2,3-dihydroxyphenyl β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-dihydroxyphenyl β-D-glucopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2-(2,3-dihydroxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₂H₁₆O₈
• 分子量: 288.254
• InChiKey: WWVGRACROSBOHO-DVYMNCLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  葡萄糖 、 邻苯三酚 在 对甲苯磺酸 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 生成 1-O-α-D-glucopyranosyl pyrogallol 、 2,3-dihydroxyphenyl β-D-glucopyranoside 、 2-O-α-D-glucopyranosyl pyrogallol 、 (2S,3R,4S,5S,6R)-2-(2,6-dihydroxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  多羟基酚与葡萄糖的直接缩合

  摘要：

  多羟基酚与游离葡萄糖在 DMSO 中的酸催化直接缩合反应得到 O-α-D-吡喃葡萄糖苷优先于其 β-端基异构体；然而，间苯三酚和间苯二酚产生了 C-β-D-吡喃葡萄糖苷。

  DOI：

  10.1246/cl.1983.1487

文献信息

• COUMESTAN-LIKE ANTIOXIDANTS AND UV ABSORBANTS
  申请人：Wagner Barbara

  公开号：US20100330009A1

  公开（公告）日：2010-12-30

  The present invention relates to derivatives of the 1H-pyrano[4,3-b]benzofuran-1-one structure and their nitrogen analogues which possess powerful antioxidant properties combined with a highly effective UV absorbing functionality in one molecule. These compounds are especially useful in cosmetical and dermatological formulations.

  本发明涉及1H-吡喴并[4,3-b]苯并呋喃-1-酮结构及其氮类似物的衍生物，这些衍生物具有强大的抗氧化性能，同时结合了高效的吸收紫外线功能在一个分子中。这些化合物在化妆品和皮肤科配方中特别有用。
• EP2296760B1
  申请人：——

  公开号：EP2296760B1

  公开（公告）日：2016-03-16
• USE OF BENZOTROPOLONE DERIVATIVES AS UV ABSORBERS AND ANTIOXIDANTS AND THEIR USE IN SUNSCREENS AND/OR COSMETIC COMPOSITIONS
  申请人：Wagner Barbara

