(3R,5S)-[10]-gingerdiol | 53254-77-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (3R,5S)-[10]-gingerdiol
• 英文别名: [10]-gingerdiol；(3R,5S)-1-(4-hydroxy-3-methoxyphenyl)tetradecane-3,5-diol
• CAS: 53254-77-6
• 化学式: C₂₁H₃₆O₄
• 分子量: 352.514
• InChiKey: LGSIUDXMEDKEPY-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  10-姜酮醇 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以44 mg的产率得到(3S,5S)-[10]-gingerdiol
  参考文献：
  名称：

  [10]-Gingerdiols as the Major Metabolites of [10]-Gingerol in Zebrafish Embryos and in Humans and Their Hematopoietic Effects in Zebrafish Embryos

  摘要：

  Gingerols are a series of major constituents in fresh ginger with the most abundant being [6]-, [8]-, and [10]-gingerols (6G, 8G, and 10G). We previously found that ginger extract and its purified components, especially 10G, potentially stimulate both the primitive and definitive waves of hematopoiesis (blood cell formation) in zebrafish embryos. However, it is still unclear if the metabolites of 10G retain the efficacy of the parent compound toward pathological anemia treatment. In the present study, we first investigated the metabolism of 10G in zebrafish embryos and then explored the biotransformation of 10G in humans. Our results show that 10G was extensively metabolized in both zebrafish embryos and humans, in which two major metabolites, (3S,5S)-[10]-gingerdiol, were identified by analysis of the MSn spectra and comparison to authentic standards that we synthesized. After 24 h of treatment of zebrafish embryos, 10G was mostly converted to its metabolites. Our results clearly indicate that the reductive pathway is a major metabolic route for 10G in both zebrafish embryos and humans. Furthermore, we investigated the hematopoietic effect of 10G and its two metabolites, which show similar hematopoietic effects as 10G in zebrafish embryos.

  DOI：

  10.1021/jf401501s

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。
• [10]-Gingerdiols as the Major Metabolites of [10]-Gingerol in Zebrafish Embryos and in Humans and Their Hematopoietic Effects in Zebrafish Embryos
  作者：Huadong Chen、Dominique N. Soroka、Jamil Haider、Karine F. Ferri-Lagneau、TinChung Leung、Shengmin Sang

  DOI：10.1021/jf401501s

  日期：2013.6.5

  Gingerols are a series of major constituents in fresh ginger with the most abundant being [6]-, [8]-, and [10]-gingerols (6G, 8G, and 10G). We previously found that ginger extract and its purified components, especially 10G, potentially stimulate both the primitive and definitive waves of hematopoiesis (blood cell formation) in zebrafish embryos. However, it is still unclear if the metabolites of 10G retain the efficacy of the parent compound toward pathological anemia treatment. In the present study, we first investigated the metabolism of 10G in zebrafish embryos and then explored the biotransformation of 10G in humans. Our results show that 10G was extensively metabolized in both zebrafish embryos and humans, in which two major metabolites, (3S,5S)-[10]-gingerdiol, were identified by analysis of the MSn spectra and comparison to authentic standards that we synthesized. After 24 h of treatment of zebrafish embryos, 10G was mostly converted to its metabolites. Our results clearly indicate that the reductive pathway is a major metabolic route for 10G in both zebrafish embryos and humans. Furthermore, we investigated the hematopoietic effect of 10G and its two metabolites, which show similar hematopoietic effects as 10G in zebrafish embryos.