(3beta,17beta)-17-[(2R,3E,5R)-5,6-二甲基-3-庚烯-2-基]雌甾-5(10),6,8-三烯-3-醇 | 516-98-3

• 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: (3beta,17beta)-17-[(2R,3E,5R)-5,6-二甲基-3-庚烯-2-基]雌甾-5(10),6,8-三烯-3-醇
• 中文别名: 新麥角甾醇
• 英文名称: neoergosterol
• 英文别名: (3S,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-13-methyl-1,2,3,4,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol
• CAS: 516-98-3
• 化学式: C₂₇H₄₀O
• 分子量: 380.614
• InChiKey: MNMJPUHGVUDRCV-DOOCTISASA-N

物化性质

• 熔点：
  152-154°
• 比旋光度：
  D17 -11° (c = 2 in chloroform)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3beta,17beta)-17-[(2R,3E,5R)-5,6-二甲基-3-庚烯-2-基]雌甾-5(10),6,8-三烯-3-醇 在 platinum(IV) oxide chromium(VI) oxide 、 盐酸 、 高氯酸 、 氢气 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 生成 3-Methoxy-19-nor-Δ^3.5.7.9,10-ergostatetraen
  参考文献：
  名称：

  类固醇研究。第LXXVII部分。22,23-二氢麦角甾醇（3β-hydroxy-19-norergosta-5,7,9-triene）的衍生物

  摘要：

  小心地氧化22,23-二氢麦角甾醇会生成3-酮和3,4-癸二酸。酮的性质是取代的β-四氢萘酮所期望的性质：例如，溴化可生成萘酚系统。二氢麦角固醇的3β-羟基很容易通过氢解作用除去。乙酸二氢麦角甾醇酯的氧化得到11-酮衍生物。

  DOI：

  10.1039/j39670001238
• 作为产物：
  描述：

  麦角固醇 生成 (3beta,17beta)-17-[(2R,3E,5R)-5,6-二甲基-3-庚烯-2-基]雌甾-5(10),6,8-三烯-3-醇
  参考文献：
  名称：

  Dasler; Bauer, Journal of Biological Chemistry, 1947, vol. 167, p. 581,586

  摘要：

  DOI：

文献信息

• 19-Norsteroids of Unnatural Configuration from Ergosterol
  作者：Ahmed H. Eimasry、Ole Gisvold

  DOI：10.1002/jps.2600590403

  日期：1970.4

  of unnatural configuration from ergosterol has been described. This method led to the preparation of 5α,8α,9α,10α-19-norpregnan-3,20-dione which possesses unnatural configuration at positions 8 and 10. The following reaction sequence was utilized to prepare this steroid. Ergosterol was photo-oxidized to give bisergostatrienol that was pyrolyzed to yield neoergosterol whose side chain was cleaved by

  已经描述了一种由麦角固醇制备具有非天然构型的19-降冰片甾体的新方法。该方法导致制备在位置8和10具有非天然构型的5α，8α，9α，10α-19-去甲泼尼松-3，20-二酮。利用以下反应序列制备该类固醇。麦角固醇被光氧化以得到比麦角固醇，其被热解以产生新麦角固醇，其新的侧链通过臭氧分解被裂解，从而产生3β-羟基-19-norpregna-5,7,9（10）-20α-醛。第一次以结晶状态获得的醛通过3β-羟基-20-吗啉代-亚甲基-19-norpregna-5,7,9（10）-三烯衍生物的臭氧分解而降解，得到3β-羟基- 19-norpregna-5,7,9（10）-triene-20-one。后者用Ru /碳还原为相应的二醇，并且其环B又用Rh /氧化铝作为催化剂在环己烷中成功氢化。用琼斯试剂将二醇氧化为二酮。尽管以前已经记录了上述某些转化，但该报告描述了大多数中间体的技术和收率上的显着改进。
• Family planning in a stemborer parasitoid: sex ratio, brood size and size-fitness relationships in <i>Parallorhogas pyralophagus</i> (Hymenoptera: Braconidae), and implications for biological control
  作者：J.S. Bernal、P.O. Gillogly、J. Griset

