Pregnenolone 是一种内源性类固醇激素,能够抑制 M1 受体和 M3 受体介导的电流,其 IC50 分别为 11.4 µM 和 6.0 µM。
靶点Pregnenolone 在剂量相关地诱导 MAP2 促进微管蛋白组装的速率和程度方面表现出作用,而 progesterone 却没有活性并抵消了 Pregnenolone 的刺激作用。Pregnenolone 引起的微管组装增加,形成一个完全正常的结构。此外,它还保持微管丰富,并在外包过程中促进细胞运动。在小鼠海马细胞株(HT-22)中,Pregnenolone 导致孕激素受体核定位显著减少。Pregnenolone 对谷氨酸和 β 淀粉样蛋白具有神经病理学的神经保护作用。
体内研究在完整雄性 SCID 小鼠和去势动物中,Pregnenolone 维持其体内增殖活性并刺激 LNCaP 肿瘤异种移植物的生长。Pregnenolone 通过激活 LNCaP 雄激素受体(AR),而不是野生型 AR,来转录。在这些动物模型中,Pregrenolone 还导致星形胶质细胞在伤口附近显著减少,并使大鼠活性星形细胞中溴脱氧尿苷掺入的水平显著降低。此外,Pregnenolone 促进了下游神经甾体 allopregnanolone 的增加,后者具有神经保护作用,能增加神经发生、减少细胞凋亡和炎症、调节下丘脑-垂体-肾上腺轴,并显着地提高 GABA(A)受体的反应性。Pregnenolone 还提高了 Pregnenolone 硫酸盐的水平,后者是积极调节 NMDA 受体的神经甾体。
化学性质Pregnenolone 是一种白色结晶粉末,熔点为 193℃,不溶于水。其溶解度(g/100ml)如下:四氯化碳 0.5、石油醚 0.1、乙酸乙酯 1.1、丙酮 0.6、氯仿 17.0、乙醇 1.9、苯 0.9、异丙醇 1.5、丙二醇 0.1、二氧六环 3.1、苄醇 8.1。
用途Pregnenolone 主要用于生化研究,并作为激素类药物黄体酮的中间体。此外,它还可用于甾体类药物中间体和甾体类药物的合成,以及用作医药黄体酮的中间体。
生产方法将乙酸妊娠双烯醇酮、乙醇与雷氏镍一起加热至 50℃左右使其溶解,然后抽真空通入氢气,反复3次后,在搅拌下通氢,在 34-36℃反应 3.5h。静置,通氮气排出氢气,滤出催化剂。将滤液浓缩回收大部分乙醇,析出结晶。将结晶投入水解锅内减压蒸尽乙醇,冷却后加入甲醇加热回流使其溶解,加入 50% 碳酸钾水溶液,回流 1.5h,减压浓缩回收甲醇,出料后冷却至 5℃以下,滤取结晶,用温水洗至中性烘干。再用 10 倍量乙醇溶解,加活性炭脱色,重结晶一次,得妊烯醇酮。
中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
5-孕烯-3alpha-醇-20-酮 | pregnenolone | 19037-28-6 | C21H32O2 | 316.484 |
去氢表雄酮 | dehydroepiandrosterone | 53-43-0 | C19H28O2 | 288.43 |
—— | 3β-formyloxypregn-5-en-20-one | 18843-28-2 | C22H32O3 | 344.494 |
胆固醇 | cholesterol | 57-88-5 | C27H46O | 386.662 |
豆甾醇 | β-sitosterol | 83-46-5 | C29H50O | 414.715 |
—— | cholesterol | —— | C27H46O | 386.662 |
孕烯醇酮醋酸酯 | Pregnenolone acetate | 1778-02-5 | C23H34O3 | 358.521 |
—— | pregn-5-en-3α-ol-20-one acetate | 5223-98-3 | C23H34O3 | 358.521 |
孕烯醇酮三甲基甲硅烷基醚 | 1-((3S,8S,9S,10R,13S,14S,17S)-10,13-Dimethyl-3-trimethylsilanyloxy-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethanone | 18919-58-9 | C24H40O2Si | 388.666 |
22(R)-羟基胆固醇 | 22(R)-Hydroxycholesterol | 17954-98-2 | C27H46O2 | 402.661 |
—— | pregnenolone acrylate | —— | C24H34O3 | 370.532 |
16-妊娠双烯醇酮 | 16-dehydropregnenolone | 1162-53-4 | C21H30O2 | 314.468 |
(3S,8S,9S,10R,13S,14S,17S)-3-羟基-10,13-二甲基-2,3,4,7,8,9,10,11,12,13,14,15,16,17-十四氢-1H-环戊并[a]菲-17-羧酸甲酯 | methyl 5-androsten-3β-ol-17β-carboxylate | 7254-03-7 | C21H32O3 | 332.483 |
醋酸去氢表雄酮 | prasterone acetate | 853-23-6 | C21H30O3 | 330.467 |
20Alpha-羟基胆固醇 | 20(S)-hydroxycholesterol | 516-72-3 | C27H46O2 | 402.661 |
—— | 3β-t-butyldimethylsilyloxy-pregn-5-en-20-one | 58701-45-4 | C27H46O2Si | 430.747 |
