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Steroid

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IdImageCOMMON NAMENAMEDATA No Lipid classINFORMANTSYMBOLFORMULAMOL.WT(average)Download cdx file / Mol format file BIOOGICAL ACTIVITY PHYSICAL AND CHEMICAL PROPERTIES SPECTRAL DATA CHROMATOGRAM DATA SOURCE CHEMICAL SYNTHESIS METABOLISM GENETIC INFORMATION NOTE REFERENCES
MELTING POINTBOILING POINTDENSITYREFRACTIVE INDEXOPTICAL ROTATIONSOLUBILITY UV SPECTRAIR SPECTRANMR SPECTRAMASS SPECTRAOTHER SPECTRA
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Allocholesterol / Coprostenol / 4:5-Coprosten-3-ol Cholest-4-en-3b-ol SST0001SteroidHideaki Nishino C27H46O1 386.654Download ChemDraw structure data 132deg (ether-methanol) << Ref. 0002>> [a]23/D=+43.7deg (c=1 in benzene) << Ref. 0002>> Freely sol in benzene, acetone, ether, chloroform, dioxane, pyridine; less sol in methanol, alcohol << Ref. 0002>> Preparation. << Ref. 0001/0002>> Separation from cholesterol. << Ref. 0003>> Deep-red color with 90% trichloroacetic acid. Positive in Rosenheim reaction, Salkowski reaction, Liebermann-Burchard reaction. << Ref. 0002>> Precipitable by digitonin. << Ref. 0004>> << Ref.0001 >> AUTHOR: Windaus,A. TITLE: Umlagerung des Cholesterins JOURNAL: Justus Liebigs Ann Chem. VOLUME: 453 PAGE: 101 -112 (1927)
<< Ref.0002 >> AUTHOR: Schoenheimer,R., and Evans,Jr.,E.A. TITLE: Allocholesterol and Epiallocholesterol JOURNAL: J.Biol.Chem. VOLUME: 114 PAGE: 567 -582 (1936)
<< Ref.0003 >> AUTHOR: Stoll,W. TITLE: Untersuchungen an Sterinen 5. Über das Allocholesterin und Seinen Nachweis. JOURNAL: Z.Physiol.Chem. VOLUME: 246 PAGE: 10 -12 (1937)
<< Ref.0004 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp45-45, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - ()
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Androsterone / Cis-androsterone / 3a-Hydroxy-17-androstanone / Androstan-3(a)-ol-17-one / 3(a)-Hydroxyetioallocholan-17-one / 3-Epihydroxyetioallocholan-17-one 3a-Hydroxy-5a-androstan-17-one SST0002SteroidHideaki Nishino C19H30O2 290.440Download ChemDraw structure data Androgenic activity. Sex determination in fetus. Maintenance of genitalia functions. << Ref. 0005/0006>> 185-185.5 degC << Ref. 0006>> [a]15/D=+87.8pm1.5deg, [a]15/5461=+107.3pm1.5deg (c=1.5379 in dioxan) << Ref. 0006>> Sol in most organic solvents. Barely sol in water. << Ref. 0007>> max. 292.5pm1.0 nm, min. 232.5pm2.5 nm (ethanol) << Ref. 0008>> Isolation from male urine. << Ref. 0005/0006>> Synthesis from cholesterol. << Ref. 0009/0010>> Not precipitated by digitonin. << Ref. 0007>> << Ref.0005 >> AUTHOR: Butenandt,A., and Tscherning,K. TITLE: Über Androsteron, ein Krystallisiertes Männliches Sexualhormon. I Isolierung und Reindarstellung aus Männerharn JOURNAL: Z.Physol.Chem. VOLUME: 229 PAGE: 167 -184 (1934)
<< Ref.0006 >> AUTHOR: von Euw,J., and Reichstein,T. TITLE: Über Bestandteile der NebennierenRinde und Verwandte Stoffe. 56. Mitteilung. Substanz V und Konfigurations-Bestimmungen in der C21O5-Gruppe JOURNAL: Helv.Chim.Acta VOLUME: 25 PAGE: 988 -1022 (1942)
<< Ref.0007 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp101-101, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0008 >> AUTHOR: Hogness,T.R., Sidwell,Jr.,A.R., and Zscheile,Jr.,F.P. TITLE: The Absorption Spectra of Compounds Related to the Sterols JOURNAL: J.Biol.Chem. VOLUME: 120 PAGE: 239 -256 (1937)
<< Ref.0009 >> AUTHOR: Ruzicka,L., Goldberg,M.W., and Brügger,H. TITLE: Zur Kenntnis der Sexualhormone I. Über die Gewinnung von 3-Chlor- und 3-Oxy-Ätio-Allocholanon-(17). Synthese einer Verbindung von den Eigenschaften des Testikelhormons JOURNAL: Helv.Chim.Acta VOLUME: 17 PAGE: 1389 -1394 (1934)
<< Ref.0010 >> AUTHOR: Marker,R.E. TITLE: Androsterone JOURNAL: J.Am.Chem.Soc. VOLUME: 57 PAGE: 1755 -1756 (1935)
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Bufotalin 16-(Acetyloxy)-3,14-dihydroxybufa-20,22-dienolide / 3b,14,16b-Trihydroxy-5b-bufa-20,22-dienolide 16-acetate SST0003SteroidHideaki Nishino C26H36O6 444.560Download ChemDraw structure data Cardiotoxic steroid. Applied for Chinese medicine named Senso as cardiotonic agent. << Ref. 0011/0012/0013/0014/0015/0016>> 269-272 degC (3-acetate), 233 degC (free) << Ref. 0013>> [a]20/D=+5.4deg (c=0.5 in CHCl3) << Ref. 0013>> Sol in alcohol, chloroform << Ref. 0017>> max. 300 nm << Ref. 0015>> 1H n.m.r. (100 MHz), employing spin-decoupling experiments, lead to the following assignments: the pyrone ring protons, d 6.17 (Ha, Doublet, Jab 9Hz, Jac 1Hz), 8.04 (Hb, Quartet, Jab 9Hz, Jbc 2.7Hz), 7.24 (Hc), while in ring D the 17a-proton Hd appeared as