  公开号：US20110123468A1

  公开（公告）日：2011-05-26

  Described is the use of benzotropolone and their derivatives, especially the compounds of formula (1); wherein R 2 , R 3 , R 4 , R 5 and R 6 independently of one another are hydrogen; OH; C 1 -C 30 alkyl, C 2 -C 30 al-kenyl, C 1 -C 30 alkoxy, C 3 -C 12 cycloalkyl or C 1 C 30 hydroxyalkyl, which may be substituted by one or more E and/or interrupted by one or more D; C 6 -C 20 aryl, which may be substituted by one or more G; C 4 -C 20 heteroaryl, which may be substituted by one or more G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 7 -C 25 aralkyl, CN, or —CO—R 17 ; C 1 -C 30 mono- or dialkylamino; COR 9 ; COOR 9 ; CONR 9 R 10 ; CN; SO 2 R 9 ; OCOOR 9 ; OCOR 9 ; NHCOOR 9 ; NR 9 COR 10 ; NH 2 ; *—(CO)—NH—(CH 2 ) n1 —(PO)—(OR 11 ) 2 ; —(CO)—O—(CH 2 ) n1 —(PO)—(OR 11 ) 2 ; sulphate; sulphonate; phosphate; phosphonate; —(CH 2 ) n2 —[O—(SO 2 )] n3 —OR 11 ; —O—(CH 2 ) n4 (CO) n5 —R 11 ; —(O) n6 —(CH 2 ) n7 —(PO)—(OR 9 ) 2 ; —(O) n6 —(CH 2 ) n7 —SO 2 —OR 9 ; halogen; organosilanyl; organo-siloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen to the benzotropolone system or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH 2 ) n —(X 1 ) 1 or 0 -benzotropolone system, wherein n=1-10 and X 1 =—O—; —(CO)—; —O—CO—; —COO—, —NH—; —S—; —SO 2 —); R 1 , R 7 and R 8 independently of one another are hydrogen; C 1 C 12 alkyl or C 3 -C 12 -cycloalkyl, which may be substituted by one or more E and/or interrupted by one or more D; C 6 -C 20 aryl, which may be substituted by one or more G; C 4 -C 20 heteroaryl, which may be substituted by one or more G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 7 -C 25 aralkyl, or COOR 9 ; COR 9 ; CONR 9 R 10 ; SO 3 R 9 ; SO 2 R 9 ; PO 3 (R 9 ) 2 ; PO 2 (R 9 ) 2 ; organosilanyl; organosiloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen to the benzotropolone system or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH 2 ) n —(X 2 ) 1 or 0 —*, wherein n=1-10 and X 2 =—C(═O)—; —O—CO—*); R 9 and R 10 independently from each other are hydrogen; C 1 C 18 alkyl or C 3 -C 12 -cycloalkyl which may be substituted by one or more E and/or interrupted by one or more D; C 6 -C 20 aryl, which may be substituted by one or more G; C 4 -C 20 heteroaryl, which may be substituted by one or more G; organosilanyl; organosiloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH 2 ) n —*, wherein n=1-10); or R 9 and R 10 together form a five or six membered ring, R 11 is hydrogen; or C 1 -C 5 alkyl; n 1 , n 2 , n 4 and n 7 independently from each other are a number from 1 to 5; n 3 , n 5 and n 6 independently from each other are a 0; or 1; D is —CO—; —COO—; —S—; —SO—; —SO2-; —O—; —NR 14 —; —S 1 R 19 R 20 —; —POR 11 —; —CR 12 ═CR 13 —; or —C≡C—; and E is —OR 18 ; —SR 18 ; —NR 14 R 15 ; —NR 14 COR 15 ; —COR 17 ; —COOR 16 ; —CONR 14 R 15 ; —CN; halogen; Or SO 3 R 18 ; SO 2 R 18 ; PO 3 (R 18 ) 2 ; PO 2 (R 18 ) 2 ; organosilanyl; organosiloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH 2 )n-(X 1 ) 1 or 0 —*, wherein n=1-10 and X1=—O—; —C(═O)—; —O—CO—; —COO—; —NH—; —S—; —SO 2 —); G is E; C 1 -C 18 alkyl, which is optionally interrupted by D; C 1 -C 18 perfluoroalkyl; C 1 -C 18 alkoxy, which is optionally substituted by E and/or interrupted by D; wherein R 12 , R 13 , R 14 and R 15 independently of each other are hydrogen; C 6 -C 18 aryl which is optionally substituted by OH, C 1 -C 18 alkyl or C 1 -C 18 alkoxy; C 1 -C 18 alkyl, which is optionally interrupted by —O—; or Ri4 and Ri5 together form a five or six membered ring, Ri6 is hydrogen; C6-Ci8aryl which is optionally substituted by OH, C 1 -C 18 alkyl or d-C 18 alkoxy; C 1 -C 18 alkyl which is optionally interrupted by —O—; R 17 is H; C 6 -C 18 aryl which is optionally substituted by OH, C 1 -C 18 alkyl or C 1 -C 18 alkoxy; or d-C 18 alkyl which is optionally interrupted by —O—; R 18 is hydrogen; C 6 -C 18 aryl, which is optionally substituted by OH, C 1 -C 18 alkyl or d-C 18 alkoxy; C 1 -C 18 alkyl, which is optionally interrupted by —O—; R 19 and R 20 independently of each other are hydrogen; C 1 -C 18 alkyl; C 6 -C 18 aryl which is optionally substituted by C 1 -C 18 alkyl; and R 21 is C 1 -C 18 alkyl; or C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl; * means, that this radical is directed to the benzotropolone moiety; for the protection of human and animal hair and skin against UV radiation.
• US8383088B2
  申请人：——

  公开号：US8383088B2

  公开（公告）日：2013-02-26
• US9707417B2
  申请人：——

  公开号：US9707417B2

  公开（公告）日：2017-07-18