LBF20107PG03: Difference between revisions
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|LipidBank=XPR1500 | |LipidBank=XPR1500 | ||
|LipidMaps=LMFA03010137 | |LipidMaps=LMFA03010137 | ||
|SysName=7- [ | |SysName=7- [ (3R,5S) -Dihydroxy-2R- (3S-hydroxy-trans-1-octenyl) -cyclopentan-1R -yl] -heptanoic acid | ||
|Common Name=&& | |Common Name=&&Prostaglandin F_1 alpha&&(8R,9S,11R,13E,15S) -9,11,15-Trihydroxyprost-13-enoic acid&& | ||
|Melting Point=102-103°C | |Melting Point=102-103°C | ||
|Optical=[ | |Optical=[ alpha ]X^{25}_D =+30°(ETHANOL) [[Reference:Pike_JE:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552|{{RelationTable/GetFirstAuthor|Reference:Pike_JE:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552}}]] | ||
|Solubility=DIETHYL ETHER, ETHYL ACETATE, METHANOL , ETHANOL [[Reference: | |Solubility=DIETHYL ETHER, ETHYL ACETATE, METHANOL , ETHANOL [[Reference:Pike_JE:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552|{{RelationTable/GetFirstAuthor|Reference:Pike_JE:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552}}]][[Reference:Bergstrom_S:Sjoevall_J:,Acta_Chem._Scand.,1960,14,1693|{{RelationTable/GetFirstAuthor|Reference:Bergstrom_S:Sjoevall_J:,Acta_Chem._Scand.,1960,14,1693}}]] | ||
|Mass Spectra=m/e 356(M | |Mass Spectra=m/e 356(M^+ ), 338, 320 [[Reference:Ramwell_PW:Shaw_JE:Clarke_GB:Grostic_MF:Kaiser_DG:Pike_JE:,Progr. Chem. Fats Other Lipids,1971,9,231|{{RelationTable/GetFirstAuthor|Reference:Ramwell_PW:Shaw_JE:Clarke_GB:Grostic_MF:Kaiser_DG:Pike_JE:,Progr. Chem. Fats Other Lipids,1971,9,231}}]] | ||
|IR Spectra=d,l-PGF1 | |IR Spectra=d,l-PGF1 alpha ; KBr : nu 3330, 1716, 967 cm^{-1} [[Reference:Miyano_M:Dorn_CR:Mueller_RA:,J. Org. Chem.,1972,37,1810|{{RelationTable/GetFirstAuthor|Reference:Miyano_M:Dorn_CR:Mueller_RA:,J. Org. Chem.,1972,37,1810}}]] | ||
|NMR Spectra= | |NMR Spectra=^1 H-NMR(ACETONE-d_6 , TMS) : delta 5.50(2H, 13-,14-CH), 3.75-4.3(m, 3H), 0.88(t, 3H) [[Reference:Ramwell_PW:Shaw_JE:Clarke_GB:Grostic_MF:Kaiser_DG:Pike_JE:,Progr. Chem. Fats Other Lipids,1971,9,231|{{RelationTable/GetFirstAuthor|Reference:Ramwell_PW:Shaw_JE:Clarke_GB:Grostic_MF:Kaiser_DG:Pike_JE:,Progr. Chem. Fats Other Lipids,1971,9,231}}]]^1 H-NMR(CD_3 OD, TMS, 300MHz): delta 4.10(1H, 9-CH), 3.81(1H, 11-CH), 2.36(1H, 10 beta -CH), 1.57(1H, 10 alpha -CH)[[Reference:De_Clercq_P:Samson_M:Tavernier_D:Van_Haver_D:Vandewalle_M:,J. Org. Chem.,1977,42,3140|{{RelationTable/GetFirstAuthor|Reference:De_Clercq_P:Samson_M:Tavernier_D:Van_Haver_D:Vandewalle_M:,J. Org. Chem.,1977,42,3140}}]] | ||
|Source=Prostaglandin F1 | |Source=Prostaglandin F1 alpha is contained in human seminal plasma in an amount of 3.6 microgram/ml [[Reference:Bergstrom_S:,Science,1967,157,382|{{RelationTable/GetFirstAuthor|Reference:Bergstrom_S:,Science,1967,157,382}}]], 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 [[Reference:Horton_EW:,Experientia,1965,21,113|{{RelationTable/GetFirstAuthor|Reference:Horton_EW:,Experientia,1965,21,113}}]]. | ||
|Chemical Synthesis=[[Reference:Miyano_M:Dorn_CR:Mueller_RA:,J. Org. Chem.,1972,37,1810|{{RelationTable/GetFirstAuthor|Reference:Miyano_M:Dorn_CR:Mueller_RA:,J. Org. Chem.,1972,37,1810}}]] {{Image200|LBF20107PG03FT0001.gif}} | |Chemical Synthesis=[[Reference:Miyano_M:Dorn_CR:Mueller_RA:,J. Org. Chem.,1972,37,1810|{{RelationTable/GetFirstAuthor|Reference:Miyano_M:Dorn_CR:Mueller_RA:,J. Org. Chem.,1972,37,1810}}]] {{Image200|LBF20107PG03FT0001.gif}} | ||
|Metabolism= | |Metabolism= | ||
|Symbol=PGF1 | |Symbol=PGF1α | ||
|Biological Activity=In terms of contraction of gastrointestinal smooth muscles, prostaglandin F1 | |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 [[Reference:Horton_EW:,Physiol. Rev.,1969,49,122|{{RelationTable/GetFirstAuthor|Reference:Horton_EW:,Physiol. Rev.,1969,49,122}}]]. Reference [[Reference:Bergstrom_S:Carlson_LA:Weeks_JR:,Pharmacol. Rev.,1968,20,1|{{RelationTable/GetFirstAuthor|Reference:Bergstrom_S:Carlson_LA:Weeks_JR:,Pharmacol. Rev.,1968,20,1}}]] contains a table for comparison of biological activities of various prostaglandins including F1 alpha . | ||
}} | }} | ||
{{Lipid/Footer}} | {{Lipid/Footer}} |
Latest revision as of 08:00, 21 October 2010
LipidBank Top (トップ) |
Fatty acid (脂肪酸) |
Glycerolipid (グリセロ脂質) |
Sphingolipid (スフィンゴ脂質) |
Journals (雑誌一覧) |
How to edit (ページの書き方) |
IDs and Links | |
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LipidBank | XPR1500 |
LipidMaps | LMFA03010137 |
CAS | |
KEGG | {{{KEGG}}} |
KNApSAcK | {{{KNApSAcK}}} |
mol | LBF20107PG03 |
Prostaglandin F1α | |
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Structural Information | |
7- [ (3R,5S) -Dihydroxy-2R- (3S-hydroxy-trans-1-octenyl) -cyclopentan-1R -yl] -heptanoic acid | |
| |
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 | |
102-103°C | |
[ α ]X25 D =+30°(ETHANOL) Pike_JE et al. | |
DIETHYL ETHER, ETHYL ACETATE, METHANOL , ETHANOL Pike_JE et al. BergstromSet al. | |
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 . | |
Miyano_M et al. | |
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 . | |
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 | ||||||||||||||||||||||||||||||||||||||||||||||||||
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