a doublet at d 2.72, J 9Hz. Because Jed and Jef were both 9Hz, He corresponded to a sextet at d 5.54 with Jeg 2 Hz. The methylene protons Hf and Hg gave signals at d 2.66 and 1.9, respectively. << Ref. 0016>> m/e: 444 (M, 5%) (M for C26H36O6=444); 384 (M-60, 100%); 336 (M-60-18, 61%); 351 (M-60-18-15, 9%); 348 (M-60-36, 10%); 341 (M-60-43, 80%); 323 (M-60-43-18, 68%). Metastable ion peaks at m/e 332.0 (440 to 384), 349.0 (384 to 366), and 303.0 (384 to 341) were observed. << Ref. 0016>> Predominant constituent of dermal gland secretion, toad poison. Component of bufotoxin. << Ref. 0011/0012/0013/0014/0015/0016/0017>> A couple of methods for partial synthesis. Prepare the 16-ketone of cinobufagin, reduce 14,15b-epoxide group with chromous acetate to yield b-hydroxy ketone and a,b-unsaturated ketone. Selectively reduce the b-hydroxy ketone with Urushibara nickel A to produce alcohol, which is acetylated to provide diacetate. Treat the diacetate with HCl in methanol to give bufotalin. Alternatively reduce first the a,b-unsaturated ketone with Urushibara nickel A to allylic alcohol. After acetylation subject the olefin to hypoiodous acid or hypobromous acid, then treat the resulting halohydrin with Urushibara nickel A. Hydrogenolyze the product to bufotalin 3b-acetate. << Ref. 0018>> << Ref.0011 >> AUTHOR: Faust,E.S. TITLE: Ueber Bufonin und Bufotalin, die Wirksamen Bestandtheile des Krötenhautdüsecretes JOURNAL: Arch.Exp.Pathol.Pharmakol. VOLUME: 47 PAGE: 278 -310 (1902)
<< Ref.0012 >> AUTHOR: Faust,E.S. TITLE: Weitere Beiträge zur Kenntniss der Wirksamen Bestandtheile des Krötenhautdrüsensecretes. JOURNAL: Arch.Exp.Pathol.Pharmakol. VOLUME: 49 PAGE: 1 -6 (1902)
<< Ref.0013 >> AUTHOR: Wieland,H., and Weil,F.J. TITLE: Über das Krötengift. JOURNAL: Ber. VOLUME: 46 PAGE: 3315 -3327 (1913)
<< Ref.0014 >> AUTHOR: Wieland,H., Hesse,G., and Hüttel,R. TITLE: Zur Kenntnis der Krötengiftstoffe. IX. Weiteres zur Konstitutionsfrage. JOURNAL: Justus Liebigs Ann Chem. VOLUME: 524 PAGE: 203 -222 (1936)
<< Ref.0015 >> AUTHOR: Meyer,K. TITLE: Über Herzaktive Krötengifte (Bufogenine). 5. Mitteilung. Konstitution des Bufotalins. JOURNAL: Helv.Chim.Acta VOLUME: 32 PAGE: 1993 -2003 (1949)
<< Ref.0016 >> AUTHOR: Pettit,G.R., Brown,P., Bruschweiler,F., and Houghton,L.E. TITLE: Structure of the Bufadienolide Bufotalin JOURNAL: J.Chem.Soc.,Chem.Commun. VOLUME: 1970 PAGE: 1566 -1567 (1970)
<< Ref.0017 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp224-224, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0018 >> AUTHOR: Kamano, Y., Pettit, G. R., and Inoue, M. TITLE: Bufadienolides. 29. Synthetic routes to bufotalin PubMed ID:4412262 JOURNAL: J Org Chem. VOLUME: 39 PAGE: 3007-3013(1974)
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Chlorogenin 5a-Spirostan-3b,6a-diol SST0004SteroidHideaki Nishino C27H44O4 432.636Download ChemDraw structure data Saponin useful as fish poisons. << Ref. 0025>> 273-276degC, 154-155degC (diacetate) << Ref. 0023>> [a]24/546 = -52deg (chloroform or isopropanol) << Ref. 0023>> Sol in methanol, isopropanol. << Ref. 0023>> d (pyridine) 0.83 (19-Me), 0.86 (18-Me), 1.12d(21-Me, J=7Hz), 1.05d (27-Me, J=7Hz), 3.30d (26-H2, J=11Hz), 3.39dd (26-H2, J=11, 3Hz), 4.45ddd (16-H, J=7, 7, 7Hz), 3.70m (3H and 6H). << Ref. 0024>> m/e 432 << Ref. 0024>> Root of amole (California soap plant, lily family, Chlorogalum pomeridianum Kunth) << Ref. 0025>> Precipitable by digitonin. << Ref. 0019>> Conversion to tigogenin. << Ref. 0023>> << Ref.0019 >> AUTHOR: Marker,R.E., and Rohrmann,E. TITLE: Sterols. LVIII. The Position of the Nuclear Hydroxyl Groups in Chlorogenin. JOURNAL: J.Am.Chem.Soc. VOLUME: 61 PAGE: 946 -949 (1939)
<< Ref.0023 >> AUTHOR: Marker,R.E., Turner,D.L., and Ulshafer,P.R. TITLE: Sterols. CXI. Sapogenins. XL. The Conversion of Chlorogenin to Tigogenin. JOURNAL: J.Am.Chem.Soc. VOLUME: 62 PAGE: 3009 -3010 (1940)
<< Ref.0024 >> AUTHOR: Chakravarty,A.K., Dhar,T.K., and Pakrashi,S.C. TITLE: Hispigenin, a Novel 22bo-Spirostane from Solanum Hispidum JOURNAL: Tetrahedron Lett. VOLUME: 1978 PAGE: 3875 -3878 (1978)
<< Ref.0025 >> AUTHOR: Liang,P., and Noller,C.R. TITLE: Saponins and Sapogenins. III. The Sapogenins Obtained from Chlorogalum Pomeridianum JOURNAL: J.Am.Chem.Soc. VOLUME: 57 PAGE: 525 -527 (1935)
