デヒドロエピアンドロステロン 化学特性,用途語,生産方法
外観
白色～わずかにうすい黄色, 結晶性粉末～粉末
溶解性
エタノールに溶け、水にほとんど溶けない。ベンゼン、エタノール、エーテルに可溶。クロロホルム、石油エーテルに難溶。
解説
デヒドロエピアンドロステロン,(3β)-3-hydroxyandrost-5-ene-17-one．C19H28O2(288.43)．略称DHEA．デヒドロイソアンドロステロンともいう．男性ホルモンの一つ．副腎皮質の網状層から分泌される．コレステロール，スチグマステロール，ジオスゲニンなどの17位の側鎖の化学的分解，微生物発酵による分解で得られる．白色の結晶．融点140～141 ℃(針状晶)，152～153 ℃(葉状晶)．[α]D＋11°(エタノール)．エタノール，エーテルに可溶，クロロホルム，石油エーテルに難溶．男性ホルモンのテストステロン，タンパク同化ホルモン，発情ホルモンなどの合成中間体として重要な化合物で，ホルモンの母とよばれることがある．弱い男性ホルモン作用がある．デヒドロエピアンドロステロンの血中濃度は約20歳で最高となり，その後，加齢とともに減少するが，歳をとっても健康な人はこのホルモン濃度が高い傾向があることから，老化防止作用があるのではないかと注目されている．
用途
薬理研究用。
効能
子宮頸管熟化促進薬, アンドロゲン受容体作動薬
説明
Dehydroepiandrosterone(DHEA) is an endogenous steroid hormone that is secreted primarily by the adrenal gland and is the most abundant sex steroid. It is a neurohormone; small quantities of DHEA are produced in the brain and declines in serum and CSF with age. (Knopman and Henderson, 2003). Metabolites of DHEA include androstenedione , which subsequently may be metabolized to testosterone or estrone which is an estradiol precursor. In addition to serving as an intermediate in the biosynthesis of sex steroids, DHEA directly modulates a number of cellular and nuclear receptors.
化学的特性
white fine crystalline powder. There are two crystal forms. Needle-like crystal, melting point 140-141oC; small leaf-like crystal, melting point 152-153oC. Has right-handedness. Soluble in alcohol, ether, benzene, slightly soluble in chloroform, petroleum ether. In case of digitonin to produce precipitation.
天然物の起源
DHEA is naturally occurring in yam (see Wild Yam, p. 596-597).
使用
Dehydroepiandrosterone (DHEA) is a major C19 steroid produced by the adrenal cortex. It is a major secretory steroidal product of the adrenal gland; secretion progresively declines with aging. May have estrogen-or androgen-like effects depending on the hormonal milieu. Intracellularly converted to androstenedione. It is used in treatment of menopausal syndrome. People living with HIV may be interested in taking DHEA for a variety of reasons, including treatment of depression, increasing bone density, decreasing arterial plaques, improvement of immune function with HIV, increased memory, and increased muscle strength.
定義
ChEBI: Dehydroepiandrosterone is an androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands. It has a role as an androgen, a human metabolite and a mouse metabolite. It is a 17-oxo steroid, an androstanoid and a 3beta-hydroxy-Delta(5)-steroid.
Manufacturing Process
To a solution of 1 gram of 16-dehydropregnenolon-3β-acetate in 10 ml pyridine is added 0.22 gram of hydroxylamine hydrochloride, and the mixture is allowed to stand at room temperature for four days. One gram of 16dehydropregnenolon-3β-acetate oxime is dissolved in 30 ml of hot dioxane, and then the solution is cooled in an ice bath until about one-half of the dioxane has solidified. Then 1 gram of phosphorus pentachloride is added and the mixture is shaken until all the dioxane has melted. The mixture is maintained at 35°C, for seventy-five minutes, then an excess of ice is added and the solution is again allowed to stand at 35°C. After about thirty minutes, a solution of 5 ml of concentrated hydrochloric acid in 10 ml of water is added, and the mixture is diluted with water, extracted with ether and the ethereal extract washed with dilute sodium hydroxide solution. The ether is removed on a steam bath and the residue is worked up to yield dehydroepiandrosterone.
世界保健機関（WHO）
The World Health Organization has no information further to the
above regarding preparations containing prasterone or to indicate that such
preparations remain available.
一般的な説明
DHEA is a major secretory steroidal product of the adrenal gland and is a hormonal precursor to both androgens and estrogens. It can also be synthesized using wild yam or soy, but there is no evidence to show that humans are able to increase DHEA levels by consuming these foods. DHEA and its sulfated metabolite, DHEA-S, are negative modulators of GABAA receptors.
健康ハザード
An experimental teratogen.Experimental reproductive effects. Questionablecarcinogen with experimental neoplastigenic data. Whenheated to decomposition it emits acrid smoke andirritating fumes.
副作用
Side effects may include acne, skin rash, GI upset, hirsuitism, hypertension, and increased HDL. In people with HIV, additional side effects may include fatigue, nasal congestion, and headaches.
安全性
Dehydroepiandrosterone should always be used under the supervision of a medical professional. It is likely safe for people with low DHEA levels to take oral supplements short-term (<6 months) to restore DHEA to normal, but long-term use and doses resulting in high DHEA levels are possibly unsafe. Side effects are often seen with higher doses and longterm use.
デヒドロエピアンドロステロン 上流と下流の製品情報
原材料
準備製品