δ-eicosalactone | 110071-67-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: δ-eicosalactone
• 英文别名: meadowlactone；6-pentadecyloxan-2-one
• CAS: 110071-67-5
• 化学式: C₂₀H₃₈O₂
• 分子量: 310.521
• InChiKey: LLPDOHGLBDHCJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  400.7±13.0 °C(Predicted)
• 密度：
  0.897±0.06 g/cm3(Predicted)
• 保留指数：
  2573.1

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  δ-eicosalactone 、 正丁醇 在 硫酸 作用下， 反应 0.02h， 生成 5-Hydroxy-icosanoic acid butyl ester
  参考文献：
  名称：

  草甸泡沫脂肪酸衍生的γ-和δ-内酯的开环率

  摘要：

  Abstractδ‐Lactones derived from meadowfoam (Limnanthes) fatty acids were reacted with amine and alcohol nucleophiles in a second‐order reaction to provide the acyclic 5‐hydroxy eicosanoic acid esters and amides. The rate of reaction for the ring opening of δ‐lactones was compared to the rate of ring opening of γ‐lactones and the rate of derivatization of meadowfoam fatty acids. δ‐Lactones showed a much larger rate for the formation of derivatives than the corresponding γ‐lactones or fatty acids. γ‐Lactone had a rate constant >7700 times larger for the formation of butyl ester than meadowfoam fatty acids. The formation of amides from δ‐lactones is even faster than the esterification reaction and requires no catalyst or solvent when conducted at the melting point of the lactone.

  DOI：

  10.1007/s11746-998-0011-1
• 作为产物：
  描述：

  溴代十四烷 、 1,2-环己二酮 在 氢氧化钾 、 sodium carbonate 、 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 为溶剂， 反应 58.0h， 以12%的产率得到δ-eicosalactone
  参考文献：
  名称：

  Sensory-Directed Identification of Creaminess-Enhancing Volatiles and Semivolatiles in Full-Fat Cream

  摘要：

  Aimed at defining the chemical nature of creaminess-related flavor compounds in dairy products on a molecular level, a full-fat cream was analyzed for sensorially active volatiles and semivolatiles by means of activity-guided screening techniques. Application of the aroma extract dilution analysis on an aroma distillate prepared from pasteurized cream (30% fat) revealed delta-decalactone, (Z)-6-dodeceno-gamma-lactone, gamma-dodecalactone, delta-dodecalactone, and 3-methylindole with by far the highest flavor dilution (FD) factors among the 34 odor-active volatiles identified. Using a complementary approach involving silica column chromatography and fractionated high-vacuum distillation combined with sensory experiments enabled the additional identification of delta-tetradecalactone, delta-hexadecalactone, gamma-tetradecalactone, gamma-hexadecalactone, and delta-octadecalactone as semivolatile flavor components in the cream fat. Although a series of lactones is present in dairy cream, spiking of cream samples with individual lactones revealed that only the delta-tetradecalactone is able to enhance the typical retronasal creamy flavor of the product when added in amounts above its theshold level of 66 mu mol/kg. Rather than contributing to the retronasal aroma of cream, first evidence was found that, particularly, gamma- and delta-octadecalactones and gamma- and delta-eicosalactones are able to influence the melting behavior of cream in the oral cavity.

  DOI：

  10.1021/jf0721545

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。
• ANTICANCER AGENTS, PERFUMES OR FOODS AND DRINKS CONTAINING $g(v)-HYDROXYFATTY ACIDS
  申请人：SODA AROMATIC COMPANY, LIMITED

  公开号：EP1249236A1

  公开（公告）日：2002-10-16

  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 ω-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, ω-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，其中含有至少一种选自具有特定化学结构的ω-羟基脂肪酸及其盐或酯、羟基氧代脂肪酸及其盐或酯、内酯、大环酮和大环二酯组成的组的化合物作为活性成分。 对于本发明中使用的上述化合物，由于杀灭癌症和抑制癌症转移的活性显著较高，具有防止癌症复发和预防癌症的效果，细胞毒性显著较低，且小剂量即可有效，因此可以提供副作用显著降低的抗癌剂。此外，与已知的抗肿瘤药物联合使用可进一步提高抑制癌症转移的活性。在本发明的抗癌剂中，ω-羟基脂肪酸很容易通过水解内酯得到高纯度的ω-羟基脂肪酸，这些内酯也是本发明的抗癌剂。
• Methods for enhancing the morphology, tone, texture and/or appearance of skin or hair using a Meadowlactone
  申请人：Wohlman Alan

  公开号：US20070092465A1

  公开（公告）日：2007-04-26

  The present invention provides inexpensive, safe and reliable methods for improving the morphology, tone, texture and/or appearance of the skin and/or hair of a mammal, preferably without using one or more surfactants (or other chemicals) that can strip away, or otherwise remove, one or more protective lipids from the skin and/or hair. These methods comprise topically applying to the skin and/or hair at least three applications on a regular basis of a composition in an effective amount including: (a) a Meadowlactone in an amount that is effective for enhancing the morphology, tone, texture and/or appearance of the skin and/or hair, and having the chemical structure set forth herein; and (b) a cosmetically acceptable base in an amount that is effective for acting as a carrier vehicle for the Meadowlactone.
• US6639089B2
  申请人：——

  公开号：US6639089B2

  公开（公告）日：2003-10-28
• US7615231B2
  申请人：——

  公开号：US7615231B2

  公开（公告）日：2009-11-10