Endrin | 72-20-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Endrin
• 英文别名: endrine；Hexadrin；(1R,2R,3R,6S,7S,8S,9S,11R)-3,4,5,6,13,13-hexachloro-10-oxapentacyclo[6.3.1.13,6.02,7.09,11]tridec-4-ene
• CAS: 72-20-8
• 化学式: C₁₂H₈Cl₆O
• 分子量: 380.913
• InChiKey: DFBKLUNHFCTMDC-GKRDHZSOSA-N

物化性质

• 熔点：
  200 °C
• 沸点：
  416.2±45.0 °C(Predicted)
• 密度：
  1.7 g/cm3
• 物理描述：
  Endrin is a white crystalline, odorless solid dissolved in a liquid carrier. It is water emulsifiable. It is toxic by inhalation, skin absorption, and/or ingestion. When heated or burned it may emit toxic hydrogen chloride and phosgene. It is used as a pesticide.
• 颜色/状态：
  WHITE, CRYSTALLINE SOLID
• 气味：
  Odorless
• 闪点：
  80 °F (commercial product may contain flammable liquid)
• 溶解度：
  Solubility in g/100 ml solvent at 25 °C: acetone 17, benzene 13.8, carbon tetrachloride 3.3, hexane 7.1, and xylene 18.3
• 蒸汽压力：
  3X10-6 mm Hg @ 20 °C
• 亨利常数：
  Henry's Law constant = 6.36X10-6 atm-cu m/mole @ 25 °C
• 稳定性/保质期：
  Endrin is stable in the presence of most alkalis but rearranges to delta-keto endrin in the presence of strong acids, in sunlight and when heated.
• 分解：
  Decomposes above 200 °C.
• 腐蚀性：
  Slightly corrosive to metals
• 气味阈值：
  1.80x10-2 ppm (perfume/flavor grade purity).
• 保留指数：
  2180 ;2157 ;2200 ;2165 ;2208.2 ;2168.7 ;2183.5 ;2185 ;2176.7 ;2164.2 ;2165 ;2183 ;2164.2 ;2183

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

在动物体内，恩德林被降解，主要是转化为9-酮恩德林和9-羟基恩德林，但也转化为5-羟基恩德林。

IN ANIMALS, ENDRIN IS DEGRADED, LARGELY TO 9-KETOENDRIN & 9-HYDROXYENDRIN, BUT ALSO TO 5-HYDROXYENDRIN.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在6天期间，雄性/大鼠服用豆油中的恩德林，通过粪便排出了66%的剂量...雌性...37%。...粪便分析显示...恩德林...抗-12-羟基恩德林...合成-12-羟基恩德林...3-羟基恩德林...12-酮恩德林...以及Δ-酮恩德林...。

IN A 6-DAY PERIOD, MALES /RATS ADMIN ENDRIN IN ARACHIS OIL/ EXCRETED IN FECES 66% DOSE ... FEMALES ... 37%. ... ANALYSIS /FECES/ REVEALED ... ENDRIN ... ANTI-12-HYDROXYENDRIN ... SYN-12-HYDROXYENDRIN ... 3-HYDROXYENDRIN ... 12-KETOENDRIN ... & DELTA-KETOENDRIN ... .

来源:Hazardous Substances Data Bank (HSDB)

代谢

在大鼠中给予恩德林后，对粪便的分析揭示了一种极性代谢物...反式-4,5-二氢异恩德林-4,5-二醇。另一种极性代谢物未被鉴定。雄性大鼠的尿液中包含了恩德林，12-酮恩德林，反-12-羟基恩德林和3-羟基恩德林（比例分别为17:19:2:1）。雌性大鼠的提取物中不包含12-酮恩德林。/建议：12-酮恩德林是最有毒的。/

/IN RATS ADMIN ENDRIN, ANALYSIS OF FECES REVEALED/ A POLAR METABOLITE ... TRANS-4,5-DIHYDROISODRIN-4,5-DIOL. ANOTHER POLAR ... NOT IDENTIFIED. ... URINE FROM MALE RATS CONTAINED ENDRIN, 12-KETOENDRIN, ANTI-12-HYDROXYENDRIN & 3-HYDROXYENDRIN (17:19:2:1, RESPECTIVELY). THE EXTRACTS FROM FEMALE RATS DID NOT CONTAIN 12-KETOENDRIN. /SRP: 12-KETOENDRIN IS THE MOST TOXIC/.

