甘草异黄酮甲 | 66056-19-7

• 物质功能分类: 天然产物 - 黄酮类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 中文名称: 甘草异黄酮甲
• 中文别名: 甘草异黄酮A
• 英文名称: licoisoflavone A
• 英文别名: phaseoluteone；3-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxychromen-4-one
• CAS: 66056-19-7
• 化学式: C₂₀H₁₈O₆
• 分子量: 354.359
• InChiKey: KCUZCRLRQVRBBV-UHFFFAOYSA-N

物化性质

• 沸点：
  635.7±55.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 海关编码：
  2914400090

制备方法与用途

生物活性方面，Licoisoflavone A 是一种异黄酮类化合物，主要来源于甘草-Julifical。其能够抑制脂质过氧化，半数抑制浓度（IC50）为 7.2 μM。

反应信息

• 作为反应物：
  描述：

  甘草异黄酮甲 、 乙酸酐 在 sodium acetate 作用下， 生成 2',4',5,7-tetraacetoxy-3'-(3-methyl-2-butenyl)isoflavone
  参考文献：
  名称：

  Synthesis of Licoisoflavone A and Related Compounds

  摘要：

  用苯甲酰氯对 2′，4′，5，7-四羟基异黄酮进行部分苯甲酰化，得到 7-苯甲酰氧基-2′，4′，5-三羟基异黄酮。将 7-（苯甲酰氧基）异黄酮与 2-甲基-3-丁烯-2-醇缩合，然后水解生成 3′-（3-甲基-2-丁烯基）异黄酮，就得到了地衣异黄酮 A。它的 5′-（3-甲基-2-丁烯基）异构体也是用类似的方法从 5-苯甲酰氧基-2′,4′,7-三羟基异黄酮合成的。

  DOI：

  10.1246/bcsj.58.136
• 作为产物：
  描述：

  2'-羟基金雀异黄素 在 吡啶 、 dilute alkali 作用下， 生成 甘草异黄酮甲
  参考文献：
  名称：

  SYNTHESES OF LICOISOFLAVONE A AND 5′-ALKENYL ISOMER

  摘要：

  用苯甲酰氯对 2′，4′，5，7-四羟基异黄酮进行部分苯甲酰化，得到 7-苯甲酰氧基-2′，4′，5-三羟基异黄酮。将 7-苯甲酰氧基异黄酮与 2-甲基-3-丁烯-2-醇缩合，然后水解生成 3′-（3-甲基-2-丁烯基）异黄酮，得到地衣异黄酮 A。

  DOI：

  10.1246/cl.1982.675

文献信息

• Fad-dependent epoxidase as a key enzyme in fungal metabolism of prenylated flavonoids
  作者：Mitsuharu Tanaka、Satoshi Tahara

  DOI：10.1016/s0031-9422(97)00322-1

  日期：1997.10

  Crude protein extracts from Botrytis cinerea preincubated with 6-prenylnaringenin (6-PN) for 20 hr catalysed the prenyl epoxidation of 7-O-methyl-luteone. The resulting epoxide was non-enzymatically and slowly converted into the corresponding dihydrofurano derivative in a buffer solution at pH 7.5. Preparation of cell-free extracts in the presence of 6-PN from the mycelia without preincubation with 6-PN hardly showed the epoxidizing activity. These facts revealed that the substrate analogue 6-PN has a role as an enzyme inducer rather than stabilizer. The enzyme reaction depends on molecular oxygen and NADPH. Low amounts of FAD were necessary for maximal enzyme activity. The enzymatic activity was not inhibited by various inhibitors of cytochrome P-450 tested, in addition to carbon monoxide and cytochrome c. The results indicated that this enzyme does not belong to the monooxygenases dependent on cytochrome P-450, but to those dependent on FAD. About half of. the total enzyme activity was found in the 125 000 g supernatant, but the specific activity for the epoxidation reaction in the 125 000 g pellet was 3.7-fold higher than in the soluble fraction. The enzyme showed high specificity to monoprenyl isoflavones. Finally, a preliminary experiment using a cell-free system from white lupin hypocotyls resulted in formation of small amounts of an epoxide corresponding to 7-O-methyl-luteone used as the substrate. (C) 1997 Elsevier Science Ltd.
• Fungitoxic dihydrofuranoisoflavones and related compounds in white lupin, Lupinus albus
  作者：Satoshi Tahara、John L. Ingham、Shiro Nakahara、Junya Mizutani、Jeffrey B. Harborne

  DOI：10.1016/s0031-9422(00)84936-5

  日期：1984.8
• PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS
  申请人：McMaster University

  公开号：US20210380513A1

  公开（公告）日：2021-12-09

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).
• [EN] METHODS FOR PROMOTING JOINT AND BONE HEALTH<br/>[FR] PROCÉDÉS FAVORISANT LA SANTÉ DES OS ET ARTICULATIONS
  申请人：CARGILL INC

  公开号：WO2007139887A2

  公开（公告）日：2007-12-06

  [EN] The present invention provides methods for promoting bone and joint health with certain compositions described herein or with optionally enriched extracts of plant material comprising such compositions. The present invention provides methods for the treatment or regulation of, bone and joint conditions such as joint inflammation, joint swelling, joint pain, gout, childhood arthritis, lupus arthritis, rheumatoid arthritis, and osteoarthritis.
  [FR] La présente invention concerne des procédés destinés à favoriser la santé des os et des articulations grâce à certaines compositions décrites ci-après ou à des extraits éventuellement enrichis de matière végétale comprenant de telles compositions. La présente invention concerne des procédés destinés au traitement ou à la régulation de maladies des os et des articulations, telles que les inflammations articulaires, les oeèmes articulaires, les douleurs articulaires, la goutte, l'arthrite juvénile, l'arthrite de lupus, l'arthrite rhumatoïde et l'ostéoarthrite.