胆甾-4,6-二烯-3beta-基苯甲酸酯 | 25485-34-1

• 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: 胆甾-4,6-二烯-3beta-基苯甲酸酯
• 英文名称: cholest-4,6-diene-3β-yl benzoate
• 英文别名: 3β-benzoyloxy-cholesta-4,6-diene；3β-Benzoyloxy-cholesta-4,6-dien；Benzoesaeure-(cholestadien-(4.6)-yl-(3β)-ester)；cholesta-4,6-dien-3β-yl benzoate；[10,13-Dimethyl-17-(6-methylheptan-2-yl)-2,3,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]benzoate；[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] benzoate
• CAS: 25485-34-1
• 化学式: C₃₄H₄₈O₂
• 分子量: 488.754
• InChiKey: KJRLFFDMSLSIGS-LLHZKFLPSA-N

物化性质

• 熔点：
  122-124 °C
• 沸点：
  573.6±29.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  胆甾-4,6-二烯-3beta-基苯甲酸酯 在 吡啶 作用下， 生成 Cholesta-2,4,6-trien
  参考文献：
  名称：

  Δ 2,4,6 -Cholestatrien。BeiBrug zum机制的HBr-Abspaltung aus 7-溴-胆固醇基苯甲酸酯

  摘要：

  1.孛DER的HBr-Abspaltung AUS7β-维奇-cholesterylbenzoat wurde ALS Nebenprodukt EIN三烯isoliert，DEM sehr wahrscheinlich死Formel EINESΔ 2,4,6- -Cholestatriens zukommt。

  DOI：

  10.1002/hlca.19510340417
• 作为产物：
  描述：

  7α-bromocholest-5-en-3β-ol benzoate 在 2,4,6-三甲基吡啶 作用下， 生成 胆甾-4,6-二烯-3beta-基苯甲酸酯
  参考文献：
  名称：

  Redel; Gauthier, Bulletin de la Societe Chimique de France, 1948, p. 607,610

  摘要：

  DOI：

文献信息

• Synthesis of perfluoroalkyl steroids as CO-emulsifying agents for 1-bromoperfluorooctane and other perfluorocompounds
  作者：C.M. Sharts、A.A. Malik、J.C. Easdon、L.A. Khawli、D.M. Long、D.F. Shellhamer、V.L. Burton、M.K. Porter、L.F. Sprague

  DOI：10.1016/s0022-1139(00)85180-5

  日期：1987.1

  substituted with perfluoroalkyl groups at C-3, C-7, and C-20 positions on the steroid nucleus are described. Synthetic methods employed included coupling of perfluoroalkylcopper with allylic bromides and Grignard reactions. Free radical additions of perfluoroalkyl iodide to unsaturated steroids and reaction of perfluoroalkyl Grignard reagents with 6-ketosteroid were unsuccessful. Perfluoroalkyl -substituted

  描述了在类固醇核的C-3，C-7和C-20位置被全氟烷基取代的类固醇的合成。所使用的合成方法包括全氟烷基铜与烯丙基溴的偶联和格氏反应。全氟烷基碘向不饱和类固醇的自由基加成以及全氟烷基格氏试剂与6-酮类固醇的反应均未成功。需要全氟烷基取代的类固醇作为全乳化全氟辛烷/水乳液中的助乳化剂进行测试，该乳液用作血液替代品（合成血液）。还报道了选择全氟辛基溴化物作为氟碳基血液替代品中的携氧剂以及使用全氟烷基取代的类固醇作为共乳化剂的基本原理。
• Die direkte Photobromierung der Cholesterylester in der Allylstellung (C7-Position). Sterine als ionoide Systeme III
  作者：H. Schaltegger

  DOI：10.1002/hlca.19500330713

  日期：——

  man Cholesterylester höchst einfach mit elementarem Brom und Licht in 7-Stellung bromieren kann, ohne dass die Doppelbindung aufgehoben oder umgelagert wird. Man erhält in ebenso guter Ausbeute wie über den Umweg mit Bromsuccinimid 7-Bromcholesterylester. Der Konstitutionsbeweis wurde durch die verschiedenen Umsetzungen des 7-β-Bromcholesterylbenzoates in bekannte Derivate erbracht.

