15-Hydroxy-12-ketopentadecanoic acid

• 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: 15-Hydroxy-12-ketopentadecanoic acid
• 英文别名: 15-hydroxy-12-oxopentadecanoic acid
• 化学式: C₁₅H₂₈O₄
• 分子量: 272.38
• InChiKey: SHXXBFGBKFKECN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  15-Hydroxy-12-ketopentadecanoic acid 、 对甲苯磺酰氯 以31%的产率得到
  参考文献：
  名称：

  DOUGAN, H.;LYSTER, D. M.;VINCENT, J. S., J. RADIOANAL. AND NUCL. CHEM.: ART., 1985, 89, N 1, 71-78

  摘要：

  DOI：
• 作为产物：
  描述：

  环氧十五烷-2,13-二酮 、 氢氧化钾 以88%的产率得到
  参考文献：
  名称：

  DOUGAN, H.;LYSTER, D. M.;VINCENT, J. S., J. RADIOANAL. AND NUCL. CHEM.: ART., 1985, 89, N 1, 71-78

  摘要：

  DOI：

文献信息

• Anticancer agents, perfumes or foods and drinks containing omega-hydroxyfatty acids
  申请人：——

  公开号：US20030055105A1

  公开（公告）日：2003-03-20

  The present invention relates to drugs and, particularly, to anticancer agents. More particularly, the present invention relates to an anticancer agents containing, as an active ingredient, at least one compound selected from the group consisting of &ohgr;-hydroxy fatty acids and salts or esters thereof, hydroxy oxo-fatty acids and salts or esters thereof, lactones, macrocyclic ketones, and macrocyclic diesters having specific chemical structures. With respect to the compounds described above used in the present invention, since the activities of killing cancer and inhibiting cancer metastasis are significantly high, the effects of preventing the recurrence of cancer and preventing cancer are exhibited, the cytotoxicity is significantly low, and a small dose is effective, it is possible to provide anticancer agents having significantly decreased side effects. Additionally, use in combination with known antitumor agents can further enhance the activity of inhibiting cancer metastasis. Among the anticancer agents of the present invention, &ohgr;-hydroxy fatty acids can be easily obtained in high purities by hydrolyzing lactones which are also the anticancer agents of the present invention.

  本发明涉及药物，特别是抗癌剂。更具体地说，本发明涉及一种抗癌剂，其含有至少一种从以下化合物组合中选择的活性成分，包括ω-羟基脂肪酸及其盐或酯、羟基酮脂肪酸及其盐或酯、内酯、大环酮和具有特定化学结构的大环二酯。对于本发明中所述的上述化合物，由于其杀灭癌细胞和抑制癌转移的活性显著高，具有预防癌症复发和预防癌症的效果，细胞毒性显著低，且小剂量就能发挥作用，因此能够提供具有显著降低副作用的抗癌剂。此外，与已知的抗肿瘤药物结合使用可以进一步增强抑制癌转移的活性。在本发明的抗癌剂中，ω-羟基脂肪酸可以通过水解也是本发明的抗癌剂的内酯轻松获得高纯度。
• .alpha.-(.omega.-cyanoalkanoyl-.gamma.-butyrolactone and method for
  申请人：Ube Industries, Ltd.

  公开号：US05023351A1

  公开（公告）日：1991-06-11

  Disclosed are .alpha.-(.omega.-Cyanoalkanoyl)-.gamma.-butyrolactone represented by the formula: ##STR1## wherein n represents an integer of 7 to 11, and a method for producing the same, which comprises reacting .omega.-cyano fatty acid ester represented by the formula: NC--(CH.sub.2).sub.n --COOR (II) wherein R represents an alkyl group having 1 to 4 carbon atoms and n has the same meaning as in the above, with .gamma.-butyrolactone in the presence of alkali metal alcoholate represented by the formula: R'OM (III) wherein R' represents an alkyl group having 1 to 4 carbon atoms and M represents an alkali metal.

  本发明涉及一种α-(ω-氰基烷酰基)-γ-丁内酯，其表示为以下式子：##STR1## 其中n表示7至11的整数，以及一种制备该化合物的方法，包括在碱金属醇盐存在下，将ω-氰基脂肪酸酯与γ-丁内酯反应，其中ω-氰基脂肪酸酯的表示式为：NC--(CH.sub.2).sub.n --COOR (II)，其中R表示1至4个碳原子的烷基，n与上述含义相同，碱金属醇盐的表示式为：R'OM (III)，其中R'表示1至4个碳原子的烷基，M表示碱金属。
• .alpha.-(.omega.-cyanoalkanoyl)-.gamma.-butyrolactone and method for
  申请人：Ube Industries, Ltd.

  公开号：US05099036A1

  公开（公告）日：1992-03-24

  Disclosed are .alpha.-(.omega.-Cyanoalkanoyl)-.gamma.-butyrolactone represented by the formula: ##STR1## wherein n represents an integer of 7 to 11, and a method for producing the same, which comprises reacting .omega.-cyano fatty acid ester represented by the formula: NC--(CH.sub.2).sub.n --COOR (II) wherein R represents an alkyl group having 1 to 4 carbon atoms and n has the same meaning as in the above, with .gamma.-butyrolactone in the presence of alkali metal alcoholate represented by the formula: R'OM (III) wherein R' represents an alkyl group having 1 to 4 carbon atoms and M represents an alkali metal.

