2-hexyl-3-hydroxydecanoic acid | 124347-07-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 2-hexyl-3-hydroxydecanoic acid
• 英文别名: 2-Hexyl-3-hydroxy-decansaeure
• CAS: 124347-07-5
• 化学式: C₁₆H₃₂O₃
• 分子量: 272.428
• InChiKey: MAJPNCZLAWPPTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  19
• 可旋转键数：
  13
• 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：

  2-hexyl-3-hydroxydecanoic acid 在 potassium hydrogensulfate 、 乙酸酐 作用下， 生成 2-hexyl-dec-2-enoic acid
  参考文献：
  名称：

  Lederer et al., Bulletin de la Societe Chimique de France, 1952, p. 413,416

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-4-heptylidene-3-hexyloxetan-2-one 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 生成 2-hexyl-3-hydroxydecanoic acid
  参考文献：
  名称：

  霉菌酸生物表面活性剂的合成及其物理和表面活性

  摘要：

  AbstractFive mycolic acids [2‐alkyl‐3‐hydroxy FA: R1C*(OH)C*HR2COOH] were synthesized using acyl chlorides with alkyl chains of different lengths (total carbon numbers of mycolic acids, 12, 16, 20, 24, 36). The relationship between the chemical structures of the mycolic acids and their surface‐active properties was determined. The acids were synthesized in three steps: (i) dimerization of acyl chloride into alkyl ketene dimer, (ii) selective reduction of C=C to C‐C by hydrogenation, and (iii) β‐lactone ring cleavage under alkaline conditions. The yields of C12‐, C16‐, C20‐, C24‐, and C36‐mycolic acid were 72, 73, 73, 73, and 73%, respectively. The critical micelle concentrations (CMC) of C12‐, C16‐, and C20‐mycolic acid were 2.2×10−4, 1.36×10−4, and 7.4×10−5 M, respectively. As the carbon number increased, the surface tension at the CMC value was also lower; the values for C12‐, C16‐ and C20‐mycolic acid were 46.54, 43.59, and 41.57 dyn/cm, respectively. The emulsifying activities of mycolic acids were determined for n‐tetradecane, n‐hexadecane, cyclohexane, and diesel oil. The results showed that C12‐mycolic acid was the best emulsifier for diesel oil, C16‐mycolic acid was the best emulsifier for n‐tetradecane and n‐hexadecane, and C20‐mycolic acid was the best emulsifier for cyclohexane. This study showed that mycolic acids having, surface‐active properties can be chemically synthesized for potential applications in the detergent/cleaning material industries, for example, in oil spill cleanup, oil recovery, textiles, pharmaceuticals, and cosmetics.

  DOI：

  10.1007/s11746-005-5170-8

文献信息

• KAMATA, TOSIXIRO;ISIGAMI, YUTAKA;VASADA, NOBUXIDEH
  作者：KAMATA, TOSIXIRO、ISIGAMI, YUTAKA、VASADA, NOBUXIDEH

  DOI：——

  日期：——
• JPH01149751A
  申请人：——

  公开号：JPH01149751A

  公开（公告）日：1989-06-12
• Novel microorganisms having oil biodegradability and method for bioremediation of oil-contaminated soil
  申请人：Park Byeong-Deog

  公开号：US20080020947A1

  公开（公告）日：2008-01-24

  Disclosed herein are novel microorganisms having excellent biodegradability and a method for the bioremediation of oil-contaminated soil. The novel microorganisms are specified as Rhodococcus baikoneurensis EN3 KCTC19082, Acinetobacter johnsonii EN67 KCTC12360 and Acinetobacter haemolyticus EN96 KCTC12361. In the bioremediation method, in addition to said novel microorganisms, various microorganisms of Nocardia sp., Gordonia sp., Rhodococcus sp. and Acinetobactor sp. can be used, and the oil biodegradation activities of these microbial strains can be increased by adding biosurfactant 2-alkyl-3-hydroxylic acid or its derivative. According to the disclosed invention, oil-contaminated soils can be purified in an effective, economical and eco-friendly manner compared to prior bioremediation methods.
• Synthesis of mycolic acid biosurfactants and their physical and surface-active properties
  作者：Myungjin Lee、Hyung Sub Gwak、Byeong Deog Park、Sung-Taik Lee

  DOI：10.1007/s11746-005-5170-8

  日期：2005.3

  AbstractFive mycolic acids [2‐alkyl‐3‐hydroxy FA: R1C*(OH)C*HR2COOH] were synthesized using acyl chlorides with alkyl chains of different lengths (total carbon numbers of mycolic acids, 12, 16, 20, 24, 36). The relationship between the chemical structures of the mycolic acids and their surface‐active properties was determined. The acids were synthesized in three steps: (i) dimerization of acyl chloride into alkyl ketene dimer, (ii) selective reduction of C=C to C‐C by hydrogenation, and (iii) β‐lactone ring cleavage under alkaline conditions. The yields of C12‐, C16‐, C20‐, C24‐, and C36‐mycolic acid were 72, 73, 73, 73, and 73%, respectively. The critical micelle concentrations (CMC) of C12‐, C16‐, and C20‐mycolic acid were 2.2×10−4, 1.36×10−4, and 7.4×10−5 M, respectively. As the carbon number increased, the surface tension at the CMC value was also lower; the values for C12‐, C16‐ and C20‐mycolic acid were 46.54, 43.59, and 41.57 dyn/cm, respectively. The emulsifying activities of mycolic acids were determined for n‐tetradecane, n‐hexadecane, cyclohexane, and diesel oil. The results showed that C12‐mycolic acid was the best emulsifier for diesel oil, C16‐mycolic acid was the best emulsifier for n‐tetradecane and n‐hexadecane, and C20‐mycolic acid was the best emulsifier for cyclohexane. This study showed that mycolic acids having, surface‐active properties can be chemically synthesized for potential applications in the detergent/cleaning material industries, for example, in oil spill cleanup, oil recovery, textiles, pharmaceuticals, and cosmetics.
• Lederer et al., Bulletin de la Societe Chimique de France, 1952, p. 413,416
  作者：Lederer et al.

  DOI：——

  日期：——