(3R,3'R,6'R)-β,ε-carotene-3,3'-diol dipropionate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3R,3'R,6'R)-β,ε-carotene-3,3'-diol dipropionate
• 英文别名: lutein dipropionate；[(1R)-3,5,5-trimethyl-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-[(1R,4R)-2,6,6-trimethyl-4-propanoyloxycyclohex-2-en-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohex-3-en-1-yl] propanoate
• 化学式: C₄₆H₆₄O₄
• 分子量: 681.012
• InChiKey: KOIIJOQUOHWOTK-KUJYJOPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.1
• 重原子数：
  50
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丙酸乙烯酯 、 叶黄素 在 lipase acrylic resin from Candida antarctica 作用下， 以 甲苯 为溶剂， 反应 96.0h， 以66.4%的产率得到(3R,3'R,6'R)-β,ε-carotene-3,3'-diol 3-propionate
  参考文献：
  名称：

  叶黄素-3-单酯的高度区域选择性酶促合成

  摘要：

  叶黄素是一种富含脂肪酸的酯衍生物的形式，是一种富含万寿菊花的叶黄素类胡萝卜素（Tagetes spp。）。本文中，我们介绍了使用脂肪酶（Novozyme 435，固定的CALB）和羧酸乙烯酯（丙酸乙烯酯和丙酸乙烯酯）区域选择性合成3- O-酰基单酯叶黄素衍生物（β-紫罗兰酮选择性，高达17：1）的酶促方法。硬脂酸酯）作为酰基供体。区域选择性源自CALB的高度立体选择性。这种方法论解决了叶黄素区域选择性单酯化的长期存在的问题，这可能使与其他单酯叶黄素类胡萝卜素的新型半合成途径成为可能。

  DOI：

  10.1016/j.tetlet.2018.10.006

文献信息

• A METHOD FOR OBTAINING STABLE MICRO-EMULSIONS OF DERIVATIVES OF OXYCAROTENOIDS OF SHORT-CHAIN ORGANIC ACIDS, MICRO-EMULSIONS OBTAINED, AND FORMULATION WHICH CONTAINS THESE
  申请人：Industrial Organica S.A. De C.V.

  公开号：EP2062570A1

  公开（公告）日：2009-05-27

  A method for obtaining stable micro-emulsions consisting of a solution of derivatives of oxycarotenoids of short-chain organic acids, comprising diacetates and dipropionates, micro-emulsions obtained, and formulation which contain these. The oxycarotenoids can thus be absorbed easily into the digestive system as micelles which have greater bioavailability than oxycarotenoids in crystalline form.

  一种获得稳定微乳剂的方法，微乳剂由短链有机酸类胡萝卜素衍生物的溶液（包括二乙酸酯和二丙酸酯）、获得的微乳剂以及含有这些衍生物的配方组成。这样，类胡萝卜素就能以胶束的形式被消化系统轻松吸收，其生物利用率高于结晶形式的类胡萝卜素。
• Compositions and applications of carotenoids of improved absorption and bioavailability
  申请人：Torres-Quiroga, Jose-Odon

  公开号：EP2468111A1

  公开（公告）日：2012-06-27

  Micro micellar form of carotenoids or xanthophylls, which show improved absorption and biovailability by living organisms, providing higher levels of carotenoids in the blood stream, and consequently are deposited at the target tissues at a faster rate, and more efficiently than crystalline carotenoids, which does not contain any crystal forms of carotenoids, and which are obtained as micro micelles after melting Lutein diacetate or Lutein dipropionate in their natural original lipid vegetable matrix, in the presence of lipids, phospholipids, fatty acids, emulsifiers and moisture, and are ingested in a dosage between 2 to 50 mg, to provide an absorption of the carotenoid solubilizate which is at least 20% above than that of crystalline carotenoids, and provides a macular pigment deposit which exceeds at least 10% of Macular Pigment Optical Density, than the deposition obtained by ingesting crystalline Lutein. Thus preventing tissue degeneration, UV light damage to skin and the retina, and in general to act as more effective and efficient antioxidants than when administered in crystalline form.

  微胶囊形式的类胡萝卜素或黄绿素，可提高生物体的吸收率和生物利用率，在血液中提供更高水平的类胡萝卜素，因此比结晶类胡萝卜素更快、更有效地沉积在目标组织中，结晶类胡萝卜素不含任何晶体形式的类胡萝卜素，是将叶黄素二醋酸酯或叶黄素二丙酸酯在其天然原始脂质植物基质中熔化后得到的微胶囊、在脂质、磷脂、脂肪酸、乳化剂和水分的存在下，以 2 至 50 毫克的剂量摄入，类胡萝卜素溶解物的吸收率比晶体类胡萝卜素的吸收率至少高出 20%，黄斑色素沉积量比摄入晶体叶黄素的沉积量至少高出 10%。因此，叶黄素可防止组织变性、紫外线对皮肤和视网膜的损害，并在总体上起到比晶体状叶黄素更有效、更高效的抗氧化剂的作用。
• Absorption and bioavailability of carotenoids, formulations and applications
  申请人：Olvera Ricardo Montoya

  公开号：US20080044475A1

  公开（公告）日：2008-02-21

  A process for obtaining a microscopic physical state of xanthophylls or oxycarotenoids derivatives forms such as diacetates or dipropionates derivatives, which are readily incorporated in the digestive system as micelles providing an improved bioavailability, as compared to the bioavailability of carotenoids that are ingested in diverse preparations that contain microscopic carotenoids crystals and a method for its application.
• COMPOSITIONS AND APPLICATIONS OF CAROTENOIDS OF IMPROVED ABSORPTION AND BIOAVAILABILITY
  申请人：Montoya-Olvera Ricardo

  公开号：US20120157547A1

  公开（公告）日：2012-06-21

  Micro micellar form of carotenoids or xanthophylls, which show improved absorption and biovailability by living organisms, providing higher levels of carotenoids in the blood stream, and consequently are deposited at the target tissues at a faster rate, and more efficiently than crystalline carotenoids, which does not contain any crystal forms of carotenoids, and which are obtained as micro micelles after melting Lutein diacetate or Lutein dipropionate in their natural original lipid vegetable matrix, in the presence of lipids, phospholipids, fatty acids, emulsifiers and moisture, and are ingested in a dosage between 2 to 50 mg, to provide an absorption of the carotenoid solubilizate which is at least 20% above than that of crystalline carotenoids, and provides a macular pigment deposit which exceeds at least 10% of Macular Pigment Optical Density, than the deposition obtained by ingesting crystalline Lutein. Thus preventing tissue degeneration, UV light damage to skin and the retina, and in general to act as more effective and efficient antioxidants than when administered in crystalline form.
• US7435846B2
  申请人：——

  公开号：US7435846B2

  公开（公告）日：2008-10-14