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|LipidBank=XPR1500
|LipidBank=XPR1500
|LipidMaps=LMFA03010137
|LipidMaps=LMFA03010137
|SysName=7- [ 3 (R) ,5 (S) -Dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) cyclopentan-1 (R) -yl ] -heptanoic acid / (8R,9S,11R,13E,15S) -9,11,15-Trihydroxyprost-13-enoic acid
|SysName=7- [ (3R,5S) -Dihydroxy-2R- (3S-hydroxy-trans-1-octenyl) -cyclopentan-1R -yl] -heptanoic acid
|Common Name=&&PROSTAGLANDIN F_1alpha&&7- [ 3 (R) ,5 (S) -Dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) cyclopentan-1 (R) -yl ] -heptanoic acid&&(8R,9S,11R,13E,15S) -9,11,15-Trihydroxyprost-13-enoic acid&&
|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  
|Reflactive=[<FONT FACE="Symbol">a</FONT>]X<sub>D</sub><sup>25</sup>=+30°(ETHANOL) [[Reference:Pike_J_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552|{{RelationTable/GetFirstAuthor|Reference:Pike_J_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552}}]]
|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:Pike_J_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552|{{RelationTable/GetFirstAuthor|Reference:Pike_J_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552}}]]
|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<SUP><FONT SIZE=-1>+</FONT></SUP>), 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}}]]
|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<FONT FACE="Symbol">a</FONT> ; KBr : <FONT FACE="Symbol">n</FONT> 3330, 1716, 967 cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP> [[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}}]]
|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=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(ACETONE-d<SUB><FONT SIZE=-1>6</FONT></SUB>, TMS) : <FONT FACE="Symbol">d</FONT> 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}}]]<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(CD<SUB><FONT SIZE=-1>3</FONT></SUB>OD, TMS, 300MHz):<FONT FACE="Symbol">d</FONT>4.10(1H, 9-CH), 3.81(1H, 11-CH), 2.36(1H, 10<FONT FACE="Symbol">b</FONT>-CH), 1.57(1H, 10<FONT FACE="Symbol">a</FONT>-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}}]]
|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 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}}
|Metabolism=
|Symbol=PGF1&alpha;
|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 .
}}
}}


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{{Lipid/Footer}}

Latest revision as of 08:00, 21 October 2010

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Upper classes: LB LBF



IDs and Links
LipidBank XPR1500
LipidMaps LMFA03010137
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20107PG03
Prostaglandin F1α
LBF20107PG03.png
Structural Information
7- [ (3R,5S) -Dihydroxy-2R- (3S-hydroxy-trans-1-octenyl) -cyclopentan-1R -yl] -heptanoic acid
  • Prostaglandin F1α
  • (8R,9S,11R,13E,15S) -9,11,15-Trihydroxyprost-13-enoic 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.
LBF20107PG03FT0001.gif
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
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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