2-[(1S,2R,10S,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]-2-oxoethyl acetate

• ChemBase ID: 53507
• Molecular Formular: C23H32O4
• Molecular Mass: 372.49778
• Monoisotopic Mass: 372.2300595
• SMILES: [C@]12(C)[C@H]([C@H]3[C@H](CC2)[C@]2(C)C(=CC(=O)CC2)CC3)CC[C@@H]1C(=O)COC(=O)C
• Canonical SMILES: CC(=O)OCC(=O)[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
• InChI: InChI=1S/C23H32O4/c1-14(24)27-13-21(26)20-7-6-18-17-5-4-15-12-16(25)8-10-22(15,2)19(17)9-11-23(18,20)3/h12,17-20H,4-11,13H2,1-3H3/t17-,18-,19-,20+,22-,23-/m0/s1
• InChIKey: VPGRYOFKCNULNK-ACXQXYJUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2R,10S,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]-2-oxoethyl acetate; 2-[(1S,2R,10S,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]-2-oxoethyl acetate
• IUPAC Traditional name: deoxycorticosterone acetate
• Synonyms: Δ^4-Pregnen-21-ol-3, 20-dione 21-acetate; 21-Acetoxy-4-pregnene-3,20-dione; 21-Acetoxyprogesterone; 21-Hydroxy-4-pregnene-3,20-dione 21-acetate; 21-Hydroxyprogesterone 21-acetate; Cortexone acetate; DOC acetate; 11-DEOXYCORTICOSTERONE ACETATE; 3,20-Dioxopregn-4-en-21-yl acetate; DESOXYCORTICOSTERONE ACETATE; Deoxycorticosterone acetate; 11-Deoxycorticosterone acetate; 4-Pregnen-21-ol-3,20-dione 21-acetate; Deoxycorticosterone acetate; 21-(Acetyloxy)-pregn-4-ene-3,20-dione; 11-Deoxycorticosterone 21-Acetate; 21-Acetoxy-3,20-diketopregn-4-ene; 21-Acetoxypregn-4-en-3,20-dione; 21-Hydroxypregn-4-ene-3,20-dione Acetate; Arcort; Bio-Corten; Cortacet; Cortate; Cortenil; Cortesan; Cortifar; Cortigen; Cortinaq; Cortiron; Cortivis; Cortixyl; DCA; DOCA; Decorten; Decortin; Decosteron; Decosterone; Decostrate; Deoxy Corticosterone Acetate; 11-去氧皮质酮乙酸酯; 21-乙酰氧基孕甾-4-烯-3,20-二酮; 21-羟基孕甾-4-烯-3,20-二酮-21-醋酸酯; 21-羟基孕酮-21-乙酸酯; DOC 乙酸酯; 乙酸脱氧肾上腺皮质固酮; 孕甾-4-烯-21-醇-3,20-二酮-21-醋酸酯; 脱氧皮质酮醋酸酯; 醋酸去氧皮质酮

Database IDs

• CAS Number: 56-47-3
• EC Number: 200-275-9
• MDL Number: MFCD00003660
• Beilstein Number: 2570798
• PubChem SID: 24870071; 162058270; 24894065; 24858764
• PubChem CID: 5952

CALCULATED PROPERTIES

• Acid pKa: 17.183268
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.7724817
• LogD (pH = 7.4): 3.7724817
• Log P: 3.7724817
• Molar Refractivity: 103.559 cm^3
• Polarizability: 40.84742 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetone: soluble (1 in 30); alcohol: soluble (1 in 50); Chloroform; chloroform: freely soluble; dioxane: slightly soluble; H2O: insoluble; Methanol; vegetable oils: slightly soluble
• Apperance: Off-White Solid
• Melting Point: 154-160; 155-161 °C; 157-161°C
• Optical Rotation: [α]20/D +175±4°, c = 1% in dioxane

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C), Protect from light
• Storage Warning: IRRITANT
• RTECS: HG0525000
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: Others

Product Information

• Purity: ≥98.0% (HPLC); 99%
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C23H32O4
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

MP Biomedicals - 05211115

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02101497

Purity: 99%
Light Sensitive
Crystalline

Sigma Aldrich - 46347

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

Toronto Research Chemicals - D232595

Adrenocortical/mineralocorticoid Steroid.

REFERENCES

• Quigley, J., et al.: Clin. Exper. Pharmacol. Physiol., 36, 724 (2009)