2(R)-Hydroxy-2-methylbutyronitrile-beta-D-glucopyranoside | 534-67-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2(R)-Hydroxy-2-methylbutyronitrile-beta-D-glucopyranoside
• 英文别名: 2-methyl-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutanenitrile
• CAS: 534-67-8
• 化学式: C₁₁H₁₉NO₆
• 分子量: 261.27
• InChiKey: WEWBWVMTOYUPHH-UHFFFAOYSA-N

物化性质

• 熔点：
  106 - 109°C
• 溶解度：
  DMSO（轻微）、甲醇（轻微）、水（轻微、加热、超声处理）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  7

ADMET

代谢

当暴露于人体肠道中的酶和肠道菌群时，毒藜碱可以分解为有毒的化学物质氢氰酸。这是通过存在于植物细胞壁中的亚麻酸酶发生的。咀嚼植物允许酶接触毒藜碱，将其转化为丙酮氰醇，然后丙酮氰醇自行分解为氢氰酸。（L630, L1240）有机腈通过肝脏中的细胞色素P450酶的作用转化为氰化物离子。氰化物迅速被吸收并在全身分布。氰化物主要通过罗丹酶或3-巯基丙酸硫转移酶代谢为硫氰酸盐。氰化物代谢物通过尿液排出。（L96）

Upon exposure to enzymes and gut flora in the human intestine, lotaustralin can decompose to the toxic chemical hydrogen cyanide. This occurs via the enzyme linamarase, which is found in the cell wall of the plant. Chewing of the plant allows the enzyme to contact the lotaustralin converting it into acetone cyanohydrin, which then spontaneously decomposes to hydrogen cyanide. (L630, L1240) Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

有机腈在体内和体外都会分解成氰化物离子。因此，有机腈的主要毒性机制是它们产生有毒的氰化物离子或氢氰酸。氰化物是电子传递链第四复合体（存在于真核细胞线粒体膜中）中的细胞色素c氧化酶的抑制剂。它与这种酶中的三价铁原子形成配合物。氰化物与这种细胞色素的结合阻止了电子从细胞色素c氧化酶传递到氧气。结果，电子传递链被中断，细胞无法再通过有氧呼吸产生ATP能量。主要依赖有氧呼吸的组织，如中枢神经系统和心脏，受到特别影响。氰化物也通过绑定过氧化氢酶、谷胱甘肽过氧化物酶、变性血红蛋白、羟钴胺素、磷酸酶、酪氨酸酶、抗坏血酸氧化酶、黄嘌呤氧化酶、琥珀酸脱氢酶和Cu/Zn超氧化物歧化酶产生一些毒性效应。氰化物与变性血红蛋白中的三价铁离子结合形成无活性的氰化变性血红蛋白。

Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

膳食中暴露于洛托乌斯酸被报告为发展葡萄糖不耐症和糖尿病的一个风险因素。它还可能引起被称为konzo的上运动神经元疾病。(L630, L1240)

Dietary exposure to lotaustralin has been reported as a risk factor in developing glucose intolerance and diabetes. It may also cause the upper motor neuron disease known as konzo. (L630, L1240)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口腔

Oral

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

氰化物中毒的表现包括快速、深大的呼吸和呼吸急促，全身无力，眩晕，头痛，头晕，混乱，抽搐/癫痫发作，最终失去意识。

Cyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97)

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• WGK Germany：
  3

制备方法与用途

lotaustralin 是一种氰苷类化合物。