3,4-环氧丁烷-1,2-二醇 | 17177-50-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3,4-环氧丁烷-1,2-二醇
• 英文名称: (+/-)-(1,2-Dihydroxyethyl)oxirane
• 英文别名: 1,2-dihydroxybut-3,4-epoxybutane；(1',2'-dihydroxyethyl)oxirane；3,4-epoxybutane-1,2-diol；butadiene diol epoxide；1,2,3,4-Diepoxybutene；butadiene diolepoxide；(1,2-Dihydroxyethyl)oxirane；1-(oxiran-2-yl)ethane-1,2-diol
• CAS: 17177-50-3
• 化学式: C₄H₈O₃
• 分子量: 104.106
• InChiKey: KRBIHOANUQUSRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2910900090

反应信息

• 作为反应物：
  描述：

  3,4-环氧丁烷-1,2-二醇 在 sodium periodate 作用下， 生成 2,3-环氧丙醛
  参考文献：
  名称：

  鸟苷和缩水甘油醛（环氧乙烷甲醛）反应的加合物结构：15 N标记研究

  摘要：

  guanonsine（的反应1A）与外消旋缩水甘油（2在pH 10下在水性介质中），得到5,9-二氢-9-氧代-3-β- d -ribofuranosylimidazo [1,2一〕嘌呤（1，Ñ 2 -乙鸟嘌呤）（3c），其7-羟甲基衍生物（3a）和亚甲基-7,7'-双-5,9-二氢-9-氧代-3-β- D-核呋喃呋喃基咪唑并[1,2- a ]嘌呤（5）; 加合物（3a）和（5）的结构由[ 1-15 N]鸟苷（15-15 N）衍生的15 N标记加合物的13 C nmr分析推导得出1b）和[ 15 NH 2 ]鸟苷（1c）。

  DOI：

  10.1039/c39860000515
• 作为产物：
  描述：

  双环氧化丁二烯 在 水 作用下， 以 水 为溶剂， 生成 3,4-环氧丁烷-1,2-二醇
  参考文献：
  名称：

  32P-postlabelling of N6-adenine adducts of epoxybutanediol in vivo after 1,3-butadiene exposure

  摘要：

  Epoxybutanediol is one of the epoxide metabolites of butadiene (BD). A pair of diastereomeric N-1-adenine adducts were formed by reacting epoxybutanediol with deoxyadenosine 5'-monophosphate (5'-dAMP). These two N-1-adenine adducts rearranged in a base-catalysed reaction to an N-6-trihydroxybutyl-adenine adduct, which was characterized by UV and mass spectroscopy. Using the P-32-postlabelling/HPLC assay the same adducts were detected in diepoxybutane (DEB)-treated DNA in vitro and in liver DNA samples from rats exposed to ED by inhalation. Adenine adducts of epoxybutanediol are probably suitable for monitoring ED exposure. (C) 1998 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0378-4274(98)00253-7

文献信息

• Preparation of 2,3,4-Trihydroxybutylarsonic Acid: A Starting Compound for Novel Arsonolipids
  作者：Maria A. Lala、Gerasimos M. Tsivgoulis、Panayiotis V. Ioannou

  DOI：10.1080/10426500701506184

  日期：2007.10.18

  Possible routes for the preparation of 2,3,4-trihydroxybutylarsonic acid, a key compound for the synthesis of novel arsonolipids, were experimentally evaluated. The best substrate was found to be 3,4-epoxybutane-1,2-diol. Its reaction with alkaline sodium arsenite, “Na 3 AsO 3 ,” gave the arsonic acid in ∼ 50% yield, as two pairs of diastereoisomers, each pair being a racemic mixture.

