6-羟基山柰酚 | 4324-55-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 6-羟基山柰酚
• 中文别名: 6-羟基山奈酚
• 英文名称: 3,4',5,6,7-pentahydroxyflavone
• 英文别名: 6-Hydroxykaempferol；6-hydoxykaempferol；3,5,6,7-tetrahydroxy-2-(4-hydroxy-phenyl)-chromen-4-one；3,5,6,7-Tetrahydroxy-2-(4-hydroxy-phenyl)-chromen-4-on；3,5,6,7,4'-Pentahydroxy-flaven-4-on；3,5,6,7-tetrahydroxy-2-(4-hydroxyphenyl)chromen-4-one
• CAS: 4324-55-4
• 化学式: C₁₅H₁₀O₇
• 分子量: 302.24
• InChiKey: LFPHMXIOQBBTSS-UHFFFAOYSA-N

物化性质

• 熔点：
  310-315 °C (decomp)
• 沸点：
  669.3±55.0 °C(Predicted)
• 密度：
  1.799±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  UDP-D-[U-(14)C]glucose 、 6-羟基山柰酚 在 petals of Rudbeckia hirta enzyme preparation 作用下， 生成
  参考文献：
  名称：

  Formation of UV-honey guides in Rudbeckia hirta

  摘要：

  The UV-honey guides of Rudbeckia hirta were investigated by UV-photography, reflectance spectroscopy, LC-MS analysis and studies of the enzymes involved in the formation of the W-absorbing flavonols present in the petals. It was shown for the first time that the typical bull's eye pattern is already established at the early stages of flower anthesis on the front side of the petal surface, but is hidden to pollinators until the buds are open and the petals are unfolded. The rear side of the petals remains W-reflecting during the whole flower anthesis. Studies on the local distribution of 19 flavonols across the petals confirmed that the majority are concentrated in the basal part of the ray flower. However, in contrast to the earlier studies, eupatolitin 3-O-glucoside (6,7-dimethoxyquercetin 3-O-glucoside) was present in both the basal and apical parts of the petals, whereas eupatolin (6,7-dimethoxyquercetin 3-O-rhamnoside) was exclusively found in the apical parts. The enzymes involved in the formation of the flavonols in R. hirta were demonstrated for the first time. These include a rare flavonol 6-hydroxylase, which was identified as cytochrome P450-dependent monooxygenase and did not accept any methylated flavonol as substrate. All enzymes were present in the basal and apical parts of the petals, although some of them clearly showed higher activities in the basal part. This indicates that the local accumulation of flavonols in R. hirta is not achieved by a locally restricted presence of the enzymes involved in flavonol formation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.04.017
• 作为产物：
  描述：

  3,4,5-三甲氧基苯酚 在 氢氧化钾 、 三氟化硼乙醚 、 碘 、 sodium acetate 、 三溴化硼 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 20.0h， 生成 6-羟基山柰酚
  参考文献：
  名称：

  Inhibitory Effects of 5,6,7-Trihydroxyflavones on Tyrosinase

  摘要：

  从一组14种羟基黄酮中，天然存在的黄酮类化合物Baicalein（1）、6-羟基芹菜素（6）、6-羟基高良姜素（13）和6-羟基山柰酚（14）对酪氨酸酶关于L-多巴显示出高抑制效果，其中每一种5,6,7-三羟基黄酮1、6、13或14作为单酚酶的辅因子。此外，6-羟基山柰酚（14）表现出最高的活性，并且与L-多巴相比是酪氨酸酶的竞争性抑制剂。5,6,7-三羟基黄酮1、6、13或14也显示出高抗氧化活性。因此，我们得出结论，5,6,7-三羟基黄酮除了其抗氧化特性外，还具有良好的脱色素抑制效果，是有用的脱色素剂。

  DOI：

  10.3390/12010086

文献信息

• Studies of the Selective<i>O</i>-Alkylation and Dealkylation of Flavonoids. XVIII. A Convenient Method for Synthesizing 3,5,6,7-Tetrahydroxyflavones
  作者：Tokunaru Horie、Takashi Kobayashi、Yasuhiko Kawamura、Isao Yoshida、Hideaki Tominaga、Kazuyo Yamashita

  DOI：10.1246/bcsj.68.2033

  日期：1995.7

  In the demethylation of 6-hydroxy-3,4′,7-trimethoxy-5-(tosyloxy)flavone with anhydrous aluminum bromide, the 5-tosyloxyl group was eliminated with bromination to give 8-bromo-3,6,7-trihydroxy-4′-methoxyflavone as the main product. When anhydrous aluminum chloride was used in the demethylation of the acetate, the 5-tosyloxyl group was cleaved prior to the demethylation to give 5,6,7-trihydroxy-3,4′-dimethoxyflavone. Demethylation of 6-hydroxy-4′,5,7-trimethoxy-3-(tosyloxy)flavone and its acetate with the bromide or chloride afforded the 5,6,7-trihydroxyflavone without the cleavage of the 3-tosyloxyl group, but was not suitable for the general synthesis of the 3,5,6,7-tetrahydroxyflavones because of the difficulty in removing the protecting group. Consequently, it was found that the direct demethylation of 3,6-dihydroxy-5,7-dimethoxyflavones with anhydrous aluminum chloride–sodium iodide in acetonitrile was the most useful general method for synthesizing 3,5,6,7-tetrahydroxyflavones. Additionally, the reported structures of two natural flavones were revised.

