cis-Zearalenone | 36455-70-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: cis-Zearalenone
• 英文别名: (S)-(-)-zearalenone；Z-zearalenone；cis-ZEN；(10'S)-zearalenone；Trans-zearalenone；(4S,12Z)-16,18-dihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraene-2,8-dione
• CAS: 36455-70-6
• 化学式: C₁₈H₂₂O₅
• 分子量: 318.37
• InChiKey: MBMQEIFVQACCCH-MIBUCLJRSA-N

物化性质

• 沸点：
  600.4±55.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)
• 碰撞截面：
  167 Ų [M-H]- [CCS Type: TW, Method: calibrated with polyalanine]

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 储存条件：
  -20°C

制备方法与用途

产品特性

玉米赤霉烯酮(Z)是由玉米赤霉菌、禾谷镰刀菌和兰线镰刀菌等真菌产生的一种具有雌激素毒性作用的真菌毒素。尽管其耐热性较强，在100°C下处理1小时才被完全破坏，但主要污染玉米、小麦、大米、大麦、小米和燕麦等谷物，尤其是玉米受感染的概率最高，也可通过饲料影响畜禽产品。

玉米赤霉烯酮对动物的作用类似雌激素，会导致体内雌激素水平过高。在急性中毒的情况下，会对神经系统、心脏、肾脏、肝脏和肺部产生毒性作用。主要机理是它会促使神经系统的亢奋，并在多个器官中形成出血点，从而导致动物突然死亡。猪是所有家畜中最敏感的动物，尤其是雌性更为敏感。

玉米赤霉烯酮中毒会导致家畜体重增长缓慢，器官重量发生变化、生育能力下降以及行为异常。常见的症状包括雌性动物不孕、流产或产弱仔；雄性动物可能出现雌性化现象。当饲料中含有的玉米赤霉烯酮浓度在1 mg/kg至5 mg/kg之间时，便会对动物产生影响。

此外，玉米赤霉烯酮还会引起中枢神经系统的中毒症状，如恶心、发冷、头痛、精神抑郁和共济失调等。根据规定，小麦和玉米中的玉米赤霉烯酮限量为60 μg/kg。

反应信息

• 作为反应物：
  描述：

  cis-Zearalenone 在 吡啶 、 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 4-acetyl-2-methyl-cis-zearalenone
  参考文献：
  名称：

  来自禾谷镰刀菌的乙酰化霉菌毒素

  摘要：

  摘要 除了玉米赤霉烯酮、脱氧雪腐镰刀菌烯醇和 15-乙酰脱氧雪腐镰刀菌烯醇外，还从玉米镰刀菌中分离出三种新的乙酰化真菌毒素：4-乙酰玉米赤霉烯酮、4-乙酰顺式玉米赤霉烯酮和 3,15-二乙酰脱氧雪腐镰刀菌烯醇。介绍了玉米赤霉烯酮衍生物的化学相关性和相关光谱数据。

  DOI：

  10.1016/0031-9422(89)85014-9
• 作为产物：
  描述：

  玉米烯酮 以 甲醇 为溶剂， 反应 70.0h， 生成 cis-Zearalenone
  参考文献：
  名称：

  来自禾谷镰刀菌的乙酰化霉菌毒素

  摘要：

  摘要 除了玉米赤霉烯酮、脱氧雪腐镰刀菌烯醇和 15-乙酰脱氧雪腐镰刀菌烯醇外，还从玉米镰刀菌中分离出三种新的乙酰化真菌毒素：4-乙酰玉米赤霉烯酮、4-乙酰顺式玉米赤霉烯酮和 3,15-二乙酰脱氧雪腐镰刀菌烯醇。介绍了玉米赤霉烯酮衍生物的化学相关性和相关光谱数据。

  DOI：

  10.1016/0031-9422(89)85014-9

文献信息

• Biomimetic Synthesis of Resorcylate Natural Products Utilizing Late Stage Aromatization: Concise Total Syntheses of the Marine Antifungal Agents 15G256ι and 15G256β
  作者：Ismael Navarro、Jean-François Basset、Séverine Hebbe、Sarah M. Major、Thomas Werner、Catherine Howsham、Jan Bräckow、Anthony G. M. Barrett

  DOI：10.1021/ja803445u

  日期：2008.8.1

  sequential reaction with potassium carbonate and methanolic hydrogen chloride to give resorcylate esters. The reaction was applied in the total synthesis of the marine antifungal agents 15G256beta (1), 15G256iota (2), and 15G256pi (3) and the mycotoxin S-(-)-zearalenone (4).

  Diketo-1,3-dioxin-2-ones 在 110 摄氏度的甲苯中加热后经历了逆狄尔斯-阿尔德反应，生成 alpha、gamma、-triketo-ketenes。这些用醇捕获以提供 2,4,6-三酮羧酸酯，其通过与碳酸钾和甲醇氯化氢的顺序反应顺利芳构化以得到间苯二酸酯。该反应用于海洋抗真菌剂 15G256beta (1)、15G256iota (2) 和 15G256pi (3) 和霉菌毒素 S-(-)-玉米赤霉烯酮 (4) 的全合成。
• Cis-zearalanone, cis-zearalenol, and cis-zearalene
  申请人：IMC Chemical Group, Inc.