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Cholestanol / b-Cholestanol Dihydroxycholesterol / 3b-Hydroxycholestan / 5a-Cholestan-3b-ol SST0005SteroidHideaki Nishino C27H48O1 388.669Download ChemDraw structure data Accumulation within the nervous system in cerebrotendinous xanthomatosis patients. << Ref. 0031>> 141.5-142degC << Ref. 0026>> [a] 22/D=+28.8deg << Ref. 0026>> Freely sol in heated alcohol, ethylether, chloroform. Approximately 1 g/100 ml alcohol or 200 ml methanol. << Ref. 0028>> 9.20(19-H), 9.36(18-H) << Ref. 0029>> Human feces, bilestones, eggs. << Ref. 0028>> Trace amount accompanied with cholesterol in animal cells, predominant sterol of sponges. << Ref. 0030>> Synthesis by reduction of cholesterol. << Ref. 0026/0027>> Precipitable by digitonin. Negative in Liebermann-Burchard reaction. << Ref. 0026/0027>> << Ref.0026 >> AUTHOR: Willstätter,R., and Mayer,E.W. TITLE: Reduktion Mit Platin und Wasserstoff. II. Über Dihydrocholesterin. JOURNAL: Ber. VOLUME: 41 PAGE: 2199 -2203 (1908)
<< Ref.0027 >> AUTHOR: Ellis,G.W., and Gardner,J.A. TITLE: On b-Cholestanol, Some of Its Derivatives and Oxidation Products. JOURNAL: Biochem.J. VOLUME: 12 PAGE: 72 -80 (1918)
<< Ref.0028 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp341-341, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0029 >> AUTHOR: Tori,K., Komeno,T., and Nakagawa,T. TITLE: Nuclear Magnetic Resonance Studies on Steroids. III. Steroidal Epoxides and Episulfides JOURNAL: J.Org.Chem. VOLUME: 29 PAGE: 1136 -1141 (1964)
<< Ref.0030 >> AUTHOR: Rosenfeld, R. S. TITLE: Analysis of sterol extracts for cholestanol PubMed ID:5323673 JOURNAL: Anal Biochem. VOLUME: 12 PAGE: 483-487(1965)
<< Ref.0031 >> AUTHOR: Menkes, J. H., Schimschock, J. R., and Swanson, P. D. TITLE: Cerebrotendinous xanthomatosis. The storage of cholestanol within the nervous system PubMed ID:5676919 JOURNAL: Arch Neurol. VOLUME: 19 PAGE: 47-53(1968)
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Coprostenol / 3b-Cholestanol / Stercorin 5b-Cholestan-3b-ol SST0006SteroidHideaki Nishino C27H48O1 388.669Download ChemDraw structure data 101degC (methanol) << Ref. 0035>> [a]18/D=+28deg (c=1.8 in chloroform) << Ref. 0036>> Sol in ethylether, chloroform, benzene. Slightly sol in methanol (1g/145 ml). Sol in water. << Ref. 0036>> Separation from cholesterol using TLC. << Ref. 0034>> Feces from human << Ref. 0032/0034>> , rat << Ref. 0033>> , and carnivorous animals. << Ref. 0036>> Synthesis by reduction of cholest-5-en-3-one with lithium aluminium hydride. << Ref. 0035/0037>> Synthesis by catalytic hydrogenation of coprostenol. << Ref. 0002/0038/0039/0040>> Approximately 360 mg/day in human feces. << Ref. 0032/0034>> Positive in Liebermann-Burchard reaction. << Ref. 0032/0033/0034>> Reduction by more than one bacterial species. << Ref. 0041>> << Ref.0002 >> AUTHOR: Schoenheimer,R., and Evans,Jr.,E.A. TITLE: Allocholesterol and Epiallocholesterol JOURNAL: J.Biol.Chem. VOLUME: 114 PAGE: 567 -582 (1936)
<< Ref.0032 >> AUTHOR: Bondzynski,S.T., and Humnicki,V. TITLE: Ueber das Schicksal des Cholesterins im Thierischen Organismus JOURNAL: Z.Physiol.Chem. VOLUME: 22 PAGE: 396 -410 (1896)
<< Ref.0033 >> AUTHOR: Wells, W. W., Coleman, D. L., and Baumann, C. A. TITLE: Intestinal sterols. I. Delta7-cholestenol and 7-dehydrocholesterol in feces PubMed ID:13259659 JOURNAL: Arch Biochem Biophys. VOLUME: 57 PAGE: 437-444(1955)
<< Ref.0034 >> AUTHOR: Samuel,P., Urivetzky,M., and Kaley,G. TITLE: Separation and Radioassay of Fecal Cholesterol and Coprosterol Using Thin-Layer Chromatography. JOURNAL: J.Chromatog. VOLUME: 14 PAGE: 508 -509 (1964)
<< Ref.0035 >> AUTHOR: Ruzicka,L., Brüngger,H., Eichenberger,E., and Meyer,J. TITLE: Polyterpene und Polyterpenoide XCI. Zur Präparativen Hersterins und Epi-Dihydro-Cholesterins. Beitrag zur Kenntnis der Räumlichen Lage der Hydroxylgruppe bei den Sterinen. JOURNAL: Helv.Chim.Acta. VOLUME: 17 PAGE: 1407 -1416 (1934)
<< Ref.0036 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp394-394, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0037 >> AUTHOR: Shoppee,C.W., and Summers,H.R. TITLE: Steroids and the Walden Inversion. Part VI. Reduction of Cholest-5-en-3-one with Lithium Alminum Hydride JOURNAL: J.Chem.Soc. VOLUME: 1950 PAGE: 687 -689 (1950)
<< Ref.0038 >> AUTHOR: Ruzicka,L., Furter,M., and Goldberg,M.W. TITLE: Über Steroide und Sexualhormone (42. Mitteilung) Zur Stereo Chemie Epimerer Steroider Alkohole Mit Einem Hydroxyl in den Stellungen 3 Odor 17. JOURNAL: Helv.Chim.Acta VOLUME: 21 PAGE: 498 -514 (1938)
<< Ref.0039 >> AUTHOR: Shoppee,C.W., Agashe, B.D., and Summers,G.H.R. TITLE: Steroids. Part XIII. Catalytic Hydrogenation of 3a- and 3b-Substituted D4-Steroids. JOURNAL: J.Chem.Soc. VOLUME: 1957 PAGE: 3107 -3112 (1957)
<< Ref.0040 >> AUTHOR: Dart,M.C., and Henbest,H.B. TITLE: Aspects of Stereochemistry. Part XV. Catalytic Hydrogenation of Cyclic Allylic Alcohols in the Presence of Sodium Nitrite. JOURNAL: J.Chem.Soc. VOLUME: 1960 PAGE: 3563 -3570 (1960)
