Dehydroepiandrosterone
Title: Dehydroepiandrosterone
CAS Registry Number: 53-43-0
CAS Name: (3b)-3-Hydroxyandrost-5-en-17-one
Additional Names: prasterone; dehydroisoandrosterone; trans-dehydroandrosterone; D5-androsten-3b-ol-17-one; DHEA
Molecular Formula: C19H28O2
Molecular Weight: 288.42
Percent Composition: C 79.12%, H 9.79%, O 11.09%
Literature References: Major secretory steroidal product of the adrenal gland; secretion progressively declines with aging. May have estrogen- or androgen-like effects depending on the hormonal milieu. Intracellularly converted to androstenedione, q.v. Isoln from male urine: Butenandt, Tscherning, Z. Physiol. Chem. 229, 167 (1934); Butenandt, Dannenbaum, ibid. 192. Prepn from cholesterol: Butenandt et al., ibid. 237, 57 (1935); Ruzicka, Wettstein, Helv. Chim. Acta 18, 986 (1935); Wallis, Fernholz, J. Am. Chem. Soc. 57, 1379, 1504 (1935); Schoeller et al., Naturwissenschaften 23, 337 (1935); from sitosterol: Oppenauer, Nature 135, 1039 (1935). High yield prepn: H. Hosoda et al., J. Org. Chem. 38, 4209 (1973). Metabolism study: P. Knapstein et al. Acta Endocrinol. 58, 261 (1968). Toxicity study of the sulfate: M. Yahara et al., J. Toxicol. Sci. 2, 161 (1977). Clinical evaluation in hormone replacement therapy: A. J. Morales et al., J. Clin. Endocrinol. Metab. 78, 1360 (1994); in systemic lupus erythematosus: R. F. van Vollenhoven et al., Arthritis Rheum. 38, 1826 (1995). Review of physiological importance: P. Ebeling, V. A. Koivisto, Lancet 343, 1479-1481 (1994). Symposium on role in aging: Ann. N.Y. Acad. Sci. 774, 1-350 (1995). Review of therapeutic potential: B. Allolio, W. Arlt, Trends Endocrinol. Metab. 13, 288-294 (2002).
Properties: Dimorphous, needles, mp 140-141°; leaflets, mp 152-153°. [a]18D +10.9° (c = 0.4 in alc). Pptd by digitonin. Sol in benzene, alcohol, ether; sparingly sol in chloroform, petr ether.
Melting point: mp 140-141°; mp 152-153°
Optical Rotation: [a]18D +10.9° (c = 0.4 in alc)
 
Derivative Type: Sulfate
CAS Registry Number: 651-48-9
Additional Names: DHEAS
Molecular Formula: C19H28O5S
Molecular Weight: 368.49
Percent Composition: C 61.93%, H 7.66%, O 21.71%, S 8.70%
Literature References: Hydrophilic storage form that circulates in the blood.
 
Derivative Type: Sodium sulfate
CAS Registry Number: 1099-87-2
Additional Names: Sodium dehydroepiandrosterone sulfate
Trademarks: Astenile (Recordati); Mylis (Kanebo)
Molecular Formula: C19H27NaO5S
Molecular Weight: 390.47
Percent Composition: C 58.44%, H 6.97%, Na 5.89%, O 20.49%, S 8.21%
Properties: White cryst powder, mp 154° (dec). Sol in methanol, slightly sol in water, abs ethanol. Practically insol in acetone, chloroform, benzene.
Melting point: mp 154° (dec)
 
Therap-Cat: In treatment of menopausal syndrome.
Keywords: Androgen.

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