(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-ene-5,17-dione

• ChemBase ID: 105422
• Molecular Formular: C21H28O5
• Molecular Mass: 360.44402
• Monoisotopic Mass: 360.193674
• SMILES: O=C(CO)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3C(=O)C[C@]12C
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)CC(=O)[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
• 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
• InChIKey: MFYSYFVPBJMHGN-ZPOLXVRWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,17-dione; (1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadec-6-ene-5,17-dione; (1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,17-dione
• IUPAC Traditional name: cortisone; (1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,17-dione
• Synonyms: 17α,21-Dihydroxy-4-pregnene-3,11,20-trione; 17α-Hydroxy-11-dehydrocorticosterone; 4-Pregnene-17α,21-diol-3,11,20-trione; Kendall’s Compound E; Reichstein’s Substance Fa; Cortisone; CYANODIHYDROPHENARSAZINE; Kendall's Compound E.; Δ^4-Pregnene-17, 21-diol-3, 11, 20-trione; CORTISONE; Kendall's compound E; Reichstein's Substance Fa; Wintersteiner's compound F; 17,21-Dihydroxy-pregn-4-ene-3,11,20-trione; 17-Hydroxy-11-dehydrocorticosterone; 11-Dehydro-17-hydroxycorticosterone; Adrenalex; Compound E; Cortisate; Cortivite; Cortogen; Cortone; NSC 9703

Database IDs

• CAS Number: 50-04-4; 53-06-5
• EC Number: 200-162-4
• MDL Number: MFCD00003610
• Beilstein Number: 1356062
• PubChem SID: 24278304; 162092505
• PubChem CID: 222786
• CHEBI ID: 16962
• CHEMBL: 111861
• Chemspider ID: 193441
• KEGG ID: D07749
• MeSH Name: Cortisone
• Unique Ingredient Identifier: V27W9254FZ
• Wikipedia Title: Cortisone

CALCULATED PROPERTIES

• Acid pKa: 12.5762005
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.6606807
• LogD (pH = 7.4): 1.6606778
• Log P: 1.6606807
• Molar Refractivity: 96.4748 cm^3
• Polarizability: 37.741665 Å^3
• Polar Surface Area: 91.67 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO; Ethanol; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 220-224 °C; 220–224 °C; 220-224°C; 223-228 °C (dec.)(lit.)

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• RTECS: GM9020000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... SERPINA6(866)
• Mechanism of Action: ACTH secretion inhibitor; Calcium mobilizer; Corticosteroid; Gluconeogenesis promoter; Glycogen deposition inhibitor; Phosphorus mobilizer

Product Information

• Purity: ≥98%
• Biological Source: Adrenal cortical hormone
• Application(s): Antiinflammatory agent; Immunosuppressive; Used in rheumatoid arthritis and rheumatic fever therapy
• Empirical Formula (Hill Notation): C21H28O5

DETAILS

MP Biomedicals - 05203904

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02190172

Crystalline

Sigma Aldrich - C2755

Biochem/physiol Actions
Cortisone is a glucocorticoid; a corticosterone analog that has approximately twice the anti-inflammatory potency as corticosterone but much lower Na2+ retention potency.
Packaging
1, 5 g in glass bottle
250 mg in glass bottle

Toronto Research Chemicals - C696500

Glucocorticoid, anti-inflammatory agent.

REFERENCES

• Honda, A., et al.: J. Biol. Chem., 268, 7759 (1993)
• Narko, K., et al.: J. Clin. Endocrinol. Metab., 86, 1765 (1993)
• Michael, A., et al.: Reproduction, 126, 425 (1993)
• drich Library of 13C and 1H FT NMR Spectra, 1992, 3, 587A; 602B, (nmr)
• Reichstein, T., Helv. Chim. Acta, 1936, 19, 1107; 1937, 20, 978, (isol, Cortisone)
• Sarett, L.H., J.A.C.S., 1948, 70, 1454, (synth)
• Rosenkranz, G. et al., J.A.C.S., 1951, 73, 4055, (synth)
• Woodward, R.B. et al., J.A.C.S., 1951, 73, 4057, (synth)
• Sarett, L.H. et al., J.A.C.S., 1952, 74, 4974, (synth)
• Hayden, A.L., Anal. Chem., 1955, 27, 1486, (ir, Cortisone)
• Green, G.F.H. et al., J.C.S., 1965, 7328, (pmr, Cortisone)
• Smit, A. et al., Rec. Trav. Chim. (J. R. Neth. Chem. Soc.), 1966, 85, 731
• Saucy, G. et al., Helv. Chim. Acta, 1967, 50, 1394, (synth, uv, ir, pmr, 10-form)
• Genard, P. et al., Steroids, 1968, 12, 763, (ms, Cortisone)
• Weeks, C.M. et al., J.A.C.S., 1973, 95, 2865, (struct)
• Hazen, G.G., J. Chem. Educ., 1980, 57, 291, (synth)
• Horiguchi, Y. et al., J.O.C., 1986, 51, 4323, (synth)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6296; 6940, (synonyms)
• Kirk, D.N. et al., J.C.S. Perkin 2, 1990, 1567, (pmr)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 727
• Muhtadi, F.J., Anal. Profiles Drug Subst., 1999, 26, 167-246, (rev)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CNS800; CNS825