6-O-arachidonoyl L-ascorbate

• 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: 6-O-arachidonoyl L-ascorbate
• 英文别名: 6-O-arachidonoyl ascorbate；[(2S)-2-[(2R)-3,4-dihydroxy-5-oxo-2H-furan-2-yl]-2-hydroxyethyl] (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• 化学式: C₂₆H₃₈O₇
• 分子量: 462.584
• InChiKey: UFPPHFKCARFQTB-PCKNPRETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  33
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  花生四烯酸 、 维生素 C 在 lipase from Candida antarctica type B (Chirazyme(R) L-2 C₂) 作用下， 以 丙酮 为溶剂， 生成 6-O-arachidonoyl L-ascorbate
  参考文献：
  名称：

  使用固定化脂肪酶的填充床反应器连续生产酰基l-抗坏血酸酯

  摘要：

  AbstractSaturated acyl (6‐O‐caproyl, lauroyl, and myristoyl) and unsaturated acyl (6‐O‐oleoyl, linoleoyl, and arachidonoyl) l‐ascorbates were continuously synthesized at 50°C using a system where a column packed with ascorbic acid powder and a packed‐bed reactor with an immobilized lipase from Candida antarctica were connected in series. A productivity of 1.6–1.9 kg/L reactor·d was achieved for at least 11 d. The surface tension of the caproyl or lauroyl l‐ascorbate in aqueous solution was measured at various temperatures and pH to estimate the critical micelle concentration (CMC) of the acyl l‐ascorbate. The CMC values were independent of temperature but dependent on the pH. The value of the caproyl ascorbate increased with an increase in pH.

  DOI：

  10.1007/s11746-003-0791-0

文献信息

• Process for producing powdered compositions containing highly unsaturated fatty acid esters of ascorbic acid and powdered compositions containing the esters
  申请人：Fukami Harukazu

  公开号：US20060160891A1

  公开（公告）日：2006-07-20

  The invention provides a process for powdering highly unsaturated fatty acid esters of ascorbic acid which are pasty and problematic in physical properties by a simple and easy means; highly unsaturated fatty acid esters of ascorbic acid which are improved in stability by powdering; and compositions containing the powdered highly unsaturated fatty acid esters of ascorbic acid. Specifically, a process for powdering a highly unsaturated fatty acid ester of ascorbic acid as represented by the general formula (I): RCO-A [wherein RCO— is acyl derived from a highly unsaturated fatty acid; and A is an ascorbic acid residue bonded through an —O— linkage resulting from an hydroxyl group of ascorbic acid], characterized by mixing a highly unsaturated fatty acid ester of ascorbic acid as represented by the general formula (I) with an aqueous solution of a water-soluble filler to form an emulsion and dehydrating and drying the emulsion by a spray drying method

  该发明提供了一种用简单易行的方法对抗坚固、物理性能有问题的抗坚固脂肪酸酯粉化的过程；通过粉化改善稳定性的抗坚固脂肪酸酯抗坚固酸；以及含有粉化的抗坚固脂肪酸酯抗坚固酸的组合物。具体来说，一种抗坚固脂肪酸酯抗坚固酸的粉化过程，其表示为通式(I)：RCO-A [其中RCO—是由抗坚固脂肪酸衍生的酰基；A是由抗坚固酸的羟基形成的—O—键连接的抗坚固酸残基]，其特征在于将抗坚固脂肪酸酯抗坚固酸按通式(I)表示的抗坚固脂肪酸酯抗坚固酸与水溶性填料的水溶液混合形成乳状液，并通过喷雾干燥方法脱水和干燥乳状液。
• [EN] SKIN CARE PRODUCTS, AS WELL AS FOODS AND BEVERAGES CONTAINING 6-O-PUFA ASCORBIC ESTERS<br/>[FR] PRODUITS POUR LES SOINS DE LA PEAU, ET ALIMENTS ET BOISSONS CONTENANT DES ESTERS 6-O-PUFA ASCORBIQUES
  申请人：SUNTORY LTD

  公开号：WO2006019186A1

  公开（公告）日：2006-02-23

  Skin care products which contain as a vitamin C component 6-O-PUFA ascorbates represented by general formula (I): RCO-A (I)where RCO- is an acyl group derived from a polyunsaturated fatty acid, and A is a residue of ascorbic acid that binds by -O- derived from the hydroxyl group in ascorbic acid. The products show improved transfer of ascorbic acid to tissues or cells, allow the functions of ascorbic acid to be exhibited efficiently, and also have the potential to show the functions of PUFAs. Also provided are foods and beverages that contain 6-O-PUFA ascorbates represented by general formula (I).

