香草醇4-O-Β-D-吡喃葡萄糖苷 | 74950-96-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 香草醇4-O-Β-D-吡喃葡萄糖苷
• 英文名称: vanilloloside
• 英文别名: vanillyl alcohol-4-O-β-D-glucopyranoside；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)-2-methoxyphenoxy]oxane-3,4,5-triol
• CAS: 74950-96-2
• 化学式: C₁₄H₂₀O₈
• 分子量: 316.308
• InChiKey: SIMPNXWTAVEOTO-RKQHYHRCSA-N

物化性质

• 熔点：
  119-121 °C
• 沸点：
  574.2±50.0 °C(Predicted)
• 密度：
  1.475±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-(beta-D-葡萄糖基)-3-甲氧基苯甲醛 在 sodium tetrahydroborate 、 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以93%的产率得到香草醇4-O-Β-D-吡喃葡萄糖苷
  参考文献：
  名称：

  丁香酚衍生糖苷的合成及其抑制血管紧张素转化酶能力的评价

  摘要：

  摘要 我们在此报告了一系列作为血管紧张素转换酶 (ACE) 抑制剂具有活性的糖苷。它们在结构上与天然化合物丁香酚相关，并表现出显着的抑制值。它们的合成很迅速，我们可以获得与这种酶复合的它们的信息对接图。丁香酚衍生的糖苷在苷元中带有羧基，是其中最活跃的（IC 50为 0.4 mM），并且在与 ACE 的对接研究中显示出良好的结合能。此外，毒性风险、理化性质和药物评分的计算预测表明，丁香酚的葡萄糖苷衍生物是一种适合用于寻找新候选药物的优化研究的化合物。

  DOI：

  10.1080/14786419.2020.1827399

文献信息

• GLYCOSIDE COMPOUND
  申请人：AJINOMOTO CO., INC.

  公开号：US20130288992A1

  公开（公告）日：2013-10-31

  Compounds of formula (I″) wherein: R 11 , R 12 , R 13 , R 14 and R 15 are hydrogen, hydroxyl, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkyl-carbonyloxy, or a G-O— group, and at least one of R 11 , R 12 , R 13 , R 14 and R 15 is a G-O— group, wherein G is a saccharide residue, X 1 is a single bond, or a methylene group, an ethylene group, a trimethylene group, a vinylene group or —CH═CH—CH 2 —, X 2 is —CO—O— or —O—CO—, p and q are integer ofs 0 to 7, and p+q=0 to 8, Y 1 is methylene, ethylene or an alkenylene group having a carbon number of 2 to 15 and 1 to 3 double bonds, and R 16 and R 17 are hydrogen, methyl or ethyl, or R 16 and R 17 form a C 3-6 cycloalkyl group, are useful as GLP-1 secretion promoting agents.

  式（I″）的化合物 其中： R11，R12，R13，R14和R15为氢，羟基，C1-6烷基，C1-6烷氧基，C1-6烷基羰氧基或G-O-基团，且R11，R12，R13，R14和R15中至少有一个是G-O-基团，其中G是糖残基， X1是单键，或亚甲基基团，乙烯基团，三亚甲基基团，乙烯基团或-CH=CH-CH2-， X2是-CO-O-或-O-CO-， p和q是0到7的整数，且p+q=0到8， Y1是亚甲基，乙烯基或碳数为2到15且具有1到3个双键的烯基基团，以及 R16和R17为氢，甲基或乙基，或R16和R17形成C3-6环烷基基团，可用作GLP-1分泌促进剂。
• Biotransformation of Benzaldehyde-Type and Acetophenone-Type Derivatives by Pharbitis nil Hairy Roots
  作者：Hideki Kanho、Sayaka Yaoya、Nobuo Kawahara、Takahisa Nakane、Yoichi Takase、Kazuo Masuda、Masanori Kuroyanagi

