(8R,8'R)-4,4'-dibenzyloxy-3,3'-dimethoxylignane-9,9'-diol | 111194-08-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 二苄基丁烷木脂素
• 英文名称: (8R,8'R)-4,4'-dibenzyloxy-3,3'-dimethoxylignane-9,9'-diol
• 英文别名: L_gthreo-2,3-bis-(4-benzyloxy-3-methoxy-benzyl)-butane-1,4-diol；L_gthreo-2,3-Bis-(4-benzyloxy-3-methoxy-benzyl)-butan-1,4-diol；(2R,3R)-2,3-bis[(3-methoxy-4-phenylmethoxyphenyl)methyl]butane-1,4-diol
• CAS: 111194-08-2
• 化学式: C₃₄H₃₈O₆
• 分子量: 542.672
• InChiKey: IOTJTTYNETYJNK-KYJUHHDHSA-N

物化性质

• 熔点：
  112-113 °C
• 沸点：
  722.6±60.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (8R,8'R)-4,4'-dibenzyloxy-3,3'-dimethoxylignane-9,9'-diol 在 甲醇 、 sodium hydroxide 、 palladium on activated charcoal 作用下， 生成 (2R,3R)-2,3-bis[(3,4-dimethoxyphenyl)methyl]butane-1,4-diol
  参考文献：
  名称：

  罗汉松科化学-III：一种新的木脂素，癸二异西里香脂醇和罗汉松心材的其他成分

  摘要：

  从罗汉松的心材中分离出一种新的木脂素，提出了新的木酚素，其名称为癸二-异西里香脂醇。已经显示该结构为2：3-双（4'-羟基-3'-甲氧基苄基）-丁丹-1：4-二醇（II，R = H），并且通过从（-）-的绝对合成来证实。苦参醇（I，R = H）。对心材提取物的进一步检查导致除先前报道的化合物马蒂固醇，α-榄香烯苷，槲皮素之外，还分离了次要成分（+）-紫杉醇，（+）-芳香金属菊酯，山奈酚和角豆蔻醇。 ，金雀异黄素和popopicatin。

  DOI：

  10.1016/s0040-4020(01)93195-3
• 作为产物：
  描述：

  (R)-(+)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone 在 lithium aluminium tetrahydride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 (8R,8'R)-4,4'-dibenzyloxy-3,3'-dimethoxylignane-9,9'-diol
  参考文献：
  名称：

  The Syntheses of (R)-(+)-b-Vanillyl-g-butyrolactone and of Chiral Lignans Therefrom

  摘要：

  DOI：

  10.3987/r-1987-05-1169

文献信息

• Antioxidant Activity of Butane Type Lignans, Secoisolariciresinol, Dihydroguaiaretic Acid, and 7,7′-Oxodihydroguaiaretic Acid
  作者：Satoshi YAMAUCHI、Toshiya MASUDA、Takuya SUGAHARA、Yuya KAWAGUCHI、Maya OHUCHI、Tatsushi SOMEYA、Jun AKIYAMA、Shiori TOMINAGA、Manami YAMAWAKI、Taro KISHIDA、Koichi AKIYAMA、Masafumi MARUYAMA

  DOI：10.1271/bbb.80461

  日期：2008.11.23

  The antioxidant activity of butane-type lignans was evaluated. Secoisolariciresinol (SECO) and dihydroguaiaretic acid (DGA) showed higher radical scavenging activity than that of 7,7′-dioxodihydroguaiaretic acid (ODGA). SECO and DGA inhibited the oxidation of unsaturated fatty acid. Both enantiomers of DGA were also lipoxygenase inhibitors, but neither enantiomer of SECO inhibited the lipoxygenase activity.

  对丁烷类木酚素的抗氧化活性进行了评估。与 7,7′-二氧二氢愈创木脂酸（ODGA）相比，仲异月桂醇（SECO）和二氢愈创木脂酸（DGA）具有更高的自由基清除活性。SECO 和 DGA 可抑制不饱和脂肪酸的氧化。DGA 的两种对映体也是脂氧合酶抑制剂，但 SECO 的两种对映体都不能抑制脂氧合酶的活性。
• [EN] PROCESS FOR THE PREPARATION OF (S,S)-SECOISOLARICIRESINOL DIGLUCOSIDE AND (R,R)-SECOISOLARICIRESINOL DIGLUCOSIDE<br/>[FR] PRÉPARATION DE (S,S)-SÉCOISOLARICIRÉSINOL DIGLUCOSIDE ET DE (R,R)-SÉCOISOLARICIRÉSINOL DIGLUCOSIDE
  申请人：LIGNAMED LLC

  公开号：WO2018231691A1

  公开（公告）日：2018-12-20

  Provided is a synthesis process for (S,S)-secoisolariciresinol diglucoside and (R,R)-secoisolariciresinol diglucoside.

  提供了一种(S,S)-丝光木素二葡萄糖苷和(R,R)-丝光木素二葡萄糖苷的合成过程。
• Preparation of (S,S)-secoisolariciresinol diglucoside and (R,R)-secoisolariciresinol diglucoside
  申请人：The Trustees of the University of Pennsylvania

  公开号：US10030040B2

  公开（公告）日：2018-07-24

  The invention relates to processes for preparing (S,S)-secoisolariciresinol diglucoside and (R,R)-secoisolariciresinol diglucoside and compositions comprising the same.

  本发明涉及制备(S,S)-科异落叶松树脂醇二葡萄糖苷和(R,R)-科异落叶松树脂醇二葡萄糖苷的工艺以及包含它们的组合物。
• Cytotoxic Activity of Dietary Lignan and Its Derivatives: Structure–Cytotoxic Activity Relationship of Dihydroguaiaretic Acid
  作者：Tuti Wukirsari、Hisashi Nishiwaki、Kosuke Nishi、Takuya Sugahara、Koichi Akiyama、Taro Kishida、Satoshi Yamauchi

  DOI：10.1021/jf5010572

  日期：2014.6.11

  Cytotoxic activities of synthesized lignan derivatives were estimated by WST-8 reduction assay against HL-60 and HeLa cells to show the structure-activity relationship. The activities of some effective compounds were examined against Colon 26 and Vero cells. Dietary secoisolariciresinol (SECO, 1) and its metabolite, 9,9'-anhydrosecoisolariciresinol (2), did not show the cytotoxic activity. On the other hand, all stereoisomers of dihydroguaiaretic acid (DGA, 9,9'-dehydroxysecoisolariciresinol, 3-5) exhibited the activity (IC50: around 30 mu M). The IC50 value of (8R,8'R)-9-butyl DGA derivative 13 was around 6 mu M. This fact means that the hydrophobic group was advantageous for higher activity at 9- and 9'-positions. By the evaluation of the effect of 7and 7'-aryl group on the activity, we discovered the highest activity of (8R,8'R)-7-(3-hydroxy-4-methoxyphenyl)-7'-(2-ethoxyphenyl) DGA derivative 47 showing around 1 mu M of IC50 value, which is about 24-fold higher activity than that of natural (8R,8'R)-DGA. The derivative of dietary lignan showed the high cytotoxic activity.
• Bioorg. Med. Chem. Lett. 2013, 23, 5325-5328
  作者：

  DOI：——

  日期：——