白花前胡甲素 | 21499-23-0

• 物质功能分类: 生物化工 - 中草药成分
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 白花前胡甲素
• 中文别名: (+)-甜茶内酯
• 英文名称: phyllodulcin
• 英文别名: (+)-phyllodulcin；3R-phyllodulcin；(R)-8-hydroxy-3-(3-hydroxy-4-methoxy-phenyl)-isochroman-1-one；(R)-8-Hydroxy-3-(3-hydroxy-4-methoxy-phenyl)-isochroman-1-on；(3R)-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-3,4-dihydroisochromen-1-one
• CAS: 21499-23-0
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: PBILBHLAPJTJOT-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  白花前胡甲素 在 咪唑 、 四丁基氟化铵 、 三溴化硼 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 13.08h， 生成 3-(3,4-二羟基苯基)-8-羟基异苯并吡喃-1-酮
  参考文献：
  名称：

  Development of Bioactive Functions in Hydrangeae Dulcis Folium. VI. Syntheses of Thunberginols A and F and Their 3'-Deoxy-Derivatives Using Regiospecific Lactonization of Stilbene Carboxylic Acid: Structures and Inhibitory Activity on Histamine Release of Hydramacrophyllols A and B.

  摘要：

  氯化铜（II）介导的 2-羧基二苯乙烯的内酯化反应进行了区域特异性反应，生成了五元内酯，而使用 N-溴代琥珀酰亚胺和阳极氧化进行的溴内酯化反应则生成了六元内酯。利用这些区域特异性内酯化反应作为关键步骤，从phyllodulcin 和 hydrangenol 合成了抗过敏和抗菌的异香豆素和苯亚甲基酞thunberginols A 和 F 及其 3'-deoxyanalogs 。根据物理化学和化学证据，从绣线菊叶中分离出了两种名为水飞蓟醇 A 和 B 的邻苯二甲酸盐，并确定了它们的立体结构，其中包括应用氯化铜（II）内酯化法从水飞蓟醇合成了水飞蓟醇 A 和 B。此外，还发现水合麦考酚 A 和 B 对抗原-抗体反应诱导的大鼠腹腔渗出细胞释放组胺具有抑制作用。

  DOI：

  10.1248/cpb.44.1890
• 作为产物：
  描述：

  (3-acetyloxy-2-ethoxycarbonylbenzyl)-triphenylphosphonium bromide 在 palladium on activated charcoal 吡啶 、 氢氧化钾 、 氢气 、 sodium ethanolate 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 29.88h， 生成 白花前胡甲素
  参考文献：
  名称：

  Enantiodifferentiation in Taste Perception of the phyllodulcins

  摘要：

  Both enantiomers of phyllodulcin 1 have been prepared. Ester 2 was synthesized in a Wittig reaction from O-benzyl isovanillin. The corresponding stilbene carboxylic acid 3 could be cyclized with CF3CO2H to produce the 3'-benzyl ether 4 of (+/-)-phyllodulcin. Acylation with (1R,4S)-camphanoyl chloride gave first 5 and after hydrogenolysis of the benzyl ether group in 5 the diastereomeric esters 6. The diastereomerically pure 8-(1R,4S)-camphanoate (+)-6 of (R)-phyllodulcin could be isolated by repeated recrystallization. With (1S,4R)-camphanoyl chloride the enantiomeric 8-(1S,4R)-camphanoate (-)-6 of O-phyllodulcin could be prepared via ent-5 from a mixture of the diastereomeric esters ent-6. Ethanolysis of (+)-6 gave (R)-phyllodulcin [(+)-1] with 99% ee. The enantiomeric (S)-(-)-1 with 98% ee could be obtained from (-)-6. While (+)-1, the enantiomer occuring in fermented leaves of amacha, has an intense sweet taste, the enantiomer (-)-1 is completely tasteless.

