(+)-(S)-17-hydroxystearic acid | 34370-59-7

• 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: (+)-(S)-17-hydroxystearic acid
• 英文别名: 17-L-Hydroxy-octadecansaeure；17-Hydroxy-octadecansaeure；17-Hydroxy-stearinsaeure；(s)-17-Hydroxy stearic acid；(17S)-17-hydroxyoctadecanoic acid
• CAS: 34370-59-7
• 化学式: C₁₈H₃₆O₃
• 分子量: 300.482
• InChiKey: CKGPXFKOAGKQDN-KRWDZBQOSA-N

物化性质

• 熔点：
  79-80 °C
• 沸点：
  436.3±18.0 °C(Predicted)
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  (+)-(S)-17-hydroxystearic acid 在 chromium(VI) oxide 作用下， 以 溶剂黄146 为溶剂， 生成 17-氧代十八酸
  参考文献：
  名称：

  HYDROXY FATTY ACID GLYCOSIDES OF SOPHOROSE FROM TORULOPSIS MAGNOLIAE

  摘要：

  在Torulopsis magnoliae菌株发酵过程中形成的油主要由部分乙酰化的2-O-β-D-葡萄糖吡喃基-D-葡萄糖吡喃糖单元组成，以β-糖苷键连接到17-L-羟基十八烷酸和17-L-羟基-9-十八烯酸上。

  DOI：

  10.1139/v61-104
• 作为产物：
  描述：

  17-羟基油酸 生成 (+)-(S)-17-hydroxystearic acid
  参考文献：
  名称：

  HYDROXY FATTY ACID GLYCOSIDES OF SOPHOROSE FROM TORULOPSIS MAGNOLIAE

  摘要：

  在Torulopsis magnoliae菌株发酵过程中形成的油主要由部分乙酰化的2-O-β-D-葡萄糖吡喃基-D-葡萄糖吡喃糖单元组成，以β-糖苷键连接到17-L-羟基十八烷酸和17-L-羟基-9-十八烯酸上。

  DOI：

  10.1139/v61-104

文献信息

• THE FERMENTATION OF LONG-CHAIN COMPOUNDS BY TORULOPSIS MAGNOLIAE: I. STRUCTURES OF THE HYDROXY FATTY ACIDS OBTAINED BY THE FERMENTATION OF FATTY ACIDS AND HYDROCARBONS
  作者：A. P. Tulloch、J. F. T. Spencer、P. A. J. Gorin

  DOI：10.1139/v62-203

  日期：1962.7.1

  The yield of extracellular glycolipid produced by Torulopsis magnoliae is increased three-to five-fold by the addition of suitable compounds to the growing culture. The supplement, which can be a long-chain acid, ester, hydrocarbon, or glyceride, is hydroxylated and converted to hydroxy fatty acid sophorosides. Fatty esters of all chain lengths from C₁₆to C₂₂, including several unsaturated esters, and even-numbered hydrocarbons from C₁₆to C₂₄are readily fermented. Shorter-chain compounds are used poorly or not at all. With compounds of 16 to 18 carbon atoms, hydroxylation occurs at the terminal or penultimate carbon atom, depending on degree of unsaturation and chain length. Substrates of more than 18 carbon atoms are mainly reduced in chain length by one or more two-carbon units and hydroxylated, giving C₁₇or C₁₈acids with the hydroxyl group on the penultimate carbon atom. The various enzymic reactions which occur during the fermentation are discussed.

  扩大培养基中添加适当化合物可将Magnoliae酵母产生的细胞外糖脂产量提高三到五倍。这种添加剂可以是长链酸、酯、碳氢化合物或甘油酯，经过羟基化后转化为羟基脂肪酸索非酮苷。从C16到C22的所有链长的脂肪酯，包括几种不饱和酯，以及从C16到C24的偶数碳氢化合物都容易发酵。较短链的化合物使用效果不佳或根本不使用。对于含有16到18个碳原子的化合物，羟基化发生在末端或次末端碳原子上，取决于不饱和度和链长。含有超过18个碳原子的底物主要通过一个或多个二碳单位减少链长并进行羟基化，从而在次末端碳原子上带有羟基的C17或C18酸。讨论了发酵过程中发生的各种酶反应。
• Structure and reactions of lactonic and acidic sophorosides of 17-hydroxyoctadecanoic acid
  作者：A. P. Tulloch、A. Hill、J. F. T. Spencer

  DOI：10.1139/v68-551

  日期：1968.11.1

  the acetate group at the 6′-position. The principal acidic component (5) (31%) also has acetate groups at the 6′- and 6″-positions but the fatty acid carboxyl group is free. The structures were deduced by a combination of glycol cleavage and nuclear magnetic resonance studies and by examination of the products of acetobrominolysis of the acetylated lactones and acid.The 2″,3″-glycol group of the lactones

  17-L-羟基十八烷酸的内酯和酸性槐糖苷混合物的主要成分的完整结构已被确定，该混合物由一种酵母属酵母产生。主要内酯组分 (1) (41%) 在 6'- 和 6"-位具有乙酸酯基团，并且脂肪酸羧基连接到 4"-位以形成大环内酯环。另一个内酯组分 (2) (8%) 与第一个不同，仅在 6'-位不存在乙酸酯基团。主要酸性组分 (5) (31%) 在 6'- 和 6''- 位也具有乙酸酯基团，但脂肪酸羧基是游离的。这些结构是通过乙二醇裂解和核磁共振研究的结合以及乙酰化内酯和酸的乙酰溴分解产物的检查推导出来的。2“，内酯的 3"-乙二醇基团对高碘酸盐和乙酸中的四乙酸铅具有抗氧化性。甲基4的乙二醇裂解速率的研究...
• Process for producing wax ester from dihydroxy fatty acid
  申请人：Awang Roila

  公开号：US20050192452A1

  公开（公告）日：2005-09-01

  A process for producing wax ester comprising of esterifying dihydroxy fatty acid preferably dihydroxystearic acid with at least one alcohol in the presence of lipase as a catalyst which is then remove by filtration. The filtered catalyst could be reuse and provides a number of cost advantages. In the preferred embodiment of the present invention, the dihydroxystearic acid is derived from palm based oleic acid and the alcohol contains 8 to 18 carbon atoms per molecules.

  一种生产蜡酯的方法，包括在脂肪酶的催化下，将二羟基脂肪酸（最好是二羟基硬脂酸）与至少一种醇酯化，然后通过过滤去除催化剂。过滤后的催化剂可以重复使用，提供了多种成本优势。在本发明的首选实施例中，二羟基硬脂酸来自基于棕榈油的油酸，而醇含有每个分子8至18个碳原子。
• Absolute Configuration and Antiprotozoal Activity of Minquartynoic Acid
  作者：Hasse Bonde Rasmussen、Søren Brøgger Christensen、Lars Peter Kvist、Arzalan Kharazmi、Andrea Gonzales Huansi

  DOI：10.1021/np990604k

  日期：2000.9.1

  Minquartynoic acid (1) was isolated as an antimalarial and antileishmanial constituent of the Peruvian tree Minquartia guianensis and its absolute configuration at C-17 established to be (+)-S through conversion to the known (+)-(S)-17-hydroxystearic acid (2) and confirmed using Mosher's method.
• US7125694B2
  申请人：——

  公开号：US7125694B2

  公开（公告）日：2006-10-24