3-(3,4-二羟基苯基)-1-(2,4,6-三羟基苯基)-1-丙酮 | 57765-66-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 3-(3,4-二羟基苯基)-1-(2,4,6-三羟基苯基)-1-丙酮
• 中文别名: 3-羟基根皮素
• 英文名称: 3-hydroxyphloretin
• 英文别名: eriodictyol dihydrochalcone；3-(3,4-Dihydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
• CAS: 57765-66-9
• 化学式: C₁₅H₁₄O₆
• 分子量: 290.273
• InChiKey: CNABJBYLQABXJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(3,4-二羟基苯基)-1-(2,4,6-三羟基苯基)-1-丙酮 生成 5,7-dihydroxy-3-(3,4-dihydroxybenzyl)chromone
  参考文献：
  名称：

  SATHYANARAYANA, S.;KRISHNAMURTY, H. G., INDIAN J. CHEM. B, 27,(1988) N0, C. 899-901

  摘要：

  DOI：
• 作为产物：
  描述：

  根皮素 以 aq. phosphate buffer 为溶剂， 反应 1.0h， 生成 3-(3,4-二羟基苯基)-1-(2,4,6-三羟基苯基)-1-丙酮
  参考文献：
  名称：

  卵磷脂（一种来自苹果的生物活性化合物）通过人类细胞色素P450酶的区域选择性羟化作用

  摘要：

  萤石素是苹果和苹果产品中的主要多酚化合物，它很有趣，因为它对人体健康具有有益的作用。主要发现它是葡糖苷，次氯嗪的一种形式。但是，尚未报道人类毛p素的代谢途径。因此，鉴定在人肝微粒体中产生的促视紫红质代谢物和使它们产生的人细胞色素P450（P450）酶很有趣。在这项研究中，使用人肝微粒体和重组人肝P450检查了人肝P450对促性腺激素的氧化作用。人肝微粒体中促绿素的主要代谢产物是3-OH促绿素，与细菌CYP102A1催化的促绿素反应相同。CYP3A4和CYP2C19的kcat值分别为3.1和5.8 min-1。但是，CYP3A4具有3。Km值比CYP2C19低3倍。CYP3A4催化的反应的催化效率比CYP2C19催化的反应高1.8倍。在最佳条件下，由CYP3A4进行的全细胞生物转化可从8 mM伞菌素中获得3-OH伞菌素的0.16 mM h-1生产力。Phloretin是CYP3A4催化的睾丸

  DOI：

  10.3390/ph13110330

文献信息

• Enzymatic Conversion of Flavonoids using Bacterial Chalcone Isomerase and Enoate Reductase
  作者：Mechthild Gall、Maren Thomsen、Christin Peters、Ioannis V. Pavlidis、Patrick Jonczyk、Philipp P. Grünert、Sascha Beutel、Thomas Scheper、Egon Gross、Michael Backes、Torsten Geißler、Jakob P. Ley、Jens-Michael Hilmer、Gerhard Krammer、Gottfried J. Palm、Winfried Hinrichs、Uwe T. Bornscheuer

  DOI：10.1002/anie.201306952

  日期：2014.1.27

  Flavonoids are a large group of plant secondary metabolites with a variety of biological properties and are therefore of interest to many scientists, as they can lead to industrially interesting intermediates. The anaerobic gut bacterium Eubacterium ramulus can catabolize flavonoids, but until now, the pathway has not been experimentally confirmed. In the present work, a chalcone isomerase (CHI) and

  黄酮类化合物是一大类具有各种生物学特性的植物次生代谢产物，因此许多科学家都对其感兴趣，因为它们会导致工业上有意义的中间体。厌氧肠细菌Eubacterium ramulus可以分解黄酮类化合物，但是直到现在，该途径还没有被实验证实。在目前的工作中，可以通过全基因组测序和基因基序搜索来鉴定查尔酮异构酶（CHI）和烯酸还原酶（ERED）。即使在有氧条件下，这两种酶也已被成功克隆并以其活性形式在大肠杆菌中表达。的分解代谢途径E.桂枝被黄烷酮的生物转化成二氢查耳酮证实。工程表达两种酶的大肠杆菌菌株用于几种黄烷酮的转化，从而强调了这种生物催化级联反应的适用性。
• AROMA COMPOSITIONS OF ALKAMIDES WITH HESPERETIN AND/OR 4-HYDROXYDIHYDROCHALCONES AND SALTS THEREOF FOR ENHANCING SWEET SENSORY IMPRESSIONS
  申请人：Ley Jakob