—— | 3β-acetoxybisnor-5-cholenic acid | 1474-14-2 | C24H36O4 | 388.547 |
孕甾-5-烯-3,20-二酮 | pregn-5-ene-3,20-dione | 1236-09-5 | C21H30O2 | 314.468 |
黄体酮 | Progesterone | 57-83-0 | C21H30O2 | 314.468 |
—— | methyl 3β-acetoxybisnorchol-5-enate | 6556-99-6 | C25H38O4 | 402.574 |
20,22-二羟基胆固醇 | 20R,22R-dihydroxycholesterol | 596-94-1 | C27H46O3 | 418.66 |
—— | 3β-acetoxy-5-etienic acid chloride | 7429-97-2 | C22H31ClO3 | 378.939 |
16-脱氢孕烯醇酮乙酸酯 | 16-dehydropregnenolone acetate | 979-02-2 | C23H32O3 | 356.505 |
—— | pregnadiene-(5,17(20)c)-diyl-(3β,20)-diacetate | 66979-17-7 | C25H36O4 | 400.558 |
—— | trans-Pregna-5,17(20)-dien-3β,20-diol-diacetat | 66979-18-8 | C25H36O4 | 400.558 |
—— | (20R,22R)-3β-(tert-butyldimethylsilyl)oxycholest-5-ene-20,22-diol | 782494-67-1 | C33H60O3Si | 532.923 |
中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
—— | pregnenolone | —— | C21H32O2 | 316.484 |
21-羟基孕烯醇酮 | 21-hydroxypregnenolone | 1164-98-3 | C21H32O3 | 332.483 |
—— | 3β-hydroxyandrost-5-ene-17β-carbaldehyde | 55029-99-7 | C20H30O2 | 302.457 |
1-[(3S,8S,9S,10R,13R,14S,17S)-3-甲氧基-10,13-二甲基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-17-基]乙酮 | pregnenolone methyl ether | 511-26-2 | C22H34O2 | 330.511 |
(3beta,20S)-20-甲酰基-3-羟基-5-孕烯 | cholest-5-en-3β-ol-22-al | 53906-49-3 | C22H34O2 | 330.511 |
去氢表雄酮 | dehydroepiandrosterone | 53-43-0 | C19H28O2 | 288.43 |
—— | 3,25-dihydroxycholest-5-en-22-one | 1397692-53-3 | C27H44O3 | 416.645 |
—— | 3β-formyloxypregn-5-en-20-one | 18843-28-2 | C22H32O3 | 344.494 |
(3S,8S,9S,10R,13S,14S,17S)-17-乙酰基-3-羟基-10,13-二甲基-1,2,3,4,8,9,11,12,14,15,16,17-十二氢环戊烯并[a]菲-7-酮 | 3β-hydroxypregn-5-ene-7,20-dione | 33530-84-6 | C21H30O3 | 330.467 |
7alpha-羟基孕烯诺龙 | 3β,7α-dihydroxy-pregn-5-en-20-one | 30626-96-1 | C21H32O3 | 332.483 |
—— | di-(pregn-5-en-20-one)-3β-yl ether | 75868-85-8 | C42H62O3 | 614.952 |
5-孕烯-3-beta,16-alpha-二醇-20-酮 | 16α-hydroxypregnenolone | 520-88-7 | C21H32O3 | 332.483 |
21-乙酰氧基孕烯醇酮 | 21-acetoxypregnenolone | 566-78-9 | C23H34O4 | 374.521 |
—— | 5-pregnen-3β-ol | 2862-58-0 | C21H34O | 302.5 |
—— | Cholest-5-en-3β-ol | 4420-91-1 | C26H44O | 372.635 |
(3S,8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(2R)-5-甲基己烷-2-基]-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-醇 | 20(R)-(3'-methyl)butyl-5-pregnen-3β-ol | 38819-44-2 | C26H44O | 372.635 |
—— | 3α-hydroxy-10.13-dimethyl-17β-ethyl-gonene-(5) | 5223-95-0 | C21H34O | 302.5 |
