3,4-二[(3-羟基苯基)甲基]四氢呋喃-2-酮 | 76543-15-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 中文名称: 3,4-二[(3-羟基苯基)甲基]四氢呋喃-2-酮
• 英文名称: enterolactone
• 英文别名: 3,4-Bis[(3-hydroxyphenyl)methyl]oxolan-2-one
• CAS: 76543-15-2
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: HVDGDHBAMCBBLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

ADMET

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  3,4-二[(3-羟基苯基)甲基]四氢呋喃-2-酮 在 重水 、 boron trifluoride - phosphoric-2H3 acid 作用下， 以 丙酮 为溶剂， 反应 20.0h， 以74%的产率得到[2,4,5,6,2',4',5',6'-2H8]-enterolactone
  参考文献：
  名称：

  Synthesis of[2H8]-enterolactone and[2H10]-enterodiol

  摘要：

  肠内酯和肠内二醇是哺乳动物体内膳食丁内酯型木脂素的主要代谢产物。研究这些化合物的生物特性和潜在健康影响需要同位素标记化合物作为定量测量的标准。肠内酯的一种简便的氘标记方法是使用D3PO4·BF3/D2O复合物在室温下交换所有八个芳香氢，甚至来自非活性间位的芳香氢，以74%的产率和99%的同位素纯度形成[2,4,5,6,2′,4′,5′,6′-2H8]-肠内酯。[2,4,5,6,9,9,2′,4′,5′,6′-2H10]-肠内二醇是通过用LiAlD4还原[2,4,5,6,2′,4′,5′,6′-2H8]-肠内酯制备的，LiAlD4在分子中引入另外两个氘原子。版权 © 2003 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.793
• 作为产物：
  描述：

  E-2-(3-Benzyloxy-4-methoxybenzylidene)butanedioic acid 1-methyl ester 在 palladium on activated charcoal 、 sodium iodide 六甲基磷酰三胺 、 氢氧化钾 、 sodium tetrahydroborate 、 正丁基锂 、 氢气 、 三溴化硼 、 potassium carbonate 、 六甲基二硅氮烷 、 calcium chloride 作用下， 以 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 、 丙酮 为溶剂， -78.0~25.0 ℃ 、344.73 kPa 条件下， 反应 18.33h， 生成 3,4-二[(3-羟基苯基)甲基]四氢呋喃-2-酮
  参考文献：
  名称：

  Ruthenium dioxide in fluoro acid medium: II. Application to the formation of steganes skeleton by oxidative phenolic coupling.

  摘要：

  Ruthenium (IV) dioxide dihydrate in fluoro acidic medium was found to be a very efficient agent for the oxidative coupling of the phenolic lignans (+/-)-presteganes A and B. Different attempts to oxidise the diphenolic dibenzylbutanolide (+/-)-HPMF were also carried out, but were unsuccessful. Likely explanation for these failures are given.

  DOI：

  10.1016/s0040-4020(01)88186-2

文献信息

• Identification of the Microbial Transformation Products of Secoisolariciresinol Using an Untargeted Metabolomics Approach and Evaluation of the Osteogenic Activities of the Metabolites
  作者：Wen-Xuan Yu、Hok-Him Tang、Jun-Jie Ye、Hui-Hui Xiao、Chung-Yan Lam、Tim-Fat Shum、Zhi-Kang Sun、Yuan-Zhen Li、Xin-Yu Zang、Wen-Chao Du、Jian-Ping Zhang、Tsz-Hung Kong、Li-Ping Zhou、Jia-Chi Chiou、Chun-Fai Kung、Kam-Wah Mok、Jing Hu、Man-Sau Wong

  DOI：10.3390/molecules28155742

  日期：——

  Secoisolariciresinol (SECO) is one of the major lignans occurring in various grains, seeds, fruits, and vegetables. The gut microbiota plays an important role in the biotransformation of dietary lignans into enterolignans, which might exhibit more potent bioactivities than the precursor lignans. This study aimed to identify, synthesize, and evaluate the microbial metabolites of SECO and to develop efficient lead compounds from the metabolites for the treatment of osteoporosis. SECO was fermented with human gut microbiota in anaerobic or micro-aerobic environments at different time points. Samples derived from microbial transformation were analyzed using an untargeted metabolomics approach for metabolite identification. Nine metabolites were identified and synthesized. Their effects on cell viability, osteoblastic differentiation, and gene expression were examined. The results showed that five of the microbial metabolites exerted potential osteogenic effects similar to those of SECO or better. The results suggested that the enterolignans might account for the osteoporotic effects of SECO in vivo. Thus, the presence of the gut microbiota could offer a good way to form diverse enterolignans with bone-protective effects. The current study improves our understanding of the microbial transformation products of SECO and provides new approaches for new candidate identification in the treatment of osteoporosis.

