(+)-anhydrosecoisolariciresinol | 316379-21-2

• 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
• 英文名称: (+)-anhydrosecoisolariciresinol
• 英文别名: divanillyltetrahydrofuran；(+)-(8S,8'S)-3,3'-dimethoxy-9,9'-epoxylignane-4,4'-diol；trans-3,4-divanillyltetrahydrofuran；3, 4-divanillyltetrahydrofuran；(S)-trans-3,4-Divanillyl-tetrahydro-furan；DVTF；(+/-)-trans-3,4-Divanillyltetrahydrofuran；4-[[(3S,4S)-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl]-2-methoxyphenol
• CAS: 316379-21-2
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: ROGUIJKVZZROIQ-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,O-双(三甲基硅烷基)三氟乙酰胺 、 (+)-anhydrosecoisolariciresinol 在 吡啶 作用下， 反应 0.33h， 生成 (3S,4S)-3,4-Bis-(3-methoxy-4-trimethylsilanyloxy-benzyl)-tetrahydro-furan
  参考文献：
  名称：

  亚麻籽粕中木脂素，异二十烷醇和松脂醇的分离和表征。

  摘要：

  描述了从亚麻籽粕中分离和鉴定木脂素，异二十烷醇，松脂醇，癸二异西里烯醇和马来甾醇（有效植物雌激素）的方法。这是在食品中检测到异二十烷醇和松脂醇的首次报道。选择的提取方法结合了用醇溶剂系统从植物基质中去除木脂素苷，然后进行酸水解以释放糖苷配基。反相高效液相色谱-二极管阵列检测系统用于酸水解甲醇提取物中280 nm处木脂素的初步分离和检测。木质素三甲基甲硅烷基醚衍生物通过气相色谱/质谱法表征。异豆香脂树脂是亚麻籽中的主要木脂素。异二十烷醇，松脂醇，

  DOI：

  10.1021/jf981359y
• 作为产物：
  描述：

  (+)-开环异落叶松树脂酚 在 triphenylphosphine hydrochloride 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以77 mg的产率得到(+)-anhydrosecoisolariciresinol
  参考文献：
  名称：

  Process for the production of (−) 3,4-divanillyl tetrahydrofuran

  摘要：

  本发明涉及一种制备(−)3,4-二香草醚四氢呋喃的方法，该方法包括(a)从印度红杉的心材和根部中通过改进的工艺分离得到(−)丝氨酸木树脂素，该工艺包括将印度红杉的心材和根部的酒精提取物在水和氯化溶剂之间分配，(b)用碱提取氯化溶剂提取物，(c)用矿酸中和后用有机溶剂提取(−)丝氨酸木树脂素，(d)从适当的有机溶剂中结晶出它，(e)将分离的(−)丝氨酸木树脂素溶解在适当的有机溶剂中，(f)在0-80℃下与三苯基膦卤化物反应1-10小时，(g)通过柱层析分离得到(−)3,4-二香草醚四氢呋喃。

  公开号：

  US06372922B1

文献信息

• Isolation and Characterization of the Lignans, Isolariciresinol and Pinoresinol, in Flaxseed Meal
  作者：Lucy P. Meagher、Gary R. Beecher、Vincent P. Flanagan、Betty W. Li

  DOI：10.1021/jf981359y

  日期：1999.8.1

  The isolation and characterization of the lignans, isolariciresinol, pinoresinol, secoisolariciresinol, and matairesinol, potent phytoestrogens, from flaxseed meal are described. This is the first report of isolariciresinol and pinoresinol being detected in a food. The extraction method selected combined the removal of the lignan glycosides from the plant matrix with an alcoholic solvent system, followed

  描述了从亚麻籽粕中分离和鉴定木脂素，异二十烷醇，松脂醇，癸二异西里烯醇和马来甾醇（有效植物雌激素）的方法。这是在食品中检测到异二十烷醇和松脂醇的首次报道。选择的提取方法结合了用醇溶剂系统从植物基质中去除木脂素苷，然后进行酸水解以释放糖苷配基。反相高效液相色谱-二极管阵列检测系统用于酸水解甲醇提取物中280 nm处木脂素的初步分离和检测。木质素三甲基甲硅烷基醚衍生物通过气相色谱/质谱法表征。异豆香脂树脂是亚麻籽中的主要木脂素。异二十烷醇，松脂醇，
• Process for the production of (−) 3,4-divanillyl tetrahydrofuran
  申请人：Council of Scientific and Industrial Research

  公开号：US06372922B1

  公开（公告）日：2002-04-16

  The present invention relates to a process for the production of (−)3,4-divanillyl tetrahydrofiran of formula (2) which comprises (a) isolating) (−) secoisolariciresinol of formula (1) from the heartwood and roots of Taxus wallichiana by an improved process which consists of partitioning of the alcoholic extract of the heartwood and roots of T. wallichiana between water and chlorinated solvent, (b) extracting the chlorinated solvent extract with alkali and (c) isolating (−) secoisolariciresinol from the alkali extract upon neutralization with mineral acid and extracting with organic solvent and (d) crystallizing it from suitable organic solvent, (e) dissolving the isolated (−) secoisolariciresinol in suitable organic solvent and (f) reacting with triphenyl phosphine halide at 0-80° C. for 1-10 hours and (g) isolating (−) 3,4-divanillyl tetrahydrofuran by column chromatography.

  本发明涉及一种制备(−)3,4-二香草醚四氢呋喃的方法，该方法包括(a)从印度红杉的心材和根部中通过改进的工艺分离得到(−)丝氨酸木树脂素，该工艺包括将印度红杉的心材和根部的酒精提取物在水和氯化溶剂之间分配，(b)用碱提取氯化溶剂提取物，(c)用矿酸中和后用有机溶剂提取(−)丝氨酸木树脂素，(d)从适当的有机溶剂中结晶出它，(e)将分离的(−)丝氨酸木树脂素溶解在适当的有机溶剂中，(f)在0-80℃下与三苯基膦卤化物反应1-10小时，(g)通过柱层析分离得到(−)3,4-二香草醚四氢呋喃。
• Identification and Stereochemical Characterization of Lignans in Flaxseed and Pumpkin Seeds
  作者：Tina Sicilia、Heike B. Niemeyer、Doris M. Honig、Manfred Metzler

  DOI：10.1021/jf0207979

  日期：2003.2.1

  Phytoestrogens of the lignan type are widely distributed in plant-derived food items and are believed to protect against hormone-dependent cancer. The richest known dietary source of lignans is flaxseed. Flaxseed has been reported to contain glycosides of secoisolariciresinol as the major lignan, together with small amounts of matairesinol, isolariciresinol, and pinoresinol. Secoisolariciresinol, but none of the other lignans, has so far been identified in pumpkin seeds. In the present study, two different methods for the hydrolysis of lignan glycosides are compared. Artifact formation and loss of lignans under acidic conditions were observed. Lariciresinol was identified by GC-MS analysis in two different types of flaxseed (Linum usitatissimum L. and Linum flavum L.) and in pumpkin seeds (Cucurbita pepo L.) for the first time. Likewise, the novel lignan demethoxy-secoisolariciresinol was tentatively identified in the flaxseed samples. Stereochemical analysis by chiral HPLC of several lignans isolated from flaxseed showed that secoisolariciresinol, matairesinol, and lariciresinol consisted predominantly of one enantiomer.
• Process for the production of (-) 3,4 divanillyl tetrahydrofuran
  申请人：Council of Scientific and Industrial Research

  公开号：EP1245570B1

  公开（公告）日：2004-12-29