—— | cholesterin | 34026-89-6 | C27H46O | 386.662 |
3-羟基-10,13-二甲基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-17-羧酸 | etienic acid | 10325-79-8 | C20H30O3 | 318.456 |
雄甾-5-烯-3-醇 | androst-5-en-3β-ol | 1476-64-8 | C19H30O | 274.447 |
—— | 3β-hydroxy-20-oxo-21,24-dinor-cholen-(5)-oic acid-(23)-ethyl ester | 28816-14-0 | C24H36O4 | 388.547 |
5,25R-胆甾烯-3beta,26-二醇 | (25R)-cholest-5-ene-3β,26-diol | 20380-11-4 | C27H46O2 | 402.661 |
—— | pregn-5,20-diene-3β-ol | 21321-88-0 | C21H32O | 300.484 |
—— | 20-methyl-pregna-5,20-dien-3β-ol | 17879-91-3 | C22H34O | 314.511 |
—— | (20(22)E)-cholesta-5,20(22)-dien-3β-ol | —— | C27H44O | 384.646 |
—— | cholesta-5,20-diene-3β-ol | 41083-90-3 | C27H44O | 384.646 |
孕烯醇酮醋酸酯 | Pregnenolone acetate | 1778-02-5 | C23H34O3 | 358.521 |
孕烯醇酮三甲基甲硅烷基醚 | 1-((3S,8S,9S,10R,13S,14S,17S)-10,13-Dimethyl-3-trimethylsilanyloxy-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethanone | 18919-58-9 | C24H40O2Si | 388.666 |
—— | pregnadiene | 22953-07-7 | C21H32O | 300.484 |
—— | 20-oxopregn-5-en-3β-yl hemisuberate | —— | C29H44O5 | 472.665 |
(3S,8S,9S,10R,13R,14S)-10,13-二甲基-2,3,4,7,8,9,11,12,14,15-十氢-1H-环戊并[a]菲-3-醇 | HAD | 1224-94-8 | C19H28O | 272.431 |
—— | (22S)-22-hydroxycampesterol | 71473-12-6 | C28H48O2 | 416.688 |
—— | pregn-5-en-20-one | 32414-75-8 | C21H32O | 300.484 |
—— | 20-oxopregn-5-en-3β-yl hemiadipate | —— | C27H40O5 | 444.612 |
17Alpha-羟基妊娠烯醇酮 | 17-Hydroxypregnenolone | 387-79-1 | C21H32O3 | 332.483 |
(3S,8S,9S,10R,13S,14S,17S)-3-羟基-10,13-二甲基-2,3,4,7,8,9,10,11,12,13,14,15,16,17-十四氢-1H-环戊并[a]菲-17-羧酸甲酯 | methyl 5-androsten-3β-ol-17β-carboxylate | 7254-03-7 | C21H32O3 | 332.483 |
—— | 20-oxopregn-5-en-3β-yl hemiglutarate | —— | C26H38O5 | 430.585 |
—— | (20R)-20,3β-dihydroxypregna-5-ene-22-aldehyde | 66007-54-3 | C22H34O3 | 346.51 |
3beta-羟基孕甾-5-烯-20-酮 3-(琥珀酸氢酯) | Pregnenolone hemisuccinate | 4598-67-8 | C25H36O5 | 416.558 |
—— | 3β,7α,11α-trihydroxypregn-5-en-20-one | 1865-73-2 | C21H32O4 | 348.483 |
20-alpha-二氢孕烯诺龙 | pregn-5-ene-3β,20α-diol | 901-56-4 | C21H34O2 | 318.5 |
5-孕烯-3beta,20Beta-二醇 | (20R)-pregn-5-ene-3β,20-diol | 901-57-5 | C21H34O2 | 318.5 |
(3S,8S,9R,10S,13S,14R,17R)-17-乙酰基-10,13-二甲基-3-磺基氧基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊并[a]菲 | pregnenolone sulfate | 1247-64-9 | C21H32O5S | 396.548 |
—— | 3β,9α-dihydroxypregn-5-en-20-one | 95001-96-0 | C21H32O3 | 332.483 |