  实验评估了制备 2,3,4-三羟基丁基胂酸（合成新型胂脂的关键化合物）的可能途径。发现最好的底物是 3,4-epoxybutane-1,2-diol。它与碱性亚砷酸钠“Na 3 AsO 3 ”反应，以约 50% 的产率得到胂酸，为两对非对映异构体，每一对都是外消旋混合物。
• Mechanisms of Formation of Adducts from Reactions of Glycidaldehyde with 2‘-Deoxyguanosine and/or Guanosine
  作者：Bernard T. Golding、Pritpal K. Slaich、Gordon Kennedy、Christine Bleasdale、William P. Watson

  DOI：10.1021/tx950057c

  日期：1996.1.1

  formed from guanosine and glycidaldehyde. The structure analysis of this adduct was also aided by 13C NMR analysis of the 15N-labeled adduct derived from [1-15N]guanosine. Analogous adducts were obtained from the reaction between glycidaldehyde and deoxyguanosine. Mechanisms of formation of the adducts from glycidaldehyde and guanosine/deoxyguanosine are proposed and supported by model studies with simple

  描述了由rac-but-3-ene-1,2-二醇方便地合成rac-缩水甘油醛和由D-甘露糖醇方便地合成（R）-缩水甘油醛。（R）-乙二醛（1）在水中与鸟嘌呤反应（pH 4-11，在较高pH下反应更快），最初产生6（S）-羟基-7（S）-（羟甲基）-3-（β-D -呋喃核糖基）-5,6,7-三氢咪唑并[1,2-α嘌呤-9（3H）-一（7a）和6（S），7（R）-二羟基-3-（β-D-呋喃核糖基）-5,6,7,8-四氢嘧啶基[1,2-α]嘌呤-10（3H）-一（8a）。前者分解为7-（羟甲基）-5,9-二氢-9-氧代-3-（β-D-核呋喃糖基）咪唑并[1,2-α]嘌呤（1,2-α）嘌呤（3a），5,9-二氢-9-氧代-3-（β-D-呋喃呋喃糖基）咪唑并[1,2-α]嘌呤（5a，1，N2-乙鸟嘌呤）和甲醛，而后者的加合物相对稳定。羟甲基在7-（羟甲基）-5的咪唑环上的位置 通过13 C NMR分
• <i>In vitro</i> and <i>in vivo</i> mutagenicity of the butadiene metabolites butadiene diolepoxide, butadiene monoepoxide and diepoxybutane
  作者：I.-D. Adler、U. Kliesch、L. Nylund、K. Peltonen

  DOI：10.1093/mutage/12.5.339

  日期：——

  Three metabolites of 1,3-butadiene, namely butadiene diolepoxide, butadiene monoepoxide and diepoxybutane, were tested in the bacterial mutation assay using Salmonella typhimurium strain TA100 with and without metabolic activation (S9 mix). All three compounds showed a mutagenic response. The bifunctional epoxide was more effective than the diolepoxide which was more effective than the monoepoxide. Toxicity appeared to follow the ranking of the chemicals for their mutagenic potency. The monoepoxide and the diolepoxide were also tested for induction of micronuclei in mouse bone marrow erythrocytes and for dominant lethal mutation induction in postmeiotic male mouse germ cells. The effects of the diepoxide in both in vivo tests have been published earlier. In the micronucleus assay, the three metabolites gave a positive response whereby the diepoxide was more effective than the monoepoxide which was more effective than the diolepoxide. In contrast to the diepoxide which was positive at a dose as low as 36 mg/kg, the monoepoxide and the diol did not show an induction of dominant lethal effects up to doses of 120 and 240 mg/kg, respectively. It is concluded that the metabolites were mutagenic in bacteria without metabolic activation and clastogenic in mouse bone marrow; only the bifunctional diepoxide, however, was active in postmeiotic male mouse germ cells.

  使用具有和不具有代谢激活（S9 mix）的鼠伤寒沙门氏菌菌株 TA100 在细菌突变测定中测试了 1,3-丁二烯的三种代谢物，即二环氧丁二烯、单环氧丁二烯和二环氧丁烷。所有三种化合物均表现出诱变反应。双官能环氧化物比二烯环氧化物更有效，而二烯环氧化物又比单环氧化物更有效。毒性似乎遵循化学物质的致突变能力的排名。还测试了单环氧化物和双环氧化物在小鼠骨髓红细胞中诱导微核以及在减数分裂后雄性小鼠生殖细胞中诱导显性致死突变。双环氧化物在两项体内测试中的作用已于早些时候发表。在微核测定中，三种代谢物给出了阳性反应，其中双环氧化物比单环氧化物更有效，而单环氧化物比双环氧化物更有效。与在低至36mg/kg的剂量下呈阳性的双环氧化物相反，单环氧化物和二醇分别在高达120和240mg/kg的剂量下没有表现出诱导显性致死作用。结论：该代谢物对未代谢激活的细菌具有致突变作用，对小鼠骨髓具有致断裂作用；然而，只有双功能双环氧化物在减数分裂后雄性小鼠生殖细胞中具有活性。
• Mutagenicity of a Glutathione Conjugate of Butadiene Diepoxide
  作者：Sung-Hee Cho、Elisabeth M. Loecken、F. Peter Guengerich

