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7,12-二甲基苯并[a]蒽 | 57-97-6

中文名称
7,12-二甲基苯并[a]蒽
中文别名
N-苄基二甲胺;N,N-二甲基苄胺;9,10-二甲基-1,2-苯并蒽;2,6-二溴苯酚-3,4,5-d3;7,12-二甲基苯并(a)蒽;7,12-二甲基苯蒽;1,4-二甲基-2,3-苯并菲;7,12-二甲基苯并蒽;9,1-二甲基-1,2-苯并蒽
英文名称
7,12-Dimethylbenz[a]anthracene
英文别名
7,12-dimethyl-1,2-benzanthracene;DMBA;7,12-dimethylbenzanthracene;7,12-dimethylbenz[a]anthacene;7,12-dimethylbenzo[a]anthracene
7,12-二甲基苯并[a]蒽化学式
CAS
57-97-6
化学式
C20H16
mdl
——
分子量
256.347
InChiKey
ARSRBNBHOADGJU-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    122-123 °C(lit.)
  • 沸点:
    183-184 °C765 mm Hg(lit.)
  • 密度:
    0.9 g/mL at 25 °C(lit.)
  • 闪点:
    130 °F
  • 物理描述:
    7,12-dimethylbenz[a]anthracene appears as yellow to greenish-yellow crystals or a yellow solid. Odorless. Maximum fluorescence at 440 nm. Bluish-violet fluorescence in UV light. (NTP, 1992)
  • 颜色/状态:
    Plates, leaflets from acetone-alcohol, faint greenish-yellow tinge
  • 气味:
    Odorless[NOAA; CAMEO Chemicals. Database of Hazardous Materials. 7,12-Dimethylbenz
  • 溶解度:
    In water, 0.061 mg/L water at 25 °C
  • 蒸汽压力:
    6.8X10-7 mm Hg at 25 °C
  • 稳定性/保质期:
    - 存在于烟气中。 - 具有致癌性。
  • 分解:
    Hazardous decomposition products formed under fire conditions - Carbon oxides.[Sigma-Aldrich; Safety Data Sheet for 7,12-Dimethylbenz
  • 保留指数:
    2711;2713;443.82;443.9;444;442.03;443.38;444.84;443.38

计算性质

  • 辛醇/水分配系数(LogP):
    5.8
  • 重原子数:
    20
  • 可旋转键数:
    0
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.1
  • 拓扑面积:
    0
  • 氢给体数:
    0
  • 氢受体数:
    0

ADMET

代谢
由于美国胰腺癌发病率高,以及胰腺癌与环境暴露的相关性,我们进行了实验来测量致癌物7,12-二甲基苯并蒽在长埃文斯雄性大鼠胰腺中的代谢。本研究检查了致癌物的体外代谢,并发现胰腺产生的水性产物与肝脏相似,然而,胰腺的代谢能力并未通过苯巴比妥或3-甲基胆蒽预处理诱导出更高的代谢。胰腺代谢产物的 高压液相色谱分析显示,5,6-环氧-7-羟甲基-12-甲基苯并蒽的相对丰度比肝脏高,而7-羟甲基-12-甲基苯并蒽和7-甲基-12-羟甲基苯并蒽的相对丰度比肝脏低。在注射后2、5、10、16、22和36小时测量了胰腺、肝脏、胆汁和血液中的致癌物水平。
Because of the high incidence of pancreatic cancer in the United States and because of the correlation of pancreatic cancer to environmental exposure, we have undertaken experiments to measure the metabolism of the carcinogen 7,12-dimethylbenzanthracene in the pancreas of the Long-Evans male rat. This study examined the in vitro metabolism of the carcinogen and found the production of aqueous products in pancreas to be similar to that in liver, however, the pancreatic capability was not induced to greater metabolism by pretreatment with either phenobarbital or 3-methylcholanthrene. High pressure liquid chromatographic analysis of the in vitro products of pancreatic metabolism demonstrated a relatively greater abundance of 5,6-epoxy-7-hydroxymethyl-12-methylbenzanthracene than the liver and a relatively less abundance of 7-hydroxymethyl-12-methylbenzanthracene and 7-methyl-12-hydroxymethylbenzanthracene than the liver. Carcinogen levels were measured in pancreas, liver, bile and blood at 2, 5, 10, 16, 22 and 36 hours after injection.
