6-O-capryloyl-D-glucopyranose | 20881-92-9

• 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-capryloyl-D-glucopyranose
• 英文别名: 6-O-octanoyl-α-D-glucopyranose；6-O-octanoylglucopyranose；6-O-octanoyl-D-glucopyranose；glucose caprylate；URB1388；[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl octanoate
• CAS: 20881-92-9
• 化学式: C₁₄H₂₆O₇
• 分子量: 306.356
• InChiKey: ZLDMSVMGGVMZGO-GQYPCLOQSA-N

物化性质

• 沸点：
  455.319±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.266±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-O-octanoyl-1,2-O-cyclohexylidene-α-D-glucofuranose 在 水 、 三氟乙酸 作用下， 反应 1.5h， 以69%的产率得到6-O-capryloyl-D-glucopyranose
  参考文献：
  名称：

  Chemoenzymatic synthesis of glucose fatty esters

  摘要：

  D-Glucose fatty esters at C-6 were obtained by chemoenzymatic synthesis involving 1,2-O-cyclohexylidene-alpha-D-glucofuranose (1) followed by hydrolysis of the cyclohexylidene protecting group. The enzymatic esterification of 1 was performed with fatty acids of variable chain lengths (C8:0 to C18:0). The kinetic of the reaction was studied for each fatty acid and the structure of the octanoyl ester was determined by H-1 and C-13 NMR spectroscopy. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00340-0

文献信息

• Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents
  作者：Raffaella Campana、Alessio Merli、Michele Verboni、Francesca Biondo、Gianfranco Favi、Andrea Duranti、Simone Lucarini

  DOI：10.3390/ph12040186

  日期：——

  A small library of sugar-based (i.e., glucose, mannose and lactose) monoesters containing hydrophobic aliphatic or aromatic tails were synthesized and tested. The antimicrobial activity of the compounds against a target panel of Gram-positive, Gram-negative and fungi was assessed. Based on this preliminary screening, the antibiofilm activity of the most promising molecules was evaluated at different

  合成并测试了一个小的糖基单糖库（即葡萄糖，甘露糖和乳糖），其中含有疏水性脂族或芳族尾巴。评估了化合物对革兰氏阳性，革兰氏阴性和真菌的靶标的抗菌活性。基于此初步筛选，在选定的食源性病原体（大肠杆菌，单核细胞增生李斯特菌，金黄色葡萄球菌，肠炎沙门氏菌）的不同发育时间，评估了最有前途的分子的抗生物膜活性。生物膜形成过程中的抗生物膜活性导致以下结果：甘露糖C10>乳糖联苯乙酸酯>葡萄糖C10>乳糖C10。其中，甘露糖C10和乳糖联苯乙酸盐分别对大肠杆菌的抑制作用为97％和92％。在MIC值下，对于所有检查的化合物，在Caco-2细胞系上均未观察到毒性。总体而言，基于这些结果，所有基于糖的单酯均显示出作为安全抗菌剂的有趣特征。尤其是，甘露糖C10和乳糖联苯乙酸酯是最有希望的药物和食品应用生物相容性和安全性防腐剂。
• Enzymatic Preparation of a Homologous Series of Long-Chain 6-<i>O</i>-Acylglucose Esters and Their Evaluation as Emulsifiers
  作者：Min-Yi Liang、Yongsheng Chen、Martin G. Banwell、Yong Wang、Ping Lan

  DOI：10.1021/acs.jafc.8b00913

  日期：2018.4.18

  fatty acid esters are nonionic surfactants that are widely exploited in the food and cosmetics industries, as well as in the oral care and medical supply fields. Accordingly, new methods for their selective synthesis and the “tuning” of their emulsifying properties are of considerable interest. Herein we report simple and irreversible enzymatic esterifications of d-glucose with seven fatty acid vinyl

  糖脂肪酸酯是非离子型表面活性剂，在食品和化妆品行业以及口腔护理和医疗供应领域得到了广泛的应用。因此，用于其选择性合成和对其乳化性能的“调节”的新方法引起了极大的兴趣。在此，我们报道了d-葡萄糖与七个脂肪酸乙烯基酯的简单且不可逆的酶促酯化反应。然后评估所得6- O-酰基葡萄糖基葡萄糖酯的起泡和乳化作用。符合预期，当烷基侧链的长度与6- O相关时-酰基葡萄糖酯增加，然后其亲水-亲脂平衡（HLB）值降低，而衍生乳液的稳定性提高。为了保持良好的发泡性能，需要长度至少为9至11个碳的烷基侧链。在最初的关于6- O-酰基葡萄糖酯的测定中，本文所述的大多数对HepG2，MCF-7，LNacp，SW549和LO-2细胞系无毒。
• One-step synthesis of carbohydrate esters as antibacterial and antifungal agents
  作者：Madher N. AlFindee、Qian Zhang、Yagya Prasad Subedi、Jaya P. Shrestha、Yukie Kawasaki、Michelle Grilley、Jon Y. Takemoto、Cheng-Wei Tom Chang

  DOI：10.1016/j.bmc.2017.12.038

  日期：2018.2

  compounds were active against a panel of bacteria and fungi, including Staphylococcus aureus, methicillin-resistant S. aureus (MRSA), Candida albicans, Cryptococcus neoformans, Aspergillus flavus and Fusarium graminearum. Unlike prior studies on carbohydrate esters that focus only on antibacterial applications, our compounds are found to be active against both bacteria and fungi. Furthermore, the synthetic

  碳水化合物酯是可生物降解的，降解的加合物是天然存在的碳水化合物和脂肪酸，对环境无害，对人体无毒。已经开发出单碳水化合物的简单的一步区域选择性酰化，其导致了多种碳水化合物酯的合成。这些酰化碳水化合物的筛选表明，几种化合物对一组细菌和真菌具有活性，包括金黄色葡萄球菌，耐甲氧西林金黄色葡萄球菌（MRSA），白色念珠菌，新型隐球菌，黄曲霉和禾谷镰刀菌。。与先前对仅专注于抗菌应用的碳水化合物酯的研究不同，我们的化合物被发现对细菌和真菌均具有活性。此外，合成方法学适合于扩大各种酰化碳水化合物的生产。鉴定出的先导化合物MAN014可以在食品加工和防腐等应用中用作抗菌剂，并用于治疗动植物的细菌和真菌疾病。
• ESTERS OF GLYCOSIDES AND A PROCESS FOR ENZYMATIC PREPARATION THEREOF
  申请人：NOVO NORDISK A/S

  公开号：EP0394280B1

  公开（公告）日：1995-04-05
• MONOESTER SUGAR DERIVATIVES AS FLAVOR MODIFIERS
  申请人：Firmenich SA

  公开号：US20210161189A1

  公开（公告）日：2021-06-03

  Compositions containing monoester derivatives of the primary alcohol residue of a sugar are generally disclosed herein, as well as their use as sweetness enhancers, bitterness maskers, sourness maskers, or astringency reducers, to improve the taste profile of a flavored article.