<< Ref.0041 >> AUTHOR: Rosenfeld,R.S., and Gallagher,T.F. TITLE: Further Studies of the Biotransformation of Cholesterol to Coprostanol. JOURNAL: Steroids VOLUME: 4 PAGE: 515 -520 (1964)
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7-Dehydrocholesterol / Provitamin D3 Cholesta-5,7-dien-3b-ol SST0007SteroidHideaki Nishino7-DHC C27H44O1 384.638Download ChemDraw structure data Immediate precursor to cholesterol. << Ref. 0051/0052>> 149-150degC << Ref. 0043>> [a]20/D=-122.5deg(benzene), -113.6deg(chloroform) << Ref. 0043/0045>> Sol in ether, chloroform. Slightly sol in methanol. Insol in water << Ref. 0045>> nm(e): min. 230 (150), max. 262.5 (740), max. 271 (1,040), min. 276 (883), max. 281.5 (1,075), min. 288 (553), max. 293 (615), max. 321 (36). << Ref. 0008>> E1%/1cm (l, nm): 39.1 (2,300), 193 (2,625), 271 (2,710), 230 (2,760), 280 (2,815), 144 (2,880), 160 (2,930), 0.9 (3,210). << Ref. 0046>> Tissues of animals << Ref. 0047>> , pig derma (5 % of total sterols) << Ref. 0048>> , Horned snail (Buccinum undatum). << Ref. 0049/0050>> Antirachitic activity as vitamin D3 after conversion to cholecalcipherol by ultraviolet irradiation and hydroxylation. << Ref. 0051/0052>> Synthesis from cholesterol via 7-bromocholesteryl ester. << Ref. 0053/0054>> Possibly excess accumulation relates to holoprosencephalic disorder. << Ref. 0055>> Precipitable by digitonin. << Ref. 0042>> << Ref.0008 >> AUTHOR: Hogness,T.R., Sidwell,Jr.,A.R., and Zscheile,Jr.,F.P. TITLE: The Absorption Spectra of Compounds Related to the Sterols JOURNAL: J.Biol.Chem. VOLUME: 120 PAGE: 239 -256 (1937)
<< Ref.0042 >> AUTHOR: Windaus,A., Lettre,H., and Schenck,Fr. TITLE: Über das 7-Dehydro-Cholesterin JOURNAL: Justus Liebigs Ann Chem. VOLUME: 520 PAGE: 98 -106 (1935)
<< Ref.0043 >> AUTHOR: Boer,A.G., Reerink,E.H., van Wijk,A., and van Niekerk,J. TITLE: A Naturally Occurring Chicken Provitamin-D. JOURNAL: Proc.Acad.Sci.Amsterdam VOLUME: 39 PAGE: 622 -632 (1936)
<< Ref.0045 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp2857-2858, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0046 >> AUTHOR: Loofbourow,J.R. TITLE: Physical Methods for Identification and Assay of Vitamins and Hormones. JOURNAL: Vitamins and Hormones VOLUME: 1 PAGE: 109 -155 (1943)
<< Ref.0047 >> AUTHOR: Deuel,Jr.,H.T.(1951) Distribution, Properties, and Chemistry of the Provitamins D and Vitamins D in the Lipids Their Chemistry and Biochemistry I (Deuel,Jr.,H.J., eds.), pp739-792, Interscience Publishers, New York TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0048 >> AUTHOR: Windaus,A., and Bock,F. TITLE: Über das Provitamin aus dem Sterin der Schweinschwarte. JOURNAL: Z.Physiol.Chem. VOLUME: 245 PAGE: 168 -170 (1937)
<< Ref.0049 >> AUTHOR: Bock,F., and Wetter,F. TITLE: Über die bei Einigen Avertebraten Vorkommenden Antirachitishen Provitamine JOURNAL: Z.Physiol.Chem. VOLUME: 256 PAGE: 33 -41 (1938)
<< Ref.0050 >> AUTHOR: Windaus,A. TITLE: The Antirachitic Provitamins in the Animal Kingdom JOURNAL: Nachr.Ges.Wiss.Göttingen, Math.-Physk.Klasse, Fachgruppe III VOLUME: 1 PAGE: 185 -192 (1936)
<< Ref.0051 >> AUTHOR: Windaus,A., Schenck,Fr., and von Werder,F. TITLE: Über das Antirachitisch Wirksame Bestrahlungsprodukt aus 7-Dehydro-Cholesterin. JOURNAL: Z.Physiol.Chem. VOLUME: 241 PAGE: 100 -103 (1936)
<< Ref.0052 >> AUTHOR: Windaus,A., Deppe,N., and Wunderlich,W. TITLE: Über Einige Bestrahlungsprodukte aus 7-Dehydro-Cholesterin. JOURNAL: Justus Liebigs Ann Chem. VOLUME: 533 PAGE: 118 -127 (1938)
<< Ref.0053 >> AUTHOR: Buisman,J.A.K., Stevens,W., and von der Vliet,J. TITLE: Investigations on Sterols. I. A New Synthesis of 7-Dehydrocholesterol (Provitamin D). JOURNAL: Rec.Trav.Chim. VOLUME: 66 PAGE: 83 -92 (1947)
<< Ref.0054 >> AUTHOR: Confalone,P.N., Kulesha,I.D., and Uskokovic,M.R. TITLE: A New Synthesis of 7-Dehydrocholesterols. JOURNAL: J.Org.Chem. VOLUME: 46 PAGE: 1030 -1032 (1981)
<< Ref.0055 >> AUTHOR: Salen, G., Shefer, S., Batta, A. K., Tint, G. S., Xu, G., Honda, A., Irons, M., and Elias, E. R. TITLE: Abnormal cholesterol biosynthesis in the Smith-Lemli-Opitz syndrome PubMed ID:8808751 JOURNAL: J Lipid Res. VOLUME: 37 PAGE: 1169-1180(1996)
