(1beta,3alpha,5beta,7alpha,12alpha)-1,3,7,12-四羟基胆烷-24-酸 | 80875-94-1

• 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
• 中文名称: (1beta,3alpha,5beta,7alpha,12alpha)-1,3,7,12-四羟基胆烷-24-酸
• 中文别名: (1β,3α,5β,7α,12α)-1,3,7,12-四羟基胆烷-24-酸
• 英文名称: 1β,3α,7α,12α-tetrahydroxy-5β-cholan-24-oic acid
• 英文别名: 1β-hydroxycholic acid；1beta-Hydroxycholic acid；(4R)-4-[(1R,3S,5S,7R,8S,9S,10S,12S,13R,14S,17R)-1,3,7,12-tetrahydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 80875-94-1
• 化学式: C₂₄H₄₀O₆
• 分子量: 424.578
• InChiKey: UYVVLXVBEQAATF-WAIVXGPNSA-N

物化性质

• 沸点：
  621.3±55.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1beta,3alpha,5beta,7alpha,12alpha)-1,3,7,12-四羟基胆烷-24-酸 在 lithium hydroxide 、 氰基磷酸二乙酯 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N-(1β,3α,7α,12α-tetrahydroxy-5β-cholan-24-oyl)-2-aminopropionic acid
  参考文献：
  名称：

  Conjugated 1.BETA.-Hydroxycholic Acid in the Urine of Newborns and Pregnant Women Measured by Radioimmunoassay Using Antisera Raised against N-(1.BETA.-Hydroxycholyl)-2-aminopropionic Acid-Bovine Serum Albumin Conjugate.

  摘要：

  用 N-(1β,3α,7α,12α-四羟基-5β-胆烷-24-酰基)-2-氨基丙酸-牛血清白蛋白（BSA）共轭物免疫家兔，制备了牛 1β-羟基胆酸抗血清。所制得的抗血清对共轭 1β-hydroxycholic acid 具有很高的亲和力（1.25-1.46×109 M-1）和特异性；对 glyco 1β-hydroxycholic acid 的交叉反应率为 100%，而对其他 1β-hydroxylated 胆汁酸的甘氨酸和牛磺酸共轭物的交叉反应率从 11.30% 到 0.23% 不等。通过放射免疫法测定了出生后 0-20 天的新生儿尿中共轭 1β- 羟基胆酸的浓度，其含量范围为 0.29 至 18.51 μg/ml，妊娠晚期妇女（<1.13 μg/ml）和正常妇女（<0.12 μg/ml）的尿中共轭 1β- 羟基胆酸的浓度范围为 0.29 至 18.51 μg/ml。

  DOI：

  10.1248/cpb.40.1835
• 作为产物：
  描述：

  胆酸甲酯 在 吡啶 、 过氧乙酸 、 4-二甲氨基吡啶 、 mercury(II) diacetate 、 水 、 溴 、 lithium 、 lithium carbonate 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 silver carbonate 、 lithium bromide 、 sodium hydroxide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 41.0h， 生成 (1beta,3alpha,5beta,7alpha,12alpha)-1,3,7,12-四羟基胆烷-24-酸
  参考文献：
  名称：

  ROR gamma modulators

  摘要：

  本发明涉及式I的化合物，或其药学上可接受的盐，用于治疗或预防、抑制或改善ROR gamma受体介导的疾病，特别是糖尿病和糖尿病相关疾病，具体而言是II型糖尿病，以及其生产方法，以及预防或治疗这些疾病的方法。

  公开号：

  US09777036B2

文献信息

• Synthesis of the 1.BETA.-hydroxylated bile acids, unusual bile acids in human biological fluids.
  作者：MASAHIKO TOHMA、REIJIRO MAHARA、HIROMI TAKESHITA、TAKAO KUROSAWA、SHIGEO IKEGAWA