  DOI：10.1079/ber200199

  日期：2001.8

  Various aspects were studied of the brood size and sex allocation strategies, and of size-fitness relationships in Parallorhogas pyralophagus (Marsh), a gregarious ectoparasitoid of Eoreuma loftini Dyar. Brood size was significantly correlated with host size; larger hosts were allocated larger broods. Brood sex ratios were fixed precisely at 1 male per 4 females, and eggs were likely to be deposited in that order; differential mortality did not contribute to this precise sex ratio. The sex allocation strategy of P. pyralophagus is likely to conform to strict, i.e. single foundress, local mate competition. Adoption of this strategy is probably influenced by a limited insemination capacity of males; a smaller proportion of females (0.09 vs. 0.21) remained virgin in broods with precise or higher sex ratios (≥0.20 males) relative to broods with lower than precise sex ratios (< 0.20 males). Moreover, all females were inseminated in most broods (60%) with precise or higher sex ratios, whereas this did not occur in broods with lower than precise sex ratios. The hypothesized occurrence of strict local mate competition in P. pyralophagus was supported also by observations that: (i) offspring brood sex ratios were independent of maternal brood sex ratios and number of parental females concurrently allocating offspring to a group of hosts, and; (ii) the rate of superparasitism under no-choice conditions was low (~20%), suggesting that rates of outbreeding in the field are low. Other results suggested that fitness in P. pyralophaguswas correlated with adult size; longevity and reproductive capacity both increased with adult size in males and females. However, adult size may be more important for females than for males because the differences in reproductive capacity between the largest and smallest individuals was up to 7.3 times greater in females versus <2 times in males.

  摘要 研究了Parallorhogas pyralophagus（Marsh）（一种Eoreuma loftini Dyar的群集外寄生虫）的育雏大小、性别分配策略以及大小适配关系等各个方面。雏的大小与寄主的大小有明显的相关性；较大的寄主被分配到较大的雏。产卵性别比例精确地固定为1雄配4雌，卵很可能按此顺序产下；不同的死亡率不会导致这种精确的性别比例。P.pyralophagus的性别分配策略很可能符合严格的本地配偶竞争，即单一雌性。采用这种策略可能受到雄性授精能力有限的影响；相对于性别比低于精确值（0.20雄性）的雏鸟，性别比精确或较高（≥0.20雄性）的雏鸟中保持处女的雌性比例较小（0.09 vs. 0.21）。此外，在大多数（60%）性别比精确或更高的雏鸟中，所有雌鸟都接受了人工授精，而在性别比低于精确的雏鸟中则没有这种情况。以下观察结果也证明了栉水母存在严格的本地配偶竞争的假设：(i)子代育雏性别比与母代育雏性别比和同时将子代分配给一组宿主的亲代雌性数量无关；(ii)无选择条件下的超级寄生率很低（约 20%），这表明野外繁殖率很低。其他结果表明，栉水母的适应性与成虫体型有关；雌雄成虫的寿命和繁殖能力都随着成虫体型的增加而增加。不过，成体大小对雌性可能比对雄性更重要，因为最大个体和最小个体之间的繁殖能力差异，雌性是雄性的7.3倍，而雄性是雌性的2倍。
• Linear polyethylenimine-sterol conjugates for gene delivery
  申请人：The University of Utah Research Foundation

  公开号：US20040137050A1

  公开（公告）日：2004-07-15

  Linear polyethylenimine was modified with sterols, such as cholesterol, in three different geometries: linear shaped (L), T-shaped (T), and a combined linear- and T-shaped (LT), to result in linear polyethylenimine-sterol conjugates. These conjugates were mixed with nucleic acids to form complexes for delivery of the nucleic acids into cells. Mammalian cells transfected with these complexes showed protein expression levels higher than linear polyethylenimine alone, and twice that of branched polyethylenimine, but without any significant loss in cell viability. Methods of making these compositions and methods of using them for gene delivery are also described.

  线性聚乙烯亚胺被固醇（如胆固醇）以三种不同的几何形状进行改性：线性形状（L）、T形状（T）和线性和T形状的组合（LT），从而形成线性聚乙烯亚胺-固醇共轭物。这些共轭物与核酸混合形成复合物，用于将核酸传递到细胞中。转染这些复合物的哺乳动物细胞显示出比单独使用线性聚乙烯亚胺更高的蛋白表达水平，且比支化聚乙烯亚胺高出一倍，但没有任何显著的细胞存活率损失。还描述了制备这些组合物的方法以及将其用于基因传递的方法。
• Barnett et al., Journal of the Chemical Society, 1940, p. 1390,1392
  作者：Barnett et al.

  DOI：——

  日期：——
• Inhoffen, Justus Liebigs Annalen der Chemie, 1932, vol. 497, p. 130,137
  作者：Inhoffen

  DOI：——

  日期：——