DL-萝卜硫素 N-乙酰基-L-半胱氨酸 | 334829-66-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: DL-萝卜硫素 N-乙酰基-L-半胱氨酸
• 中文别名: DL-萝卜硫素N-乙酰基-L-半胱氨酸；环己羧酸,4-乙炔基-,反-
• 英文名称: sulforaphane-N-acetyl-cysteine
• 英文别名: SFN-NAC；D,L-Sulforaphane N-Acetyl-L-cysteine；(2R)-2-acetamido-3-(4-methylsulfinylbutylcarbamothioylsulfanyl)propanoic acid
• CAS: 334829-66-2
• 化学式: C₁₁H₂₀N₂O₄S₃
• 分子量: 340.489
• InChiKey: IIHBKTCHILXGOT-KMYGYIBBSA-N

物化性质

• 熔点：
  106-108°C
• 密度：
  1.371±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（轻微加热）、甲醇（轻微）、水（轻微、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  172
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  三芥子酸甘油酯 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 DL-萝卜硫素 N-乙酰基-L-半胱氨酸
  参考文献：
  名称：

  Synthesis of isothiocyanate-derived mercapturic acids

  摘要：

  Twelve mercapturic acids derived from saturated and unsaturated aliphatic and aromatic isothiocyanates were synthesised, by adding isothiocyanate to a solution of N-acetyl-L-cysteine and sodium bicarbonate, in a typical yield of 77%. Isothiocyanates were synthesised first by adding the corresponding alkyl bromide to phthalimide potassium salt. The obtained N-alkyl-phthalimide was hydrazinolysed yielding the alkyl amine, which subsequently was reacted with thiophosgene yielding the isothiocyanate with an overall yield of 16%. Mercapturic acids in urine can serve as a biomarker of intake to determine the health promoting potential of isothiocyanates present in cruciferous vegetables. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00141-7

文献信息

• Discovery of a crystalline sulforaphane analog with good solid-state stability and engagement of the Nrf2 pathway in vitro and in vivo
  作者：Jeffrey Boehm、Roderick Davis、Claudia E. Murar、Tindy Li、Brent McCleland、Shuping Dong、Hongxing Yan、Jeffrey Kerns、Christopher J. Moody、Anthony J. Wilson、Alan P. Graves、Mary Mentzer、Hongwei Qi、John Yonchuk、Jen-Pyng Kou、Joseph Foley、Yolanda Sanchez、Patricia L. Podolin、Brian Bolognese、Catherine Booth-Genthe、Marc Galop、Lawrence Wolfe、Robin Carr、James F. Callahan

  DOI：10.1016/j.bmc.2018.12.026

  日期：2019.2

  The antioxidant natural product sulforaphane (SFN) is an oil with poor aqueous and thermal stability. Recent work with SFN has sought to optimize methods of formulation for oral and topical administration. Herein we report the design of new analogs of SFN with the goal of improving stability and drug-like properties. Lead compounds were selected based on potency in a cellular screen and physicochemical properties. Among these, 12 had good aqueous solubility, permeability and long-term solid-state stability at 23 degrees C. Compound 12 also displayed comparable or better efficacy in cellular assays relative to SFN and had in vivo activity in a mouse cigarette smoke challenge model of acute oxidative stress.
• Synthesis of isothiocyanate-derived mercapturic acids
  作者：Martijn Vermeulen、Binne Zwanenburg、Gordon J.F Chittenden、Hans Verhagen

  DOI：10.1016/s0223-5234(03)00141-7

  日期：2003.7

  Twelve mercapturic acids derived from saturated and unsaturated aliphatic and aromatic isothiocyanates were synthesised, by adding isothiocyanate to a solution of N-acetyl-L-cysteine and sodium bicarbonate, in a typical yield of 77%. Isothiocyanates were synthesised first by adding the corresponding alkyl bromide to phthalimide potassium salt. The obtained N-alkyl-phthalimide was hydrazinolysed yielding the alkyl amine, which subsequently was reacted with thiophosgene yielding the isothiocyanate with an overall yield of 16%. Mercapturic acids in urine can serve as a biomarker of intake to determine the health promoting potential of isothiocyanates present in cruciferous vegetables. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.