2-[(1R,2S,10S,11S,13R,14Z,15S,17S)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-ylidene]-2-hydroxyacetaldehyde

• ChemBase ID: 166713
• Molecular Formular: C22H27FO4
• Molecular Mass: 374.4457832
• Monoisotopic Mass: 374.18933756
• SMILES: C1=CC(=O)C=C2[C@]1([C@@]1([C@@H](CC2)[C@H]2[C@](C[C@@H]1O)(/C(=C(\O)/C=O)/[C@@H](C2)C)C)F)C
• Canonical SMILES: O=C/C(=C/1\[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)F)/O
• InChI: InChI=1S/C22H27FO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-21(13,3)22(15,23)18(27)10-20(16,2)19(12)17(26)11-24/h6-7,9,11-12,15-16,18,26-27H,4-5,8,10H2,1-3H3/b19-17-/t12-,15+,16+,18+,20+,21+,22+/m1/s1
• InChIKey: TYYMPHSFTLTHRI-KNUORSFASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,2S,10S,11S,13R,14Z,15S,17S)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-ylidene]-2-hydroxyacetaldehyde
• IUPAC Traditional name: 2-[(1R,2S,10S,11S,13R,14Z,15S,17S)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-ylidene]-2-hydroxyacetaldehyde
• Synonyms: (11β,16α)-9-Fluoro-11,20-dihydroxy-16-methyl-3-oxopregna-1,4,17(20)-trien-21-al; 9-Fluoro-11β,20-dihydroxy-16α-methyl-3-oxopregna-1,4,17(20)-trien-21-al; Dexamethasone-Δ17,20 21-Aldehyde

Database IDs

• CAS Number: 6762-51-2
• PubChem SID: 162260846
• PubChem CID: 71315848

CALCULATED PROPERTIES

• Acid pKa: 8.911779
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.3039887
• LogD (pH = 7.4): 2.2909963
• Log P: 2.3041568
• Molar Refractivity: 102.3604 cm^3
• Polarizability: 38.714367 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 226-230°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D298790

A degradation and metabolic intermediate of Dexamethasone (D298800). A Dexamethasone enol aldehyde as inflammation inhibitor.

REFERENCES

• Weiss, G., et al.: J. Clin. Endocrinol. Metab., 43, 696 (1976)
• Hirschmann R., et al.: Steroids, 57, 579 (1976)