(1-acetyloxy-3-hexadecanoyloxypropan-2-yl) (9E,12E)-octadeca-9,12-dienoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (1-acetyloxy-3-hexadecanoyloxypropan-2-yl) (9E,12E)-octadeca-9,12-dienoate
• 化学式: C₃₉H₇₀O₆
• 分子量: 635.0
• InChiKey: GAKUNXBDVGLOFS-AVYWLMTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.1
• 重原子数：
  45
• 可旋转键数：
  36
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

文献信息

• METHOD FOR PRODUCING 1-PALMITOYL-2-LINOLEOYL-3-ACETYL GLYCEROL
  申请人：ENZYCHEM LIFESCIENCES CORPORATION

  公开号：US20210107857A1

  公开（公告）日：2021-04-15

  Disclosed is a method for producing 1-palmitoyl-2-linoleoyl-3-acetyl glycerol of high purity with high yield by carrying out acetylation of 1-palmitoyl glycerol with acetic anhydride or a mixture of acetic anhydride and acetyl chloride. The method for producing 1-palmitoyl-2-linoleoyl-3-acetyl glycerol comprises the steps of: preparing 1-palmitoyl-3-acetyl glycerol intermediate of Chemical formula 2 in the specification by reacting 1-palmitoyl glycerol of Chemical formula 1 in the specification and an acetylating agent selected from the group consisting of (i) acetic anhydride and (ii) a mixture of acetic anhydride and acetyl chloride; and reacting the 1-palmitoyl-3-acetyl glycerol intermediate and linoleic acid.

  本方法披露了一种高纯度、高产率生产1-棕榈酰-2-亚油酰-3-乙酰甘油的方法，通过使用乙酸酐或乙酰氯或乙酸酐和乙酰氯混合物对1-棕榈酰甘油进行乙酰化。生产1-棕榈酰-2-亚油酰-3-乙酰甘油的方法包括以下步骤：通过将规范中的化学式1的1-棕榈酰甘油与来自以下组的乙酰化剂（i）乙酸酐和（ii）乙酸酐和乙酰氯混合物中选择的一种反应，制备规范中的化学式2的1-棕榈酰-3-乙酰甘油中间体；然后将1-棕榈酰-3-乙酰甘油中间体与亚油酸反应。
• [EN] PROCESS FOR REGIOSELECTIVE PREPARATION OF GLYCEROL, DERIVATIVE AND INTERMEDIATE THEREFOR<br/>[FR] PROCEDE DE PREPARATION STEREOSELECTIVE DE DERIVES DE GLYCEROL ET PRODUITS INTERMEDIAIRES UTILISES DANS CE PROCEDE
  申请人：ENZYCHEM CO LTD

  公开号：WO2005090274A1

  公开（公告）日：2005-09-29

  Disclosed is a process for regioselective preparation of l-palmitoyl-2-linoleoyl-3-acetylglycerol which is known as having activities for proliferation of hematopoietic stem cells and megakaryocytes, and an intermediate for the same. The process for preparation of l-palmitoyl-2-linoleoyl-3-acetylglycerol includes the steps of obtaining (2-alkoxy-2-methyl-[l,3]-dioxolane-4-yl)methanol by reacting glycerol and trialkylorthoacetate; obtaining 1-acetyl glycerol by hydrolyzing (2-alkoxy-2-methyl-[l,3]-dioxolane-4-yl)methanol; obtaining l-palmitoyl-3-acetyl glycerol by reacting 1-acetyl glycerol and palmitic acid derivative; and reacting l-palmitoyl-3-acetyl glycerol and linoleic acid derivative. l-palmitoyl-2-linoleoyl-3-acetylglycerol can also be prepared by the steps of obtaining l-palmitoyl-3-acetyl glycerol by hydrolyzing palmitic acid (2-alkoxy-2-methyl-[l,3] dioxolane- 4-yl)methyl ester; and reacting l-palmitoyl-3-acetyl glycerol and linoleic acid derivative.