  公开号：US20080242740A1

  公开（公告）日：2008-10-02

  The invention primarily relates to aroma compositions of (i) certain saliva-stimulating alkamides having a tingling, pungent and/or hot flavor (such as for example pellitorines, spilanthol) with (ii) hesperetin (5,7-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-chroman-4-one) or the enantiomers and/or salts thereof and/or (iii) 4-hydroxydihydrochalcones (3-(4-hydroxyphenyl)-1-phenylpropan-1-ones) and/or the salts thereof, the use thereof to enhance the sweet flavor of sweet-tasting substances or the sweet odor impression of aroma substances which give rise to a sweet odor impression, but in particular to enhance the sweet initial flavor or odor (initial sweetness). The invention thus relates to the use of said aroma compositions as general sweetness enhancers and enhancers of initial sweetness. The invention further relates to certain preparations which contain an effective amount of said aroma compositions of (i) alkamides (such as in particular pellitorines, spilanthol) with (ii) hesperetin or the enantiomers and/or salts thereof and/or (iii) 4-hydroxydihydrochalcones and/or the salts thereof and methods for enhancing the sweet flavor or initial sweetness of a sweet-tasting substance or the sweet odor impression or initial sweetness of an aroma substance which gives rise to a sweet odor impression. The invention also relates to the use of certain alkamides (i) to enhance the initial sweetness of a preparation comprising (ii) hesperetin or the enantiomers and/or salts thereof and/or (iii) 4-hydroxydihydrochalcones and/or the salts thereof and (b) sweet-tasting substances and/or (c) aroma substances which give rise to a sweet odor impression.

  该发明主要涉及具有刺激唾液分泌的辣味、刺激性和/或辛辣风味的某些唾液激发烷酰胺（例如佩利托林、斯皮兰托尔）与（ii）橙皮素（5,7-二羟基-3-(3-羟基-4-甲氧基苯基)-4-羟基-香豆素）或其对映体和/或盐以及（iii）4-羟基二氢黄烷酮（3-(4-羟基苯基)-1-苯基丙酮）和/或其盐的香气组合物，其用途是增强甜味物质的甜味或产生甜味印象的香料物质的甜味印象，尤其是增强甜味的初始风味或香气（初始甜味）。该发明因此涉及将所述香气组合物用作一般甜味增强剂和初始甜味增强剂。该发明还涉及含有有效量所述香气组合物的某些配方（i）烷酰胺（例如特别是佩利托林、斯皮兰托尔）与（ii）橙皮素或其对映体和/或盐以及（iii）4-羟基二氢黄烷酮和/或其盐的方法，用于增强甜味物质的甜味或初始甜味或产生甜味印象的香料物质的甜味印象或初始甜味。该发明还涉及使用某些烷酰胺（i）来增强含有（ii）橙皮素或其对映体和/或盐以及（iii）4-羟基二氢黄烷酮和/或其盐的配方的初始甜味以及（b）甜味物质和/或（c）产生甜味印象的香料物质的初始甜味。
• [EN] METHOD FOR THE SYNTHESIS OF ASPALATHIN AND ANALOGUES THEREOF<br/>[FR] PROCÉDÉ DE SYNTHÈSE D'ASPALATHINE ET DE SES ANALOGUES
  申请人：SOUTH AFRICAN MEDICAL RES COUNCIL

  公开号：WO2011064726A1

  公开（公告）日：2011-06-03

  A method of synthesising Aspalathin and its analogues or derivatives is disclosed. The method comprises synthesising a compound of formula 1 or its analogues or derivatives (I) wherein each of R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 is independently selected from the group consisting of -H, -OH, hydrocarbyl groups, saccharide moieties and -OR15; R15 is selected from the group consisting of hydrogen, a hydrocarbyl group (e.g. methoxy or ethoxy), an acyl group and a benzyl group; and R11, R12, R13 and R14 are independently selected from the group consisting of -H, hydrocarbyl groups, saccharide moieties, an acyl group and a benzyl group. The method comprises the step of coupling a sugar to a dihydrochalcone, chalcone or flavanone, or coupling the sugar to an intermediate for producing a dihydrochalcone, chalcone or flavanone followed by coupling of the sugar-intermediate adduct to a further intermediate for producing a dihydrochalcone, chalcone or flavanone, and transforming the product thereof into a compound of formula 1 or an analogue or derivative thereof.

