(1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

• ChemBase ID: 73248
• Molecular Formular: C21H28O2
• Molecular Mass: 312.44582
• Monoisotopic Mass: 312.20893014
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)(O)C#C)C)C
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
• InChI: InChI=1S/C21H28O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h1,13,16-18,23H,5-12H2,2-3H3/t16-,17+,18+,19+,20+,21+/m1/s1
• InChIKey: CHNXZKVNWQUJIB-CEGNMAFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one; (1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: ethinyl testosterone; (1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one; ethisterone
• Synonyms: Ethisterone; Ethisterone; 17α-Hydroxypregn-4-en-20-yn-3-one; Ethinone; Gestoral; Lucorteum Oral; Lutocyclol; Nalutoral; Nugestoral; Pranone; Pregnin; Prodoxan; Progestab; Progestoral; Trosinone; Ethnyltestosterone; 17-Ethynyltestosterone; Ethynyltestosterone; Pregneninolone; 17α-Ethynyltestosterone; 17 β-Hydroxy-4,17α-pregnen-20-yn-3-one; (8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one; 17α-Ethynyltestosterone; 17β-Hydroxy-4,17α-pregnen-20-yn-3-one; 4,17α-Pregnen-17β-ol-20-yn-3-one; 17α-乙炔睾酮; 17β-羟基-4,17α-孕甾烯-20-炔基-3-酮; 4,17α-孕甾烯-17β-醇-20-炔基-3-酮; 炔孕酮

Database IDs

• CAS Number: 434-03-7
• EC Number: 207-096-5
• MDL Number: MFCD00003656
• Beilstein Number: 1889895
• PubChem SID: 162038168; 24894377; 24869998
• PubChem CID: 5284557
• ATC CODE: G03DC04
• CHEMBL: 241694
• Chemspider ID: 4447612
• Unique Ingredient Identifier: P201BVY1MJ Verifiedfields = changed
• Wikipedia Title: Ethisterone

CALCULATED PROPERTIES

• Acid pKa: 17.594933
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.517275
• LogD (pH = 7.4): 3.517275
• Log P: 3.517275
• Molar Refractivity: 91.8996 cm^3
• Polarizability: 35.84699 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: Off-White Solid
• Melting Point: 263-269 °C(lit.); 272-275°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS: TU5570250
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 61
• Safety Statements: 53-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Pharmacology Properties

• Target: Estrogen receptor
• Mechanism of Action: Progestogen

Product Information

• Purity: ≥99% (HPLC)
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Application(s): Orally effective progestational steroid, about one-third the activity of progesterone by subcutaneous route but more active orally
• Empirical Formula (Hill Notation): C21H28O2

DETAILS

MP Biomedicals - 05213985

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02157955

Crystalline

Selleck Chemicals - S2611

Biological Activity:

Sigma Aldrich - E1001

包装
25, 100 g in glass bottle

Sigma Aldrich - 46272

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

Toronto Research Chemicals - E890445

Synthetic progestogen; metabolite of Danazol; intermediate in the synthesis of Spironolactone.

REFERENCES

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• Szegvari, D., et al.: Anal. Bioanal. Chem., 375, 713 (2003)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 592A, (nmr)
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• Inhoffen, H.H., Ber., 1939, 72, 595, (synth)
• Dorfman, R.I. et al., Endocrinology (Baltimore), 1948, 42, 77, (metab)
• Desaulles, P.A. et al., Acta Endocrinol., 1962, 40, 217; 1964, 47, 444, (pharmacol)
• Akhrem, A.A. et al., Izv. Akad. Nauk SSSR, Ser. Khim., 1971, 3, 601, (pmr)
• Horvath, G. et al., Adv. Mass Spectrom., 1978, 7B, 1280, (ms)
• Gunatilaka, A. et al., Chem. Comm., 1978, 980, (synth)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6284, (synonyms)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1184
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, GEK500