  公开了一种用于选择性区域制备l-棕榈酰-2-亚油酰-3-乙酰甘油的过程，该甘油被认为具有促进造血干细胞和巨核细胞增殖的活性，以及用于制备该甘油的中间体。制备l-棕榈酰-2-亚油酰-3-乙酰甘油的过程包括以下步骤：通过将甘油和三烷基正醋酸酯反应得到(2-烷氧基-2-甲基-[1,3]-二氧兰-4-基)甲醇；通过水解(2-烷氧基-2-甲基-[1,3]-二氧兰-4-基)甲醇得到1-乙酰甘油；通过将1-乙酰甘油和棕榈酸衍生物反应得到l-棕榈酰-3-乙酰甘油；通过将l-棕榈酰-3-乙酰甘油和亚油酸衍生物反应得到l-棕榈酰-2-亚油酰-3-乙酰甘油。l-棕榈酰-2-亚油酰-3-乙酰甘油也可以通过以下步骤制备：通过水解棕榈酸(2-烷氧基-2-甲基-[1,3]二氧兰-4-基)甲酯得到l-棕榈酰-3-乙酰甘油；然后将l-棕榈酰-3-乙酰甘油和亚油酸衍生物反应。
• PHARMACEUTICAL COMPOSITION CONTAINING EXTRACTS OF CERVUS NIPPON ANTLERS HAVING GROWTH-STIMULATING ACTIVITIES OF HEMATOPOIETIC STEM CELLS AND MEGAKARYOCYTES
  申请人：Jhon, Gil Ja

  公开号：EP1061932A1

  公开（公告）日：2000-12-27
• [EN] PHARMACEUTICAL COMPOSITION CONTAINING EXTRACTS OF CERVUS NIPPON ANTLERS HAVING GROWTH-STIMULATING ACTIVITIES OF HEMATOPOIETIC STEM CELLS AND MEGAKARYOCYTES<br/>[FR] COMPOSITION PHARMACEUTIQUE CONTENANT DES EXTRAITS DE BOIS DE CERVUS NIPPON POSSEDANT UNE ACTIVITE DE STIMULATION DE LA CROISSANCE DES CELLULES SOUCHES HEMATOPOIETIQUES ET DES MEGACARYOCYTES
  申请人：BUKWANG PHARM. IND. CO., LTD.

  公开号：WO1999026640A1

  公开（公告）日：1999-06-03

  (EN) The present invention relates to a pharmaceutical composition having growth-stimulating effects on hematopoietic stem cells and megakaryocytes, containing a specific extract or $i(Cervus nippon) antlers, especially a chloroform extract of $i(Cervus nippon) antlers and to a biologically active compound isolated from the extracts of $i(Cervus nippon) antlers, to a process for preparing the biologically active compounds and to a pharmaceutical composition containing the biological active compounds. The biologically active compounds have monoacetyl diglyceride structure with various side branches as shown in formula (I) where R1 is 9-octadecenoyl and R2 is hexadecanoyl (KJ-1), or R1 is hexadecanoyl and R2 is 9-octadecenoyl (KJ-2), or R1 is hexadecanoyl and R2 is 9,12-octadecadienoyl (KJ-3), or R1 is hexadecanoyol and R2 is 9,12,15-optadecatrienoyl (KJ-4), or R1 is hexadecanoyl and R2 is 5,8,11,14-eicosatetraenoyl (KJ-5).(FR) La présente invention concerne une composition pharmaceutique possédant des effets de stimulation de la croissance des cellules souches hématopoïétiques et des mégacaryocytes, et contenant un extrait spécifique des bois du $i(Cervus nippon), en particulier un extrait chloroformique des bois du $i(Cervus nippon). L'invention concerne également un procédé de préparation de composés biologiquement actifs isolés à partir des extraits de bois du $i(Cervus nippon) et une composition pharmaceutique contenant ces composés biologiquement actifs. Lesdits composés présentent une structure de monoacétyl-diglycéride à plusieurs ramifications latérales illustrée dans la formule (I) dans laquelle R1 est un 9-octadécénoyle et R2 est un hexadécanoyle (KJ-1), ou R1 est un hexadécanoyle et R2 est un 9-octadécénoyle (KJ-2), ou R1 est un hexadécanoyle et R2 est un 9,12-octadécadiènoyle (KJ-3), ou R1 est un hexadécanoyle et R2 est un 9,12,15-octadécatriènoyle (KJ-4), ou R1 est un hexadécanoyle et R2 est un 5,8,11,14-eicosatétraènoyle (KJ-5).