6-O-galloyl-D-glucopyranose | 7253-25-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-O-galloyl-D-glucopyranose
• 英文别名: 6-mono-O-galloyl glucose；6-O-Galloyl-D-glucose；glucose 6-O-gallate；glucose-6-O-gallate；glucose-6-gallate；[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• CAS: 7253-25-0
• 化学式: C₁₃H₁₆O₁₀
• 分子量: 332.264
• InChiKey: VGVDLJNNDOFWKT-KPCWAIEQSA-N

物化性质

• 沸点：
  703.2±60.0 °C(Predicted)
• 密度：
  1.804±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  177
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  pimentol 在 盐酸 作用下， 反应 0.25h， 生成 6-O-galloyl-D-glucopyranose
  参考文献：
  名称：

  Ericifolin: An eugenol 5-O-galloylglucoside and other phenolics from Melaleuca ericifolia

  摘要：

  Ericifolin, an eugenol 5-O-beta-(6'-O-galloylglucopyranoside) possessing the naturally unknown phenolic moiety, 5-hydroxyeugenol, together with the two new phenolics, 2-O-p-hydroxybenzoyl-6-O-galloyl-(alpha/beta)-C-4(1)-glucopyranose and 3-methoxyellagic acid 4-O-rhamnopyranoside have been isolated from the antibacterial leaves extract of Melaleuca ericifolia. In addition, 19 known phenolics were also separated and characterized. All structures were elucidated on the basis of analysis of H-1, C-13 NMR, HMQC, HMBC and FTMS spectral data. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2007.03.010

文献信息

• Expanding Rutinosidase Versatility: Acylated Quercetin Glucopyranosides as Substrates
  作者：Katerina Brodsky、Lucie Petrásková、Michal Kutý、Pavla Bojarová、Helena Pelantová、Vladimír Křen

  DOI：10.1002/cctc.202400028

  日期：——

  Aspergillus niger rutinosidase (AnRut) efficiently cleaved a library of rutin glycomimetics - isoquercitrin acylated at C-6′ of its glucosyl moiety. The substrates tested included isoquercitrin substituted at glucosyl C-6′ with acetyl, benzoyl, phenylacetyl, phenylpropanoyl, cinnamyl, vanillyl, galloyl, 4-hydroxybenzoyl, and 3-(4-hydroxy-3-O-methylphenyl)propanoyl. AnRut showed the ability to transglycosylate

  黑曲霉芦丁糖苷酶 (AnRut) 有效地裂解芦丁糖模拟物文库 - 在其葡萄糖基部分的 C-6' 处酰化的异槲皮苷。测试的底物包括在葡萄糖基C-6'处被乙酰基、苯甲酰基、苯乙酰基、苯丙酰基、肉桂基、香草基、没食子酰基、4-羟基苯甲酰基和3-(4-羟基-3-O-甲基苯基)丙酰基取代的异槲皮苷。 AnRut 显示出与底物 6'-O-乙酰基异槲皮苷和 6'-O-苯甲酰基异槲皮苷底物进行糖基转移的能力，得到正丁基 6-乙酰基-β-d-吡喃葡萄糖苷和正丁基 6-苯甲酰基-β-d -吡喃葡萄糖苷。
• Tyrosyl-DNA Phosphodiesterase I Inhibitors from the Australian Plant <i>Macropteranthes leichhardtii</i>
  作者：Li-Wen Tian、Yunjiang Feng、Trong D. Tran、Yoko Shimizu、Tom Pfeifer、Paul I. Forster、Ronald J. Quinn

  DOI：10.1021/acs.jnatprod.5b00211

  日期：2015.7.24

  Mass-directed isolation of the CH2Cl2/MeOH extract from the bark of an Australian plant, Macropteranthes leichhardtii, resulted in the purification of a new phenylpropanoid glucoside, macropteranthol (1), together with four known analogues (2-5). The structure of compound 1 was elucidated by NMR and MS data analyses and quantum chemical calculations. Compounds 3 and 5 showed inhibitory activity against tyrosyl-DNA phosphodiesterase I with IC50 values of similar to 1.0 mu M.
• Biosynthesis of 1,2,3,6-tetra-O-galloyl-β-d-glucose
  作者：Sigrid Hagenah、Georg G. Gross

  DOI：10.1016/s0031-9422(00)95148-3

  日期：1993.2

  An enzyme that catalysed the beta-glucogallin (1-O-galloyl-beta-D-glucose)-dependent galloylation of 1,2,6-tri-O-galloyl-beta-D-glucose to 1,2,3,6-tetra-O-galloyl-beta-D-glucose was partially purified from leaves of oak (Quercus robur). This acyltransferase had a M(r) of ca 380 000, and pH and temperature optima of 6.0 and 55-degrees, respectively, and was most stable between pH 4.0 and 6.5. In addition to the natural substrates beta-glucogallin (donor) and 1,2,6-trigalloylglucose (acceptor), 1,3,6-trigalloylglucose (which is not an intermediate in the biosynthesis of hydrolysable tannins in oak and sumac) was an equally efficient acceptor molecule; in both cases, 1,2,3,6-tetragalloylglucose was the reaction product. Based on the physiological role of this new enzyme, the systematic name 'beta-glucogallin: 1,2,6-tri-O-galloyl-beta-D-glucose 3-O-galloyltransferase' (EC 2.3.1.-) is proposed.
• KASHIWADA, YOSHIKI;NONAKA, GEN-ICHIRO;NISHIOKA, ITSUO, PHYTOCHEMISTRY, 27,(1988) N 5, 1469-1472
  作者：KASHIWADA, YOSHIKI、NONAKA, GEN-ICHIRO、NISHIOKA, ITSUO

  DOI：——

  日期：——
• Ericifolin: An eugenol 5-O-galloylglucoside and other phenolics from Melaleuca ericifolia
  作者：S.A.M. Hussein、A.N.M. Hashim、R.T. El-Sharawy、M.A. Seliem、M. Linscheid、U. Lindequist、M.A.M. Nawwar

  DOI：10.1016/j.phytochem.2007.03.010

  日期：2007.5

  Ericifolin, an eugenol 5-O-beta-(6'-O-galloylglucopyranoside) possessing the naturally unknown phenolic moiety, 5-hydroxyeugenol, together with the two new phenolics, 2-O-p-hydroxybenzoyl-6-O-galloyl-(alpha/beta)-C-4(1)-glucopyranose and 3-methoxyellagic acid 4-O-rhamnopyranoside have been isolated from the antibacterial leaves extract of Melaleuca ericifolia. In addition, 19 known phenolics were also separated and characterized. All structures were elucidated on the basis of analysis of H-1, C-13 NMR, HMQC, HMBC and FTMS spectral data. (C) 2007 Elsevier Ltd. All rights reserved.