threo-9,10-Dihydroxy-hexadecansaeure | 2027-46-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: threo-9,10-Dihydroxy-hexadecansaeure
• 英文别名: threo-9.10-dihydroxy-palmitic acid；threo-9.10-Dihydroxy-palmitinsaeure；Niedrigerschmelzende 9.10-Dihydroxy-palmitinsaeure；(9R,10R)-9,10-dihydroxyhexadecanoic acid
• CAS: 2027-46-5；16343-85-4；16343-86-5；29242-09-9；93635-23-5
• 化学式: C₁₆H₃₂O₄
• 分子量: 288.428
• InChiKey: MHWBJDVXYSGJET-HUUCEWRRSA-N

物化性质

• 熔点：
  85-86 °C
• 沸点：
  458.0±25.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  threo-9,10-Dihydroxy-hexadecansaeure 在 甲醇 、 sodium 作用下， 生成 (+/-)-erythro-11,12-dibromo-octadecanoic acid ethyl ester
  参考文献：
  名称：

  Effect of Dietary Omega-3 Fatty Acids and Chronic Ethanol Consumption on Reverse Cholesterol Transport in Rats

  摘要：

  We previously showed that chronic ethanol feeding reads to a decrease of apolipoprotein E (apoE) in high-density lipoprotein (HDL), whereas supplementing this diet with 2.8% of total dietary calories as omega 3-fatty acids (omega 3FAs) restores HDL-apoE to the control values. Since HDL containing apoE plays a major role in reverse cholesterol transport (RCT), we measured the effects chronic ethanol intake and omega 3-FAs -FAs on RCT in the present study. Four groups of rats, control normal fat (CN), alcohol-normal fat (AN), control omega 3FA fat (CF), and alcohol-omega 3FA fat (AF), were fed their respective diets for 8 weeks, after which hepatocytes and HDLs from each group were evaluated for RCT capacity (cholesterol efflux from macrophages end uptake by liver cells). Compared with the control diet (CN), chronic ethanol (AN) feeding inhibited the cholesterol efflux capacity of HDL by 21% (P <.01), whereas w3FA feeding (2.8% of total dietary calories) stimulated this capacity by 79% (P <.01) and 25% (P <.01) in CF and AF rats, respectively. With respect to cholesterol uptake by the liver, there were no significant 3-way or 4-way interactions between the 4 factors, HDL-alcohol, MDL-fish oil, hepatocyte-alcohol, and hepatocyte-fish oil. The main effects for HDL-alcohol, HDL-fish oil, and hepatocyte-alcohol were all highly significant (P =.0001,.0001, and .007, respectively). There was a significant HDL-alcohol and HDL-fish oil interaction (P =.0001). Hepatocyte-alcohol was not a factor in any 2-way interactions. Our study indicates no evidence of an interaction between the effects of omega 3FAs end the effects of alcohol on hepatocytes in terms of RCT function. Thus, feeding as little as 2.8% of the total dietary calories as w3FA not only restored the impaired RCT function of HDL caused by chronic ethanol intake, but also enhanced by severalfold the ability of HDL to promote RCT even in normal animals. Copyright (C) 2000 by W.B. Saunders Company.

  DOI：

  10.1016/s0026-0495(00)80017-7
• 作为产物：
  描述：

  棕榈油酸 在 甲酸 、 双氧水 作用下， 生成 threo-9,10-Dihydroxy-hexadecansaeure
  参考文献：
  名称：

  Effect of Dietary Omega-3 Fatty Acids and Chronic Ethanol Consumption on Reverse Cholesterol Transport in Rats

  摘要：

  We previously showed that chronic ethanol feeding reads to a decrease of apolipoprotein E (apoE) in high-density lipoprotein (HDL), whereas supplementing this diet with 2.8% of total dietary calories as omega 3-fatty acids (omega 3FAs) restores HDL-apoE to the control values. Since HDL containing apoE plays a major role in reverse cholesterol transport (RCT), we measured the effects chronic ethanol intake and omega 3-FAs -FAs on RCT in the present study. Four groups of rats, control normal fat (CN), alcohol-normal fat (AN), control omega 3FA fat (CF), and alcohol-omega 3FA fat (AF), were fed their respective diets for 8 weeks, after which hepatocytes and HDLs from each group were evaluated for RCT capacity (cholesterol efflux from macrophages end uptake by liver cells). Compared with the control diet (CN), chronic ethanol (AN) feeding inhibited the cholesterol efflux capacity of HDL by 21% (P <.01), whereas w3FA feeding (2.8% of total dietary calories) stimulated this capacity by 79% (P <.01) and 25% (P <.01) in CF and AF rats, respectively. With respect to cholesterol uptake by the liver, there were no significant 3-way or 4-way interactions between the 4 factors, HDL-alcohol, MDL-fish oil, hepatocyte-alcohol, and hepatocyte-fish oil. The main effects for HDL-alcohol, HDL-fish oil, and hepatocyte-alcohol were all highly significant (P =.0001,.0001, and .007, respectively). There was a significant HDL-alcohol and HDL-fish oil interaction (P =.0001). Hepatocyte-alcohol was not a factor in any 2-way interactions. Our study indicates no evidence of an interaction between the effects of omega 3FAs end the effects of alcohol on hepatocytes in terms of RCT function. Thus, feeding as little as 2.8% of the total dietary calories as w3FA not only restored the impaired RCT function of HDL caused by chronic ethanol intake, but also enhanced by severalfold the ability of HDL to promote RCT even in normal animals. Copyright (C) 2000 by W.B. Saunders Company.

