5-(β-D-glucopyranosyloxy)-2-hydroxybenzoic acid | 1820-89-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(β-D-glucopyranosyloxy)-2-hydroxybenzoic acid
• 英文别名: Gentisic acid 5-O-β-D-glucopyranoside；genistic acid 5-O-β-D-glucopyranoside；gentisic acid 5-O-β-D-glucoside；gentisic acid-5-O-β-D-glucoside；Gentisic acid β-D-glucoside；(3-Carboxy-4-hydroxy-phenyl)-β-D-glucopyranosid；5-(beta-D-glucopyranosyloxy)-2-hydroxybenzoic acid；2-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoic acid
• CAS: 1820-89-9
• 化学式: C₁₃H₁₆O₉
• 分子量: 316.265
• InChiKey: CBTFERBMQQAROP-BZNQNGANSA-N

物化性质

• 沸点：
  647.4±55.0 °C(Predicted)
• 密度：
  1.686±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  22
• 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：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-(β-D-glucopyranosyloxy)-2-hydroxybenzoic acid 在 β-glucosidase 作用下， 反应 168.0h， 生成 2,5-二羟基苯甲酸
  参考文献：
  名称：

  来自 Boreava orientalis 的羟基苯甲酸

  摘要：

  新型愈创木脂酰甘油醚、苏式-愈创木脂酰甘油-8'-香草酸醚、焦儿茶酸、焦儿茶酸3-O-β-d-葡萄糖苷、龙胆酸、龙胆酸5-O-β-d-葡萄糖苷、香草酸和香草酸酸性 4-O-β-d-葡萄糖苷是从东方柏的果实中鉴定出来的。在 UV、质量、1H 和 13C NMR 光谱数据的基础上进行结构解析，包括 2D 位移相关和选择性 INEPT 实验。

  DOI：

  10.1016/0031-9422(95)00059-g
• 作为产物：
  描述：

  2,3,4,6-四-O-苯基-Alpha-D-吡喃葡萄糖基三氯乙酰亚氨酸 在 palladium on activated charcoal barium dihydroxide 、 氢氧化钾 、 三氟化硼乙醚 、 水 、 氢气 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 149.0h， 生成 5-(β-D-glucopyranosyloxy)-2-hydroxybenzoic acid
  参考文献：
  名称：

  Synthesis of antioxidative and anti-inflammatory drugs glucoconjugates

  摘要：

  Glucoconjugates of (+/-)-ibuprofen, (+/-)-alpha-tocopherol (vitamin E), gentisic acid, gallic acid, 2,6-bis(tert-butyl)-4-thiophenol, and N-acetyl-L-cysteine were prepared with the objective of increasing the bioavailability of such antioxidant and anti-inflammatory drugs. The O-glucosides were synthesized using benzylated alpha-D-glucopyranosyl trichloracetimidate as glycosyl donor. For the synthesis of the S-glucosides, the glycosyl donor 1,2,3,4,6-penta-O-acetyl-beta-D-glucopyranose provided higher yields than the corresponding O-acetylated imidate. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00311-0

文献信息

• Isolation and characterization of phenolic compounds from Coptidis Rhizoma.
  作者：SHOJI YAHARA、MAYUMI SATOSHIRO、ITSUO NISHIOKA、TETSURO NAGASAWA、HIKOKICHI OURA

  DOI：10.1248/cpb.33.527

  日期：——

  Six phenolic compounds were isolated from Coptidis Rhizoma and were identified as 3-(3', 4'-dihydroxyphenyl)-(2R)-lactic acid, 3-(3', 4'-dihydroxyphenyl)-(2R)-lactic acid 4'-O-β-D-glucopyranoside, 3', 4'-dihydroxyphenethyl alcohol 1-O-β-D-glucopyranoside, gentisic acid 5-O-β-D-glucopyranoside, 4-O-feruloyl-D-quinic acid and 5-O-feruloyl-D-quinic acid.