来源:Hazardous Substances Data Bank (HSDB)
代谢
大鼠肝细胞溶质的同质3α-羟基类固醇-二氢二醇脱氢酶催化多种多环芳烃反式二氢二醇的NADP依赖性氧化,并已被认为参与它们的解毒。本研究考察了甲基团对酶促苯并(a)蒽 (BA) 反式二氢二醇氧化速度和立体化学过程的影响。BA和7-甲基苯并(a)蒽 (7-MBA) 的外消旋反式-3,4-二氢二醇被纯化的脱氢酶完全消耗,表明两种对映体都是底物。然而,50%的(±)-反式-3,4-二氢二醇的12-甲基苯并(a)蒽 (12-MBA) 和7,12-二甲基苯并(a)蒽 (DMBA) 被氧化,这表明在每种情况下只有一个对映体被利用。在低底物浓度下,BA、12-MBA和DMBA的反式-3,4-二氢二醇的酶促氧化遵循简单的一级动力学。相比之下,7-MBA的3,4-二氢二醇的氧化为高级反应,这是由于每种对映体氧化速率的差异。为每种反应估计的速率常数表明,位于7位的非湾区甲基比对位于12位的湾区甲基对氧化速率的增强作用更大(分别为10倍和4倍)。DMBA的3,4-二氢二醇,它同时具有非湾区和湾区甲基,其氧化速率比未甲基化母体烃快30倍以上。通过圆二色光谱法分配了优先氧化二氢二醇的绝对立体化学。对于DMBA和12-MBA的3,4-二氢二醇,被氧化的对映体具有3S,4S的配置。在7-MBA 3,4-二氢二醇的圆二色光谱中观察到了一个大的负Cotton效应,这表明在快速氧化这个外消旋底物的阶段结束时,脱氢酶对3S,4S对映体表现出部分立体化学偏好。这些结果表明,BA在C-7位的甲基化大大增强了3S,4S-二氢二醇的氧化,而C-12位的湾区甲基化完全阻止了3R,4R-对映体的氧化。在体内通过这种方式对甲基化多环芳烃反式二氢二醇进行快速、立体选择性的氧化可能会显著影响它们的致癌性。
The homogeneous 3 alpha-hydroxysteroid-dihydrodiol dehydrogenase of rat liver cytosol catalyzes the NADP-dependent oxidation of a wide variety of polycyclic aromatic trans-dihydrodiols and has been implicated in their detoxification. This study examined the influence of methyl groups on the velocity and stereochemical course of enzymatic benz(a)anthracene (BA) trans-dihydrodiol oxidation. The racemic trans-3,4-dihydrodiols of BA and 7-methylbenz(a)anthracene (7-MBA) were completely consumed by the purified dehydrogenase, indicating that both stereoisomers are substrates. However, 50% of the ( +/- )-trans-3,4-dihydrodiols of 12-methylbenz(a)anthracene (12-MBA) and 7,12-dimethylbenz(a)-anthracene (DMBA) were oxidized, suggesting that only one stereoisomer is utilized in each case. At low substrate concentrations, enzymatic oxidation of the trans-3,4-dihydrodiols of BA, 12-MBA, and DMBA followed simple first-order kinetics. By contrast, oxidation of the 3,4-dihydrodiol of 7-MBA was of higher order, due to differences in the rate of oxidation of each stereoisomer. Rate constants estimated for each reaction indicate that the non-bay-region methyl group at position 7 has a greater enhancing effect on the rate of oxidation than the bay-region methyl group at position 12 (10- versus 4-fold, respectively). The 3,4-dihydrodiol of DMBA, which possesses both non-bay- and bay-region methyl groups, is oxidized more than 30 times faster than the unmethylated parent hydrocarbon. The absolute stereochemistry of the preferentially oxidized dihydrodiols was assigned by circular dichroism spectrometry. For the 3,4-dihydrodiols of DMBA and 12-MBA, the stereoisomer oxidized has the 3S,4S configuration. A large negative Cotton effect was observed in the circular dichroism spectrum of the 7-MBA 3,4-dihydrodiol which remained at the end of the rapid phase of oxidation of this racemic substrate, indicating that the dehydrogenase displays partial stereochemical preference for the 3S,4S enantiomer. These results suggest that methylation of BA at C-7 greatly enhances the oxidation of the 3S,4S-dihydrodiol, while the presence of a bay-region methyl group at C-12 completely blocks the oxidation of the 3R,4R-stereoisomer. Rapid, stereoselective oxidation of methylated polycyclic aromatic trans-dihydrodiols by this route in vivo may significantly influence their carcinogenicity.