  DOI：

  10.1016/0957-4166(95)00367-x

文献信息

• [EN] AMINO ACID DERIVATIVES AND THEIR USE AS FLAVOR MODIFIERS<br/>[FR] DÉRIVÉS D'ACIDES AMINÉS ET LEUR UTILISATION EN TANT QUE MODIFICATEURS DE GOÛT
  申请人：FIRMENICH & CIE

  公开号：WO2021209345A1

  公开（公告）日：2021-10-21

  The present invention provides derivatives of glutamine of formula (I) and derivatives of arginine of formula (II), and the use of such compounds as flavor modifiers. The invention further provides the use of such derivatives of glutamine and arginine to enhance the salty and umami taste of ingestible compositions as ingestible compositions that include such derivatives of glutamine and arginine and bulking agents.

  本发明提供了公式(I)的谷氨酰衍生物和公式(II)的精氮酸衍生物，以及将这些化合物用作风味调节剂的用途。该发明进一步提供了利用这些谷氨酰和精氮酸衍生物增强可摄入组合物的咸味和鲜味的用途，作为包含这些谷氨酰和精氮酸衍生物以及增稠剂的可摄入组合物。
• [EN] ORGANIC COMPOUNDS<br/>[FR] COMPOSÉS ORGANIQUES
  申请人：GIVAUDAN SA

  公开号：WO2021102896A1

  公开（公告）日：2021-06-03

  Disclosed are TRPM8 modulators as defined by formula (I) for achieving a cooling effect on skin and mucousa.

  公开了根据式(I)定义的TRPM8调节剂，用于在皮肤和粘膜上实现降温效果。
• [EN] SUBSTITUTED AZACYLES AS TRMP8 MODULATORS<br/>[FR] AZACYLES SUBSTITUÉS EN TANT QUE MODULATEURS DE TRPM8
  申请人：GIVAUDAN SA

  公开号：WO2021074281A1

  公开（公告）日：2021-04-22

  Disclosed are TRPM8 modulators as defined by formula (I) for achieving a cooling effect on skin and mucousa.

  公开的是根据公式(I)定义的TRPM8调节剂，用于实现皮肤和粘膜的冷却效果。
• 1H-pyrrole-2,4-dicarbonyl-derivatives and their use as flavoring agents
  申请人：IMAX Discovery GmbH

  公开号：EP2832233A1

  公开（公告）日：2015-02-04

  The present invention primarily relates to 1H-pyrrole-2,4-dicarbonyl-derivatives of Formula (I) wherein R1, R2, R3, Z. Z' and J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) or of a mixture of compounds of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

  本发明主要涉及式(I)的1H-吡咯-2,4-二羰基衍生物，其中R1、R2、R3、Z、Z'和J按描述定义，及其混合物，以及用作调味剂的使用。根据本发明的化合物适用于生产、赋予或增强鲜味。本发明进一步涉及包含式(I)化合物或式(I)化合物混合物的有效量的调味混合物、口腔消费的组成物以及即食、即用和半成品，以及用于生产、赋予、改变和/或增强特定风味印象的特定方法。
• Imidazo[1,2-a]pyridine-ylmethyl-derivatives and their use as flavoring agents
  申请人：IMAX Discovery GmbH

  公开号：EP2832234A1

  公开（公告）日：2015-02-04

  The present invention primarily relates to imidazo[1,2-a]pyridine-ylmethyl-derivatives of Formula (I) wherein R1, R2, X, W e J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

  本发明主要涉及式(I)的咪唑[1,2-a]吡啶基甲基衍生物，其中R1、R2、X、W和J如描述中定义，以及涉及它们的混合物和使用它们作为调味剂。根据本发明的化合物适合于产生、赋予或增强鲜味。本发明进一步涉及调味混合物、口腔摄入的配方以及包含有效量的式(I)化合物的即食、即用和半成品，以及用于生产、赋予、改变和/或增强特定风味印象的特定方法。