  从黄连中分离出六种酚类化合物，经鉴定为 3-(3'，4'-二羟基苯基)-(2R)-乳酸、3-(3'，4'-二羟基苯基)-(2R)-乳酸 4'-O-β-D-Glucopyranoside 、3'，4'-二羟基苯乙醇 1-O-β-D-吡喃葡萄糖苷、龙胆酸 5-O-β-D-吡喃葡萄糖苷、4-O-阿魏酰-D-奎宁酸和 5-O-阿魏酰-D-奎宁酸。
• TOPICAL AGENT FOR DERMATOLOGICAL USE
  申请人：Nakayama Hiroki

  公开号：US20110014141A1

  公开（公告）日：2011-01-20

  The objective of the present invention was to enhance the skin whitening effects and blackening prevention effects and supply safe and stable topical agents for dermatological use. For that purpose 4-Hydroxyphenyl-α-D-glucopyranoside was combined with auxiliary agents such as ascorbic acid and its derivatives, crude drugs and its extracts, hydroxycarboxylic acid and its salts, oil soluble glycyrrhiza extract, gentian extract, phenol derivatives and their salts, placenta extract, kojic acid and its derivatives, glucosamine and its derivatives, azelaic acid and its derivatives, retinol and its derivatives, pyridoxin and its derivatives, tocopherol and its derivatives, chitosan and its decomposition products, caffeic acid derivatives, hydroxycinnamate and its derivatives, Umbelliferae plant extracts, mycelial cultures and their extracts, plant leaves and their extracts.

  本发明的目的是增强皮肤美白效果和黑色素生成的预防效果，并提供安全稳定的用于皮肤科的局部制剂。为此，4-羟基苯基-α-D-葡萄糖苷与辅助剂如抗坏血酸及其衍生物、天然药物及其提取物、羟基羧酸及其盐、油溶性甘草提取物、龙胆提取物、酚类衍生物及其盐、胎盘提取物、曲酸及其衍生物、葡萄糖胺及其衍生物、癸二酸及其衍生物、视黄醇及其衍生物、吡哆醇及其衍生物、生育酚及其衍生物、壳聚糖及其分解产物、咖啡酸衍生物、羟基肉桂酸及其衍生物、伞形科植物提取物、菌丝培养物及其提取物、植物叶片及其提取物相结合。
• Topical agent for dermatological use containing 4-hydroxyphenyl-alpha-D-glucopyranoside
  申请人：PENTAPHARM Ltd.

  公开号：EP1859835A2

  公开（公告）日：2007-11-28

  The objective of the present invention was to enhance the skin whitening effects and blackening prevention effects and supply safe topical agents for dermatological use. For that purpose a topical composition comprising 4-hydroxyphenyl-alpha-D-glucopyranoside and UV absorber is manufactured.

  本发明的目的是增强皮肤美白效果和防止变黑效果，并提供安全的皮肤病外用制剂。为此，制造了一种由 4-羟基苯基-α-D-吡喃葡萄糖苷和紫外线吸收剂组成的外用组合物。
• PHARMACEUTICAL PREPARATION FOR EXTERNAL APPLICATION TO SKIN COMPRISING PHOSPHORYLATED SUGAR
  申请人：Ezaki Glico Co., Ltd.

  公开号：EP1932514A1

  公开（公告）日：2008-06-18

  Provided is an external preparation for skin, comprising a phosphorylated saccharide. The phosphorylated saccharide may be an inorganic salt of a phosphorylated saccharide. The phosphorylated saccharide may be a calcium, magnesium, potassium, zinc, iron or sodium salt. Also provided is an external preparation for skin, comprising a phosphorylated saccharide and a second component, wherein the second component is selected from the group consisting of moisturizing agents, whitening components, ultraviolet absorbents, anti-inflammatory agents, cell-activating agents and antioxidants. The moisturizing agent may be ascorbic acid or an ascorbic acid derivative.

  本文提供了一种皮肤外用制剂，其中包含一种磷酸化糖。磷酸化糖可以是磷酸化糖的无机盐。磷酸化糖可以是钙、镁、钾、锌、铁或钠盐。还提供了一种皮肤外用制剂，包括磷酸化糖和第二种成分，其中第二种成分选自保湿剂、美白成分、紫外线吸收剂、消炎剂、细胞活化剂和抗氧化剂组成的组。保湿剂可以是抗坏血酸或抗坏血酸衍生物。
• Phenolic glucoside gallates from quercus mongolica and q. acutissima
  作者：Kanji Ishimaru、Gen-Ichiro Nonaka、Itsuo Nishioka

  DOI：10.1016/s0031-9422(00)82367-5

  日期：1987.1