2-[(1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate

• ChemBase ID: 105401
• Molecular Formular: C24H31FO6
• Molecular Mass: 434.4977432
• Monoisotopic Mass: 434.21046693
• SMILES: O=C(OCC(=O)[C@]1(O)[C@]2(C[C@H](O)[C@]3(F)[C@@]4(C(=CC(=O)C=C4)CC[C@H]3[C@@H]2C[C@H]1C)C)C)C
• Canonical SMILES: CC(=O)OCC(=O)[C@@]1(O)[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
• InChI: InChI=1S/C24H31FO6/c1-13-9-18-17-6-5-15-10-16(27)7-8-21(15,3)23(17,25)19(28)11-22(18,4)24(13,30)20(29)12-31-14(2)26/h7-8,10,13,17-19,28,30H,5-6,9,11-12H2,1-4H3/t13-,17+,18+,19+,21+,22+,23+,24+/m1/s1
• InChIKey: AKUJBENLRBOFTD-RPRRAYFGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate; 2-[(1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0?,?.0??,??]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate
• IUPAC Traditional name: decadron-LA
• Synonyms: Dexamethasone 21-acetate; 9α-Fluoro-16α-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione-21-acetate; 9α-Fluoro-16α-methylprednisolone-21-acetate; Prednisolone F acetate; DEXAMETHASONE-21-ACETATE; (11β,16α)-21-(Acetyloxy)-9-fluoro-11,17-dihydroxy-16-methyl-pregna-1,4-diene-3,20-dione; 9-Fluoro-11β,17,21-trihydroxy-16α-methyl-pregna-1,4-diene-3,20-dione 21-Acetate; Decadronal; Dectancyl; Dex-Cortidelt Acetate; Dexa-Cortisyl; NSC 39471; 21-O-Acetyl Dexamethasone; 9α-氟-16α-甲基-11β,17α,21-三羟基--1,4-孕甾二烯-3,20-二酮-21-乙酸酯; 9α-氟-16α-甲基氢化泼尼松龙-21-乙酸酯; 泼尼松龙乙酸酯; 地塞米松 21-乙酸酯

Database IDs

• CAS Number: 1177-87-3
• EC Number: 214-646-8
• MDL Number: MFCD00027407
• Beilstein Number: 2342608
• PubChem SID: 24869880; 24893562; 162093650
• PubChem CID: 236702

CALCULATED PROPERTIES

• Acid pKa: 12.440784
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.122695
• LogD (pH = 7.4): 2.1226912
• Log P: 2.1226952
• Molar Refractivity: 111.6444 cm^3
• Polarizability: 43.471127 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Off-White Solid
• Melting Point: 238-240 °C(lit.)
• Optical Rotation: [α]20/D +85±3°, c = 1% in dioxane

Safety Information

• Storage Condition: 2-8°C
• RTECS: TU4050000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 43
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (HPLC); ≥99%
• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C24H31FO6
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

MP Biomedicals - 02190041

Crystalline

Sigma Aldrich - D1881

Biochem/physiol Actions
An anti-inflammatory glucocorticoid.

Sigma Aldrich - 46166

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - A168480

Protected Dexamethasone, a glucocorticoid anti-inflammatory agent.

REFERENCES

• Liu, Y., et al.: Anal. Bioanal. Chem., 395, 591 (2009)
• Rodgers, A., et al.: Chem. Res. Toxicol., 23, 724 (2009)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2009)