来源:Hazardous Substances Data Bank (HSDB)
代谢
早期的研究表明,苯并[a]蒽(BA)、7-甲基苯并[a]蒽(7-MBA)和12-甲基苯并[a]蒽(12-MBA)在中位蒽环位置或L区域发生生物烷基化取代反应,导致强烈致癌物7,12-二甲基苯并[a]蒽(7,12-DMBA)的生物合成。这些结果支持了这一假设:对于大多数,甚至是所有未取代的多环芳烃致癌物,在中位蒽环位置或L区域引入烷基团是一种对强致癌活性的结构要求。在这里,我们报告了L区域甲基衍生物7-MBA、12-MBA和7,12-DMBA在大鼠肝脏胞质制剂中被氧化成羟甲基衍生物,而没有明显的环位置氧化。
Earlier studies ... demonstrated that benz[a]anthracene (BA), 7-methylbenz[a]anthracene (7-MBA) and 12-methylbenz[a]anthracene (12-MBA) undergo a bio-alkylation substitution reaction in the meso-anthracenic position(s) or L-region leading to the biosynthesis of the potent carcinogen 7,12-dimethylbenz[a]anthracene (7,12-DMBA). These results support the hypothesis that for most, if not all, unsubstituted polycyclic aromatic hydrocarbon carcinogens, the chemical or biochemical introduction of an alkyl group in the meso-anthracenic position(s) or L-region is a structural requirement for strong carcinogenic activity. Here we report that the L-region methyl derivatives 7-MBA, 12-MBA and 7,12-DMBA are oxidized to hydroxymethyl derivatives by a rat liver cytosol preparation without any apparent oxidation of the ring positions.
来源:Hazardous Substances Data Bank (HSDB)
代谢
在大鼠、豚鼠、猪和仓鼠中产生8,9-二氢-8,9-二羟基-7,12-二甲基苯并蒽、7-羟甲基-12-甲基苯并蒽、12-羟甲基-7-甲基苯并蒽。/根据表格/
Yields 8,9-dihydro-8,9-dihydroxy-7,12-dimethylbenzanthracene, 7-hydroxymethyl-12-methylbenzanthracene, 12-hydroxymethyl-7-methylbenzanthracene in rat, guinea pig, pig and hamster. /From table/
来源:Hazardous Substances Data Bank (HSDB)
代谢
7,12-二甲基苯并[a]芘已知的人类代谢物包括苯并[a]芘-8,9-二醇, 7,12-二甲基-, 7-羟甲基-12-甲基苯并[a]芘, 7,12-二甲基苯并[a]芘-5,6-二醇, 苯并[a]芘-3,4-二醇, 7,12-二甲基-, 12-羟甲基-7-甲基苯并[a]芘, 以及苯并[a]芘-2-醇, 7,12-二甲基-.
7,12 Dimethylbenzanthracene has known human metabolites that include Benz(a)anthracene-8,9-diol, 7,12-dimethyl-, 7-Hydroxymethyl-12-methylbenz[a]anthracene, 7,12-Dimethylbenz(a)anthracene-5,6-diol, BENZ(a)ANTHRACENE-3,4-DIOL, 7,12-DIMETHYL-, 12-Hydroxymethyl-7-methylbenz(a)anthracene, and BENZ(a)ANTHRACEN-2-OL, 7,12-DIMETHYL-.
