(6R)-6-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(5R)-5-羟基-2-亚甲基环己亚基]亚乙基]-7a-甲基-2,3,3a,5,6,7-六氢-1H-茚-1-基]-2-羟基-2-甲基庚烷-3-酮 | 74886-61-6

• 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: (6R)-6-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(5R)-5-羟基-2-亚甲基环己亚基]亚乙基]-7a-甲基-2,3,3a,5,6,7-六氢-1H-茚-1-基]-2-羟基-2-甲基庚烷-3-酮
• 中文别名: 联锡基环戊基锰三羰基
• 英文名称: 25-Hydroxy-24-oxovitamin D3
• 英文别名: 24-oxo-25-hydroxyvitamin D₃；25-Hydroxy-24-oxocalciol；(6R)-6-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]-2-hydroxy-2-methylheptan-3-one
• CAS: 74886-61-6
• 化学式: C₂₇H₄₂O₃
• 分子量: 414.629
• InChiKey: DDZHNKIBJQESJA-AHMPPUFCSA-N

物化性质

• 沸点：
  554.3±35.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6R)-6-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(5R)-5-羟基-2-亚甲基环己亚基]亚乙基]-7a-甲基-2,3,3a,5,6,7-六氢-1H-茚-1-基]-2-羟基-2-甲基庚烷-3-酮 、 氢(+1)阳离子 、 氧气 、 [2Fe-2S]¹⁺ 生成 1,25-二羟基-24-氧代-维他命D3 、 水 、 [2Fe-2S]²⁺
  参考文献：
  名称：

  Expression of human CYP27B1 inEscherichia coliand characterization in phospholipid vesicles

  摘要：

  CYP27B1 is a mitochondrial cytochrome P450 that catalyses the hydroxylation of 25‐hydroxyvitamin D3 at the C1α‐position to give the hormonally active form of vitamin D3, 1α,25‐dihydroxyvitamin D3. We successfully expressed human CYP27B1 in Escherichia coli and partially purified this labile enzyme and carried out a detailed characterization of its kinetic properties in a reconstituted membrane environment. The phospholipid concentration did not affect the enzyme activity in the vesicle‐reconstituted system, although it was influenced by the phospholipid composition, with the addition of cardiolipin lowering the Km for 25‐hydroxyvitamin D3. These data are consistent with the enzyme accessing substrate from the hydrophobic domain of the vesicle membrane. Cardiolipin also caused the appearance of inhibition of activity at high substrate concentrations. This substrate inhibition fitted a model for one catalytic and two inhibitory sites on the enzyme for the binding of substrate. The Km for human adrenodoxin was observed to decrease with decreasing substrate concentration, with the catalytic efficiency (kcat/Km) being largely independent of adrenodoxin concentration. Human CYP27B1 was also active on 25‐hydroxyvitamin D2 and on intermediates of the CYP24A1‐mediated inactivation pathway, 24R,25‐dihydroxyvitamin D3, 24‐oxo‐25‐hydroxyvitamin D3 and 24‐oxo‐23,25‐dihydroxyvitamin D3, with all these substrates showing comparable kcat values of 50–71 min−1, similar to 25‐hydroxyvitamin D3. The latter two substrates gave higher Km values than that for 25‐hydroxy‐vitamin D3. The present study shows that human CYP27B1 can be partially purified in an active form with the enzyme displaying high activity towards a range of substrates in a phospholipid vesicle‐reconstituted system that mimics the inner‐mitochondrial membrane.

  DOI：

  10.1111/j.1742-4658.2012.08736.x
• 作为产物：
  描述：

  3β,25-dihydroxy-24-oxocholesta-5,7-diene 生成 (6R)-6-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(5R)-5-羟基-2-亚甲基环己亚基]亚乙基]-7a-甲基-2,3,3a,5,6,7-六氢-1H-茚-1-基]-2-羟基-2-甲基庚烷-3-酮
  参考文献：
  名称：

  Synthesis of 25-hydroxy-24-oxovitamin D3,a new metabolite of vitamin D3.

  摘要：

  介绍了 25-hydroxy-24-oxovitamin D3 的合成方法。该化合物在所有方面都与天然产物相同。

  DOI：

  10.1248/cpb.29.1187

文献信息

• [EN] COCRYSTALS OF STEROID AND SECOSTEROID COMPOUNDS AND COMPOSITIONS COMPRISING THEM<br/>[FR] CO-CRISTAUX DE COMPOSÉS STÉROÏDES ET SÉCOSTÉROÏDES ET COMPOSITIONS LES COMPRENANT
  申请人：CENTER FOR INTELLIGENT RES IN CRYSTAL ENGINEERING S L

  公开号：WO2021105147A1

  公开（公告）日：2021-06-03

  It is provided a cocrystal of a compound of formula (I) or of a compound formula (II) wherein X and Y are independently selected from -CH2- and -C(CH2)-, provided that al least one of X or Y is -CH2-; R1 is -CHCH3-Zm-Wn-(CH2)o-Tp-S, wherein Z is O, and m is 0 or 1; W is R4CH CHR5, wherein either R4 and R5 are H and the dashed line indicates that there is a single bond, or R4 and R5 together are forming a bond and the dashed line indicates that there is a double bond, and n is 0 or 1; o is 0, 1 or 3; T is selected from the group consisting of -CHR6-, -C(O), wherein R6 is -OH or -CH3, and p is 0 or 1; S is selected from the group consisting of H, (C1-C3) alkyl optionally substituted by -OH, (C1-C3) haloalkyl optionally substituted by -OH, cyclopropyl, or; and R2 is -H or -OH; R3 is H or CH3; and the dashed line in formula (II) indicates a single or a double bond; and a hydrogen bond donor coformer which is a phenolic compound. It is also provided a composition comprising the cocrystal and a personal care product comprising the composicion.

