Cortisone
Title: Cortisone
CAS Registry Number: 53-06-5
CAS Name: 17,21-Dihydroxypregn-4-ene-3,11,20-trione
Additional Names: 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
Additional Names: 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.

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