3-O-acetyltaxifolin | 78834-97-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3-O-acetyltaxifolin
• 英文别名: dihydroquercetin 3-acetate；[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-2,3-dihydrochromen-3-yl] acetate
• CAS: 78834-97-6
• 化学式: C₁₇H₁₄O₈
• 分子量: 346.293
• InChiKey: NPWRSXJQDKRXOR-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 3-O-acetyltaxifolin 以 吡啶 为溶剂， 生成 taxifolin pentaacetate
  参考文献：
  名称：

  Potential sweetening agents of plant origin. 13. An intensely sweet dihydroflavonol derivative based on a natural product lead compound

  摘要：

  The dihydroflavonol dihydroquercetin 3-acetate (1) was isolated as a sweet constituent of the young shoots of Tessaria dodoneifolia (Hook. & Arn.) Cabrera (Compositae). Compound 1 and dihydroquercetin 3-acetate 4'-(methyl ether) (2), a novel synthetic analogue of this natural product lead compound, were rated by a taste panel as being 80 and 400 times sweeter than a 2% w/v sucrose solution, respectively. Synthetic dihydroquercetin 4'-(methyl ether) (3) showed a reduced sweetness intensity when compared to 2, while (+)-dihydroquercetin (4) was devoid of sweetness. Dihydroflavonol derivatives 1-3 represent a new class of potentially noncaloric and noncariogenic intense sweeteners.

  DOI：

  10.1021/jm00401a030
• 作为产物：
  描述：

  taxifolin pentaacetate 在 sodium sulfite 作用下， 以 甲醇 为溶剂， 反应 41.0h， 以70%的产率得到3-O-acetyltaxifolin
  参考文献：
  名称：

  Crystal structures of dihydroquercetin 3-acetate and dihydroquercetin 3,3'4',7-tetraacetate: hydrogen bonding in 5-hydroxyflavanones

  摘要：

  二氢槲皮素3-醋酸酯和二氢槲皮素3,3',4',7-四醋酸酯的分子结构是通过单晶X射线分析确定的。将它们的晶体数据与16种已知的5-羟基黄酮类化合物进行比较，显示了分子内O(5)-H···O(4)=C氢键的存在，以及两个芳香环几乎垂直取向和杂环环的偏好沙发构象。化合物3的晶体包装模式中的主要稳定力是分子间氢键。关键词：晶体结构、二氢槲皮素、黄酮类化合物、氢键。

  DOI：

  10.1139/v99-140

文献信息

• [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。
• Epimerization, transacylation and bromination of dihydroquercetin acetates; synthesis of 8-bromodihydroquercetin
  作者：Eberhard Kiehlmann、Monica Szczepina

  DOI：10.2478/s11532-011-0032-8

  日期：2011.6.1

  acetyl transfer. Dhq 7,3′,4′-triacetate yields exclusively dhq 3′,4′-di- and 3,7,3′,4′-tetraacetate under these conditions. The acetylation/deacetylation reactions are accompanied by partial epimerization: 3 new acetates with 2,3-cis stereochemistry (dhq 3-, 3,7,3′,4′-tetra- and penta-) were identified. Dhq and its 3,7,3′,4′-tetraacetate undergo regiospecific dibromination at C-6 and C-8 with excess N-bromosuccinimide

  二氢槲皮素 (dhq) 及其 3-乙酸酯在没有碱催化剂的情况下与乙酸酐反应，生成部分乙酰化产物的混合物。三种新酯通过 NMR 光谱表征为 dhq 3,7,3'-三乙酸酯、3,7,4'-三乙酸酯和 5,7,3',4'-四乙酸酯。在其熔点，纯 dhq 3,7,3',4'-四乙酸酯通过分子间乙酰转移部分转化为 dhq 3,3',4'-三乙酸酯和 dhq 五乙酸酯。在这些条件下，Dhq 7,3',4'-三乙酸酯仅产生 dhq 3',4'-二-和 3,7,3',4'-四乙酸酯。乙酰化/去乙酰化反应伴随着部分差向异构化：鉴定出 3 种具有 2,3-顺式立体化学（dhq 3-, 3,7,3',4'-tetra- 和 penta-）的新乙酸酯。Dhq 及其 3,7,3',
• Five diterpenes and other constituents from nine Baccharis species
  作者：Ferdinand Bohlmann、Christa Zdero、Michael Grenz、Autar K. Dhar、Harold Robinson、Robert M. King

  DOI：10.1016/0031-9422(81)85107-2

  日期：1981.1

  Abstract The investigation of nine Baccharis species afforded, in addition to known compounds, three new clerodane derivatives related to bacchotricuneatin B, two ent -labdane derivatives, two 3-acetoxyflavanones, a benzofuran derivative and a chromene. The overall picture of the chemistry of this large genus is still not very clear.

  摘要 除已知化合物外，对九种 Baccharis 的研究还提供了三种与 bacchotricuneatin B 相关的新克罗丹衍生物、两种 ent-labdane 衍生物、两种 3-乙酰氧基黄烷酮、一种苯并呋喃衍生物和一种色烯。这个大属的化学整体图仍然不是很清楚。
• FLAVANONE DERIVATIVES AND THEIR USE AS SWEETNESS ENHANCERS
  申请人：Firmenich SA

  公开号：US20220273012A1

  公开（公告）日：2022-09-01

  The present disclosure generally provides a class of flavanone derivatives and their use as sweetness enhancers. In some aspects, the disclosure provides certain compositions that include such flavanone derivatives, such as compositions that include such flavanone derivatives and one or more other sweeteners. In some other aspects, the disclosure provides methods of reducing the caloric content of a sweetened article, such as a sweetened food or beverage product.

  本公开说明通常提供一类黄酮酮衍生物及其作为增甜剂的用途。在某些方面，本说明提供包括这种黄酮酮衍生物的某些组合物，例如包括这种黄酮酮衍生物和一个或多个其他甜味剂的组合物。在其他一些方面，本说明提供减少含糖物品（例如含糖食品或饮料产品）的卡路里含量的方法。
• Methods for the enzymatic modification of steviol glycosides, modified steviol glycosides obtainable thereby, and the use thereof as sweeteners
  申请人：Rijksuniversiteit Groningen

  公开号：US10731195B2

  公开（公告）日：2020-08-04

  The present invention relates generally to the production of steviol glycosides. Provided is a method for enzymatically providing a modified steviol glycoside, comprising incubating a steviol glycoside substrate in the presence of sucrose and the glucansucrase GTF180 of Lactobacillus reuteri strain 180, or a mutant thereof having the desired transglycosylation activity. Also provided are modified steviol glycosides obtainable by a method of the invention, and the use thereof as low-glycemic sweetener.

  本发明一般涉及甜菊醇苷的生产。本发明提供了一种酶法提供改性甜菊醇苷的方法，包括在蔗糖和具有所需转糖活性的重酵母乳杆菌 180 株的葡聚糖酶 GTF180 或其突变体存在的情况下培养甜菊醇苷底物。本发明还提供了可通过本发明方法获得的改性甜菊糖苷，以及将其用作低糖甜味剂的方法。