(-)-phyllodulcin | 172588-04-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (-)-phyllodulcin
• 英文别名: 3S-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；(S)-8-Hydroxy-3-(3-hydroxy-4-methoxyphenyl)isochroman-1-one；(3S)-8-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-3,4-dihydroisochromen-1-one
• CAS: 172588-04-4
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: PBILBHLAPJTJOT-AWEZNQCLSA-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

反应信息

• 作为反应物：
  描述：

  盐酸 、 (-)-phyllodulcin 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Asahina; Asano, Chemische Berichte, 1931, vol. 64, p. 1252,1254, 1255

  摘要：

  DOI：
• 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 (-)-phyllodulcin
  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

• Süßmittelreduzierte Produkte, Aromamischungen dafür sowie Verfahren zum Herstellen solcher Produkte
  申请人：Symrise AG

  公开号：EP2298084A1

  公开（公告）日：2011-03-23

  Aromamischung, umfassend (i) einen oder mehrere süß schmeckende Stoffe, ausgewählt aus der Gruppe der natürlich vorkommenden süß schmeckenden Stoffe und deren physiologisch verträglichen Salzen ohne Phyllodulcin und dessen physiologisch verträglichen Salzen, und (ii) Phyllodulcin und/oder eines oder mehrere dessen physiologisch verträgliche Salze, wobei das Verhältnis des Sucroseäquivalenz der Konzentration des Stoffes oder der Stoffe der Gruppe (i) zur Sucroseäquivalenz der Konzentration des Stoffes oder der Stoffe der Gruppe (i) ≥ 2 ist.

  一种调味组合物，包括 (i) 一種或多種甜味物質，選自天然甜味物質及其生理上可接受 的鹽類，但不包括植物多糖及其生理上可接受的鹽類、 和 (ii) 植柔素和/或其一种或多种生理上可接受的盐、 其中第(i)组一种或多种物质浓度的蔗糖当量与第(i)组一种或多种物质浓度的蔗糖当量之比≥2。
• Reduced-sweetener products, flavoring mixtures for said reduced-sweetener products and process for the production of products of this type
  申请人：Reichelt Katharina

  公开号：US10624372B2

  公开（公告）日：2020-04-21

  A flavoring mixture, comprising (i) one or more sweet-tasting substances, selected from the group of naturally occurring sweet-tasting substances and the physiologically compatible salts thereof without phyllodulcin and the physiologically compatible salts thereof, and (ii) phyllodulcin and/or one or more of the physiologically compatible salts thereof, wherein the ratio of the sucrose equivalence of the concentration of the substance or substances of group (i) to the sucrose equivalence of the concentration of the substance or substances of group (i) is ≥2.

  一种调味混合物，包括 (i) 一种或多种甜味物质，选自天然甜味物质及其生理相容盐类，但不包括植醇霉素及其生理相容盐类、 和 (ii) 植柔素和/或一种或多种生理相容盐、 其中第(i)组物质浓度的蔗糖当量与第(i)组物质浓度的蔗糖当量之比≥2。
• REDUCED-SWEETENER PRODUCTS, FLAVORING MIXTURES FOR SAID REDUCED-SWEETENER PRODUCTS AND PROCESS FOR THE PRODUCTION OF PRODUCTS OF THIS TYPE
  申请人：Reichelt Katharina

  公开号：US20110076239A1

  公开（公告）日：2011-03-31

  A flavoring mixture, comprising (i) one or more sweet-tasting substances, selected from the group of naturally occurring sweet-tasting substances and the physiologically compatible salts thereof without phyllodulcin and the physiologically compatible salts thereof, and (ii) phyllodulcin and/or one or more of the physiologically compatible salts thereof, wherein the ratio of the sucrose equivalence of the concentration of the substance or substances of group (i) to the sucrose equivalence of the concentration of the substance or substances of group (i) is ≧2.
• Asahina; Asano, Chemische Berichte, 1931, vol. 64, p. 1252,1254, 1255
  作者：Asahina、Asano

  DOI：——

  日期：——
• Enantiodifferentiation in Taste Perception of the phyllodulcins
  作者：Reinhard Zehnter、Hans Gerlach

  DOI：10.1016/0957-4166(95)00367-x

  日期：1995.11

  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.