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Desmosterol / 24-Dehydrocholesterol / Desmesterol Cholesta-5,24-dien-3b-ol SST0008SteroidHideaki Nishino C27H44O1 384.638Download ChemDraw structure data One of precursors to cholesterol in animals. << Ref. 0056/0057/0058>> 120.5-121.0degC (methanol) << Ref. 0057>> 117-118degC. << Ref. 0059>> 120-122degC << Ref. 0060>> [a]/D=-37.9deg, [a]27/D=-40.2 (c=1 in chloroform) << Ref. 0057>> Sol in ether, benzene, chloroform, ethanol. << Ref. 0061>> max. 320nm (E1%/1cm, 240), 433nm (E1%/1cm, 154), min. 256nm (E1%/1cm, 93), 393nm (E1%/1cm, 109), (7times10-7 M in 97% sulfate) << Ref. 0057>> 1125, 1012, 900 cm-1 (THP ether) << Ref. 0057/0058/0060>> 41 (18-CH3), doublet centered at 51 (J=6Hz, 21-CH3), 61 (19-CH3), 97 and 102 (26.27 methyls), 210(3a-H) and 303(24-H), 320(6-H) << Ref. 0057/0058/0060>> m/e: 91(31%), 93(48%), 95(52%), 105(37%), 107(41%), 109(33%), 117(12%), 119(44%), 121(34%), 123(15%), 129(100%), 130(17%), 131(20%), 133(26%), 135(17%), 143(20%), 145(32%), 147(22%), 149(13%), 159(25%), 161(18%), 173(12%), 213(13%), 245(12%) << Ref. 0058>> Rat skin << Ref. 0056>> Chick embryo << Ref. 0057>> Red algae (Rhodophyceae) << Ref. 0058>> Barnacle << Ref. 0059>> Synthesis from 3b-hydroxybisnorcholenic acid and 3b-hydroxynorcholenic acid by lithium-ethylamine-induced hydrogenolysis of the methyl ether derivatives of allyl alcohol. << Ref. 0060>> Synthesis from 3b-acetoxy-23,24-dinorchol-5-en-22-ol by coupling reaction between dimethylallyllithium and a bromide. << Ref. 0062>> Synthesis from 16a, 17a-epoxypregnenolone by employing the potassium-assisted oxy-Cope rearrangement as a key stereodirecting process at C-20. << Ref. 0063>> Possibly excess accumulation relates to lethal multiple malformations. << Ref. 0064>> Conversion to cholesterol in vivo. << Ref. 0056>> << Ref.0056 >> AUTHOR: Stokes, W. M., Hickey, F. C., and Fish, W. A. TITLE: Sterol metabolism. I. The occurrence of desmosterol (24-dehydrocholesterol) in rat skin and its conversion in vivo to cholesterol PubMed ID:13549424 JOURNAL: J Biol Chem. VOLUME: 232 PAGE: 347-359(1958)
<< Ref.0057 >> AUTHOR: Stokes, W. M., Fish, W. A., and Hickey, F. C. TITLE: Metabolism of cholesterol in the chick embryo. II. Isolation and chemical nature of two companion sterols PubMed ID:13319360 JOURNAL: J Biol Chem. VOLUME: 220 PAGE: 415-430(1956)
<< Ref.0058 >> AUTHOR: Idler, D. R., Saito, A., and Wiseman, P. TITLE: Sterols in red algae (Rhodophyceae) PubMed ID:5643148 JOURNAL: Steroids. VOLUME: 11 PAGE: 465-473(1968)
<< Ref.0059 >> AUTHOR: Fargerlund,U.H.M., and Idler,D.R. TITLE: Marine Sterols. IV. 24-Dehydrocholesterol: Isolation from a Barnacle and Synthesis by the Wittig Reaction. JOURNAL: J.Am.Chem.Soc. VOLUME: 79 PAGE: 6473 -6475 (1957)
<< Ref.0060 >> AUTHOR: Dasgupta, S. K., Crump, D. R., and Gut, M. TITLE: New preparation of desmosterol PubMed ID:4853344 JOURNAL: J Org Chem. VOLUME: 39 PAGE: 1658-1662(1974)
<< Ref.0061 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp460-460, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0062 >> AUTHOR: Apfel,M.A. TITLE: A New Synthesis for D24-Sterols: Preparation of Cholesta-5,24-Dien-3b-Ol (Desmosterol). JOURNAL: J.Org.Chem. VOLUME: 43 PAGE: 2284 -2285 (1978)
<< Ref.0063 >> AUTHOR: Koreeda,M., Tanaka,Y., and Schwartz,A. TITLE: Stereochemically Controlled Synthesis of Steroid Side Chains: Synthesis of Desmosterol. JOURNAL: J.Org.Chem. VOLUME: 45 PAGE: 1172 -1174 (1980)
<< Ref.0064 >> AUTHOR: FitzPatrick, D. R., Keeling, J. W., Evans, M. J., Kan, A. E., Bell, J. E., Porteous, M. E., Mills, K., Winter, R. M., and Clayton, P. T. TITLE: Clinical phenotype of desmosterolosis PubMed ID:9450875 JOURNAL: Am J Med Genet. VOLUME: 75 PAGE: 145-152(1998)
9
a-Ecdysone 2,3,14,22,25-Pentahydroxycholest-7-en-6-one SST0009SteroidHideaki Nishino C27H44O6 464.635Download ChemDraw structure data Molting hormone of insects. << Ref. 0065/0066/0068/0069/0075>> 238-239degC << Ref. 0067/0068>> [a]20/578 = +62deg << Ref. 0067>> Sol in ethanol. << Ref. 0065>> max. 243nm (e=11,600), 293nm (e=15,800) << Ref. 0065/0068>> KBr (/cm): 1658, 1652 << Ref. 0069>> n max. 73(18-H), 107(19-H), 124 and 131(21-H), 138(26-H and 27-H) cps << Ref. 0070>> m/e (t-190deg): 446(3%), 428(29), 418(2), 413(2), 410(3), 372(3), 359(4), 348(8), 330(15), 315(18), 300(23), 279(17), 267(5), 255(8),250(13), 249(10), 99(100), 81(61) << Ref. 0071>> Silkworm (Bombyx mori) << Ref. 0072>> Rhizomes (Polypodium vulgare L.). << Ref. 0073>> Bracken (Pteridium aquilium L.) << Ref. 0074>> Synthesis from stigma-22-ene-3,6-dione by dividing three partial structure, A-ring, B, C-ring, and side chain. << Ref. 0068>> Synthesis from 3b-hydroxy-23,24-bisnorchol-5-en-22-oic acid, readily available starting material. << Ref. 0070>> Synthesis from (20S)-2b,3b-diacetoxy-20-formyl-5b-pregn-7-en-6-one by Grinard reaction with 2-methyl-3-butyn-2-oltetrahydropyran-2-yl ether, followed by hydrogenation of the triple bond, removal of the protecting groups, and hydroxylation in 14a-position. << Ref. 0071>> Synthesis from methyl 14a-hydroxy-2b,3b-isopropylidenedioxy-6-oxo-22,23-bisnor-5b-chol-7-enoate. << Ref. 0074>> << Ref.0065 >> AUTHOR: Karlson, P., Hoffmeister, H., Hummel, H., Hocks, P., and Spiteller, G. TITLE: [On the chemistry of ecdysone. VI. Reactions of ecdysone molecules] PubMed ID:5849855 JOURNAL: Chem Ber. VOLUME: 98 PAGE: 2394-2402(1965)