  DOI：10.1021/tx100304f

  日期：2010.10.18

  The mutagenicity and carcinogenicity of the important commodity chemical 1,3-butadiene are attributed to the epoxide products. We confirmed our previous work showing that expression of rat glutathione (GSH) transferase 5-5 enhances the mutagenicity of butadiene diepoxide in Salmonella typhimurium TA 1535. A GSH butadiene diepoxide conjugate was isolated and fully characterized by mass spectrometry and nuclear magnetic resonance as S-(2-hydroxy-3,4-epoxybutyl)GSH. The conjugate had a t(1/2) of 2.6 h (pH 7.4, 37 degrees C) and was considerably more mutagenic than butadiene diepoxide or monoepoxide in S. typhimurium. We propose that the GSH conjugate may be a major species involved in butadiene genotoxicity, not a detoxication product.
• Identification of Novel Metabolites of Butadiene Monoepoxide in Rats and Mice
  作者：Kevan A. Richardson、Melanie M. C. G. Peters、René H. J. J. J. Megens、Paul A. van Elburg、Bernard T. Golding、Peter J. Boogaard、William P. Watson、Nico J. van Sittert

  DOI：10.1021/tx970175v

  日期：1998.12.1

  Differences in the metabolism of 1,3-butadiene (Bd) in rats and mice may account for the observed species difference in carcinogenicity. Previous studies of the metabolic fate of Ed have identified epoxide formation as a key metabolic transformation which gives 1,2-epoxy-3-butene (BMO), although some evidence of aldehyde metabolites is reported. In this study, male Sprague-Dawley rats and male B6C3F1 mice received single doses of [4-C-14]BMO at 1, 5, 20, and 50 mg/kg of body weight (0.014, 0.071, 0.286, and 0.714 mmol/kg of body weight). Analysis of urinary metabolites indicated that both species preferentially metabolize BMO by direct reaction with GSH when given by ip administration. The excretion of (R)-2-(N-acetyl-L-cystein-S-yl)-1-hydroxybut-3-ene (IIa), 1-(N-acetyl-L-cystein-S-yl)-2-(S)-hydroxybut-3-ene (IIb), 1-(N-acetyl-L-cystein-S-yl)-2-(R)-hydroxybut-3-ene (IIc), and (S)-2-(N-acetyl-L-cystein-S-yl)- 1-hydroxybut-3-ene (IId) accounted for 48-64% of urinary radioactivity in rats and 46-54% in mice. The metabolites originating from the R-stereoisomer of BMO (IIc and IId) predominated over those arising from the S-stereoisomer (IIa and IIb) in both species. IIc was formed preferentially in mice and IId in rats. The corresponding mercaptoacetic acids, S-(1-hydroxybut-3-en-2-yl)mercaptoacetic acid (IIf) and S-(2-hydroxybut-3-en-1-yl)mercaptoacetic acid (IIg), were identified only in mouse urine (ca. 20% of the recovered radioactivity,, 4-(N-Acetyl-L-cystein-S-yl)- 1,2-dihydroxybutane (Ia), a metabolite derived from hydrolysis of BMO, accounted for 10-17% of the radioactivity in rat and 6-10% in mouse urine. 4-(N-Acetyl-L-cystein-S-yl)-2-hydroxybutanoic acid (1b), 3-(N-acetyl-L-cystein-S-yl)propan-1-ol (Ic), and 3-(N-acetyl-L-cystein-S-yl)propanoic acid (Id:). also derived from the hydrolysis of RR IO, were only present in the rat. Metabolites of 1,2,3,4-diepoxybutane (DEB) were not detected after administration of BMO in rat or mouse urine. This study showed both quantitative and qualitative differences in the metabolism of BMO with varying doses and between species. The data aid in the safety evaluation of Ed and contribute to the interpretation of mathematical models developed for quantitative risk assessment and extrapolation of animals to humans.