Heratomin;6-[(3-甲基-2-丁烯-1-基)氧基]-2H-呋喃并[2,3-h]-1-苯并吡喃-2-酮 | 61265-06-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: Heratomin;6-[(3-甲基-2-丁烯-1-基)氧基]-2H-呋喃并[2,3-h]-1-苯并吡喃-2-酮
• 中文别名: 6-[(3-甲基-2-丁烯-1-基)氧基]-2H-呋喃并[2,3-H]-1-苯并吡喃-2-酮
• 英文名称: heratomin
• 英文别名: 6-(3-methylbut-2-enoxy)furo[2,3-h]chromen-2-one
• CAS: 61265-06-3
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: DSDJMMMGDPDPIX-UHFFFAOYSA-N

物化性质

• 密度：
  1.242

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

ADMET

毒理性

• 毒性总结

许多呋喃香豆素的作用机制是基于它们能够与DNA和其他细胞组分如RNA、蛋白质以及膜中存在的几种蛋白质（如磷脂酶A2和C、钙依赖性和cAMP依赖性蛋白激酶以及表皮生长因子）形成光加合物。呋喃香豆素在DNA碱基对之间插入，并在紫外线A照射后给出环加成物。Heratomin也是昆虫细胞色素P450的抑制剂。

The mechanism of action many furocoumarins is based on their ability to form photoadducts with DNA and other cellular components such as RNA, proteins, and several proteins found in the membrane such as phospholipases A2 and C, Ca-dependent and cAMPdependent protein-kinase and epidermal growth factor. Furocoumarins intercalate between base pairs of DNA and after ultraviolet-A irradiation, giving cycloadducts. Heratomin is aloso an inhibitor of insect cytochromes P450. (L579)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

未列入国际癌症研究机构(IARC)名录。IARC评估了其他呋喃香豆素类物质，将8-甲氧基补骨脂素归类为对人类致癌(第1组)，将5-甲氧基补骨脂素归类为可能对人类致癌(第2A组)，以及某些其他呋喃香豆素类物质归类为对人类致癌性无法分类(第3组)。(L135)

Not listed by IARC. IARC has assessed other furocoumarins, classifying 8-methoxypsoralen as carcinogenic to humans (Group 1), 5-methoxypsoralen as possibly carcinogenic to humans (Group 2A), and certain other furocoumarins as not being classifiable as to their carcinogenicity to humans (Group 3). (L135)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

呋喃香豆素中的8-甲氧基补骨脂素对人类具有致癌性，5-甲氧基补骨脂素也可能具有致癌性（L135）。一些来自小鼠研究的证据表明，当与UVA辐射暴露结合时，其他呋喃香豆素也具有致癌性（A15105）。SKLM认为，由于食用含有呋喃香豆素的食物通常量仍然显著低于光毒性剂量范围，因此由食用这些食物引起的皮肤癌的额外风险是不显著的。然而，不能排除食用某些食物，特别是芹菜和欧防风，可能会由于储存、加工和生产条件而导致呋喃香豆素浓度显著增加，从而可能食用到光毒性剂量（L2157）。已知呋喃香豆素光化学疗法会引起多种副作用，包括红斑、水肿、色素沉着过度和皮肤过早老化。呋喃香豆素的所有光生物效应都源于它们的光化学反应。因为许多可溶于饮食或水的呋喃香豆素是细胞色素P450的强抑制剂，所以当与其他药物一起服用时，它们也会引起不良反应。

The furocoumarin 8-methoxypsoralen is carcinogenic to humans, and possibly 5-methoxypsoralen as well (L135). There is some evidence from mouse studies that other furocoumarins are carcinogenic when combined with exposure to UVA radiation (A15105). The SKLM regards the additional risk of skin cancer arising from the consumption of typical quantities of furocoumarin-containing foods, which remain significantly below the range of phototoxic doses, as insignificant. However, the consumption of phototoxic quantities cannot be ruled out for certain foods, particularly celery and parsnips, that may lead to significant increases in furocoumarin concentrations, depending on the storage, processing and production conditions. (L2157) Furocoumarin photochemotherapy is known to induce a number of side-effects including erythema, edema, hyperpigmentation, and premature aging of skin. All photobiological effects of furocoumarins result from their photochemical reactions. Because many dietary or water soluble furocoumarins are strong inhibitors of cytochrome P450s, they will also cause adverse drug reactions when taken with other drugs.

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 海关编码：
  2932999099

反应信息

• 作为产物：
  描述：

  6-(3-methyl-2-butenoxy)-2-oxo-(2,3,4H)-furo<2,3-h><1>benzopyran 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以12%的产率得到Heratomin;6-[(3-甲基-2-丁烯-1-基)氧基]-2H-呋喃并[2,3-h]-1-苯并吡喃-2-酮
  参考文献：
  名称：

  Two regiocomplementary approaches to angular furanocoumarins with chromium carbene complexes: synthesis of sphondin, thiosphondin, heratomin, and angelicin

  摘要：

  DOI：

  10.1021/ja00230a023

文献信息

• WULFF, WILLIAM D.;MCCALLUM, J. STUART;KUNNG, FEN-ANN, J. AMER: CHEM. SOC., 110,(1988) N2, C. 7419-7434
  作者：WULFF, WILLIAM D.、MCCALLUM, J. STUART、KUNNG, FEN-ANN

  DOI：——

  日期：——
• Two regiocomplementary approaches to angular furanocoumarins with chromium carbene complexes: synthesis of sphondin, thiosphondin, heratomin, and angelicin
  作者：William D. Wulff、J. Stuart. McCallum、Fen Ann. Kunng

  DOI：10.1021/ja00230a023

  日期：1988.10