<< Ref.0066 >> AUTHOR: Huber, R., and Hoppe, W. TITLE: [On the chemistry of ecdysone. VII. Analysis of the crystal and molecular structure of the molting hormone in insects, ecdysone, using the automized folding molecule method] PubMed ID:5849856 JOURNAL: Chem Ber. VOLUME: 98 PAGE: 2403-2424(1965)
<< Ref.0067 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp547-547, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0068 >> AUTHOR: Mori,H., Shibata,K., Tsuneda,K., and Sawai,M. TITLE: Synthesis of Ecdysone. JOURNAL: Chem.Pharm.Bull. VOLUME: 16 PAGE: 563 -566 (1968)
<< Ref.0069 >> AUTHOR: Kaplanis, J. N., Thompson, M. J., Robbins, W. E., and Bryce, B. M. TITLE: Insect hormones: alpha ecdysone and 20-hydroxyecdysone in bracken fern PubMed ID:6037858 JOURNAL: Science. VOLUME: 157 PAGE: 1436-1438(1967)
<< Ref.0070 >> AUTHOR: Siddall, J. B., Marshall, J. P., Bowers, A., Cross, A. D., Edwards, J. A., and Fried, J. H. TITLE: Synthetic studies on insect hormones. I. Synthesis of the tetracyclic nucleus of ecdysone PubMed ID:5900550 JOURNAL: J Am Chem Soc. VOLUME: 88 PAGE: 379-380(1966)
<< Ref.0071 >> AUTHOR: Kerb, U., Schulz, G., Hocks, P., Wiechert, R., Furlenmeier, A., Furst, A., Langemann, A., and Waldvogel, G. TITLE: [On the synthesis of ecdysone. IV. On insect hormones. The synthesis of the natural skin shedding hormone] PubMed ID:5924992 JOURNAL: Helv Chim Acta. VOLUME: 49 PAGE: 1601-1606(1966)
<< Ref.0072 >> AUTHOR: Butenandt,A., and Karlson,P. TITLE: Über die Isolierung eines Metamorphose-Hormons der Insekten in Kristallisierter Form. JOURNAL: Z.Natureforsch VOLUME: 9 PAGE: 389 -391 (1954)
<< Ref.0073 >> AUTHOR: Heinrich, G., and Hoffmeister, H. TITLE: [Ecdysone as companion substance of ecdysterone in Polypodium vulgare L] PubMed ID:6077902 JOURNAL: Experientia. VOLUME: 23 PAGE: 995-(1967)
<< Ref.0074 >> AUTHOR: Iddall, J. B., Cross, A. D., and Fried, J. H. TITLE: Steroids. CCXCII. Synthetic studies on insect hormones. II. The synthesis of ecdysone PubMed ID:5902567 JOURNAL: J Am Chem Soc. VOLUME: 88 PAGE: 862-863(1966)
<< Ref.0075 >> AUTHOR: Ashburner, M. TITLE: Chromosomal action of ecdysone PubMed ID:6250033 JOURNAL: Nature. VOLUME: 285 PAGE: 435-436(1980)
10
b-Ecdysone / 20-Hydroxyecdysone / Ecdysterone / Crustecdysone / Isoinokosterone 2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one SST0010SteroidHideaki Nishino C27H44O7 480.634Download ChemDraw structure data Molting and metamorphosis hormone for Insecta and Crustacea. Much potent than a-ecdysone. << Ref. 0077>> 240-242degC (methanol-ethylacetate) << Ref. 0079>> [a]28/D = +63deg(c=1.0, methanol) << Ref. 0080>> Sol in methanol, ethanol. << Ref. 0080>> max. 243nm (e= 10,300), 240nm (ethanol, e= 12,670), 242nm (methanol, e= 12,400) << Ref. 0067/0079/0077>> n KBr/max. 1656, 1615, 1387, 1229, 1053, 917, 878 /cm << Ref. 0079>> Pyridine-d5: 1.07(19-H), 1.20(18-H), 1.36(26- and 27-H), 1.56(21-H), 6.17(7-H) << Ref. 0079>> m/e: 480 (ecdysone+0), 462 (M-H2O), 444 (M-2H2O), 426 (M-3H2O), 408 (M-4H2O) << Ref. 0077>> Silkworm (Bombyx mori) << Ref. 0077>> Crawfish (crayfish) (Jasus lalandei) << Ref. 0078>> Achyranthis radix (as phytoecdysone) << Ref. 0080>> Australia timber tree (Podocarpus elatus) << Ref. 0081>> Lemmaphyllum microphyllum, Trillium smallii << Ref. 0082>> Synthesis from hydroxylated aldehyde precursor, (20S)-2b,3b-diacetoxy-5a-hydroxy-20-methoxycarbonylpregn-7-en-6-one. << Ref. 0079>> Synthesis from 20b-hydroxy-5a-pregnane-3,6-dione via 2b,3b-diacetoxy-5a-pregn-7-ene-6,20-dione. << Ref. 0083>> Stereospecific synthesis from 20bbenzoyloxy-5-pregnen-3b-ol. << Ref. 0084>> Stereocontrolled total synthesis from 2b,3b,20b,-triacetoxy-5a-pregnan 6-one via acetylene-cationcyclization. << Ref. 0085>> The complete structure of natural b-ecdysone determined by a three-dimensional X-ray analysis using convolution molecule method. << Ref. 0076>> << Ref.0067 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp547-547, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0076 >> AUTHOR: Dammeier, B., and Hoppe, W. TITLE: [The crystal and molecular structure analysis of the insectmoulting hormone 20-hydroxyecdysone (Ecdysterone)] PubMed ID:5154405 JOURNAL: Chem Ber. VOLUME: 104 PAGE: 1660-1673(1971)