来源:Hazardous Substances Data Bank (HSDB)

代谢

/ENDRIN ADMIN TO RATS IN 6 DAY STUDY/ ... MAJOR METABOLITE IN FEMALE RAT URINE /WAS/ IDENTICAL TO 12-HYDROXYENDRIN O-SULFATE. IN TISSUES /ANALYZED/ 12-KETOENDRIN /WAS/ MAJOR CMPD IN FAT OF MALES; ENDRIN IN FEMALES /BUT/ 12-KETOENDRIN WAS ALSO PRESENT. IN LIVER OF MALES NO ENDRIN /WAS DETECTED/ & 12-KETOENDRIN /WAS/ MAJOR METABOLITE. 六天内给大鼠内服恩德林的研究...雌性大鼠尿液中的主要代谢物与12-羟基恩德林O-硫酸盐相同。在分析的组织中，12-酮恩德林是雄性脂肪中的主要化合物；雌性中是恩德林，但12-酮恩德林也存在。在雄性肝脏中没有检测到恩德林，而12-酮恩德林是主要的代谢物。

/ENDRIN ADMIN TO RATS IN 6 DAY STUDY/ ... MAJOR METABOLITE IN FEMALE RAT URINE /WAS/ IDENTICAL TO 12-HYDROXYENDRIN O-SULFATE. IN TISSUES /ANALYZED/ 12-KETOENDRIN /WAS/ MAJOR CMPD IN FAT OF MALES; ENDRIN IN FEMALES /BUT/ 12-KETOENDRIN WAS ALSO PRESENT. IN LIVER OF MALES NO ENDRIN /WAS DETECTED/ & 12-KETOENDRIN /WAS/ MAJOR METABOLITE.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

癌症分类：D组 不可归入人类致癌性类别

Cancer Classification: Group D Not Classifiable as to Human Carcinogenicity

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

分类：D；无法归类为人类致癌性。分类依据：内吸磷的口服给药在两种品系的小鼠的任一性别中均未产生致癌作用。国家癌症研究所（NCI）的生物鉴定提示雄性和雌性大鼠有反应，尽管NCI报告了无证据结论。几个生物鉴定的不充分性使报告的阴性结果的可信度受到质疑。这些不充分性和NCI生物鉴定中的提示性反应不支持E组的分类；相反，D组的分类最能反映这些模棱两可的数据。人类致癌性数据：不充分。动物致癌性数据：不充分。

CLASSIFICATION: D; not classifiable as to human carcinogenicity. BASIS FOR CLASSIFICATION: Oral administration of endrin did not produce carcinogenic effects in either sex of two strains of mice. An NCI bioassay was suggestive of responses in male and female rats although NCI reported a no evidence conclusion. The inadequacies of the several bioassays call into question the strength of the reported negative findings. These inadequacies and the suggestive responses in the NCI bioassay do not support a Group E classification; rather a Group D classification best reflects the equivocal data. HUMAN CARCINOGENICITY DATA: Inadequate. ANIMAL CARCINOGENICITY DATA: Inadequate.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

没有关于人类的数据。动物致癌性证据不足。总体评估：第3组：该物质对人类致癌性无法分类。

No data are available in humans. Inadequate evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

A4：不能分类为人类致癌物。

A4: Not classifiable as a human carcinogen.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

国际癌症研究机构致癌物：恩德林

IARC Carcinogenic Agent:Endrin

来源:International Agency for Research on Cancer (IARC)

吸收、分配和排泄

... ENDRIN比DIELDRIN更快地从血浆中被清除，因为ENDRIN有更快的胆汁排泄。

... ENDRIN IS CLEARED MUCH MORE RAPIDLY FROM PLASMA THAN DIELDRIN BECAUSE OF MORE RAPID BILIARY EXCRETION.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在施用(14)C-恩德林到棉株上部叶面十二周后，回收了33%的施用放射性，其中26%在叶子和叶内，其余在植物的其他部分和土壤中。

