. LBF20107PG18 See above. Tanaka_T et al. 1987


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