<< Ref.0077 >> AUTHOR: Hocks,P., and Wiechert,R. TITLE: 20-Hydroxy-Ecdyson, Isoliert aus Insekten. JOURNAL: Tetrahedron Lett. VOLUME: 1966 PAGE: 2989 -2993 (1966)
<< Ref.0078 >> AUTHOR: Hampshire,F., and Horn,D.H.S. TITLE: Structure of Crustecdysone, a Crustacean Moulting Hormone. JOURNAL: J.Chem.Soc., Chem Commun. VOLUME: 1966 PAGE: 37 -38 (1966)
<< Ref.0079 >> AUTHOR: Hüppi,G., and Siddall,J.B. TITLE: Steroids. CCCXXXIII. Synthetic Studies on Insect Hormones. V. The Synthesis of Crustecdysone (20-Hydroxyecdysone). JOURNAL: J.Am.Chem.Soc. VOLUME: 89 PAGE: 6790 -6792 (1967)
<< Ref.0080 >> AUTHOR: Takemoto,T., Ogawa,S., and Nishimoto,N. TITLE: Isolation of the Moulting Hormones of Insects from Achyranthis Radix. JOURNAL: Yakugaku Zasshi VOLUME: 87 PAGE: 325 -327 (1967)
<< Ref.0081 >> AUTHOR: Galbraith,M.N., and Horn,D.H.S. TITLE: An Insect-Moulting Hormone from a Plant. JOURNAL: J.Chem.Soc., Chem.Commun. VOLUME: 1966 PAGE: 905 -906 (1966)
<< Ref.0082 >> AUTHOR: Horn, D. H., Fabbri, S., Hampshire, F., and Lowe, M. E. TITLE: Isolation of crustecdysone (20R-hydroxyecdysone) from a crayfish (Jasus lalandei H. Milne-Edwards) PubMed ID:5685865 JOURNAL: Biochem J. VOLUME: 109 PAGE: 399-406(1968)
<< Ref.0083 >> AUTHOR: Kerb,U., Wiechert,R., Furlenmeier,A., and Fürst,A. TITLE: Über eine Synthese des Crustecdysons (20-Hydroxyecdyson). JOURNAL: Tetrahedron Lett. VOLUME: 1968 PAGE: 4277 -4280 (1968)
<< Ref.0084 >> AUTHOR: Mori, H., and Shibata, K. TITLE: Synthesis of ecdysterone PubMed ID:5347599 JOURNAL: Chem Pharm Bull (Tokyo). VOLUME: 17 PAGE: 1970-1973(1969)
<< Ref.0085 >> AUTHOR: Kametani,T., Tsubuki,M., and Nemoto,H. TITLE: A Stereocontrolled Total Synthesis of 2b,3b,20b-Triacetoxy-5a-Pregnan-6-One. A Total Synthesis of 20-Hydroxyecdysone. JOURNAL: Tetrahedron Lett. VOLUME: 21 PAGE: 4855 -4856 (1980)
11
Equilin 3-Hydroxyestra-1,2,5(10),7-tetraen-17-one / 1,3,5,7-Estratetraen-3-ol-17-one SST0011SteroidHideaki Nishino C18H20O2 268.350Download ChemDraw structure data Weaker than estron, stronger than estriol. << Ref. 0091>> Clinically available because of mild estrogenic hormone activity. << Ref. 0093>> 237-239degC << Ref. 0087>> 238-240degC << Ref. 0088>> 237-240degC << Ref. 0089>> [a]15/D=+308 (dioxane) << Ref. 0088>> [a]25/D=+304deg(dioxane) << Ref. 0087>> [a]/D=+295deg(c=1 in ethanol) << Ref. 0089>> max. 283-285nm << Ref. 0090>> 282nm (ethanol) << Ref. 0089>> loge=3.36 (282nm) << Ref. 0089>> Urine of mares. << Ref. 0088/0091>> Synthesis from 19-nortestosterone acetate via four intermediates. << Ref. 0089>> Relatively simple synthesis from dienone compound. << Ref. 0092>> Synthesis from estratetraene via several novel steroid intermediates and reactions. << Ref. 0093>> Total synthesis from estra-1,3,5(10),8-tetraenes by oxidation with m-chloroperbenzoic acid, rearrangement of the resulting epoxide with acid, catalytic hydrogenation, and dehydration. << Ref. 0094>> Synthesis by conversion of equilenine. << Ref. 0095/0096>> << Ref.0087 >> AUTHOR: Pearlman,W.H., and Wintersteiner,O. TITLE: Estrogens with Oxygen in Ring B I. 7-Ketoestrone and 7-Hydroxyestrone. JOURNAL: J.Biol.Chem. VOLUME: 130 PAGE: 35 -45 (1939)
<< Ref.0088 >> AUTHOR: Girard,A., Sandulesco,G., Fridenson,A., and Rutgers,J.-J. TITLE: Sur Une Nouvelle Hormone Sexuelle Cristallisee. JOURNAL: Compt.rend. VOLUME: 195 PAGE: 981 -984 (1932)
<< Ref.0089 >> AUTHOR: Zderic,J.A., Bowers,A., Carpio,H., and Djerassi,C. TITLE: Steroids. XCVI. The Synthesis of Equilin. JOURNAL: J.Am.Chem.Soc. VOLUME: 80 PAGE: 2596 -2597 (1958)
<< Ref.0090 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp570-570, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0091 >> AUTHOR: Cartland,G.F., and Meyer,R.K. TITLE: A Study of Equilin Prepared from Pregnant Mare Urine. JOURNAL: J.Biol.Chem. VOLUME: 112 PAGE: 9 -14 (1935)
<< Ref.0092 >> AUTHOR: Bagri,J.F., Morand,P.F., Wiesner,K., and Gaudry,R. TITLE: A Simple Synthesis of Equilin. JOURNAL: Tetrahedron Lett. VOLUME: 1964 PAGE: 387 -389 (1964)
<< Ref.0093 >> AUTHOR: Stein,R.P., Buzby,Jr.,G.C., and Smith,H. TITLE: A New Total Synthesis of Equilin. JOURNAL: Tetrahedron Lett. VOLUME: 1966 PAGE: 5015 -5020 (1966)
<< Ref.0094 >> AUTHOR: Stein, R. P., Buzby, G. C., Jr., and Smith, H. TITLE: Totally synthetic steroid hormones. XX. Novel total syntheses of equilin and equilenin PubMed ID:5433528 JOURNAL: Tetrahedron. VOLUME: 26 PAGE: 1917-1933(1970)
<< Ref.0095 >> AUTHOR: Bailey,E.J., Gale,A., Phillipps,G.H., Siddons,P.T., and Smith,G. TITLE: Syntheses of Equilenin, Equilin, and 17b-Hydroxyoestr-4-En-3-One. JOURNAL: J.Chem.Soc., Chem.Commun. VOLUME: 1967 PAGE: 1253 -1254 (1967)
