Centrolobol; (R)-(-)-1,7-双对羟基苯基-3-庚醇 | 30359-01-4

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 中文名称: Centrolobol; (R)-(-)-1,7-双对羟基苯基-3-庚醇
• 中文别名: (R)-(-)-1,7-双对羟基苯基-3-庚醇
• 英文名称: (3R)-1,7-bis(4'-hydroxyphenyl)-3-heptanol
• 英文别名: 3-hydroxy-1,7-bis(4-hydroxyphenyl)heptane；(-)-centrolobol；(-)-(R)-centrolobol；Centrolobol；4-[(5R)-5-hydroxy-7-(4-hydroxyphenyl)heptyl]phenol
• CAS: 30359-01-4
• 化学式: C₁₉H₂₄O₃
• 分子量: 300.398
• InChiKey: UYJAYWZGEZOHRU-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2907299090

反应信息

• 作为反应物：
  描述：

  Centrolobol; (R)-(-)-1,7-双对羟基苯基-3-庚醇 在 aluminum isopropoxide 作用下， 以 环己酮 、 甲苯 为溶剂， 生成 1,7-bis(4'-hydroxyphenyl)-3-heptanone
  参考文献：
  名称：

  Studies on the constituents of aceraceae plants. VII. Diarylheptanoids from Acer griseum and Acer triflorum.

  摘要：

  一种名为aceroside IX (1) 的二苯庚烷类糖苷，化学式为C30H40O12, [α]D -63.5°，从灰背枫 (Acer griseum) 和三花枫 (A. triflorum) 的树皮中分离得到。另一种名为aceroside X (2) 的二苯庚烷类糖苷，化学式为C25H31O8，熔点121°， [α]21D -29.7°，以及表儿茶素，从灰背枫的树皮中分离得到，并通过薄层色谱在三花枫中检测到。在酸水解后，1生成了一种新的二苯庚烷类化合物acerogenin G (3)，化学式为C19H22O3，经过鉴定为(-)-centrolobol (5) 的酮衍生物，并产生葡萄糖和阿比糖。在部分水解过程中，1得到aceroside X (2) 和阿比糖。通过对3及其单甲基醚 (6) 的质谱分析结果，发现aceroside IX 的糖基通过与acerogenin G (3) 的C-4"位点的酚羟基结合。后者通过对1进行甲基化后酸水解生成。根据碳-13核磁共振谱分析，并与aceroside VIII (7) 的谱图比较，确定acerosides (1) 和X (2) 分别为acerogenin G 的4"-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside 和4"-O-β-D-glucopyranoside。

  DOI：

  10.1248/cpb.38.1506
• 作为产物：
  描述：

  (5S)-1,7-bis(4-hydroxyphenyl)-5-hydroxyheptan-3-one 在 sodium tetrahydroborate 、 对甲苯磺酰肼 作用下， 以 甲醇 为溶剂， 以9 mg的产率得到Centrolobol; (R)-(-)-1,7-双对羟基苯基-3-庚醇
  参考文献：
  名称：

  桔梗苷和 (-)-Centrolobol 的绝对构型

  摘要：

  通过 13C NMR 光谱确定桔梗苷的绝对构型为 S。在此建立的基础上，先前分配给 (-)-centrolobol 的 C-3 处手性的 S-构型被修改为 R-构型。

  DOI：

  10.1246/bcsj.58.2423

文献信息

• Studies on the Constituents of Aceraceae Plants. XII. Two New Diarylheptanoid Glycosides from Acer triflorum.
  作者：Satoru SHIRATORI、Seiji NAGUMO、Takao INOUE、Masahiro NAGAI、Hyung Joon CHI

  DOI：10.1248/cpb.42.960

  日期：——

  Two new diarylheptanoid glycosides, named aceroside XII (7), C30H42O12, [α]D 70.3°, and aceroside XIII (8), C25H34O8, [α]D -40.2°, were isolated along with triterpenoids and caffeoyl esters from the branches of Acer triflorum KOM. (Aceraceae). On acid hydrolysis, 7 yielded (-)-centrolobol (9), glucose and apiose. On partial hydrolysis, 7 gave 8 and apiose. Acerosides XII (7) and XIII (8) were determined to be the 4''-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside and the 4''-O-β-D-glucopyranoside of (-)-centrolobol, respectively, on the basis of chemical and spectral evidence.

