6-ketoestriol triacetate | 36614-98-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 6-ketoestriol triacetate
• 英文别名: 3,16α,17β-triacetoxy-estra-1,3,5(10)-trien-6-one；3,16α,17β-Triacetoxy-oestra-1,3,5(10)-trien-6-on；6-ketoestriol-3,16,17-triacetate；Estra-1,3,5(10)-trien-6-one, 3,16,17-tris(acetyloxy)-, (16alpha,17beta)-；[(8R,9S,13S,14S,16R,17R)-3,17-diacetyloxy-13-methyl-6-oxo-8,9,11,12,14,15,16,17-octahydro-7H-cyclopenta[a]phenanthren-16-yl] acetate
• CAS: 36614-98-9
• 化学式: C₂₄H₂₈O₇
• 分子量: 428.482
• InChiKey: YKXHUDXDHCUGIF-STZDCXSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-ketoestriol triacetate 在 吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 4.5h， 生成 Succinic acid mono-((6S,8R,9S,13S,14S,16R,17R)-3,16,17-triacetoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-6-yl) ester
  参考文献：
  名称：

  Bridge-heterologous chemiluminescence enzyme-linked immunosorbent assay of estriol 3-sulfate in pregnancy plasma

  摘要：

  A facile and sensitive chemiluminescence enzyme-linked immunosorbent assay (ELISA) of estriol 3-sulfate using a bridge-heterologous system was established. 6 alpha-Hydroxyestriol 3-sulfate 6-hemisuccinate was synthesized as a novel hapten. Antisera were raised in mate guinea-pigs against 6 alpha-hydroxyestriol 3-sulfate 6-hemisuccinate-bovine serum albumin (BSA) and 6-oxoestriol 3-sulfate O-carboxymethyloxime-BSA conjugates. Both haptens were coupled to horseradish peroxidase as an enzyme-label reagent. For separation of free and estriol 3-sulfate bound to the antibody, the crude globulin fractions of these antisera were immobilized to CNBr-activated Sepharose-4B. The enzyme activity was measured by chemiluminescent reaction using amino-butylethyl-isoluminol and hydrogen peroxide as a substrate. The immobilized antibody raised against 6 alpha-hydroxyestriol 3-sulfate 6-hemisuccinate-BSA exhibited a high affinity and an excellent specificity for estriol. 3-sulfate. The two bridge-heterologous ELISAs were more sensitive than the homologous systems. The specificity and sensitivity (10 pg) of the bridge-heterologous chemiluminescence ELISAs was comparable to those of the radioimmunoassays (RIAs). Results obtained by the ELISA and the RIA in pregnancy plasmas showed excellent correlation between ELISA and RIA (r = 0.96). (Steroids 63:516-522, 1998) (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(98)00061-0
• 作为产物：
  描述：

  雌三醇 3,16a,17b-三乙酸酯 在 CrO₃-3.5-dimethylpyrazole 作用下， 以 二氯甲烷 为溶剂， 反应 4.75h， 以49%的产率得到6-ketoestriol triacetate
  参考文献：
  名称：

  Chromic anhydride-3,5-dimethylpyrazole complex: An efficient reagent for oxidation of steroidal estrogens to 6-oxo-derivatives

  摘要：

  An efficient procedure for the oxidation of steroidal estrogens to the corresponding 6-oxo-derivatives is described. The oxidative process involves the use of 3,5-dimethylpyrazole-chromium trioxide complex at low temperature (-20 degrees). Under these conditions, only the 6-oxo-derivative and the unreacted starting material were obtained and the latter could be subjected to oxidation once again to obtain additional amount of 6-oxo-derivative.