来源:NORMAN Suspect List Exchange
毒理性
  • 毒性总结
识别和使用:7,12-二甲基苯并(a)蒽 (DMBA) 是一种固体。它主要用于实验医学中的研究化学品。人类暴露和毒性:7,12-DMBA 是最强大的合成致癌物之一。在人类中,当涂抹在皮肤上时,它可能是一个启动剂。在人类细胞培养中进行的代谢激活试验中,DMBA 显示出较低的诱变效应,但在没有激活的情况下测试时,几乎没有效果。动物研究:50天大的雌性大鼠喂食 DMBA,剂量为每千克体重112或133毫克,几周内就出现了全血细胞减少症,伴有造血和淋巴前体细胞的严重抑制。每周静脉注射 DMBA 在叙利亚仓鼠中产生了皮肤黑素细胞瘤和前胃、肠道、卵巢、皮下皮肤以及淋巴网状组织的肿瘤。单次腹腔注射 DMBA(剂量为每千克80毫克,溶于玉米油中)破坏了小鼠卵巢中的原始卵母细胞。DMBA 显著增强了鸟类的整体胚胎毒性。在啮齿动物细胞试验中,未激活的 DMBA 显示出较弱的诱变效应,而激活的 DMBA 显示出中等诱变效应。它还导致姐妹染色单体交换和染色体畸变。哺乳动物细胞转化试验表明,代谢激活的 DMBA 略微呈阳性。生态毒性研究:至少145条孔雀鱼(6到11天大)的王蛇品系(Poecilia reticulata)每周暴露于 DMBA 6小时,持续4周。暴露于中高浓度的孔雀鱼出现了肝脏肿瘤。除了肝脏肿瘤,DMBA 暴露的孔雀鱼还出现了几种其他类型的病变。
IDENTIFICATION AND USE: 7,12-Dimethylbenz(a)anthracene (DMBA) is a solid. It is used mainly as a research chemical in experimental medicine. HUMAN EXPOSURE AND TOXICITY: 7,12-DMBA is one of the most powerful synthetic carcinogens. In humans, it may be an initiator when applied to the skin. Low mutagenic effects were noted for DMBA when tested in human cell cultures with metabolic activation, but practically no effects were noted when tested without activation. ANIMAL STUDIES: After 50-day-old female rats were fed DMBA at either 112 or 133 mg/kg body wt, pancytopenia accompanied by severe depression of hematopoietic and lymphoid precursors developed within weeks. Weekly intravenous injection of DMBA produced dermal melanocytomas and tumors of the forestomach, intestine, ovary, skin subcutis, and lymphoreticular tissue in the Syrian hamster. DMBA admin in single ip doses of 80 mg/kg in corn oil destroyed primordial oocytes in mouse ovaries. DMBA, significantly enhances the overall embryotoxicity in avian species. In rodent cell tests, nonactivated DMBA exhibits weak and activated DMBA moderate mutagenic effects. It also causes sister chromatid exchanges and chromosomal aberrations. Mammalian cell transformation tests for DMBA were slightly positive with metabolic activation. ECOTOXICITY STUDIES: Groups of at least 145 guppies (6 to 11 days old) of the king cobra strain (Poecilia reticulata) were exposed for 6 hours each week for 4 weeks to DMBA. Hepatic neoplasms developed in guppies exposed to the intermediate and high concentration. In addition to liver neoplasms, several other types of lesions developed in DMBA exposed guppies.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 相互作用
由于一些流行病学研究以及在老鼠身上的启动/促进研究表明,随着磁场暴露的增加,乳腺癌的发病率可能上升,因此研究了50赫兹和60赫兹的磁场是否能够促进由7,12-二甲基苯并(a)蒽(DMBA)给药启动的大鼠乳腺肿瘤。在13周和26周的全身体暴露研究中,对雌性Sprague-Dawley大鼠进行了考察。在一项启动/促进研究中,雌性Sprague-Dawley大鼠从50天大开始,每周接受4剂5毫克/只的DMBA,并暴露于1或5高斯场强的50赫兹磁场或1高斯场强的60赫兹磁场13周,没有证据表明磁场促进了乳腺肿瘤的发展。所有DMBA组的乳腺肿瘤发生率和多发性限制了此检测方法检测磁场促进效果的能力。在另一项启动/促进研究中,雌性Sprague-Dawley大鼠从50天大开始,每周接受4剂2毫克/只的DMBA,并暴露于1或5高斯场强的50赫兹磁场13周,同样没有证据表明磁场促进了乳腺肿瘤的发展。在另一项启动/促进研究中,雌性Sprague-Dawley大鼠在50天大时接受单次10毫克/只的DMBA剂量,然后暴露于1或5高斯场强的50赫兹磁场或1高斯场强的60赫兹磁场26周,同样没有证据表明磁场促进了乳腺肿瘤的发展。