  本发明涉及一种α-(ω-氰基脂肪酰基)-γ-丁内酯，其化学式为：##STR1## 其中n表示7至11的整数，以及一种制备方法，该方法包括在碱金属醇盐的存在下，将ω-氰基脂肪酸酯与γ-丁内酯反应，所述ω-氰基脂肪酸酯的化学式为：NC--(CH.sub.2).sub.n --COOR (II)，其中R表示具有1至4个碳原子的烷基，n与上述相同，所述碱金属醇盐的化学式为：R'OM (III)，其中R'表示具有1至4个碳原子的烷基，M表示碱金属。
• Alpha-(omega-cyanoalkanoyl)-gamma-butyrolactone and method for producing the same
  申请人：UBE INDUSTRIES, LTD.

  公开号：EP0402063A2

  公开（公告）日：1990-12-12

  Disclosed are α-(ω-Cyanoalkanoyl)-γ-butyrolactone represented by the formula: wherein n represents an integer of 7 to 11, and a method for producing the same, which comprises reacting ω-cyano fatty acid ester represented by the formula: NC-(CH₂)n-COOR      (II) wherein R represents an alkyl group having 1 to 4 carbon atoms and n has the same meaning as in the above, with γ-butyrolactone in the presence of alkali metal alcoholate represented by the formula: R′OM      (III) wherein R′ represents an alkyl group having 1 to 4 carbon atoms and M represents an alkali metal.

  所公开的α-(ω-氰基烷酰基)-γ-丁内酯由式表示： 其中 n 代表 7 至 11 的整数、 以及一种生产该物质的方法，其中包括使由式.NC-(CH₂)代表的ω-氰基脂肪酸酯反应： NC-(CH₂)n-COOR (II) 其中 R 代表具有 1 至 4 个碳原子的烷基，n 的含义与上文相同、 与γ-丁内酯在碱金属醇酸酯存在下进行反应，碱金属醇酸酯的代表式为 R′OM (III) 其中 R′代表具有 1 至 4 个碳原子的烷基，M 代表碱金属。
• PROCESSES FOR PREPARING 2-($g(v)-ALKOXYCARBONYLALKANOYL)-4-BUTANOLIDES, $g(v)-HYDROXY-($g(v)-3)-KETO FATTY ESTERS, AND DERIVATIVES THEREOF
  申请人：SODA AROMATIC COMPANY, LIMITED

  公开号：EP0970952A1

  公开（公告）日：2000-01-12

  In industrial production of ω-hydroxyaliphatic acid being an important intermediate for large cyclic lactone-based perfumes, using dicarboxylate ester which is inexpensive and readily obtainable, a method, with high yield and improved selectively, for making a 2-(ω-alkoxycarbonylalkanoyl)-4-butanolide and an alkaline metal salt thereof, an ester of ω-hydroxy-(ω-3)-ketoaliphatic acid as a novel compound and a derivative thereof, and a method for making the same are provided. Condensation reaction of γ-butyrolactone with a dicarboxylate ester represented by the general formula (1) ROOC(CH2)nCOOR wherein n is an integer of 7 to 13 and R is an alkyl group forms a condensation solution containing an alkaline metal salt of 2-(ω-alkoxycarbonylalkanoyl)-4-butanolide represented by the general formula (3): wherein n is an integer of 7 to 13, R is an alkyl group, and M is an alkaline metal; the solution is extracted with water or an aqueous alkaline solution and subjected to hydrolysis and decarboxylation to form an alkaline metal salt of ω-hydroxy-(ω-3)-ketoaliphatic acid represented by the general formula (5): wherein n is an integer of 7 to 13 and M is an alkaline metal; and the compound is selectively and effectively separated and recovered and then acidified to form an ω-hydroxy-(ω-3)-ketoaliphatic acid represented by the general formula (10): wherein n is an integer of 7 to 13.

  在工业生产中，ω-羟基脂肪酸是大型环内酯基香水的重要中间体，利用价格低廉且容易获得的二羧酸酯，一种高产率和改进选择性的方法，用于制造2-(ω-烷氧基羰基烷酰基)-4-丁内酯及其碱金属盐、提供了制造 2-(ω-烷氧基羰基烷酰基)-4-丁内酯及其碱金属盐、作为新型化合物的 ω-hydroxy-(ω-3)-ketoaliphatic acid 的酯及其衍生物的方法。 γ-丁内酯与通式(1)ROOC(CH2)nCOOR 表示的二羧酸酯（其中 n 为 7 至 13 的整数，R 为烷基）的缩合反应形成含有通式(3)表示的 2-(ω-烷氧基羰基烷酰基)-4-丁内酯的碱金属盐的缩合溶液： 其中 n 为 7 至 13 的整数，R 为烷基，M 为碱金属；该溶液用水或碱性水溶液萃取并进行水解和脱羧，以形成通式(5)代表的 ω-羟基-(ω-3)-酮脂肪族酸的碱金属盐： 其中 n 为 7 至 13 的整数，M 为碱金属；并选择性地有效分离和回收该化合物，然后酸化形成通式 (10) 所代表的ω-羟基-(ω-3)-酮脂族酸： 其中 n 为 7 至 13 的整数。