  DOI：

  10.1016/s0026-0495(00)80017-7

文献信息

• Optical and geometric isomers of some fatty acids with vicinal hydroxy groups
  作者：D. F. Ewing、C. Y. Hopkins

  DOI：10.1139/v67-206

  日期：1967.6.1

  resolved by means of the brucine salts into the optically active forms. Levorotatory threo-11,12-dihydroxyeicosanoic acid was obtained from the corresponding racemate by crystallization of the ephedrine salts.The conformation of the geometric isomers of certain dihydroxy long-chain acids and their derivatives was studied by means of nuclear magnetic resonance spectra. There was a small but significant

  外消旋 threo-9,10-dihydroxypalmitic 酸通过 brucine 盐分解成旋光形式。通过麻黄碱盐的结晶，从相应的外消旋体中获得左旋苏式-11,12-二羟基二十烷酸。利用核磁共振光谱研究了某些二羟基长链酸及其衍生物的几何异构体的构象。与 (±)-赤藓酸中的 CH 质子的化学位移相比，(±)-苏氨酸中的 CH 质子的化学位移存在微小但显着的差异。这在 9,10-二羟基棕榈酸、9,10-二羟基硬脂酸和 11,12-二羟基二十烷酸中观察到。对于相同酸的 O-异亚丙基衍生物中的 CH 质子，观察到类似但更大的化学位移差异 (0.49 ppm)。
• Boughton et al., Journal of the Chemical Society, 1952, p. 671,674
  作者：Boughton et al.

  DOI：——

  日期：——
• GULACAR, FAZIL O.;BUCHS, ARMAND;SUSINI, ALBERTO, J. CHROMATOGR., 479,(1989) N, C. 61-72
  作者：GULACAR, FAZIL O.、BUCHS, ARMAND、SUSINI, ALBERTO

  DOI：——

  日期：——
• Effect of Dietary Omega-3 Fatty Acids and Chronic Ethanol Consumption on Reverse Cholesterol Transport in Rats
  作者：Philippe Marmillot、Manjunath N. Rao、Qing-Hong Liu、Stuart J. Chirtel、M.R. Lakshman

  DOI：10.1016/s0026-0495(00)80017-7

  日期：2000.4

  We previously showed that chronic ethanol feeding reads to a decrease of apolipoprotein E (apoE) in high-density lipoprotein (HDL), whereas supplementing this diet with 2.8% of total dietary calories as omega 3-fatty acids (omega 3FAs) restores HDL-apoE to the control values. Since HDL containing apoE plays a major role in reverse cholesterol transport (RCT), we measured the effects chronic ethanol intake and omega 3-FAs -FAs on RCT in the present study. Four groups of rats, control normal fat (CN), alcohol-normal fat (AN), control omega 3FA fat (CF), and alcohol-omega 3FA fat (AF), were fed their respective diets for 8 weeks, after which hepatocytes and HDLs from each group were evaluated for RCT capacity (cholesterol efflux from macrophages end uptake by liver cells). Compared with the control diet (CN), chronic ethanol (AN) feeding inhibited the cholesterol efflux capacity of HDL by 21% (P <.01), whereas w3FA feeding (2.8% of total dietary calories) stimulated this capacity by 79% (P <.01) and 25% (P <.01) in CF and AF rats, respectively. With respect to cholesterol uptake by the liver, there were no significant 3-way or 4-way interactions between the 4 factors, HDL-alcohol, MDL-fish oil, hepatocyte-alcohol, and hepatocyte-fish oil. The main effects for HDL-alcohol, HDL-fish oil, and hepatocyte-alcohol were all highly significant (P =.0001,.0001, and .007, respectively). There was a significant HDL-alcohol and HDL-fish oil interaction (P =.0001). Hepatocyte-alcohol was not a factor in any 2-way interactions. Our study indicates no evidence of an interaction between the effects of omega 3FAs end the effects of alcohol on hepatocytes in terms of RCT function. Thus, feeding as little as 2.8% of the total dietary calories as w3FA not only restored the impaired RCT function of HDL caused by chronic ethanol intake, but also enhanced by severalfold the ability of HDL to promote RCT even in normal animals. Copyright (C) 2000 by W.B. Saunders Company.