Because some epidemiology studies and initiation/promotion studies in rats have suggested a potential for increased breast cancer rates with increasing magnetic field exposure, the ability of 50- and 60-Hz magnetic fields to promote mammary gland tumors initiated by the administration of 7,12-dimethylbenz(a)anthracene (DMBA) was examined in female Sprague-Dawley rats in 13- and 26-week whole-body exposure studies. ... In an initiation/promotion study in which female Sprague-Dawley rats were initiated by four weekly doses of 5 mg DMBA per rat beginning at 50 days of age and exposed to 50-Hz magnetic fields at 1 or 5 G field intensities or to 1 G 60-Hz magnetic fields for 13 weeks, there was no evidence that magnetic fields promoted the development of mammary gland neoplasms. The prevalence and multiplicity of mammary gland carcinomas in all DMBA groups limited the ability of this assay to detect a promoting effect of magnetic fields. In an initiation/promotion study in which female Sprague-Dawley rats were initiated by four weekly doses of 2 mg DMBA per rat beginning at 50 days of age and exposed to 50-Hz magnetic fields at 1 or 5 G field intensities for 13 weeks, there was no evidence that magnetic fields promoted the development of mammary gland neoplasms. In an initiation/promotion study in which female Sprague-Dawley rats were initiated by a single 10 mg DMBA dose at 50 days of age and then exposed to 50-Hz magnetic fields at 1 or 5 G field intensities or to 1 G 60-Hz magnetic fields for 26 weeks, there was no evidence that magnetic fields promoted the development of mammary gland neoplasms.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 相互作用
目标是研究紫外线B辐射(UVR-B)和二甲基苯并蒽(DMBA)作用下肿瘤性病变的诱导。四十只Wistar大鼠被分配到四个组(每组十只动物),根据处理程序:A组接受UVR-B照射,B组接受局部DMBA,C组接受UVR-B+DMBA,D组作为对照组,观察期为十周。在第十周,它们进行了皮肤活检和组织病理学检查。计算表皮的平均厚度并进行统计分析。与对照组相比,所有组的表皮厚度都有显著增加,然而C组的厚度测量值最大(p<0.01)。暴露于紫外线B辐射的人群可能会遭受可能发展为癌症的皮肤病变。与二甲基苯并蒽等碳氢化合物结合,增加了恶性的可能性。
/The objective was/ to investigate the induction of neoplastic lesions under the action of ultraviolet B radiation (UVR-B) and dimethylbenzanthracene (DMBA). Forty Wistar rats were assigned to four groups (ten animals each), according to the procedure: group A received UVR-B irradiation, group B received topic DMBA, group C, UVR-B+DMBA and group D as control, observed for ten weeks. In the tenth week they went through a skin biopsy and histopathological study. The average thickness of the epidermis was calculated and evaluated statistically. Macroscopic lesions in group B were more of inflammatory kind compared to group A. Group C presented more injuries with neoplastic features than the others (p<0.01). Histologically there was a significant increase in thickness of the epidermis of all groups compared to control, however the greatest thickness measures occurred in Group C (p<0.01). The population exposed to ultraviolet B radiation is subject to suffer skin lesions that can develop into cancer. The association with hydrocarbons as the dimethyl benzanthracene increases the possibility of malignancy. ...