  从三叶金合欢（Acer triflorum KOM.，槭树科）的枝条中分离出两种新的二芳基庚酮苷，分别命名为 Aceroside XII (7)，C30H42O12，[α]D 70.3°和 Aceroside XIII (8)，C25H34O8，[α]D -40.2°，以及三萜类化合物和咖啡酰酯。酸水解时，7 生成 (-)-centrolobol (9)、葡萄糖和芹糖。部分水解时，7 得到 8 和芹糖。根据化学和光谱证据，确定 Acerosides XII (7) 和 XIII (8) 分别是 (-)-centrolobol 的 4''-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside 和 4''-O-β-D-glucopyranoside。
• PHARMACEUTICAL COMPOSITION FOR PREVENTION AND/OR TREATMENT OF BONE DISEASE, FUNCTIONAL FOOD OR HEALTH FOOD COMPRISING THE COMPOSITION, AND PHARMACEUTICAL PREPARATION COMPRISING THE COMPOSITION AS ACTIVE INGREDIENT
  申请人：Akihisa, Toshihiro

  公开号：EP2050442A1

  公开（公告）日：2009-04-22

  The present invention provides a highly safe pharmaceutical composition for preventing and/or treating bone disease, a pharmaceutical preparation comprising thereof, a health food comprising thereof, a functional food comprising thereof. Since the present invention comprises the arylheptanoid compound shown in the following formula (I) and the derivatives thereof, it enables to prevent and/or treat the bone disease. (In the formula (I), R1 and R5 are a functional group selected from the group consisting of a hydrogen atom, alkyl group having carbon numbers 1 to 3, monosaccharide and disaccharide; R2, R3, and R4 are a functional group selected from the group consisting of a hydrogen atom, an oxygen atom, alkyl group having carbon numbers 1 to 3, monosaccharide and disaccharide; R5 may be bound on meta-position against heptylene group of another aryl group to form a ring.)

  本发明提供了一种用于预防和/或治疗骨病的高安全性药物组合物、由其组成的药物制剂、由其组成的保健食品、由其组成的功能性食品。由于本发明包含下式（I）所示的芳基庚烷类化合物及其衍生物，因此能够预防和/或治疗骨病。 (在式(I)中，R1和R5是选自氢原子、碳原子数为1至3的烷基、单糖和二糖的官能团；R2、R3和R4是选自氢原子、氧原子、碳原子数为1至3的烷基、单糖和二糖的官能团；R5可与另一芳基的庚基在元位置上结合形成环)。
• Identification of Centrolobol as the Platyphylloside Metabolite Responsible for the Observed Effect on in Vitro Digestibility of Hay
  作者：Kerstin Sunnerheim、Katharina Bratt

  DOI：10.1021/jf040135e

  日期：2004.9.1

  Syntheses of the metabolites from platyphylloside, a phenol causing digestibility inhibition in rumen fluid, have been performed to identify the active metabolite. 1,7-Bis(4'-hydroxyphenyl)-3-heptanone (3-platyphyllone), racemic, and the two enantiomers of 1,7-bis(4'-hydroxyphenyl)-3-heptanol (centrolobol) and 1,7-bis(4-hydroxyphenyl)heptane (platyphyllane) were synthesized and tested regarding digestibility inhibition in vitro in cow rumen fluid. All compounds tested induced a decreased digestion. Centrolobol was found to be the metabolite causing the observed effect, and (R)-centrolobol was found to be the enantiomer formed in the rumen liquor in vitro.
• Nagai, Masahiro; Kenmochi, Naoki; Fujita, Masao, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 3, p. 1056 - 1060
  作者：Nagai, Masahiro、Kenmochi, Naoki、Fujita, Masao、Furukawa, Naoko、Inoue, Takao

  DOI：——

  日期：——
• Pharmaceutical composition for prevention and/or treatment of bone disease, functional food or health food comprising the composition, and pharmaceutical preparation comprising the composition as active ingredient
  申请人：Akihisa, Toshihiro

  公开号：EP2407160B1

  公开（公告）日：2016-07-27