  DOI：10.1248/cpb.53.361

  日期：——

  The glucosylation of some coumarin and flavone derivatives on incubation with the hairy roots of morning glory (Pharbitis nil) was previously reported. We further studied the biotransformation of benzaldehyde- and acetophenone-type derivatives. Vanillin and isovanillin were reduced to alcoholic derivatives and glucosylated at the phenolic and the alcoholic hydroxyl groups. In the case of 3,4-dihydroxybenzaldehyde, the formyl group was reduced and the 3-hydroxyl or 4-hydroxyl groups were glucosylated to give monoglucosides. The 3-hydroxyl group was predominantly glucosylated to the 4-hydroxyl group. 4-β-D-Glucopyranosyloxy-3-methoxybenzylalcohol was obtained in low yield. In time-course experiments with vanillin, it was found that the high-level reduction of the formyl group and glucosylation of the phenolic hydroxyl group occurred, and finally 4-O-β-D-glucopyranosylvanillylalcohol was obtained as the main product. In the case of 3,4-dimethoxybenzaldehyde, 3,4,5-trimethoxybenzaldehyde, and salicylaldehyde, the formyl groups were reduced, and then the hydroxyl groups at the benyl position were glucosylated to give alcoholic glucosides in relatively high yields. In 4-hydroxy-3-methoxyacetophenone, the 4-hydroxyl group was glucosylated and two dimerized glucosides, biphenyl and biphenylether types, were obtained in low yields. In acetophenone, 1-β-D-glucopyranosyloxy-1-phenylethane and 2-β-D-glucopyranosyloxyacetophenone were obtained. As mentioned above P. nil hairy roots showed various biotransformative activities including glucosylation of phenolic and benzylic hydroxyl groups, reduction of the formyl group near the benzene ring, and phenol oxidation dimerization. The glucosylation reaction was especially interesting for the production of valuable glucosides.

  之前已有研究报告显示，某些香豆素和黄酮衍生物在与牵牛花毛根（Pharbitis nil）孵育时发生了葡萄糖化反应。我们进一步研究了苯甲醛和乙酰苯酮类衍生物的生物转化。香草醛和异香草醛被还原为醇类衍生物，并分别在酚羟基和醇羟基上发生了葡萄糖化。在3,4-二羟基苯甲醛的情况下，甲醛基被还原，而3-羟基或4-羟基则被葡萄糖化，从而生成单糖苷。3-羟基主要葡萄糖化为4-羟基。4-β-D-葡萄糖吡喃酯氧基-3-甲氧基苄醇的产率较低。在与香草醛的时间过程实验中，发现甲醛基的高水平还原和酚羟基的葡萄糖化同时发生，最终获得了4-O-β-D-葡萄糖吡喃醇香草醇作为主要产物。在3,4-二甲氧基苯甲醛、3,4,5-三甲氧基苯甲醛和水杨醛的情况下，甲醛基被还原后，苄位的羟基被葡萄糖化，生成的醇类葡萄糖苷的产率相对较高。在4-羟基-3-甲氧基乙酰苯酮中，4-羟基被葡萄糖化，并生成了两种二聚葡萄糖苷，即联苯和联苯醚类，产率较低。在乙酰苯酮中，得到1-β-D-葡萄糖吡喃酯氧基-1-苯乙烯和2-β-D-葡萄糖吡喃酯氧基乙酰苯酮。如上所述，P. nil毛根显示了多种生物转化活性，包括酚羟基和苄羟基的葡萄糖化、苯环附近甲醛基的还原以及酚氧化二聚化。葡萄糖化反应尤其值得关注，因为它能够产生有价值的葡萄糖苷。
• Glycosylation of Vanillin and 8-Nordihydrocapsaicin by Cultured Eucalyptus perriniana Cells
  作者：Daisuke Sato、Yuki Eshita、Hisashi Katsuragi、Hiroki Hamada、Kei Shimoda、Naoji Kubota