  在无水溴化铝的脱甲基反应中，6-羟基-3,4′,7-三甲氧基-5-(托烯氧基)黄酮的5-托烯氧基基团在溴化作用下被消除，生成8-溴-3,6,7-三羟基-4′-甲氧基黄酮作为主要产物。当使用无水氯化铝进行醋酸酯的脱甲基反应时，5-托烯氧基基团在脱甲基前被切断，生成5,6,7-三羟基-3,4′-二甲氧基黄酮。6-羟基-4′,5,7-三甲氧基-3-(托烯氧基)黄酮及其醋酸酯与溴化物或氯化物的脱甲基反应生成5,6,7-三羟基黄酮，而不切断3-托烯氧基基团，但由于去除保护基团的困难，不适合于3,5,6,7-四羟基黄酮的一般合成。因此，发现采用无水氯化铝-碘化钠在乙腈中对3,6-二羟基-5,7-二甲氧基黄酮进行直接脱甲基反应是合成3,5,6,7-四羟基黄酮的最有效的一般方法。此外，修订了两种天然黄酮的已报告结构。
• [EN] CONSTRUCTS AND METHODS FOR BIOSYNTHESIS OF GALANTHAMINE<br/>[FR] CONSTRUCTIONS ET PROCÉDÉS POUR LA BIOSYNTHÈSE DE LA GALANTHAMINE
  申请人：DONALD DANFORTH PLANT SCI CT

  公开号：WO2015196100A1

  公开（公告）日：2015-12-23

  The present disclosure relates generally to the identification of enzymes within the Amaryllidaceae alkaloid biosynthetic pathway as well as to engineering transgenic organisms for the production of galanthamine and/or hemanthamine and/or lycorine. Disclosed herein is the isolation and characterization of cDNAs and encoded norbelladine 4'-0-methyltransferase, CYP96T1-3, and norbelladine synthase/reductase involved in the biosynthesis of galanthamine and haemanthamine. The invention relates to a transgenic plant, comprising within its genome, and expressing, a heterologous nucleotide sequence coding for a class I O-methyltransferase, wherein the O-methyltransferase is norbelladine 4'-0-methyltransferase. In one embodiment, the norbelladine 4'-0-methyltransferase is selected from among NpN40MT1, NpN40MT2, NpN40MT3, NpN40MT4, and NpN40MT5. The invention further contemplates a method of making a transgenic plant.

  本公开涉及总体上识别阿马里利达斯碱生物合成途径中的酶，以及为生产迎春碱和/或血红碱和/或石蒜碱而工程化转基因生物。本公开揭示了所述cDNA的分离和表征，以及编码的norbelladine 4'-0-甲基转移酶、CYP96T1-3和norbelladine合成酶/还原酶，这些酶参与了迎春碱和血红碱的生物合成。该发明涉及一种转基因植物，其基因组中包含并表达了编码I类O-甲基转移酶的异源核苷酸序列，其中O-甲基转移酶是norbelladine 4'-0-甲基转移酶。在一个实施例中，norbelladine 4'-0-甲基转移酶从NpN40MT1、NpN40MT2、NpN40MT3、NpN40MT4和NpN40MT5中选择。该发明进一步考虑了一种制备转基因植物的方法。
• METHOD AND SYSTEM FOR EFFECTING CHANGES IN PIGMENTED TISSUE
  申请人：Moazed Kambiz Thomas

  公开号：US20110280909A1

  公开（公告）日：2011-11-17

  Methods and systems are described for a rapid and sustainable change in the pigment melanin content of melanocytes of the iris stroma, thereby to change the color of the eye. Also described are nanoparticle compositions for lightening the pigmented tissues or treating a pigmented tissue related disease.

  描述了一种快速和可持续改变虹膜基质黑色素含量的黑色素细胞的方法和系统，从而改变眼睛的颜色。还描述了用于淡化有色组织或治疗有色组织相关疾病的纳米颗粒组合物。
• Method and system for effecting changes in pigmented tissue
  申请人：Moazed Kambiz Thomas

  公开号：US20120207809A1

  公开（公告）日：2012-08-16

  Methods and systems are described for a rapid and sustainable change in the pigment melanin content of melanocytes of the iris stroma, thereby to change the color of the eye. Also described are compositions for lightening or darkening the pigmented tissues or treating a pigmented tissue disease.

  本文描述了一种快速和可持续改变虹膜基质黑素细胞中黑色素含量的方法和系统，从而改变眼睛的颜色。还描述了用于使色素组织变浅或变深或治疗色素组织疾病的组合物。
• Agent for lowering prolactin
  申请人：——

  公开号：US20040138297A1

  公开（公告）日：2004-07-15

  The present invention relates to a prolactin lowering drug containing at least one bicyclic diterpene of the labdane type. 1 wherein R1=H, C 1 to C 3 alkyl or C 1 to C 3 acyl.

  本发明涉及一种降低催乳素的药物，其中至少含有一种拉布烷类双环二萜。 1 其中 R1=H, C 1 至 C 3 烷基或 C 1 至 C 3 酰基。