—— | (20R)-22-Oxo-23,24-dinor-5-cholen-3β-yl-acetat | 15626-16-1 | C24H36O3 | 372.548 |
—— | cholest-5-ene-3β,22(S),25-triol | 63163-38-2 | C27H46O3 | 418.66 |
—— | cholest-5-ene-3,22,25-triol | 76793-29-8 | C27H46O3 | 418.66 |
—— | 6-deoxoteasterone | 85707-12-6 | C28H48O3 | 432.687 |
—— | (2E)-1-((10R,13S)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3(β)-hydroxy-10,13-dimethyl-1H-cyclopenta[α]phenanthren-17(β)-yl)-3-phenylprop-2-en-1-one | 120793-61-5 | C28H36O2 | 404.593 |
1-[(3S,8R,9S,10R,13S,14S,17R)-3,17-二羟基-10,13-二甲基-1,2,3,4,7,8,9,11,12,14,15,16-十二氢环戊烯并[a]菲-17-基]-2-羟基乙烷酮 | 3β,17α,21-Trihydroxy-5-pregnen-20-one | 1167-48-2 | C21H32O4 | 348.483 |
—— | 3β-<(tetrahydro-2H-pyran-2-yl)oxy>-5-pregnen-20-one | 35961-41-2 | C26H40O3 | 400.602 |
雄烯二醇 | 5-androstenediol | 521-17-5 | C19H30O2 | 290.446 |
雄甾-5-烯-3-beta,17-alpha-二醇 | androst-5-ene-3β,17α-diol | 1963-03-7 | C19H30O2 | 290.446 |
—— | (20R)-3β,20,25-trihydroxy-cholest-5-en-22-one | 99529-72-3 | C27H44O4 | 432.644 |
20-甲基孕甾-5-烯-3,20-二醇 | 3β,20-dihydroxy-20-methylpregn-5-ene | 20976-92-5 | C22H36O2 | 332.527 |
—— | 21,21-difluoro-20-methylpregna-5,20-dien-3β-ol | —— | C22H32F2O | 350.492 |
20Alpha-羟基胆固醇 | 20(S)-hydroxycholesterol | 516-72-3 | C27H46O2 | 402.661 |
—— | (3S,8S,9S,10R,13S,14S,17S)-17-((S)-2-hydroxy-7-methyloctan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol | 947330-00-9 | C28H48O2 | 416.688 |
—— | 20α-hydroxycholesterol | 7484-22-2 | C27H46O2 | 402.661 |
—— | O-benzyl-pregnenolone | 104948-25-6 | C28H38O2 | 406.609 |
—— | 3β-trifluoroacetoxy-pregn-5-en-20-one | 33202-38-9 | C23H31F3O3 | 412.493 |
—— | cholest-5-ene-3,20,25-triol | 74803-93-3 | C27H46O3 | 418.66 |
(20S)-20-氨基孕甾-5-烯-3beta-醇 | 20α-amino-5-pregnen-3β-ol | 5035-10-9 | C21H35NO | 317.515 |
—— | (20R)-20-aminopregn-5-en-3β-ol | 5087-58-1 | C21H35NO | 317.515 |
—— | 7β,15β-dihydroxypregn-4-en-3,20-dione | 601-90-1 | C21H30O4 | 346.467 |
—— | 6β-methylpregn-4-en-3β-ol | 155874-95-6 | C22H36O | 316.527 |
去氧皮质酮 | 21-Hydroxyprogesterone | 64-85-7 | C21H30O3 | 330.467 |
—— | 2-(3β-hydroxyandrost-5-en-17β-yl)-5-methyl-2,5-hexanediol | 1397692-47-5 | C26H44O3 | 404.634 |
6-羟基黄体酮 | 6ζ-hydroxypregn-4-ene-3,20-dione | 604-20-6 | C21H30O3 | 330.467 |
4-孕烯-6-beta-醇-3,20-二酮 | 6β-hydroxypregn-4-en-3,20-dione | 604-19-3 | C21H30O3 | 330.467 |
—— | 6α-Hydroxyprogesterone | 604-20-6 | C21H30O3 | 330.467 |
—— | methyl 3β-acetoxy-5-cholen-24-oate | 63814-50-6 | C27H42O4 | 430.628 |
