queretaroic acid | 511-82-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: queretaroic acid
• 英文别名: (2S,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 511-82-0
• 化学式: C₃₀H₄₈O₄
• 分子量: 472.709
• InChiKey: CZWBKSDPBWNHGO-AHJCBHEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 queretaroic acid 以 甲醇 为溶剂， 生成 methyl queretaroate
  参考文献：
  名称：

  New Triterpenic Saponins from the Aerial Parts of Medicago arabica (L.) Huds

  摘要：

  The reinvestigation of saponin composition from Medicago arabica from Italy allowed the detection of nineteen (1-19) saponins. All of them were purified by reverse-phase chromatography and their structures elucidated by spectroscopic and spectrometric (1D and 2D NMR; ESI-MS/MS) and chemical methods. Fourteen were known saponins, previously found in other plants including other Medicago, species. They have been identified as glycosides of oleanolic acid, 2 beta,3 beta-dihydroxyolean-12-en-28-oic acid, hederagenin, bayogenin and soyasapogenol B. Five saponins, identified as 3-O-[-alpha-L-arabinopyranosyl(1 -> 2)-beta-D-glucuronopyranosyl]-30-O-beta-D-glucopyranosyl 2 beta,3 beta,30-trihydroxyolean-12-en-28-oic acid (1), 3-O-[alpha-L-arabinopyranosyl(1 -> 2)-beta- -D-glucuronopyranosyl]-30-O-[beta-D-glucopyranosyl]3 beta,30-dihydroxyolean-12-en-28-oic acid (2), 3-O-[beta-D-glucuronopyranosyl]-30-O-[alpha-L-arabinopyranosyl(1 -> 2)-beta-D-glucopyranosyl]2 beta,3 beta,30-trihydroxyolean-12-en-28-oic acid (3), 3-O-[beta-D-glucuronopyranosyl]-30-O[alpha-L-arabinopyranosyl(1 -> 2)-beta-D-glucopyranosyl] 3 beta,30-dihydroxyolean-12-en-28-oic acid (4) and 3-O-[beta-D-glucuronopyranosyl]-30-O-[beta-D-glucopyranosyl] 2 beta,3 beta,30-trihydroxyolean-12-en-28-oic acid (5), are reported here as new natural compounds. These new saponins, possessing a hydroxy group at the 30-methyl position of the triterpenic skeleton, have never been previously found in the genus Medicago.

  DOI：

  10.1021/jf8036984
• 作为产物：
  描述：

  methyl queretaroate 在 氢氧化钾 作用下， 以 乙二醇 为溶剂， 生成 queretaroic acid
  参考文献：
  名称：

  Sapogenins of Clerodendron serratum

  摘要：

  DOI：

  10.1016/s0040-4020(01)82903-3

文献信息

• Hydroxylation of Oleanolic Acid to Queretaroic Acid by Cytochrome P450 from<i>Nonomuraea recticatena</i>
  作者：Yoshikazu FUJII、Shinji HIROSUE、Tadashi FUJII、Naoki MATSUMOTO、Hitosi AGEMATU、Akira ARISAWA

  DOI：10.1271/bbb.60126

  日期：2006.9.23

  A gene for cytochrome P450 (moxA) from Nonomuraea recticatena, coexpressed with camAB for pseudomonad redox partners in Escherichia coli, hydroxylated oleanolic acid to produce queretaroic acid. When we used the P450-induced whole-cell as a catalyst, only a small amount of queretaroic acid was produced, probably due to poor permeability of oleanolic acid into the E. coli cell. In an alternative approach with the cell-free reaction system, the conversion ratio increased up to 17%.

  来自 Nonomuraea recticatena 的细胞色素 P450 (moxA) 基因，与大肠杆菌中假单胞菌氧化还原伙伴的 camAB 共表达，羟基化齐墩果酸产生槲皮酸。当我们使用P450诱导的全细胞作为催化剂时，仅产生少量的克雷塔酸，这可能是由于齐墩果酸进入大肠杆菌细胞的渗透性差。在使用无细胞反应系统的替代方法中，转化率提高了 17%。
• Biotransformation of oleanolic and maslinic acids by Rhizomucor miehei
  作者：Antonio Martinez、Francisco Rivas、Alberto Perojil、Andres Parra、Andres Garcia-Granados、Antonia Fernandez-Vivas

  DOI：10.1016/j.phytochem.2013.05.011

  日期：2013.10

  Microbial transformation of oleanolic acid by Rhizomucor miehei produced three metabolites. A known compound, a 30-hydroxyl derivative (queretaroic acid), and two 7 beta,30- and 1 beta,30-dihydroxylated metabolites, respectively. The action of the same fungus (R. miehei) on maslinic acid produced an olean-11-en-28,13 beta-olide derivative, a metabolite hydroxylated at C-30, an 11-oxo derivative, and two metabolites with an 11 alpha,12 alpha-epoxy group, hydroxylated or not at C-30. Their structures were elucidated by extensive analyses of their spectroscopic data, and also by chemical correlations. (C) 2013 Elsevier Ltd. All rights reserved.
• Terpenoids. XXIV.¹ The Structure of the Cactus Triterpene Queretaroic Acid
  作者：Carl Djerassi、J. A. Henry、A. J. Lemin、T. Rios、G. H. Thomas

  DOI：10.1021/ja01596a060

  日期：1956.8
• TRITERPENOID SAPOGENIN PRODUCTION IN PLANT AND MICROBIAL CULTURES
  申请人：VIB VZW

  公开号：EP2847346A1

  公开（公告）日：2015-03-18
• US9994883B2
  申请人：——

  公开号：US9994883B2

  公开（公告）日：2018-06-12