Home > Name List By other > (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10, 13-dimethyl-1,2,6,7,8,9,12,14,15, 16-decahydrocyclopenta[a]phenan...

CAS No 53-06-5 , (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,
13-dimethyl-1,2,6,7,8,9,12,14,15,
16-decahydrocyclopenta[a]phenanthrene-3,11-dione

  • Name: (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,
    13-dimethyl-1,2,6,7,8,9,12,14,15,
    16-decahydrocyclopenta[a]phenanthrene-3,11-dione
  • Synonyms: Cortone; Cortivite; Cortisate;Kendall's compound E; Cortogen;(8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,
    13-dimethyl-1,2,6,7,8,9,12,14,15,
    16-decahydrocyclopenta[a]phenanthrene-3,11-dione; Andreson; Cortisal; Reichstein's substance FA; Cortistal;
  • CAS Registry Number:
  • Flash Point: 311.2°C
  • Boiling Point: 567.8°Cat760mmHg
  • Density: 1.28g/cm3
  • Refractive index: 210 ° (C=1, EtOH)
  • Safety Statements: Human teratogenic effects by ingestion and possibly other routes: developmental abnormalities of the eye and ear, craniofacial area, musculoskeletal system, cardiovascular system and other neonatal measures or effects. Other experimental teratogenic effects. Additional reproductive effects in experimental animals. Mutation data reported. When heated to decomposition it emits acrid smoke and fumes. See also CORTISOL.
  • Hazard Symbols: Damaging side effects, e.g., sodium retention from ingestion.
  • Flash Point: 311.2°C
  • EINECS: 200-162-4
  • Molecular Weight: 360.44402
  • InchiKey: MFYSYFVPBJMHGN-ZPOLXVRWSA-N
  • InChI: InChI=1S/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,
    17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-15,18,22,26H,3-8,10-11H2,
    1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1
  • Molecular Formula: C21H28O5
  • Molecular Structure:CAS No:53-06-5 (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,<br />13-dimethyl-1,2,6,7,8,9,12,14,15,<br />16-decahydrocyclopenta[a]phenanthrene-3,11-dione

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  • IUPAC NAME-(8S,9S,10R,13S,14S,17R)-17-Hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione MOLECULAR FORMULA-C21H28O5 MOLAR MASS-360.44 g mol?1
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References of (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,
13-dimethyl-1,2,6,7,8,9,12,14,15,
16-decahydrocyclopenta[a]phenanthrene-3,11-dione
Title: Cortisone
CAS Registry Number: 53-06-5
CAS Name: 17,21-Dihydroxypregn-4-ene-3,11,20-trione
Synonyms: 17-hydroxy-11-dehydrocorticosterone; 11-dehydro-17-hydroxycorticosterone; D4-pregnene-17a,21-diol-3,11,20-trione; Kendall's compound E; Wintersteiner's compound F; Reichstein's substance Fa
Molecular Formula: C21H28O5
Molecular Weight: 360.44
Percent Composition: C 69.98%, H 7.83%, O 22.19%
Literature References: Isoln from suprarenal glands: Pfiffner et al., J. Biol. Chem. 111, 585 (1935); 116, 291 (1936); Mason et al., ibid. 114, 613 (1936); Reichstein, Helv. Chim. Acta 19, 1107 (1936); Kuizenga, Cartland, Endocrinology 24, 526 (1939). Synthesis of the monoacetate from desoxycholic acid: Sarett, J. Biol. Chem. 162, 601 (1946). Further development of prepn methods: Meystre, Wettstein, Experientia 3, 185 (1947); Helv. Chim. Acta 30, 1037, 1256 (1947); Reichstein et al., ibid. 26, 562, 705, 721 (1943); 27, 821 (1944); Reichstein, US 2403683 (1946); Kendall et al., J. Biol. Chem. 166, 345 (1946); Gallagher, US 2447325 (1948); Peterson, Murray, J. Am. Chem. Soc. 74, 1871 (1952); Perlman, ibid. 2126; Sarett, ibid. 70, 1454 (1948); 71, 2443 (1949); Mattox, Kendall, ibid. 70, 882 (1948). Stereospecific total synthesis: Sarett et al., ibid. 74, 4974 (1952).
Properties: Rhombohedral platelets from 95% alcohol, mp 220-224° (some decompn) when heated in evac capillary. [a]D25 +209° (c = 1.2 in 95% alcohol); [a]25546 +269° (c = 0.125 in benzene); [a]25546 +248° (c = 0.1 to 0.2 in alcohol). uv max: 237 nm (e 1.4′104) see Mason et al., J. Biol. Chem. 116, 267 (1936); Wintersteiner, Pfiffner, ibid. 291. Fairly sol in cold methanol, ethanol, acetone; much less sol in ether, benzene, chloroform; slightly sol in water (28 mg/100 ml at 25°). The water soln is neutral. Gives orange-red soln with intense green fluorescence in concd H2SO4. Reduces Benedict's soln on heating.
Melting point: mp 220-224° (some decompn) when heated in evac capillary
Optical Rotation: [a]D25 +209° (c = 1.2 in 95% alcohol); [a]25546 +269° (c = 0.125 in benzene); [a]25546 +248° (c = 0.1 to 0.2 in alcohol)
Absorption maximum: uv max: 237 nm (e 1.4′104) see Mason et al., J. Biol. Chem. 116, 267 (1936); Wintersteiner, Pfiffner, ibid. 291
 
Derivative Type: 21-Acetate
CAS Registry Number: 50-04-4
Synonyms: Cortisone acetate
Trademarks: Cortistab (Abbott); Cortisyl (Aventis); Cortogen (Schering-Plough); Cortone (Merck & Co.)
Molecular Formula: C23H30O6
Molecular Weight: 402.48
Percent Composition: C 68.64%, H 7.51%, O 23.85%
Properties: Flat needles from acetone; clusters of radiating rods from chloroform. Becomes opaque at 70-100°, mp 235-238° with slight sintering at 230°. [a]D25 +164° (c = 0.5 in acetone), [a]D25 +208 to +217° (dioxane). uv max: 238 nm (e 1.58′104), see Sarett, J. Biol. Chem. 162, 630 (1946). Soly at 25° in water: 2.2 mg/100 ml; in propylene glycol 44 mg/100 ml; in chloroform 182 mg/g. Reduces ammoniacal silver nitrate soln at room temp. Sol in sulfuric acid giving a yellow soln without fluorescence (difference from hydrocortisone acetate).
Melting point: mp 235-238° with slight sintering at 230°
Optical Rotation: [a]D25 +164° (c = 0.5 in acetone); [a]D25 +208 to +217° (dioxane)
Absorption maximum: uv max: 238 nm (e 1.58′104)
 
Derivative Type: 21-Cyclopentanepropionate
CAS Registry Number: 509-00-2
Molecular Formula: C29H40O6
Molecular Weight: 484.62
Percent Composition: C 71.87%, H 8.32%, O 19.81%
Properties: Needles from diisopropyl ether, mp 158-161°. [a]D20 +190° (chloroform). uv max (ethanol): 239 nm (e 16350). Sol in ether, glycols, vegetable oils, especially sesame, peanut, and corn oils.
Melting point: mp 158-161°
Optical Rotation: [a]D20 +190° (chloroform)
Absorption maximum: uv max (ethanol): 239 nm (e 16350)
 
Therap-Cat: Glucocorticoid.
Therap-Cat-Vet: Glucocorticoid, anti-inflammatory agent.
Keywords: Glucocorticoid.