  DOI：10.3390/molecules17055013

  日期：——

  Glycosylation of vanilloids such as vanillin and 8-nordihydrocapsaicin by cultured plant cells of Eucalyptus perriniana was studied. Vanillin was converted into vanillin 4-O-β-D-glucopyranoside, vanillyl alcohol, and 4-O-β-D-glucopyranosylvanillyl alcohol by E. perriniana cells. Incubation of cultured E. perriniana cells with 8-nor- dihydrocapsaicin gave 8-nordihydrocapsaicin 4-O-β-D-glucopyranoside

  研究了 Eucalyptus perriniana 培养的植物细胞对香草醛和 8-去甲二氢辣椒素等香草素的糖基化作用。香草醛被 E. perriniana 细胞转化为香草醛 4-O-β-D-吡喃葡萄糖苷、香草醇和 4-O-β-D-吡喃葡萄糖基香草醇。培养的 E. perriniana 细胞与 8-去甲二氢辣椒素一起孵育得到 8-去甲二氢辣椒素 4-O-β-D-吡喃葡萄糖苷和 8-去甲二氢辣椒素 4-O-β-D-龙胆二糖苷。
• Glycoside compound
  申请人：AJINOMOTO CO., INC.

  公开号：US09175028B2

  公开（公告）日：2015-11-03

  Compounds of formula (I″) wherein: R11, R12, R13, R14 and R15 are hydrogen, hydroxyl, C1-6 alkyl, C1-6 alkoxy, C1-6 alkyl-carbonyloxy, or a G-O— group, and at least one of R11, R12, R13, R14 and R15 is a G-O— group, wherein G is a saccharide residue, X1 is a single bond, or a methylene group, an ethylene group, a trimethylene group, a vinylene group or —CH═CH—CH2—, X2 is —CO—O— or —O—CO—, p and q are integer ofs 0 to 7, and p+q=0 to 8, Y1 is methylene, ethylene or an alkenylene group having a carbon number of 2 to 15 and 1 to 3 double bonds, and R16 and R17 are hydrogen, methyl or ethyl, or R16 and R17 form a C3-6 cycloalkyl group, are useful as GLP-1 secretion promoting agents.

  化合物的公式为（I'')，其中： R11，R12，R13，R14和R15为氢，羟基，C1-6烷基，C1-6烷氧基，C1-6烷基羰氧基或G-O-基团，且R11，R12，R13，R14和R15中至少有一个为G-O-基团，其中G为糖残基，X1为单键或亚甲基，乙烯基，三亚甲基，乙烯基或-CH═CH-CH2-，X2为-CO-O-或-O-CO-，p和q为0到7的整数，且p + q = 0到8，Y1为亚甲基，乙烯基或具有2到15个碳原子和1到3个双键的烯烃基团，R16和R17为氢，甲基或乙基，或R16和R17形成C3-6环烷基团，可用作GLP-1分泌促进剂。
• Scalable total synthesis of natural vanillin-derived glucoside ω-esters
  作者：David L. Avetyan、Andrey Shatskiy、Markus D. Kärkäs、Elena V. Stepanova

  DOI：10.1016/j.carres.2022.108683

  日期：2022.12

  vanillin-derived glucoside ω-esters using a mild acidic deacetylation as the key synthetic step, providing the final products in the total yields of 10–50% and general purity of >95%. Additionally, the first operationally simple and sustainable synthesis of litseafoloside B was realized on large scale, avoiding the use of toxic solvents and reagents, providing an attractive alternative to isolation of

  通过香兰素基糖苷配基的直接糖基化或香兰素后期衍生化，实现了香兰素苷、豆芽苷和一系列天然存在的香兰素苷 ω-酯的首次全合成。所有糖苷配基及其片段都是从香兰素作为唯一的芳香族前体合成的。随后，这些中间体被用于构建各种香兰素衍生的葡糖苷 ω-酯，使用温和的酸性脱乙酰作为关键合成步骤，提供总收率为 10-50% 且一般纯度 >95% 的最终产品。此外，第一次大规模实现了操作简单且可持续的山楂苷 B 合成，避免了使用有毒溶剂和试剂，为从植物来源中分离这种化合物和其他类似化合物提供了一种有吸引力的替代方法。