  已经表明，胆甾醇酯可以很容易地在7位上被元素溴和光溴化，而双键不被破坏或重新排列。获得的收率与用溴代琥珀酰亚胺，7-溴胆固醇酯的绕行率一样好。通过将7-β-溴胆固醇基苯甲酸酯向已知衍生物的各种转化来提供构成的证明。
• Blood pressure, heart rate, hormonal and other acute responses to rubber-ring castration and tail docking of lambs
  作者：A Peers、DJ Mellor、EM Wintour、M Dodic

  DOI：10.1080/00480169.2002.36251

  日期：2002.4

  AIM: To examine cardiovascular, hormonal and other physiological responses of 2-month-old lambs to rubber-ring castration and tail docking.METHODS: Twenty-two male lambs, well accustomed to handling and prepared with femoral artery and jugular vein cannulae, were studied during a 5 h control period and, at least 2 days later, for 1 h before and 4 h after castration and tail docking using rubber rings. Pressure recordings were made via femoral cannulae and blood samples for analysis of plasma constituents were taken from jugular cannulae.RESULTS: Mean systolic, diastolic and mean arterial blood pressure, heart rate and the plasma concentrations of adrenocorticotropic hormone (ACTH) and cortisol all increased markedly during the first 1 h after ring castration and tail docking. Although plasma ACTH and cortisol concentrations had returned to control levels by 2.5-3 h, blood pressures and heart rate were still elevated 4 h after ring application. In contrast, there were no significant changes in mean plasma concentrations of renin, electrolytes, minerals, glucose, lactate, urea, creatinine, total carbon dioxide and total proteins, plasma osmolality or the haematocrit after ring application. There were no significant changes in the mean values for any parameter during the 5 h control period or the I h period before ring application.CONCLUSION: Systolic, diastolic and mean arterial blood pressure and heart rate may be more sensitive than plasma ACTH or cortisol concentrations as indices of low-grade pain induced by ring castration and tail docking. Alternatively, it is possible that by 4 h after ring placement a small shift in sympathetic tone still persists in the absence of low-grade pain.
• Evidence of toxic side effects of perfluorohexyloctane after vitreoretinal surgery as well as in previously established in vitro models with ocular cell types
  作者：Sylvia Mertens、Jürgen Bednarz、Katrin Engelmann

  DOI：10.1007/s00417-002-0561-0

  日期：2002.12

  Background: Cases of ocular irritation have been observed after early clinical trials using perfluorohexyl octane (F6H8) as endotamponade. In our clinic two of three eyes developed severe inflammatory-like reactions after intermediate-term tamponade. These cases will be depicted, serving as background for the experimental study. To elucidate possible toxic effects of F6H8 on different ocular cell types and corneal tissue we applied our previously established in vitro models to investigate effects of F6H8 on cultured ocular cells in comparison with perfluorodecaline. Methods: Vitality and proliferation of cultured human corneal endothelial cells (HCEC) and human retinal pigment epithelial cells (RPE) were measured after incubation with F6H8 or perfluorodecaline for up to 5 days. Vitality was evaluated using the Live/Dead assay, and proliferation was determined according to BrdU incorporation. Additionally the endothelium of donor corneas was incubated with F6H8 for 5 days and endothelial cell morphology was documented. Results: After 5 days incubation with F6H8, cultures of RPE and HCEC showed significantly lower extinctions for vital cells as well as a non-significant decrease in proliferation compared with controls. Analysis by means of fluorescence microscopy after treatment with F6H8 or perfluorodecaline revealed decreased cell densities (F6H8 > perfluorodecaline) within contact areas. The endothelium of donor corneas incubated in presence of F6H8 developed circumscribed necrotic areas. Conclusions: Decreased amounts of vital cells cannot be explained solely by mechanical effects or nutritional deficit due to direct contact, since F6H8 has a lower specific weight than perfluorodecaline. The ability of the remaining cells to proliferate revealed that they were not irreversibly damaged. Due to the high lipophilicity of F6H8 interactions with cellular lipoprotein membranes as well as other toxic effects have to be considered and should further be investigated prior to clinical use.
• Ponomarev, N. E.; Dvorko, G. F., Journal of general chemistry of the USSR, 1991, vol. 61, # 22, p. 388 - 400
  作者：Ponomarev, N. E.、Dvorko, G. F.

  DOI：——

  日期：——