  DOI：10.1248/cpb.34.2890

  日期：——

  1β-Hydoxylated lithocholic (10a), deoxycholic (10b), chenodeoxycholic (10c) and cholic (10d) acids were synthesized from the corresponding bile acid methyl esters (1a-d) as starting materials. The Δ1-unsaturated ketones (6a, e-g) were prepard from the 3-oxo bile acid esters (2a-d) via reductive debromination of their 2, 4-dibromides (3a, e-g) with chromous acetate and dehydrobromination with lithium carbonate-lithium bromide, and oxidized with alkaline hydrogen peroxide to give the 1β-2β-epoxyketones (7a, e-g). Reductive cleavage of the epoxides (7a, e-g) and subsequent reduction with sodium borohydride afforded the 1β, 3α-dihydroxy compounds (9a, e-g), which were hydrolyzed to the 1β-hydroxylated bile acids (10a-d). 1β, 3α, 12α-Trihydroxy-5β-cholan-24-oic acid (10b) was identified in the urine of healthy men and patients with kidney disease by gas chrmatography-mass spectrometric analysis. Novel 1β, 3α, 7α-trihydroxy-(10c) and 1β, 3α, -7α, 12α-tetrahydroxy-5β-cholan-24-oic acids (10d) were detected in human meconium.

  1β-羟基胆酸（10a）、脱氧胆酸（10b）、鹅去氧胆酸（10c）和胆酸（10d）是从相应的胆酸甲酯（1a-d）作为起始原料合成的。Δ1-不饱和酮（6a、e-g）是通过用乙酸铬还原脱除其2,4-二溴化物（3a、e-g）的溴，并用碳酸锂-溴化锂脱氢，然后用碱性过氧化氢氧化，得到1β-2β-环氧酮（7a、e-g）。环氧物（7a、e-g）的还原裂解和随后的硼氢化钠还原反应得到1β,3α-二羟基化合物（9a、e-g），后者被水解为1β-羟基胆酸（10a-d）。通过气相色谱-质谱分析，在健康男性和肾脏疾病患者的尿液中鉴定出1β,3α,12α-三羟基-5β-胆烷-24-酸（10b）。在人类胎粪中检测到新的1β,3α,7α-三羟基-（10c）和1β,3α,7α,12α-
• Measurement of Conjugated 1.BETA.-Hydroxycholic Acid in Urine of Newborns by Specific Radio-immunoassay.
  作者：Shigeo IKEGAWA、Tsuyoshi MURAI、Teruki YOSHIMURA、Zhen-Zhi Xu、Masahiko TOHMA

  DOI：10.1248/cpb.40.701

  日期：——

  Anti-tauro 1β-hydroxycholic acid antisera were prepared by immunizing rabiits with N-(1β-3α-7α-12α-tetrahydroxy-5β-cholan-24-oyl)glycine bovine serum albumin conjugate. The immunoglobulin G fraction was obtained by ammonium sulfate precipitation, followed by diethylaminoethyl cellulose column chromatography. The antibody was characterized using [2^3H]tauro 1β-hydroxycholic acid which has a high affinity (Ka=1.09×109M-1) and reasonable specificity. Cross-reactivity for glyco 1β-hydroxycholic acid was 100% and those for other 1β-hydroxylated bile acids ranged from 4.32 to 29.6%. Concentrations of conjugated 1β-hydroxycholic acid in urine of newborns at 0-20d after birth were determined by radioimmunoassay to be significant (0.2-11.1 μg/ml), exhibiting a tendency to increase during the 20d after birth.

  用 N-(1β-3α-7α-12α-四羟基-5β-胆烷-24-酰)甘氨酸牛血清白蛋白结合物免疫rabiits，制备了抗牛 1β-羟基胆酸抗血清。通过硫酸铵沉淀法获得免疫球蛋白 G 部分，然后进行二乙氨基乙基纤维素柱层析。使用[2^3H]牛磺 1β-羟基胆酸对抗体进行了表征，该抗体具有高亲和力（Ka=1.09×109M-1）和合理的特异性。与 glyco 1β-hydroxycholic acid 的交叉反应率为 100%，与其他 1β-hydroxylated 胆汁酸的交叉反应率为 4.32% 至 29.6%。经放射免疫测定，新生儿出生后 0-20 天尿液中共轭 1β- 羟基胆酸的浓度显著（0.2-11.1 μg/ml），在出生后 20 天内呈上升趋势。
• Synthesis of the 1.BETA.-hydroxylated bile acids and identification of 1.BETA.,3.ALPHA.,7.ALPHA.-trihydroxy- and 1.BETA.,3.ALPHA.,7.ALPHA.,12.ALPHA.-tetrahydroxy-5.BETA.-cholan-24-oic acids in human meconium.
  作者：Masahiko Tohma、Reijiro Mahara、Hiromi Takeshita、Takao Kurosawa、Shigeo Ikegawa、Hiroshi Nittono