<< Ref.0096 >> AUTHOR: Marshall,D.J., and Deghenghi,R. TITLE: A New Direct Synthesis of Equilin from Equilenin. Potassium-Ammonia Reduction of Some Non-Conjugated Double Bonds. JOURNAL: Can.J.Chem. VOLUME: 47 PAGE: 3127 -3131 (1969)
12
Ergosterol / Ergosterin / Provitamin D2 Ergosta-5,7,22-trien-3b-ol SST0012SteroidHideaki Nishino C28H44O1 396.648Download ChemDraw structure data Antirachitic activity as 1,25-dihydroxyergocalciferol. << Ref. 0102>> 168degC (alcohol) << Ref. 0098>> bp0.01 = 250degC << Ref. 0098>> [a] 20/D=-135deg (c=1.2 in chloroform), [a] 20/546=-171deg(chloroform) << Ref. 0099>> Sol in heated chloroform, benzene. Slightly sol in methanol, ethanol, ether, petroleum ether. Insol in water. << Ref. 0050>> max. nm (e); 262 (6,940); 271 (10,000); 282 (10,600); 293 (6,060). min. nm (e); 230 (1,430); 263 (6,850); 275.5 (8,580); 289 (5,450); 317.5 (35) << Ref. 0008>> E 1%/1cm: nm(e); 36.1 (2,300); 175 (2,620); 173 (2,630); 253 (2,710); 217 (2,755); 268 (2,820); 138 (2,890); 158 (2,930); 0.8 (3,175) << Ref. 0046>> Ergots, yeasts, Chlorella, molds. << Ref. 0100/0101>> Trypanosoma, soil amoeba, Lycopodium complanatum. << Ref. 0102>> Precipitable by digitonin. Positive in Rosenheim reaction. << Ref. 0097>> << Ref.0008 >> AUTHOR: Hogness,T.R., Sidwell,Jr.,A.R., and Zscheile,Jr.,F.P. TITLE: The Absorption Spectra of Compounds Related to the Sterols JOURNAL: J.Biol.Chem. VOLUME: 120 PAGE: 239 -256 (1937)
<< Ref.0046 >> AUTHOR: Loofbourow,J.R. TITLE: Physical Methods for Identification and Assay of Vitamins and Hormones. JOURNAL: Vitamins and Hormones VOLUME: 1 PAGE: 109 -155 (1943)
<< Ref.0050 >> AUTHOR: Windaus,A. TITLE: The Antirachitic Provitamins in the Animal Kingdom JOURNAL: Nachr.Ges.Wiss.Göttingen, Math.-Physk.Klasse, Fachgruppe III VOLUME: 1 PAGE: 185 -192 (1936)
<< Ref.0097 >> AUTHOR: Chung,C.K. TITLE: Über die Konstitution des Ergosterins. JOURNAL: Justus Liebigs Ann Chem. VOLUME: 500 PAGE: 270 -280 (1933)
<< Ref.0098 >> AUTHOR: Bills,C.E., and Honeywell,E.M. TITLE: Antiricketic Substances. VIII. Studies on Highly Purified Ergosteroles and Its Esters. JOURNAL: J.Biol.Chem. VOLUME: 80 PAGE: 15 -23 (1928)
<< Ref.0099 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp574-574, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0100 >> AUTHOR: Bills,C.E. TITLE: Physiology of the Sterols, Including Vitamin D. JOURNAL: Physiol.Rev. VOLUME: 15 PAGE: 1 -97 (1935)
<< Ref.0101 >> AUTHOR: Tanret,C. TITLE: Ergosterol and Fongisterol. JOURNAL: Ann.Chim.Phys. VOLUME: 15 PAGE: 313 -330 (1908)
<< Ref.0102 >> AUTHOR: Bekemeier, H., and Benad, A. TITLE: [On the annual rhythm of the efficacy of antirachitic and toxic doses of vitamin D] PubMed ID:5321600 JOURNAL: Int Z Vitaminforsch. VOLUME: 35 PAGE: 247-257(1965)
13
b-Estradiol / Cis-estradiol / Estradiol / 3,17-Epidihydroxyestratriene / Dihydrofollicular hormone / Dihydrofolliculin / Dihydroxyestrin / Dihydrotheelin / Compudose 365 / Dihydromenformon / Dimenformon / Diogyn / Estrovite / Femestral / Gynergon / Gynoestryl / Lamdiol / Macrodiol / Oestergon / Ovahormon / Ovasterol / Ovocyclin / Ovocylin / Perlatanol / Primofol / Profoliol / Progynon-dh Estra-1,3,5(10)-triene-3b,17b-diol SST0013SteroidHideaki Nishino C18H24O2 272.382Download ChemDraw structure data Most potent estrogenic activity. << Ref. 0103>> 173-179degC << Ref. 0104>> [a]25/D= from +76 to +83deg(dioxane) << Ref. 0104>> Hardly sol in water. Sol in organic solvents like alcohol, acetone, dioxane. Slightly sol in vegetable oil. << Ref. 0104>> max. 225, 280nm << Ref. 0104>> e=2,120 (281nm), E1%/1cm=78 << Ref. 0105>> Ovary, placenta, testis, adrenal cortex of animals. << Ref. 0104>> Total synthesis from the optically active CD-building block and m-methoxyphenacyl bromide << Ref. 0106>> or (+)-carboxylic acid. << Ref. 0107>> Very weak estrogenic activity in 17a-form. << Ref. 0103>> << Ref.0103 >> AUTHOR: Maccorquodale,D.W., Thayer,S.A., and Doisy,E.A. TITLE: The Isolation of the Principal Estrogenic Substance of Liquor Folliculi. JOURNAL: J.Biol.Chem. VOLUME: 115 PAGE: 435 -448 (1936)
<< Ref.0104 >> AUTHOR: Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp583-583, MERCK & CO., Inc. Rahway, N.J. TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0105 >> AUTHOR: Sober,H.A., (1968) Section F Steroids in Handbook of Biochemistery Selected Data for Molecular Biology (Sober,H.A., eds.) ppF11-F11, The Chemical Rubber, Cleveland TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0106 >> AUTHOR: Eder,U., Gibian,H., Haffer,G., Neef,G., Sauer,G., and Wiechert,R. TITLE: Total Synthesis of Optically Active Steroids, XIV Synthesis of Estradiol. JOU