  公开号：US04052414A1

  公开（公告）日：1977-10-04

  Cis isomers of compounds represented by the formula ##STR1## are prepared by electromagnetic irradiation (about 2800 to 3500 angstroms wavelength) of their respective trans isomers. The cis isomers of the compounds of this invention are of the class of compounds known to exhibit anabolic and estrogenic activity and may be employed as animal growth promoting agents.

  通过电磁辐射（大约在2800到3500埃波长）其相应的反式异构体，制备了由公式##STR1##表示的化合物的顺式异构体。本发明的化合物的顺式异构体属于已知具有合成代谢和雌激素活性的化合物类，可用作动物生长促进剂。
• <i>In Vitro</i> Phase I Metabolism of <i>cis</i>-Zearalenone
  作者：Sarah S. Drzymala、Antje J. Herrmann、Ronald Maul、Dietmar Pfeifer、Leif-Alexander Garbe、Matthias Koch

  DOI：10.1021/tx500312g

  日期：2014.11.17

  The present study investigates the in vitro phase I metabolism of cis-zearalenone (cis-ZEN) in rat liver microsomes and human liver microsomes. cis-ZEN is an often ignored isomer of the trans-configured Fusarium mycotoxin zearalenone (transZEN). Upon the influence of (UV-) light, trans-ZEN isomeriXes to cis-ZEN. Therefore, cis-ZEN is also present in food and feed. The aim of our.study was to evaluate the in vitro phase I metabolism of cis-ZEN in comparison to that of trans-ZEN. As a result, an extensive thetabolizatiOn cis-ZEN is observed for rat and human liver inicrosoines as analyzed by,IIPLC-MS/MS and high- HO resolution MS. Kinetic Investigations based on the substrate depletion approach showed no significant difference in rate cis-zearalenone constants and half-live for,cis and trans-ZEN in rat microsomes. In contrast, cis-ZEN Wa, depleted about 1.4-fold faster than transZEN in human microgornes. The metabolite pattern of cis-ZEN revealecLa total of 10 phase I'metabolites. Its reduction products, a- and 13-cis-zearalenol (beta and fl-cis-ZEL), were found as metabolites in both species, with a-cis-ZEI, being a major metabolite in rat liver microsomes. Both compounds were identified' by co-chromatography with synthesized authentic standards. A further major metabolite in rat microsomes was Monohydroxylated cis-ZEN. In human rnicrOsornes, monohydroxylated cis-ZEN is the single dominant peak of the metabolite profile. Our study discloses three metabolic pathways for cis-ZEN: reduction of the keto-group, monohydroxylation, and a combination of both. Because these routes have been reported for trans-ZEN, we conclude that the phase I metabolism of cis-ZEN is essentially similar to that of its trans isomer. As trans-ZEN is prone to metabolic activation, leading to the formation of more estrogenic metabolites, the novel metabolitWof cisZEN reported in this study, in particular a-cis-ZEL, might also show higheri estrogenicity.
• Determination of the conformation of E and Z zearalenone and Their 7α- and 7β-Hydroxy Congeners
  作者：Mirjana Gelo、Zlata Raza、Vitomir Šunjić、Jia Guo、Günther Snatzke

  DOI：10.1016/s0957-4166(00)86149-2

  日期：1991.1

  The CD spectra of some resorcylic acid macrocyclic lactones (RAL) are reported. The spectra of the E,Z-isomeric ketones 1,6 are very similar in shape and magnitude. The Cotton effects of the 7-alpha-alcohols 2 and 7 are also of the same shape, but the DELTA-epsilon-values of 7 are only ca. 50% of those of the others. The E-7-beta-ol 3 gives a completely different CD, whereas in the Z-series 8 shows a similar CD curve as 6 and 7, but with again reduced magnitude. The CDs of the acetates 4 and 5 are very similar to those of the corresponding alcohols 2 and 3, resp. The effect of the 7-alpha- and 7-beta-hydroxy or acetoxy group on the absolute conformation of the "chain" from C(5) to C(10) is thus transmitted to the absolute value of the torsional angle of the inherently chiral chromophore C(11)-C(12)-C(12a)-C(1a)-C(= O)O in 2,3 and 4,5, resp. The CD spectra of the E,Z-isomers do not exhibit straightforward correlation with the configuration around the C = C double bond.
• MUNOZ, L.;CASTRO, J. L.;CARDELLE, M.;CASTEDO, L.;RIGUERA, R., PHYTOCHEMISTRY, 28,(1989) N 1, C. 83-85
  作者：MUNOZ, L.、CASTRO, J. L.、CARDELLE, M.、CASTEDO, L.、RIGUERA, R.

  DOI：——

  日期：——