  Secoisolariciresinol (SECO) 是存在于各种谷物、种子、水果和蔬菜中的主要木质素之一。肠道微生物群在膳食木质素向肠木质素的生物转化过程中发挥着重要作用，而肠木质素可能比前体木质素表现出更强的生物活性。本研究旨在鉴定、合成和评估 SECO 的微生物代谢物，并从代谢物中开发治疗骨质疏松症的高效先导化合物。在不同的时间点，SECO 与人体肠道微生物群在厌氧或微氧环境中进行发酵。利用非靶向代谢组学方法对微生物转化产生的样本进行了代谢物鉴定分析。鉴定并合成了九种代谢物。研究了它们对细胞活力、成骨细胞分化和基因表达的影响。结果表明，其中五种微生物代谢物的潜在成骨作用与 SECO 相似或更好。结果表明，肠木质素可能是 SECO 在体内产生骨质疏松效应的原因。因此，肠道微生物群的存在可能是形成具有骨保护作用的多种肠木质素的良好途径。目前的研究增进了我们对 SECO 微生物转化产物的了解，并为确定治疗骨质疏松症的新候选物质提供了新方法。
• Bis-hydroxybenzyl derivatives, processes for their preparation and pharmaceutical composition containing same
  申请人：AKZO N.V.

  公开号：EP0038600A1

  公开（公告）日：1981-10-28

  The invention relates to compounds of the formula's: and salts thereof, in which R, and R2 may be the same or different groups selected from hydroxy, and etherified hydroxy and an esterified hydroxy group, having valuable anti-inflammatory, lipid lowering activities, and immunomodulating properties.

  本发明涉及式的化合物： 及其盐类，其中 R 和 R2 可以是相同或不同的基团，选自羟基、醚化羟基和酯化羟基，具有重要的抗炎、降脂活性和免疫调节特性。
• Anti-proliferative composition
  申请人：Nutricia N.V.

  公开号：EP1314438A1

  公开（公告）日：2003-05-28

  Non-estrogen-dependent hyperproliferation of cells in animals or humans can be prevented or treated by means of a pharmaceutical or nutritional composition containing a combination of a) two or more inhibitors of the G1/S phase of the cell cycle; and b) two or more inhibitors of the G2/M phase of the cell cycle; and c) two or more inhibitors of protein tyrosine kinase activity. Especially, component a) comprises two or more compounds selected from flavanolignans, carotenoids and isoflavone; component b) comprises two or more compounds selected from flavanolignans, hydroxylated stilbenes, isoflavones and apigenin; and component c) comprises two or more compounds selected from flavanolignans and isoflavones.

  动物或人体内非雌激素依赖性细胞过度增殖可通过含有以下成分组合的药物或营养组合物来预防或治疗 a) 细胞周期 G1/S 期的两种或两种以上抑制剂；以及 b) 细胞周期 G2/M 期的两种或两种以上抑制剂；以及 c) 两种或两种以上蛋白酪氨酸激酶活性抑制剂。 特别是，成分 a) 包括两种或两种以上选自黄烷木质素、类胡萝卜素和异黄酮的化合物；成分 b) 包括两种或两种以上选自黄烷木质素、羟基化芪、异黄酮和芹菜素的化合物；成分 c) 包括两种或两种以上选自黄烷木质素和异黄酮的化合物。
• Process for purification and isolation of estrogens
  申请人：Dr. Reddy's Laboratories Ltd.

  公开号：US10143938B2

  公开（公告）日：2018-12-04

  The present application relates to a method for obtaining a mixture of estrogens from the pregnant mare's urine.

  本申请涉及一种从怀孕母马尿液中获取雌激素混合物的方法。
• Separation of cresol from mares' urine
  申请人：Solvay Pharmaceuticals GmbH

  公开号：US20030215953A1

  公开（公告）日：2003-11-20

  A method of separating cresol from mares' urine by pervaporation using pore-free polymeric silicone membranes in which starting urine solutions containing high-quality and -quantity conjugated estrogens with a reduced or substantially removed cresol content are provided which are advantageously suitable for obtaining natural mixtures of conjugated estrogens from pregnant mares' urine.

  一种利用无孔聚合硅胶膜通过渗透蒸发从母马尿液中分离甲酚的方法，该方法提供的起始尿液含有优质和定量的共轭雌激素，甲酚含量降低或基本去除，非常适合从怀孕母马的尿液中获得天然的共轭雌激素混合物。