[10]-姜烯酚 | 36752-54-2

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: [10]-姜烯酚
• 中文别名: 10-姜烯酚
• 英文名称: [10]-shogaol
• 英文别名: 10-shogaol；1-(4-Hydroxy-3-methoxyphenyl)tetradec-4-en-3-one
• CAS: 36752-54-2
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: FADFGCOCHHNRHF-UHFFFAOYSA-N

物化性质

• 沸点：
  476.8±35.0 °C(Predicted)
• 密度：
  0.996±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、甲醇；

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• WGK Germany：
  2

制备方法与用途

生物活性

• Shogaol 是一种从生姜中提取的抗氧化剂，能够促进皮肤细胞增殖和迁移。
• Shogaol1 抑制 COX-2 酶，其 IC50 值为 7.5 μM，并具有抗增殖作用。

靶点 COX-2 IC50：7.5 μM

化学性质
无色至微黄色液体，可溶于甲醇、乙醇、DMSO 等有机溶剂，来源于生姜。

用途
用于含量测定、鉴定及药理实验等。

反应信息

• 作为反应物：
  描述：

  [10]-姜烯酚 、 腺嘌呤 在 caesium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 以30%的产率得到5-(6-amino-9H-purin-9-yl)-1-(4-hydroxy-3-methoxyphenyl)tetradecan-3-one
  参考文献：
  名称：

  Identification of unprecedented purine-containing compounds, the zingerines, from ginger rhizomes (Zingiber officinale Roscoe) using a phase-trafficking approach

  摘要：

  Three unprecedented purine-containing compounds, named [6]-, [8]-, and [10]-zingerines as they are 5-(6-amino-9H-purin-9-yl) analogs of [6]-, [8]-, and [10]-gingerols, respectively, were isolated from a methanolic extract of ginger rhizomes using a phase trafficking-based method that utilizes solid phase reagents allowing for fast and selective simultaneous separation of basic, acidic, and neutral components of natural products extracts. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2011.03.007
• 作为产物：
  描述：

  (+/-)-[10]-姜酚 在 potassium fluoride 、 C₅₀H₃₄F₁₂O₆ 作用下， 以 甲苯 为溶剂， 反应 192.0h， 以47%的产率得到10-姜酮醇
  参考文献：
  名称：

  通过使用阳离子结合催化剂的对映选择性脱水进行β-羟基羰基化合物的动力学拆分：轻松获得对映纯手性醇醛

  摘要：

  通过使用阳离子结合的宋氏低聚乙二醇（oligoEG）催化剂，以氟化钾（KF）为基础，开发了通过对映选择性脱水过程开发的外消旋β-羟基羰基（aldol）化合物的实用且高度对映选择性的非酶动力学拆分方法。在温和的反应条件下，极高的选择性因子（s =高达2393）可分离出多种外消旋醇醛。该协议易于扩展。它为合成对映体纯形式的多种生物学和药学上相关的手性醇醛提供了另一种方法。例如，外消旋姜醇可以以极高的效率（s> 240），在一个步骤中同时提供对映体纯的姜黄醇和相应的Shogaols。这种动力学拆分过程的显着效果可归因于在由手性催化剂，底物和KF产生的密闭超分子手性笼中的系统协同氢键催化。

  DOI：

  10.1021/acs.orglett.8b00547

文献信息

• REDUCED SODIUM FOOD PRODUCT
  申请人：GENERAL MILLS, INC.

  公开号：EP3466930A1

  公开（公告）日：2019-04-10

  The present invention relates to the use of a compound according to Formula B3: where: R1 and R2 are each independently OH or C1-C3 alkoxy, and R3 is selected from the group consisting of (i) C10-C20 unsubstituted straight or branched chain alkenyl with one or more double bonds; and (ii) where X, Y and Z are independently CH, CH2, CO or CHOR5 where R5 is H or C1-C3 alkyl, provided that if one of X or Y are CH then Z is also CH, and where R4 is C1-C8 straight or branched chain unsubstituted alkyl or where n is 1-5, provided that if R4 is C1-C8 straight or branched chain alkyl, then Y is CHOR5 where R5 is C1-C3 alkyl; for substituting sodium chloride in food products.

