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|SysName=7- [ 3 (R) -Hydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl-5-oxocyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid
|SysName=7- [ 3 (R) -Hydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl-5-oxocyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid
|Common Name=&&Prostaglandin E2&&
|Common Name=&&Prostaglandin E2&&
|Melting Point=65-66°C <<1001>>
|Melting Point=65-66°C [[Reference:Corey_EJ:Schaaf_TK:Huber_W:Koelliker_U:Weinshenker_NM:,J. Am. Chem. Soc.,1970,92,397|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Schaaf_TK:Huber_W:Koelliker_U:Weinshenker_NM:,J. Am. Chem. Soc.,1970,92,397}}]]
|Reflactive=[<FONT FACE="Symbol">a</FONT>]X<sub>D</sub><sup>26</sup>=-61.0°(C=1.0, TETRAHYDROFURAN) <<1001>>
|Reflactive=[<FONT FACE="Symbol">a</FONT>]X<sub>D</sub><sup>26</sup>=-61.0°(C=1.0, TETRAHYDROFURAN) [[Reference:Corey_EJ:Schaaf_TK:Huber_W:Koelliker_U:Weinshenker_NM:,J. Am. Chem. Soc.,1970,92,397|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Schaaf_TK:Huber_W:Koelliker_U:Weinshenker_NM:,J. Am. Chem. Soc.,1970,92,397}}]]
|Solubility= ETHYL ACETATE,THF,CHLOROFORM<<1002/1006>>. STABILITIES: to be stable under neutral condition. to decompose to PGA2 under acidic and to PGB2 under basic conditions <<1004/1005>>
|Solubility= ETHYL ACETATE,THF,CHLOROFORM[[Reference:Donaldson_RE:Saddler_JC:Byrn_S:McKenzie_AT:Fuchs_PL:,J. Org. Chem.,1983,48,2167|{{RelationTable/GetFirstAuthor|Reference:Donaldson_RE:Saddler_JC:Byrn_S:McKenzie_AT:Fuchs_PL:,J. Org. Chem.,1983,48,2167}}]][[Reference:Sih_CJ:Heather_JB:Sood_R:Price_P:Peruzzotti_G:Lee_LF:Lee_SS:,J. Am. Chem. Soc.,1975,97,865|{{RelationTable/GetFirstAuthor|Reference:Sih_CJ:Heather_JB:Sood_R:Price_P:Peruzzotti_G:Lee_LF:Lee_SS:,J. Am. Chem. Soc.,1975,97,865}}]]. STABILITIES: to be stable under neutral condition. to decompose to PGA2 under acidic and to PGB2 under basic conditions [[Reference:Karim_SM:Devlin_J:Hillier_K:,Eur. J. Pharmacol.,1968,4,416|{{RelationTable/GetFirstAuthor|Reference:Karim_SM:Devlin_J:Hillier_K:,Eur. J. Pharmacol.,1968,4,416}}]][[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}}]]
|Mass Spectra=d,l-mixture ; 334(M<SUP><FONT SIZE=-1>+</FONT></SUP>-18), 316, 298, 190 <<1003>>
|Mass Spectra=d,l-mixture ; 334(M<SUP><FONT SIZE=-1>+</FONT></SUP>-18), 316, 298, 190 [[Reference:Chen_SML:Schaub_RE:Grudzinskas_CV:,J. Org. Chem.,1978,43,3450|{{RelationTable/GetFirstAuthor|Reference:Chen_SML:Schaub_RE:Grudzinskas_CV:,J. Org. Chem.,1978,43,3450}}]]
|IR Spectra=d,l-mixture ; 3400, 1710, 970cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP> <<1003>>
|IR Spectra=d,l-mixture ; 3400, 1710, 970cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP> [[Reference:Chen_SML:Schaub_RE:Grudzinskas_CV:,J. Org. Chem.,1978,43,3450|{{RelationTable/GetFirstAuthor|Reference:Chen_SML:Schaub_RE:Grudzinskas_CV:,J. Org. Chem.,1978,43,3450}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP><SUP><FONT SIZE=-1>3</FONT></SUP>C-NMR(CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>) : 214.71(C9),178.39(C1), 136.62(C14), 131.52(C13), 130.91(C5), 126.69(C6), 73.19(C15), 72.13(C11), 54.55(C12), 53.51(C8), 46.23(C10), 37.00 (C16), 33.56(C2), 31.73(C18), 26.47(C4), 25.20(C7,17), 24.60(C3), 22.64(C19), 14.04. <<1002>>. <SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>) : <FONT FACE="Symbol">d</FONT>5.67(dd, J=6.6Hz, 15.4, 1H, 14-CH), 5.57(dd, J=8.1, 15.4Hz, 1H, 13-CH), 5.40(m, 2H, 5.6-CH), 4.12(q, J=6.5, 6.7, 6.8Hz, 1H, 15-CH), 4.06(q, J=8.1, 8.2, 8.3Hz, 1H, 11-CH), 2.72(dd, J= <<1002>>
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP><SUP><FONT SIZE=-1>3</FONT></SUP>C-NMR(CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>) : 214.71(C9),178.39(C1), 136.62(C14), 131.52(C13), 130.91(C5), 126.69(C6), 73.19(C15), 72.13(C11), 54.55(C12), 53.51(C8), 46.23(C10), 37.00 (C16), 33.56(C2), 31.73(C18), 26.47(C4), 25.20(C7,17), 24.60(C3), 22.64(C19), 14.04. [[Reference:Donaldson_RE:Saddler_JC:Byrn_S:McKenzie_AT:Fuchs_PL:,J. Org. Chem.,1983,48,2167|{{RelationTable/GetFirstAuthor|Reference:Donaldson_RE:Saddler_JC:Byrn_S:McKenzie_AT:Fuchs_PL:,J. Org. Chem.,1983,48,2167}}]]. <SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>) : <FONT FACE="Symbol">d</FONT>5.67(dd, J=6.6Hz, 15.4, 1H, 14-CH), 5.57(dd, J=8.1, 15.4Hz, 1H, 13-CH), 5.40(m, 2H, 5.6-CH), 4.12(q, J=6.5, 6.7, 6.8Hz, 1H, 15-CH), 4.06(q, J=8.1, 8.2, 8.3Hz, 1H, 11-CH), 2.72(dd, J= [[Reference:Donaldson_RE:Saddler_JC:Byrn_S:McKenzie_AT:Fuchs_PL:,J. Org. Chem.,1983,48,2167|{{RelationTable/GetFirstAuthor|Reference:Donaldson_RE:Saddler_JC:Byrn_S:McKenzie_AT:Fuchs_PL:,J. Org. Chem.,1983,48,2167}}]]
}}
}}