  含有维生素C成分6-O-PUFA抗坏血酸酯的护肤产品，其一般化学式表示为（I）：RCO-A（I），其中RCO-是源自多不饱和脂肪酸的酰基，A是源自抗坏血酸的羟基结合的残基。这些产品表现出抗坏血酸向组织或细胞的传递得到改善，使抗坏血酸的功能能够有效展现，并且还具有展示多不饱和脂肪酸功能的潜力。还提供了含有一般化学式（I）表示的6-O-PUFA抗坏血酸酯的食品和饮料。
• [EN] ASCORBATE ESTERS OF OMEGA-3 FATTY ACIDS<br/>[FR] ESTERS D'ASCORBATE D'ACIDES GRAS OMÉGA 3
  申请人：JIVA PHARMA INC

  公开号：WO2014134053A1

  公开（公告）日：2014-09-04

  The present invention provides ascorbate esters of omega-3 fatty acids as their pharmaceutically-acceptable salts and pharmaceutically- acceptable formulations for use as dietary supplements with enhanced antioxidant properties, in improving the effectiveness of other drugs and in treatment of hypertriglyceridemia, hypercholestolemia, diabetes, psychiatric and neurological disorders, attention deficit and hyperactivity disorder, and as cosmeceuticals.

  本发明提供了抗坏血酸酯化的ω-3脂肪酸及其药学上可接受的盐和制剂，用作具有增强抗氧化性能的膳食补充剂，在提高其他药物的有效性以及治疗高三酰甘油血症、高胆固醇血症、糖尿病、精神和神经障碍、注意力缺陷和多动症以及作为化妆品成分。
• Skin Care Products, As Well As Foods And Beverages Containing 6-O-Pufa Ascorbic Esters
  申请人：Fukami Harukazu

  公开号：US20080319058A1

  公开（公告）日：2008-12-25

  Skin care products which contain as a vitamin C component 6-O-PUFA ascorbates represented by general formula (I): RCO-A   (I) where RCO— is an acyl group derived from a polyunsaturated fatty acid, and A is a residue of ascorbic acid that binds by —O— derived from the hydroxyl group in ascorbic acid. The products show improved transfer of ascorbic acid to tissues or cells, allow the functions of ascorbic acid to be exhibited efficiently, and also have the potential to show the functions of PUFAs. Also provided are foods and beverages that contain 6-O-PUFA ascorbates represented by general formula (I).

  含有维生素C成分6-O-PUFA抗坏血酸酸酯的护肤品，其通式表示为(I)：RCO-A  (I)，其中RCO—是由多不饱和脂肪酸衍生的酰基，而A是由抗坏血酸中羟基衍生的—O—结合的抗坏血酸残基。该产品显示了抗坏血酸向组织或细胞的转移得到了改善，能够有效地展示抗坏血酸的功能，并具有展示PUFA功能的潜力。还提供了含有通式(I)表示的6-O-PUFA抗坏血酸酸酯的食品和饮料。
• Skin Care Products, As Well As Foods and Beverages Containing 6-O-PUFA Ascorbic Esters
  申请人：FUKAMI Harukazu

  公开号：US20100003208A1

  公开（公告）日：2010-01-07

  Skin care products which contain as a vitamin C component 6-O-PUFA ascorbates represented by general formula (I): RCO-A  (I) where RCO— is an acyl group derived from a polyunsaturated fatty acid, and A is a residue of ascorbic acid that binds by —O— derived from the hydroxyl group in ascorbic acid. The products show improved transfer of ascorbic acid to tissues or cells, allow the functions of ascorbic acid to be exhibited efficiently, and also have the potential to show the functions of PUFAs. Also provided are foods and beverages that contain 6-O-PUFA ascorbates represented by general formula (I).

  含有维生素C成分6-O-PUFA抗坏血酸酸盐的护肤品，其通式表示为(I):RCO-A  (I)，其中RCO—是由多不饱和脂肪酸衍生的酰基，A是由抗坏血酸中羟基衍生的-O-结合的抗坏血酸残基。该产品显示了抗坏血酸酸的有效转移到组织或细胞，使抗坏血酸酸的功能得到有效发挥，并具有展示PUFAs功能的潜力。还提供了含有通式(I)的6-O-PUFA抗坏血酸酸盐的食品和饮料。