  DOI：

  10.1016/0039-128x(83)90145-9

文献信息

• Synthesis of estriol monoglucoside derivatives, new haptens for production of specific antisera.
  作者：TOSHIO NAMBARA、JUNICHI GOTO、HIROKO FURUYAMA、HIROAKI KATO

  DOI：10.1248/cpb.26.591

  日期：——

  For the purpose of obtaining antisera used for direct radioimmunoassay of estriol glucuronides, two new haptens, estriol 3- and 16-glucoside derivatives possessing a carboxyl group, have been synthesized. Condensation of estriol 3-carboxymethyl ether with 1-bromo-1-deoxy-α-D-glucopyranose tetraacetate in the presence of cadmium carbonate provided the 16-glucoside together with a small amount of the 17-isomer. The Koenigs-Knorr reaction with 6-oxoestriol 16, 17-diacetate under similar conditions afforded the 3-glucoside which in turn was led to the 6-(O-carboxymethyl) oxime. Removal of the protecting groups in estriol 3- and 16-glucoside derivatives was effected by treatment with methanolic alkali to yield the desired compounds.

  为了获得用于直接放射免疫测定雌三醇葡萄糖醛酸苷的抗血清，我们合成了两种新的抗原--具有一个羧基的雌三醇 3-和 16-葡萄糖苷衍生物。在碳酸镉存在下，雌三醇 3-羧甲基醚与 1-溴-1-脱氧-α-D-吡喃葡萄糖四乙酸酯缩合，得到 16-葡萄糖苷和少量 17-异构体。在类似条件下与 6-氧代雌三醇 16、17-二乙酸酯发生柯尼希斯-克诺尔反应，可得到 3-葡萄糖苷，进而生成 6-（O-羧甲基）肟。用甲醇碱处理可去除雌三醇 3-和 16-葡萄糖苷衍生物中的保护基团，从而得到所需的化合物。
• Total estriol fluorescence polarization immunoassay
  申请人：ABBOTT LABORATORIES

  公开号：EP0200960A1

  公开（公告）日：1986-11-12

  The present invention is directed to a homogeneous fluorescence polarization immunoassay for determining total estriol content in body fluids, to the various components needed for preparing and carrying out such an assay, and to methods of making these components. Specifically, tracers, immunogens and antibodies are disclosed, as well as methods for preparing them. The assay is conducted by measuring the degree of polarization of plane polarized light that has been passed through a sample containing antiserum and tracer. The combination of antiserum and tracer used will possess excellent cross-reactivity to estriol-3-sulfate, eliminating the need for enzyme hydrolysis of this conjugate to free estriol.

  本发明涉及一种测定体液中总雌三醇含量的均相荧光偏振免疫测定法，涉及制备和进行这种测定所需的各种成分，以及制备这些成分的方法。 具体地说，本发明公开了示踪剂、免疫原和抗体，以及制备它们的方法。 该测定法是通过测量穿过含有抗血清和示踪剂的样品的平面偏振光的偏振程度来进行的。 所使用的抗血清和示踪剂的组合将对雌三醇-3-硫酸盐具有极好的交叉反应性，从而无需用酶水解这种共轭物来生成游离雌三醇。
• Synthesis of 6 alpha-functionalized estriol haptens and protein conjugate thereof
  申请人：Bayer Corporation

  公开号：EP0916676A1

  公开（公告）日：1999-05-19

  Disclosed are 6α-derivatized estriol compounds which, when conjugated to a protein, are useful in the in vivo preparation of antibodies specific to estriol. When labeled with a detectable label, the estriol derivatives are useful as haptens in a competitive immunoassay for estriol which demonstrate superior sensitivity with respect to estriol specific antibodies.

  本发明公开了 6α 衍生物化的雌三醇化合物，当这些化合物与蛋白质连接时，可用于体内制备雌三醇特异性抗体。 当用可检测的标签标记时，雌三醇衍生物可用作雌三醇竞争性免疫测定中的触价物，其灵敏度优于雌三醇特异性抗体。
• 6.alpha.- and 6.beta.-Hydroxyestriol. Synthesis, configurational assignments, and spectral properties
  作者：Elizabeth P. Burrows、David L. Di Pietro、Howard E. Smith

  DOI：10.1021/jo00798a006

  日期：1972.12
• Synthesis of 6-ketoestriol and 6-hydroxyestriol
  作者：Stanley Kushinsky、Wilmonte Nasutavicus

  DOI：10.1016/0003-9861(59)90578-8

  日期：1959.9