Revision as of 00:00, 12 December 2008


Upper classes: LB LBF



IDs and Links
LipidBank XPR1401
LipidMaps LMFA03010003
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20207PG23
Prostaglandin E2
LBF20207PG23.png
Structural Information
7- [ 3 (R) -Hydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl-5-oxocyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid
  • Prostaglandin E2
Formula C20H32O5
Exact Mass 352.224974134
Average Mass 352.46508
SMILES C(CC[C@@H](O)C=C[C@H]([C@H]1CC=CCCCC(O)=O)[C@@H](CC1=O)O)CC
Physicochemical Information
65-66°C Corey_EJ et al.
ETHYL ACETATE,THF,CHLOROFORM Donaldson_RE et al. Sih_CJ et al.. STABILITIES: to be stable under neutral condition. to decompose to PGA2 under acidic and to PGB2 under basic conditions Karim_SM et al. Pike_JEet al.
Spectral Information
Mass Spectra d,l-mixture ; 334(M+-18), 316, 298, 190 Chen_SML et al.
UV Spectra
IR Spectra d,l-mixture ; 3400, 1710, 970cm-1 Chen_SML et al.
NMR Spectra 13C-NMR(CDCl3) : 214.71(C9),178.39(C1), 136.62(C14), 131.52(C13), 130.91(C5), 126.69(C6), 73.19(C15), 72.13(C11), 54.55(C12), 53.51(C8), 46.23(C10), 37.00 (C16), 33.56(C2), 31.73(C18), 26.47(C4), 25.20(C7,17), 24.60(C3), 22.64(C19), 14.04. Donaldson_RE et al.. 1H-NMR(CDCl3) : d5.67(dd, J=6.6Hz, 15.4, 1H, 14-CH), 5.57(dd, J=8.1, 15.4Hz, 1H, 13-CH), 5.40(m, 2H, 5.6-CH), 4.12(q, J=6.5, 6.7, 6.8Hz, 1H, 15-CH), 4.06(q, J=8.1, 8.2, 8.3Hz, 1H, 11-CH), 2.72(dd, J= Donaldson_RE et al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20207PG23 See above. Bergstrom_S 1967
n.a. LBF20207PG23 See above. Bergstrom_S et al. 1968
n.a. LBF20207PG23 See above. Chen_SML et al. 1978
n.a. LBF20207PG23 See above. Corey_EJ et al. 1970
n.a. LBF20207PG23 See above. Donaldson_RE et al. 1983
n.a. LBF20207PG23 See above. Funk_CD 1993
n.a. LBF20207PG23 See above. Hansen_HS 1976
n.a. LBF20207PG23 See above. Herschman_HR 1996
n.a. LBF20207PG23 See above. Karim_SM et al. 1968
n.a. LBF20207PG23 See above. Negishi_M et al. 1995
n.a. LBF20207PG23 See above. Pike_JE et al. 1969
n.a. LBF20207PG23 See above. Sih_CJ et al. 1975
n.a. LBF20207PG23 See above. Smith_WL et al. 1996
n.a. LBF20207PG23 See above. Urade_Y et al. 1995
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