TWELVE WK AFTER APPLICATION OF (14)C ENDRIN TO UPPER LEAF SURFACES OF COTTON PLANTS, 33% OF THE APPLIED RADIOACTIVITY WAS RECOVERED, 26% ON & IN THE LEAVES & THE REMAINDER IN THE OTHER PLANT PARTS & SOIL.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

恩德林在牛的体脂中积累，并且以小量排泄在它们的牛奶中。

ENDRIN IS ACCUM IN THE BODY FAT OF COWS & IS EXCRETED IN SMALL AMT IN THEIR MILK.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

与其他有机氯杀虫剂相比，VERY LITTLE ENDRIN在动物体内的储存非常少。

VERY LITTLE ENDRIN, AS COMPARED TO OTHER ORGANOCHLORINE INSECTICIDES, IS STORED IN ANIMALS.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1
• 安全说明：
  S22,S33,S36,S7
• 危险类别码：
  R67,R38,R24,R28,R50/53,R11,R23/24/25,R39/23/24/25,R65
• 危险类别：
  6.1(a)
• 危险品运输编号：
  UN 2761

SDS

第一部分：化学品名称

制备方法与用途

用途

用于致癌和毒性研究、杀虫剂以及有机合成领域。

反应信息

• 作为反应物：
  描述：

  Endrin 在 盐酸 作用下， 以 二丁醚 为溶剂， 生成 endrin ketone
  参考文献：
  名称：

  Skeletal Rearrangements in Reactions of Isodrin and Endrin

  摘要：

  DOI：

  10.1021/ja01505a024
• 作为产物：
  描述：

  isodrin 在 potassium fluoride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以92%的产率得到Endrin
  参考文献：
  名称：

  Evaluation of lipase from Candida rugosa in the resolution of endo-(±)-1,8,9,10,11,11-hexachloropentacyclo[6.2.1.13,6.02,7.05,9]dodecan-4-alcohol

  摘要：

  endo-(+/-)-1,8,9,10,11,11-Hexachloropentacyclo[6.2.1.1.(3.6).0(2.7).0(5.9)]dodecan-4-ol (+/-)-7 and exo-(+/-)-1,8,9,10,11,11-hexachloropentacyclo[6.2.1.1(3.6).0(2.7).0(5.9)]dodecan-4-ol (+/-)-4 have been prepared and the enantiomeric enrichment capacity of the lipase from Candida rugosa in the transesterification with vinyl acetate of these compounds was evaluated. It was verified that the lipase recognize only the alcohol (+/-)-7, producing endo-(+)-1,8,9,10,11,11-hexachloropentacyclo[6.2.1.1(3.6).0(2.7).0(5.9)]dodecan-4-yl acetate (+)-8 with ee >95% and conversion of 44% as the only product. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00259-6

文献信息

• Amine induced photodehalogenation of cyclodiene insecticides
  作者：P. Dureja、S.K. Mukerjee

  DOI：10.1016/s0040-4039(00)98905-6

  日期：1985.1

  The syn-Cl atom of the geminal bridge of cyclodiene insecticides and their metabolites, is dechlorinated stereoselectively by photolysis in the presence of amines.

  环二烯杀虫剂及其代谢产物双桥的syn-Cl原子在胺存在下通过光解被立体选择性地脱氯。
• 946. Cyclisations and rearrangements in the isodrin–aldrin series
  作者：C. W. Bird、R. C. Cookson、E. Crundwell

  DOI：10.1039/jr9610004809

  日期：——
• Onuska,F.I.; Comba,M.E., Biomedical Mass Spectrometry, 1975, vol. 2, p. 169 - 175
  作者：Onuska,F.I.、Comba,M.E.

  DOI：——

  日期：——
• Dureja, P.; Walia, S.; Mukerjee, S. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 898 - 899
  作者：Dureja, P.、Walia, S.、Mukerjee, S. K.

  DOI：——

  日期：——
• Wolodkowitsch et al., Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2837; engl. Ausg. S. 2797
  作者：Wolodkowitsch et al.

  DOI：——

  日期：——

表征谱图