—— | 3β-t-butyldimethylsilyloxy-pregn-5-en-20-one | 58701-45-4 | C27H46O2Si | 430.747 |
3-叔-丁基二甲基硅烷基氧基孕烯诺龙 | (3beta,17alpha)-3-{[tert-Butyl(dimethyl)silyl]oxy}pregn-5-en-20-one | 58701-45-4 | C27H46O2Si | 430.7 |
—— | 3β-acetoxyetienic acid | 7150-18-7 | C22H32O4 | 360.494 |
—— | 3α-hydroxy-5α-pregn-1-en-20-one | 38398-23-1 | C21H32O2 | 316.484 |
孕甾-5-烯-3,20-二酮 | pregn-5-ene-3,20-dione | 1236-09-5 | C21H30O2 | 314.468 |
—— | (21E)-3β-hydroxy-21-(p-cyanobenzylidene)pregn-5-en-20-one | 1365727-80-5 | C29H35NO2 | 429.602 |
11Alpha-孕酮 | 11-alpha-hydroxyprogesterone | 80-75-1 | C21H30O3 | 330.467 |
—— | (21E)-3β-hydroxy-21-(4'-chlorobenzylidene)pregn-5-en-20-one | 1365727-53-2 | C28H35ClO2 | 439.038 |
—— | 9α-hydroxyprogesterone | 15981-54-1 | C21H30O3 | 330.467 |
—— | 2α-methylpregn-4-en-3β-ol | 155875-02-8 | C22H36O | 316.527 |
黄体酮 | Progesterone | 57-83-0 | C21H30O2 | 314.468 |
—— | (21E)-3β-hydroxy-21-(4'-bromobenzylidene)pregn-5-en-20-one | 1365727-61-2 | C28H35BrO2 | 483.489 |
—— | pregn-5-en-3β-yl hemipimelate | —— | C28H44O4 | 444.655 |
19-羟孕酮 | 19-Hydroxyprogesterone | 596-63-4 | C21H30O3 | 330.467 |
—— | 3β-Acetoxy-20-methylene-5-pregnene | 38388-16-8 | C24H36O2 | 356.549 |
—— | (E)-3-(4-fluorophenyl)-1-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)prop-2-en-1-one | 1338000-54-6 | C28H35FO2 | 422.583 |
—— | 3β-((triisopropylsilyl)oxy)pregn-5-en-20-one | 241139-90-2 | C30H52O2Si | 472.827 |
—— | 17α-Hydroperoxy-5-pregnen-3β-ol-20-on | 34069-59-5 | C21H32O4 | 348.483 |
—— | 3β-hydroxypregn-5-en-20-one hydrazone | 86770-54-9 | C21H34N2O | 330.514 |
20,22-二羟基胆固醇 | 20R,22R-dihydroxycholesterol | 596-94-1 | C27H46O3 | 418.66 |
(3beta,22S)-二羟基胆固醇 | (20R,22S)-cholest-5-ene-3β,20,22-triol | 26649-05-8 | C27H46O3 | 418.66 |
肾上腺酮 | Corticosterone | 50-22-6 | C21H30O4 | 346.467 |
—— | (21E)-3β-hydroxy-21-(4'-isopropylbenzylidene)pregn-5-en-20-one | 1365727-49-6 | C31H42O2 | 446.673 |
—— | pregna-5,20(22)-diene-3β-yl laurate | 478622-95-6 | C34H56O2 | 496.817 |
—— | (2E)-1-((10R,13S)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3(β)-hydroxy-10,13-dimethyl-1H-cyclopenta[α]phenanthren-17(β)-yl)-3-o-tolylprop-2-en-1-one | 1338000-50-2 | C29H38O2 | 418.62 |
19,21-二羟基-孕甾-4-烯-3,20-二酮 | 19-hydroxydeoxycorticosterone | 2394-23-2 | C21H30O4 | 346.467 |
—— | 3β-chloro-5-pregnen-20-one | 1906-01-0 | C21H31ClO | 334.93 |
—— | 15β-hydroxyprogesterone | —— | C21H30O3 | 330.467 |