  公开了一种合成Aspalathin及其类似物或衍生物的方法。该方法包括合成式1或其类似物或衍生物（I）的化合物，其中R1、R2、R3、R4、R5、R6、R7、R8、R9和R10中的每一个都是独立地选自-H、-OH、烃基、糖基和-OR15的群组；R15选自氢、烃基（例如甲氧基或乙氧基）、酰基和苄基的群组；R11、R12、R13和R14独立地选自-H、烃基、糖基、酰基和苄基的群组。该方法包括将糖与二氢黄烷酮、黄烷酮或黄酮偶联，或将糖与产生二氢黄烷酮、黄烷酮或黄酮的中间体偶联，然后将糖-中间体加合物与产生二氢黄烷酮、黄烷酮或黄酮的进一步中间体偶联，并将其产物转化为式1或其类似物或衍生物的化合物。
• Method for the Synthesis of Aspalathin and Analogues Thereof
  申请人：Van der Westhuizen Jan Hendrik

  公开号：US20130018182A1

  公开（公告）日：2013-01-17

  A method of synthesising Aspalathin and its analogues or derivatives is disclosed. The method comprises synthesising a compound of formula 1 or its analogues or derivatives: wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 is independently selected from the group consisting of —H, —OH, hydrocarbyl groups, saccharide moieties and —OR 15 ; R 15 is selected from the group consisting of hydrogen, a hydrocarbyl group (e.g. methoxy or ethoxy), an acyl group and a benzyl group; and R 11 , R 12 , R 13 and R 14 are independently selected from the group consisting of —H, hydrocarbyl groups, saccharide moieties, an acyl group and a benzyl group. The method comprises the step of coupling a sugar to a dihydrochalcone, chalcone or flavanone, or coupling the sugar to an intermediate for producing a dihydrochalcone, chalcone or flavanone followed by coupling of the sugar-intermediate adduct to a further intermediate for producing a dihydrochalcone, chalcone or flavanone, and transforming the product thereof into a compound of formula 1 or an analogue or derivative thereof.

  公开了一种合成Aspalathin及其类似物或衍生物的方法。该方法包括合成式1或其类似物或衍生物的化合物：其中R1、R2、R3、R4、R5、R6、R7、R8、R9和R10中的每一个都是独立选择自羟基、烃基、糖基团和—OR15的群组；R15选择自氢、烃基（例如甲氧基或乙氧基）、酰基和苄基；而R11、R12、R13和R14则独立选择自—H、烃基、糖基团、酰基和苄基的群组。该方法包括将糖与二氢黄烷酮、黄烷酮或黄酮偶联，或将糖与用于产生二氢黄烷酮、黄烷酮或黄酮的中间体偶联，然后将糖-中间体加合物偶联到用于产生二氢黄烷酮、黄烷酮或黄酮的进一步中间体上，并将其转化为式1或其类似物或衍生物的化合物。
• Aroma Composition to Reduce or Suppress Undesirable Bitter and Astringent Taste Impressions of Sweeteners
  申请人：Riess Thomas

  公开号：US20100151055A1

  公开（公告）日：2010-06-17

  The invention concerns an aroma composition to reduce or suppress a bitter or astringent impression in the oral cavity, comprising (i) one or more sweeteners and (ii) one or more specific bitter-masking aroma substances and/or flavourings and optionally (iii) one or more sweetness intensifying aroma substances and/or sweeteners and optionally (iv) one or more inactive substances or carriers. The invention also concerns a preparation, containing such an aroma composition, the use of an aroma composition for reducing or eliminating a bitter and astringent effect of an artificial sweetener and a corresponding method for reducing or eliminating the bitter and astringent effect of a sweetener.

  本发明涉及一种香气组合物，用于减少或抑制口腔中的苦涩或涩感，包括（i）一种或多种甜味剂和（ii）一种或多种特定的苦味掩蔽香气物质和/或调味料，以及可选的（iii）一种或多种增强甜味的香气物质和/或甜味剂，以及可选的（iv）一种或多种不活性物质或载体。本发明还涉及一种制剂，包含这样的香气组合物，使用香气组合物来减少或消除人工甜味剂的苦涩和涩感效果以及相应的方法。