  提供了一种化合物的共晶体，该化合物具有公式（I）或化合物公式（II），其中X和Y独立地选自-CH2-和-C（CH2）-，前提是至少有一个X或Y是-CH2-；R1为-CHCH3-Zm-Wn-（CH2）o-Tp-S，其中Z为O，m为0或1；W为R4CH CHR5，其中R4和R5中的任何一个可以是H，虚线表示存在单键，或者R4和R5一起形成键，虚线表示存在双键，n为0或1；o为0，1或3；T从以下组中选择：-CHR6-，-C（O），其中R6为-OH或-CH3，p为0或1；S从以下组中选择：H，（C1-C3）烷基，可选地被-OH取代，（C1-C3）卤代烷基，可选地被-OH取代，环丙基，或；R2为-H或-OH；R3为H或CH3；公式（II）中的虚线表示单键或双键；以及作为氢键供体的辅体，其为酚类化合物。还提供了一种包含该共晶体的组合物和包含该组合物的个人护理产品。
• New 25-hydroxy-24-oxocholestane derivatives and preparation thereof
  申请人：TEIJIN LIMITED

  公开号：EP0015122A1

  公开（公告）日：1980-09-03

  The novel 25-hydroxy-24-oxocholestane derivatives of this invention can easily be converted to 24,25-dihydroxycholecalciferol or 1α,24,25-trihydroxycholecalciferol which is known as useful for medicine controlling the calcium metabolism of warm-blooded animals. Moreover, 25-hydroxy-24-oxocholestane derivatives can be converted to novel 25-hydroxy-24- oxocholecalciferol expressed by the following formula and novel 1 α,25-dihydroxy-24-oxocholecalciferol of the formula

  本发明的新型 25-hydroxy-24-oxocholestane 衍生物可以很容易地转化为 24,25-二羟基胆钙化醇或 1α,24,25-三羟基胆钙化醇，后者是众所周知的用于控制温血动物钙代谢的药物。此外，25-羟基-24-氧代胆甾烷衍生物可转化为新型 25-羟基-24-氧代胆钙化醇，如下式所示 和新型 1 α,25-二羟基-24-氧代胆钙化醇，其式为
• Composition for solid pharmaceutical preparations of active vitamins D3 and process for preparation thereof
  申请人：TEIJIN LIMITED

  公开号：EP0116755A1

  公开（公告）日：1984-08-29

  This invention is concerned with a composition for solid pharmaceutical preparations of active vitamins D3, having the remarkably improved stability of active vitamins D3. and an extremely advantageous process for the preparation thereof from the industrial viewpoint. The composition of this invention is a composition for solid pharmaceutical preparations of active vitamins D3 prepared by forming an outer layer comprising active vitamins D3 and an excipient, which is readily soluble in an organic solvent, around an inner layer comprising an excipient which is slightly soluble in an organic solvent.

  本发明涉及一种活性维生素 D3 固体药物制剂组合物，其活性维生素 D3 的稳定性显著提高。本发明的组合物是一种用于活性维生素 D3 固体药物制剂的组合物，其制备方法是在由活性维生素 D3 和赋形剂（易溶于有机溶剂）组成的外层和由微溶于有机溶剂的赋形剂组成的内层周围形成一个外层。
• Pharmaceutical composition for external use containing active type vitam D3
  申请人：TEIJIN LIMITED

  公开号：EP0177920A2

  公开（公告）日：1986-04-16

  A pharmaceutical composition for external application to the skin of a warm-blooded animal comprising (A) a pharmaceutically effective amount of an active-type vitamin D3, and (B) a substantially water-free carrier containing the active-type vitamin D3 dissolved or uniformly dispersed therein.

  一种用于温血动物皮肤外用的药物组合物，包括 (A) 有效药用量的活性型维生素 D3，和 (B) 基本不含水的载体，其中含有溶解或均匀分散的活性型维生素 D3。
• Composition for injection of active type vitamins D3
  申请人：TEIJIN LIMITED

  公开号：EP0215596A2

  公开（公告）日：1987-03-25

  A composition for the injection of active type vitamins D₃ comprising a lyophilized product of active type vitamins D₃ and an excipient. This composition has good stability of active type vitamins D₃ and is effective as an injection preparation. This composition can be easily prepared.

  一种用于注射活性维生素 D₃ 的组合物，由活性维生素 D₃ 的冻干产品和赋形剂组成。 这种组合物具有良好的活性维生素 D₃ 稳定性，作为注射制剂效果显著。 这种组合物易于制备。