  DOI：10.1248/cpb.33.3071

  日期：——

  The 1β-hydroxylated lithocholic (1), deoxycholic (2), chenodeoxycholic (3) and cholic acids (4) were synthesized from the corresponding bile acids as starting materials. These unusual bile acids in human meconium were determined by the selected ion monitoring in gas chromatography-mass spectrometry, and novel 1β-hydroxychenodeoxycholic (3) and 1β-hydroxycholic acids (4) were identified in significant amounts of 10.6% and 5.8%, respectively, of the total bile acids.

  以相应的胆汁酸为起始原料合成1β-羟基化石胆酸(1)、脱氧胆酸(2)、鹅去氧胆酸(3)和胆酸(4)。通过气相色谱-质谱法中的选择离子监测来测定人胎便中的这些不寻常胆汁酸，并鉴定出新型 1β-羟基鹅去氧胆酸 (3) 和 1β-羟基胆酸 (4)，含量分别为 10.6% 和 5.8% ，总胆汁酸。
• Dual electrode system for a continuous analyte sensor
  申请人：DexCom, Inc.

  公开号：US10299712B2

  公开（公告）日：2019-05-28

  Disclosed herein are systems and methods for a continuous analyte sensor, such as a continuous glucose sensor. One such system utilizes first and second working electrodes to measure additional analyte or non-analyte related signal. Such measurements may provide a background and/or sensitivity measurement(s) for use in processing sensor data and may be used to trigger events such as digital filtering of data or suspending display of data.

  本文公开了用于连续分析传感器（如连续葡萄糖传感器）的系统和方法。其中一种系统利用第一和第二工作电极测量额外的分析或非分析相关信号。此类测量可提供用于处理传感器数据的背景和/或灵敏度测量，并可用于触发事件，如数据的数字滤波或暂停显示数据。
• Systems and methods for CGM-based bolus calculator for display and for provision to medicament delivery devices
  申请人：DexCom, Inc.

  公开号：US11222724B2

  公开（公告）日：2022-01-11

  Disclosed are systems and methods for secure and seamless set up and modification of bolus calculator parameters for a bolus calculator tool by a health care provider (HCP). In one aspect, a method for enabling HCP set up of a bolus calculator includes providing a server accessible by both an HCP and a patient; upon login by the HCP, displaying, or transmitting for display, a fillable form, the fillable form including one or more fields for entry of one or more bolus calculator parameters; receiving data from the fillable form, the data corresponding to one or more bolus calculator parameters; and upon login by the patient, transmitting data to a device associated with the patient, the transmitted data based on the received data, where the transmitted data corresponds to one or more of the bolus calculator parameters in a format suitable for entry to a bolus calculator.

  所公开的是用于医疗服务提供者（HCP）安全、无缝地设置和修改药量计算器工具的药量计算器参数的系统和方法。在一个方面，使医护人员能够设置药量计算器的方法包括：提供一个医护人员和患者都能访问的服务器；医护人员登录后，显示或传输显示可填写表格，可填写表格包括一个或多个用于输入一个或多个药量计算器参数的字段；接收来自可填写表格的数据，该数据与一个或多个药量计算器参数相对应；患者登录后，将数据传输到与患者相关的设备，传输的数据基于接收到的数据，其中传输的数据与一个或多个药量计算器参数相对应，其格式适合输入到药量计算器中。