  本发明涉及根据式 B3 所述化合物的用途： 其中 R1 和 R2 各自独立地为 OH 或 C1-C3 烷氧基，以及 R3 选自以下组别 (i) 具有一个或多个双键的 C10-C20 未取代直链或支链烯基；和 (ii) 其中 X、Y 和 Z 独立地为 CH、CH2、CO 或 CHOR5，其中 R5 为 H 或 C1-C3 烷基，但如果 X 或 Y 之一为 CH，则 Z 也为 CH，且其中 R4 为 C1-C8 未取代的直链或支链烷基，或 其中 n 为 1-5，但如果 R4 为 C1-C8 直链或支链烷基，则 Y 为 CHOR5，其中 R5 为 C1-C3 烷基； 用于替代食品中的氯化钠。
• REDUCED SODIUM FOOD PRODUCTS
  申请人：GENERAL MILLS, INC.

  公开号：EP2954037B1

  公开（公告）日：2018-04-11
• Synergistic pharmaceutical compositions useful in prevention and treatment of beta-amyloid protein-induced disease
  申请人：Kim S. H. L. Darrick

  公开号：US20070003641A1

  公开（公告）日：2007-01-04

  Disclosed are combinations of natural and synthetic turmeric, ginger, ginko biloba, sage, and rosemary compounds suitable for treatment of beta-amyloid-disease induced disease that have synergistic anti-βA peptide effects when members of the five groups of compounds are combined. Suitable members of the compounds include both natural compounds derived from extracts of each of Curcuma sp., Zingiber sp., Ginkgo biloba, Salvia sp., or Rosmarinus sp. as well as synthetic homologues and analogues of such natural compounds. Sage and rosemary derived compounds suitable alone for treatment of beta-amyloid induced disease is also described.
• Use of a liquid cooling sensate to provide a pungent, warming or tingling sensate composition
  申请人：Moza Ashok K

  公开号：US20080038386A1

  公开（公告）日：2008-02-14

  The present invention is directed to a sensate composition consisting of a liquid cooling composition, and at least one warming, tingling, or pungent sensate ingredient of either synthetic or natural origin which provides enhanced warming, tingling, or pungent properties. The liquid cooling sensate of the invention is a eutectic mixture of 2-Isopropyl-N,2,3-trimethylbutyramide and N-Ethyl-p-menthane-3-carboxamide, or at least one cooling agent selected from the group consisting of N-(2-hydroxyethyl)-2,3-dimethyl-2-isopropylbutanamide, N-(3-ethoxypropyl)-2,3-dimethyl-2-isopropylbutanamide, N-(3-isopropoxypropyl)-2,3-dimethyl-2-isopropylbutanamide, N-(3-butoxypropyl)-2,3-dimethyl-2-isopropylbutanamide,N-Ethyl-2,2-diisopropylbutanamide, N-(1,1-dimethyl-2-hydroxyethyl)-2,2-diethylbutanamide, N-(2-ethoxyethyl)-2,3-dimethyl-2-isopropylbutanamide and N-(3-methoxypropyl)-2,3-dimethyl-2-isopropylbutanamide. The warming, tingling, or pungent sensate of the invention consists of at least one component that is an isothiocyanate and/or an amide or a natural product that contains at least one warming, tingling, or pungent principle that is an isothiocyanate and/or an amide. The present invention is further directed to a method of using the sensate composition in a food, pharmaceutical or personal care product.
• Pharmaceutical Compositions Useful In Prevention and Treatment of Beta-Amyloid Protein-Induced Disease
  申请人：Kim S.H.L. Darrick

  公开号：US20080085932A1

  公开（公告）日：2008-04-10

  The invention provides methods for treating beta-Amyloid protein-induced disease, pharmaceutical compositions and compounds useful for the same, and the use of these compounds for the manufacture of a medicament for treating the same. More particularly, the invention relates to the use of natural product compounds isolated from turmeric, gingko biloba , and ginger, and synthetic chemical analogues thereof, for the treatment of a beta-Amyloid protein-induced disease.