6'-O-lauroyl-β-maltose

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 6'-O-lauroyl-β-maltose
• 英文别名: 6'-O-lauroylmaltose；lauroyl(-6)Glc(a1-4)b-Glc；[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl dodecanoate
• 化学式: C₂₄H₄₄O₁₂
• 分子量: 524.606
• InChiKey: RHKKOJKFAQAUGX-YCULTEQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  36
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  196
• 氢给体数：
  7
• 氢受体数：
  12

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  麦芽糖	Maltose	16984-36-4	C12H22O11	342.3
  D-(+)-纤维二糖	Maltose	133-99-3	C12H22O11	342.3
  麦芽糖	D-maltose	69-79-4	C12H22O11	342.3

反应信息

• 作为产物：
  描述：

  月桂酸 、 D-(+)-纤维二糖 在 immobilized Candida antarctica lipase B (Novozym 435) 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 72.0h， 生成 6'-O-lauroyl-β-maltose
  参考文献：
  名称：

  A simple approach for the selective enzymatic synthesis of dilauroyl maltose in organic media

  摘要：

  A selective synthesis of dilauroyl maltose was developed using lipase-catalyzed condensation of lauric acid and maltose in two-solvent Mixtures. The characteristics of different solvent combination were tested and it was found that the combination of acetone with n-hexane has a good selectivity for the synthesis of dilauroyl maltose. The highest diester conversion of 69% (i.e. 36.5 g/L of dilauroyl maltose) was obtained under optimal conditions: 25.65 g/L maltose, 60 g/L lauric acid, 60 g/L molecular sieve and 10 g/L lipase at 150 rpm and 50 degrees C for 72 h in 10 mL of mixed solvent of acetone:n-hexane (60:40, v/v). (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2009.11.003

文献信息

• Comparative Study of the Emulsifying Properties of a Homologous Series of Long-Chain 6′-<i>O</i>-Acylmaltose Esters
  作者：Ya-Ru Ma、Martin G. Banwell、Rian Yan、Ping Lan

  DOI：10.1021/acs.jafc.8b02391

  日期：2018.8.22

  the facile enzymatic preparation of a homologous series of 6′-O-acylmaltose esters and an in-depth evaluation of them revealing that their surfactant properties and thermal stabilities are largely determined by the length of the fatty acid chain. In the first such comparison, we show that the foaming and emulsifying effects of certain of these maltose monoesters are superior to those of their sucrose-derived

  源自蔗糖和脂肪酸等可再生资源的乳化剂是大量的商品化学品，目前通过传统的化学合成技术生产，缺乏以选择性和高效方式形成最理想的（蔗糖）单酯的能力。由替代的，结构更简单但仍然丰富的二糖（如麦芽糖）开发新的乳化剂（表面活性剂）可能是解决此问题的方法。在此，我们报告了一系列6'- O同源酶的简便制备-酰基麦芽糖酯及其深入评估表明，它们的表面活性剂性质和热稳定性在很大程度上取决于脂肪酸链的长度。在第一个这样的比较中，我们表明某些麦芽糖单酯的起泡和乳化作用优于蔗糖衍生和商业开发的对应物。这样，麦芽糖酯作为乳化剂具有很大的潜力，例如可用于食品工业。
• A Simple Procedure for the Regioselective Synthesis of Fatty Acid Esters of Maltose, Leucrose, Maltotriose and n-Dodecyl Maltosides
  作者：Manuel Ferrer、M Angeles Cruces、Francisco J Plou、Manuel Bernabé、Antonio Ballesteros

  DOI：10.1016/s0040-4020(00)00319-7

  日期：2000.6

  The enzymatic acylation of several di- and trisaccharides with acyl donors ranging from 8 to 18 carbon atoms was carried out by transesterification with the corresponding vinyl esters. The reaction was performed in 2-methyl-2-butanol/dimethylsulfoxide mixtures using the lipase from Humicola lanuginosa (immobilized on Celite). Maltose, maltotriose and n-dodecyl maltosides were specifically acylated in the primary hydroxyl of the non-reducing-end glucose moiety; the acylation of leucrose occurred preferentially in the primary hydroxyl of the glucose ring. (C) 2000 Elsevier Science Ltd. All rights reserved.
• A simple approach for the selective enzymatic synthesis of dilauroyl maltose in organic media
  作者：Chengsheng Jia、Jia Zhao、Biao Feng、Xiaoming Zhang、Wenshui Xia

  DOI：10.1016/j.molcatb.2009.11.003

  日期：2010.3

  A selective synthesis of dilauroyl maltose was developed using lipase-catalyzed condensation of lauric acid and maltose in two-solvent Mixtures. The characteristics of different solvent combination were tested and it was found that the combination of acetone with n-hexane has a good selectivity for the synthesis of dilauroyl maltose. The highest diester conversion of 69% (i.e. 36.5 g/L of dilauroyl maltose) was obtained under optimal conditions: 25.65 g/L maltose, 60 g/L lauric acid, 60 g/L molecular sieve and 10 g/L lipase at 150 rpm and 50 degrees C for 72 h in 10 mL of mixed solvent of acetone:n-hexane (60:40, v/v). (C) 2009 Elsevier B.V. All rights reserved.