(1S,2R,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl acetate

• ChemBase ID: 131835
• Molecular Formular: C21H30O3
• Molecular Mass: 330.4611
• Monoisotopic Mass: 330.21949482
• SMILES: CC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C)C
• Canonical SMILES: CC(=O)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/C21H30O3/c1-13(22)24-19-7-6-17-16-5-4-14-12-15(23)8-10-20(14,2)18(16)9-11-21(17,19)3/h12,16-19H,4-11H2,1-3H3/t16-,17-,18-,19-,20-,21-/m0/s1
• InChIKey: DJPZSBANTAQNFN-PXQJOHHUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• IUPAC Traditional name: (1S,2R,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate; testosterone, acetate
• Synonyms: Aceto-Sterandryl; Aceto-Testoviron; Amolisin; Androtest A; Farmatest; Perandren; Perandrone A; Testiculosterone; Testolent; 17β-Acetoxy-4-androsten-3-one; 17β-Hydroxy-4-androsten-3-one 17-acetate; 4-Androsten-17β-ol-3-one 17-acetate; Deposteron; 17β-Acetoxy-4-androsten-3-one solution; 17β-Hydroxy-4-androsten-3-one 17-acetate solution; 4-Androsten-17β-ol-3-one 17-acetate solution; Deposteron solution; Testosterone acetate solution; Testosterone acetate; 17β-乙酰氧基-4-雄甾烯-3-酮 溶液; 17β-羟基-4-雄甾烯-3-酮-17-乙酸酯 溶液; 4-雄甾烯-17β-醇-3-酮-17-乙酸酯 溶液; 醋酸睾酮 溶液; 睾酮乙酸酯 溶液; 17β-乙酰氧基-4-雄甾烯-3-酮; 17β-羟基-4-雄甾烯-3-酮-17-乙酸酯; 4-雄甾烯-17β-醇-3-酮-17-乙酸酯; 醋酸睾酮; 睾酮乙酸酯

Database IDs

• CAS Number: 1045-69-8
• EC Number: 213-876-6; 200-835-2
• MDL Number: MFCD00021154
• Beilstein Number: 2062555
• PubChem SID: 24888691; 24870575; 162226112
• PubChem CID: 92145

CALCULATED PROPERTIES

• Acid pKa: 19.086855
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.8065486
• LogD (pH = 7.4): 3.8065486
• Log P: 3.8065486
• Molar Refractivity: 93.5813 cm^3
• Polarizability: 37.086353 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 139-141 °C
• Flash Point: 2 °C; 35.6 °F
• Optical Rotation: [α]20/D +88±2°, c = 1% in ethanol

Safety Information

• RTECS: XA3061500
• European Hazard Symbols: Flammable (F); Toxic (T); Harmful (Xn)
• UN Number: 2811
• German water hazard class: 2; 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 11-20/21/22-36; 45-63-22
• Safety Statements: 16-36/37; 53-22-26-36
• GHS Pictograms: GHS02; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H302-H319-H332; H302-H350-H361
• GHS Precautionary statements: P201-P281-P308 + P313; P210-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; 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
• RID/ADR: UN 2811 6.1/PG 2
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada; USDEA Schedule III; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada; USDEA Schedule IIIN; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Androgen

Product Information

• Purity: ≥99.0% (HPLC)
• Concentration: 100 ng/μL in acetonitrile
• Grade: purum; VETRANAL™, analytical standard
• Application(s): Androgen
• Empirical Formula (Hill Notation): C21H30O3

DETAILS

Sigma Aldrich - 86510

Other Notes
Sales restrictions may apply

Sigma Aldrich - 32676

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

Sigma Aldrich - 46924

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

REFERENCES

• Ruzicka, L. et al., Helv. Chim. Acta, 1936, 19, 99; 842; 1141
• Bots, J.P.L., Rec. Trav. Chim. (J. R. Neth. Chem. Soc.), 1958, 77, 1010, (synth, uv, ir)
• Johnson, W.S. et al., J.A.C.S., 1960, 82, 3409, (synth, uv, ir)
• Chinn, L.J., J.O.C., 1962, 27, 54, (synth)
• Birmingham, M.K. et al., Steroids, 1963, 1, 463, (ir)
• Korenman, S.G. et al., J. Biol. Chem., 1964, 239, 1004, (isol)
• Knox, L.H. et al., J.O.C., 1964, 29, 2187, (pmr)
• Chinn, L.J. et al., J.O.C., 1965, 30, 4165, (synth, pmr)
• Halkes, S.J. et al., Rec. Trav. Chim. (J. R. Neth. Chem. Soc.), 1965, 84, 889, (pmr)
• Saucy, G. et al., Helv. Chim. Acta, 1971, 54, 2517, (synth)
• Grant, J.K., Pfizer Med. Monogr., 1971, 6, 193, (rev)
• Isaacs, N.W. et al., J.C.S. Perkin 2, 1972, 2335, (cryst struct)
• Roberts, P.J. et al., J.C.S. Perkin 2, 1973, 1978, (cryst struct)
• Brooks, R.V., Clin. Endocrinol. Metab., 1975, 4, 503, (rev)
• Hanson, J.R. et al., J.C.S. Perkin 1, 1975, 1956, (cryst struct)
• IARC Monog., 1979, 21, 519, (tox, rev)
• Rizvi, S.Q.A. et al., J.O.C., 1981, 46, 1127, (cmr)
• Mller, M. et al., Tetrahedron, Suppl., 1981, 257, (synth, uv, ir, pmr)
• Ihara, M. et al., J.C.S. Perkin 1, 1986, 117, (synth)
• Fujiwara, H. et al., J.C.S. Perkin 2, 1990, 97, (cmr)
• Kirk, D.N. et al., J.C.S. Perkin 2, 1990, 1567, (pmr)
• Signoret, J.P., J. Steroid Biochem., 1991, 39, 639, (biochem)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1196
• Bcskei, Z. et al., Acta Cryst. C, 1996, 52, 2899, (cryst struct)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, TBF500; TBG000; TBF600; TBF750