3-(BETA-D-葡萄糖基)-2-羟基苯甲酸甲酯 | 53827-68-2

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 环羧酸
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(BETA-D-葡萄糖基)-2-羟基苯甲酸甲酯
• 英文名称: 2-hydroxy-3-O-β-D-glucosyloxy benzoic acid methyl ester
• 英文别名: methyl 3-(β-D-glucopyranosyloxy)-2-hydroxybenzoate；Methyl 3-β-D-glucopyranosyloxysalicylate；3-(beta-D-Glucopyranosyloxy)-2-hydroxybenzoic acid methyl ester；methyl 2-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate
• CAS: 53827-68-2
• 化学式: C₁₄H₁₈O₉
• 分子量: 330.292
• InChiKey: VSTYNZNDJYVPKL-RRZLQCMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 在 sodium hydroxide 作用下， 生成 sweroside 、 3-(BETA-D-葡萄糖基)-2-羟基苯甲酸甲酯
  参考文献：
  名称：

  来自大叶龙胆的酰基类环烯醚萜类化合物和抗真菌成分

  摘要：

  LC-UV-质谱法和生物测定法对大叶龙胆根的含水丙酮提取物进行共导向分馏，得到了三种新的色烯衍生物和两种新的和六种已知的二环环烯醚酮，以及苦力酮、苦参酚 I、β-谷甾醇、豆甾醇、豆蔻甾醇、β-谷甾醇-3-O-龙胆二糖苷、α-香树脂醇、齐墩果酸、异卵磷脂、龙胆二糖和2-羟基-3-(1-β-D-吡喃葡萄糖基)羟基苯甲酸甲酯。根据光谱和化学证据确定了新产品的结构为 2-甲氧基泛叶酸和大叶苷 AD。六种已知的类环烯醚萜苷是龙胆苦苷、猪脑苷、6'-O-β-D-葡糖基龙胆苦苷、6'-O-β-D-葡糖苷、三氟苷和灵多苷。新的酸（2-甲氧基链烷酸），它的甲酯，kurarinone 和 kushenol I 被证明对植物病原真菌 Cladosporium cucumerinum 具有活性。甲酯和 kurarinone 也抑制人类致病酵母白色念珠菌的生长。研究了构效关系。因此，在苯甲酸（2,2-二甲基-2H-

  DOI：

  10.1016/0031-9422(96)00149-5

文献信息

• 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。
• Skin whitening agents containing glycosides
  申请人：SHISEIDO COMPANY LIMITED

  公开号：EP0649648A2

  公开（公告）日：1995-04-26

  An external preparation for skin comprising at least one of the glycosides of hydroxysalicylic acid and/or the glycosides of aliphatic esters of hydroxysalicylic acid represented by the following general formula 1; wherein R₁ represents one selected from the group consisting of a saturated hydrocarbon group and an unsaturated hydrocarbon group which have 1 to 20 carbon atoms and which may be of either a straight-chain or a branched-chain, one of R₂ and R₃ represents a sugar residue and the other hydrogen. The external preparation for skin has an excellent whitening effect and/or an excellent skin care effect.

  一种皮肤外用制剂，包含至少一种由以下通式 1 代表的羟基水杨酸苷和/或羟基水杨酸脂族酯苷； 其中 R₁ 代表选自饱和烃基和不饱和烃基组成的组中的一种，饱和烃基和不饱和烃基具有 1 至 20 个碳原子，可以是直链或支链，R₂ 和 R₃ 中的一个代表糖残基，另一个代表氢。 这种皮肤外用制剂具有极佳的美白效果和/或极佳的护肤效果。
• 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：EP1932514B1

  公开（公告）日：2018-11-14
• Topical agent for dermatological use
  申请人：——

  公开号：US20030198610A1

  公开（公告）日：2003-10-23

  The objetive 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-&agr;-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 derivative, 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.