diacetyl-[6]-gingerdiol | 143615-75-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: diacetyl-[6]-gingerdiol
• 英文别名: (3R,5S)-3,5-Diacetoxy-1-(4-hydroxy-3-methoxyphenyl)decane；[6]-gingerdioldiacetate；(3R,5S)-1-(4-hydroxy-3-methoxyphenyl)decane-3,5-diyl diacetate；Diacetoxy-6-gingerdiol；[(3R,5S)-3-acetyloxy-1-(4-hydroxy-3-methoxyphenyl)decan-5-yl] acetate
• CAS: 143615-75-2
• 化学式: C₂₁H₃₂O₆
• 分子量: 380.481
• InChiKey: PXBFKEHWQRAQQD-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diacetyl-[6]-gingerdiol 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 甲基二乙酰氧基-6-姜二醇
  参考文献：
  名称：

  Gingerdiol related compounds from the rhizomes of Zingiber officinale

  摘要：

  [6]-Gingerdiol and four analogues, (3R,5S)-5-acetoxy-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decane, (3R,5S)-3-acetoxy-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decane,(3R,5S)-3,5-diacetoxy-1-(4-hydroxy-3-methoxyphenyl)decane and (3R,5S)-3,5-diacetoxy-1-(3,4-dimethoxyphenyl)decane, were isolated from the rhizomes of Zingiber officinale. Their structures were established by chemical and spectroscopic evidence.

  DOI：

  10.1016/0031-9422(92)83147-q
• 作为产物：
  描述：

  6]-姜二醇 在 甲醇 、 4-二甲氨基吡啶 、 氢气 、 palladium(II) hydroxide 、 sodium hydride 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 8.0h， 生成 diacetyl-[6]-gingerdiol
  参考文献：
  名称：

  Synthesis of gingerol and diarylheptanoids

  摘要：

  The synthesis of gingerol 1 and related compounds 2-5 along with diarylheptanoids 6-8 has been accomplished using a Keck allylation, Crimmins' aldol reaction, aldehyde coupling with acetylene, and chelation controlled reductions as the key reactions. The absolute configuration of these molecules was confirmed by preparing their acetonide derivatives and by comparison of the NMR data with natural compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.010

文献信息

• [EN] GINGEROL COMPOUNDS AND THEIR USE AS FLAVOR MODIFIERS<br/>[FR] COMPOSÉS DE GINGÉROL ET LEUR UTILISATION EN TANT QUE MODIFICATEURS D'ARÔME
  申请人：FIRMENICH & CIE

  公开号：WO2021094268A1

  公开（公告）日：2021-05-20

  The present disclosure relates to gingerol compounds, whether in their diol form or as a derivative, and their use to enhance the salty taste or the umami taste of a flavored article. The disclosure also provides compositions and flavored products containing such compounds. In some embodiments, the flavored products have reduced amounts of salt or umami-enhancing compounds (glutamates, arginates, purinic ribonucleotides, such as inosine monophosphate (IMP) and guanosine monophosphate (GMP)), relative to comparable flavored products that do not incorporate the gingerol compounds. The disclosure further provides methods of making monoacetate or diacetate derivatives of gingerol diols.

  本公开涉及姜酚化合物，无论是以它们的二醇形式还是作为衍生物，并且它们的用途是增强调味品的咸味或鲜味。该公开还提供了含有这些化合物的组合物和调味产品。在某些实施例中，相对于不含姜酚化合物的类似调味产品，这些调味产品的盐或鲜味增强化合物（谷氨酸盐、精氨酸盐、嘌呤核苷酸盐，例如肌苷酸酸（IMP）和鸟苷酸酸（GMP））的含量减少。该公开还提供制备姜酚二醇的单醋酸酯或双醋酸酯衍生物的方法。
• Synthesis of gingerol and diarylheptanoids
  作者：Gowravaram Sabitha、Chitti Srinivas、Teega Rammohan Reddy、Kurra Yadagiri、Jhillu Singh Yadav

  DOI：10.1016/j.tetasy.2011.11.010

  日期：2011.12

  The synthesis of gingerol 1 and related compounds 2-5 along with diarylheptanoids 6-8 has been accomplished using a Keck allylation, Crimmins' aldol reaction, aldehyde coupling with acetylene, and chelation controlled reductions as the key reactions. The absolute configuration of these molecules was confirmed by preparing their acetonide derivatives and by comparison of the NMR data with natural compounds. (C) 2011 Elsevier Ltd. All rights reserved.
• Gingerdiol related compounds from the rhizomes of Zingiber officinale
  作者：Hiroe Kikuzaki、Saiu-Mei Tsai、Nobuji Nakatani

  DOI：10.1016/0031-9422(92)83147-q

  日期：1992.5

  [6]-Gingerdiol and four analogues, (3R,5S)-5-acetoxy-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decane, (3R,5S)-3-acetoxy-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decane,(3R,5S)-3,5-diacetoxy-1-(4-hydroxy-3-methoxyphenyl)decane and (3R,5S)-3,5-diacetoxy-1-(3,4-dimethoxyphenyl)decane, were isolated from the rhizomes of Zingiber officinale. Their structures were established by chemical and spectroscopic evidence.