Steroid

DATA No : SST0128 INFORMANT : Hideaki Nishino

NAME : Androst-4-ene-3,11,17-trione

COMMON NAME	:	Adrenosterone / Reichstein's Substance G
SYMBOL	:
FORMULA	:	C₁₉H₂₄O₃ MOL.WT (average) : 300.392

BIOLOGICAL ACTIVITY

Total synthesis from 6-methoxy a-tetralone. (Ref. 0568) Preparation from Reichstein's Substance E, Fa. (Ref. 0198/0295)

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:	220-224bC (alcohol) (Ref. 0483)

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:	[a]20/D=+2623 (anhydrous alcohol); [a]25/5461=+3645 (c=0.18% in anhydrous alcohol) (Ref. 0483/0271)

DENSITY	:

SOLUBILITY	:	Sol in water, 9.85(23),15.2(37) mg/100ml alcohol, acetone, ether. (Ref. 0568)

SPECTRAL DATA

UV SPECTRA	:	UVmax: 235nm (Ref. 0483)

IR SPECTRA	:

NMR SPECTRA	:

MASS SPECTRA	:

OTHER SPECTRA	:	Crystallographic analysis. (Ref. 0569)

CHROMATOGRAM DATA

SOURCE

Bovine adrenal cortex. (Ref. 0271/0270/0483)

CHEMICAL SYNTHESIS

Metabolism of adrenosterone-1,2-³H in control and hypothyroid patients. (Ref. 0570)

METABOLISM

Androgenic activity. (Ref. 0483/0270/0271/0198/0295)

GENETIC INFORMATION

NOTE

REFERENCES

[0198]

AUTHOR	:	Steiger,M., and Reichstein,T.
TITLE	:	Über Bestandteile der Nebennieren-Rinde IX. (Die Funktion des letzten Sauerstoffatoms)
JOURNAL	:	Helv.Chim.Acta
VOL	:	20 PAGE : 817 -827 (1937)

[0270]

AUTHOR	:	Reichstein,T.
TITLE	:	Über Bestandteile der Nebennieren-Rinde VI. Trennungsmethoden, sowie Isolierung der Substanzen F. a. H und J.
JOURNAL	:	Helv. Chim. Acta
VOL	:	19 PAGE : 1107 -1126 (1936)

[0271]

AUTHOR	:	Mason,H.L.,Myers,C.S.,and Kendall,E.C.
TITLE	:	Chemical studies of the suprarenal cortex. II. The identification of a substance which possesses the qualitative action of cortin; Its conversion into a diketone closely related to androstenedione.
JOURNAL	:	J. Biol. Chem.
VOL	:	116 PAGE : 267 -276 (1936)

[0295]

AUTHOR	:	Reichstein,T.
TITLE	:	Über Bestandteile der Nebennierenrinde (X). Zur Kenntnis des Cortico-sterons.
JOURNAL	:	Helv. Chim. Acta
VOL	:	20 PAGE : 953 -969 (1937)

[0483]

AUTHOR	:	Reichstein,T.
TITLE	:	Über Cortin, das Hormon der Nebennieren-rinde. I. Mitteilung.
JOURNAL	:	Helv. Chim. Acta
VOL	:	19 PAGE : 29 -63 (1936)

[0568]

AUTHOR	:	Velluz, L., Nomine, G., Mathieu, J., Toromanoff, E., Bertin, D., Bucourt, R., and Tessier, J.
TITLE	:	[On a pathway suitable for the total synthesis of cortisone-type steroids.] PubMed ID:13841633
JOURNAL	:	C R Hebd Seances Acad Sci.
VOL	:	250 PAGE : 1293-1294 (1960)

[0569]

AUTHOR	:	Ohrt,J.M.,Haner,B.A.,and Norton,D.A.
TITLE	:	Crystal data (II) for some androstanes.
JOURNAL	:	Acta Cryst.
VOL	:	19 PAGE : 479 -479 (1965)

[0570]

AUTHOR	:	Bradlow, H. L., Fukushima, D. K., Kozuma, K., Zumoff, B., Hellman, L., and Gallagher, T. F.
TITLE	:	Metabolism of adrenosterone PubMed ID:6057562
JOURNAL	:	Steroids.
VOL	:	10 PAGE : 233-244 (1967)