3-O-nonyl-L-ascorbic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 3-O-nonyl-L-ascorbic acid
• 英文别名: (2R)-2-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-3-nonoxy-2H-furan-5-one
• 化学式: C₁₅H₂₆O₆
• 分子量: 302.368
• InChiKey: OUWGIJDQBKOLQQ-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲磺酸壬酯 、 维生素 C 在 碳酸氢钠 作用下， 以 二甲基亚砜 为溶剂， 反应 15.0h， 以70%的产率得到3-O-nonyl-L-ascorbic acid
  参考文献：
  名称：

  Regioselective Synthesis of 3-O-Alkyl Ethers of Ascorbic Acid without Protecting Groups in a Single Step

  摘要：

  The direct alkylation of L-ascorbic acid (vitamin C) with alkyl mesylates using sodium hydrogen carbonate as a base without protecting groups proceeds regioselectively and yields the corresponding 3-O-alkyl ethers of L-ascorbic acid exclusively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01013-3

文献信息

• EXTERNAL PREPARATION FOR SKIN
  申请人：Shiseido Company, Ltd.

  公开号：EP2292208A1

  公开（公告）日：2011-03-09

  Problem To provide an external preparation for skin containing an alkylresorcinol and being excellent in temperature stability (especially high-temperature stability) and photostability. Means for Resolution An external preparation for skin comprising (a) from 0.01 to 5% by mass of 4-isobutyl resorcinol or a salt thereof, and (b) from 0.01 to 5% by mass of one or more selected from L-ascorbic acid or a salt thereof and a 3-O-alkyl-L-ascorbic acid or a salt thereof. If desired, (c) one or more compounds selected from (c-1) a sterol skeleton-having compound (e.g., POE phytosterols, POE cholestanols), (c-2) a vitamin E derivative, (c-3) a compound such as polyglycerin fatty acid esters, polyoxybutene-polyglycerin alkyl ethers, sucrose fatty acid esters, and (c-4) a sorbitan skeleton-having compound may be incorporated in the preparation.

  问题 提供一种含有烷基间苯二酚的皮肤外用制剂，其温度稳定性（尤其是高温稳定性）和光稳定性极佳。解决方法 一种皮肤外用制剂，其成分包括：(a) 0.01%-5%（按重量计）的 4-异丁基间苯二酚或其盐；(b) 0.01%-5%（按重量计）的一种或多种选自 L-抗坏血酸或其盐和 3-O-烷基-L-抗坏血酸或其盐的化合物。如果需要，(c) 一种或多种选自 (c-1) 固醇骨架化合物（如 POE 植物固醇、POE 胆甾醇）、(c-2) 维生素 E 衍生物、(c-3) 聚甘油脂肪酸酯、聚氧丁烯-聚甘油烷基醚、蔗糖脂肪酸酯和 (c-4) 山梨坦骨架化合物的化合物可加入制剂中。
• External Preparation For Skin
  申请人：Shinto Keisuke

  公开号：US20110213030A1

  公开（公告）日：2011-09-01

  An external preparation for skin containing an alkylresorcinol and being excellent in temperature stability (especially high-temperature stability) and photostability. More particularly an external preparation for skin comprising (a) from 0.01 to 5% by mass of 4-isobutyl resorcinol or a salt thereof, and (b) from 0.01 to 5% by mass of one or more selected from L-ascorbic acid or a salt thereof and a 3-O-alkyl-L-ascorbic acid or a salt thereof. If desired, (c) one or more compounds selected from (c-1) a sterol skeleton-having compound (e.g., POE phytosterols, POE cholestanols), (c-2) a vitamin E derivative, (c-3) a compound such as polyglycerin fatty acid esters, polyoxybutene-polyglycerin alkyl ethers, sucrose fatty acid esters, and (c-4) a sorbitan skeleton-having compound may be incorporated in the preparation.
• US8486997B2
  申请人：——

  公开号：US8486997B2

  公开（公告）日：2013-07-16
• Regioselective Synthesis of 3-O-Alkyl Ethers of Ascorbic Acid without Protecting Groups in a Single Step
  作者：Uwe Beifuss、Olaf Kunz、Gundula Voss

  DOI：10.1016/s0040-4020(99)01013-3

  日期：2000.1

  The direct alkylation of L-ascorbic acid (vitamin C) with alkyl mesylates using sodium hydrogen carbonate as a base without protecting groups proceeds regioselectively and yields the corresponding 3-O-alkyl ethers of L-ascorbic acid exclusively. (C) 2000 Elsevier Science Ltd. All rights reserved.