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 相互作用
十字花科蔬菜含有高量的葡萄糖苷酸,其代谢物被认为可以增强排毒作用。西班牙黑萝卜(SBR)含有比其他十字花科植物多4倍的葡萄糖苷酸。本研究检验了给小鼠喂食含有20% SBR的饮食2周是否能增强7,12-二甲基苯并(a)蒽(DMBA)的代谢并抑制DMBA介导的骨髓毒性。与对照饮食相比,喂食SBR的小鼠的I相和II相解毒酶的表达显著增加。DMBA给药后6小时,喂食SBR饮食的小鼠血液中的DMBA水平显著低于喂食对照饮食的小鼠。DMBA对喂食对照饮食的小鼠的骨髓细胞的减少程度显著大于喂食SBR饮食的小鼠。集落形成实验表明,喂食SBR饮食的小鼠1)淋巴前B祖细胞减少较少,2)在168小时时CFU-preB祖细胞恢复较多,3)在6小时时CFU-GM祖细胞减少较少。因此,喂食了2周20% SBR饮食的小鼠解毒酶表达增加,DMBA代谢加快,DMBA诱导的骨髓毒性降低。总的来说,这些结果支持了SBR中的葡萄糖苷酸对急性毒性具有保护作用的假设。
Vegetables of the Cruciferae family contain high levels of glucosinolates, metabolites of which are believed to enhance detoxification. Spanish black radishes (SBR) contain 4x more glucosinolates than other crucifers. This study examined whether feeding mice a diet containing 20% SBR for 2 wk could enhance metabolism of 7,12-dimethylbenz(a)anthracene (DMBA) and inhibit DMBA-mediated bone marrow toxicity. Expression of Phase I and II detoxification enzymes was significantly greater for mice fed SBR than control diet. Six hours after DMBA administration, the blood levels of DMBA in mice fed the SBR diet were significantly lower than mice fed a control diet. DMBA reduced bone marrow cells in mice fed control diet to a significantly greater extent than mice fed the SBR diet. Colony forming assays demonstrated that mice on the SBR diet had 1) less reduction in lymphoid CFU-preB progenitor cells, 2) greater recovery of CFU-preB progenitor cells at 168 hr, and 3) less reduction of CFU-GM progenitor cells at 6 hr. Therefore, mice fed a 20% SBR diet for 2 wk had greater expression of detoxification enzymes, faster metabolism of DMBA, and a reduction in DMBA-induced bone marrow toxicity. Overall, these results support the hypothesis that glucosinolates in SBR are protective against acute toxicity.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 相互作用
人类淋巴细胞暴露于B[a]P、DMBA、Trp-P-1和MX这四种诱变剂的二元混合物中1小时,有无S9混合物的情况。通过台盼蓝染料评估细胞活力,并通过彗星试验评估遗传毒性。所有烃类与呋喃酮都表现出效果。无论有无S9,烃类之间的最毒相互作用都被观察到。在没有S9的情况下,B[a]P和Trp-P-1之间以及DMBA和Trp-P-1之间在代谢活性下观察到协同作用。只有在没有S9的情况下,Trp-P-1+DMBA之间观察到拮抗作用,而在有S9的情况下,Trp-P-1+MX和MX+DMBA之间观察到拮抗作用。观察到尾部长度随剂量增加而增加。一半的培养物显示出遗传损伤和细胞损伤的增加。...
Human lymphocytes were exposed to binary mixtures of the mutagens B[a]P, DMBA, Trp-P-1 and MX for 1 hour with or without S9. Viability was assessed with trypan blue dye and the genotoxicity by the comet assay. All of the hydrocarbon showed an effect with furanone. With and without S9, the most toxic interactions were observed between hydrocarbons. Synergistic interaction was observed without S9 between B [a] P and Trp-P-1 and between DMBA and Trp-P-1 with metabolic activity. Without S9 antagonistic interaction was observed only between Trp-P-1+DMBA, and with S9 between Trp-P-1+MX and MX+DMBA. It observed an increase dose dependent in tail length. Half the cultures showed genotoxic damage and increased cell damage. ...
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
动物研究表明... 7,12-二甲基苯并(a)蒽...很容易从小肠吸收并倾向于主要分布在体内脂肪和脂肪组织,如乳腺中。...在大鼠通过胃管给予标记的.../化合物/后,放射性物质的分布进行了研究。发现主要的排泄途径是通过胆汁进入粪便。在体内脂肪、卵巢和肾上腺中,放射性物质的保留相当持久。
Studies in animals indicate that ... 7,12-dimethylbenz(a)anthracene ... readily absorbed from intestinal tract and tends to localize primarily in body fat and fatty tissues such as breast. ... The distribution of radioactivity in rats after admin of labeled ... /cmpd/ by stomach tube was ... studied. Major route of excretion was found to occur via the bile into the feces. There was rather prolonged retention of radioactivity in body fat, ovaries, and adrenals.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
7,12-DMBA 以 20 mg/kg 的剂量口服给予大鼠,溶解在淋巴中乳糜微粒的脂质部分中。
7,12-DMBA orally administered to rats at 20 mg/kg dissolved in the lipid fraction of the chylomicrons in the lymph.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
48小时口服给药后,90%被小鼠排出。用3-甲基胆蒽预处理小鼠略微增加了7,12-DMBA消除的初始速率,但在48小时后,残留的7,12-DMBA量与非预处理小鼠相同。与非预处理的小鼠相比,预处理小鼠的尿液和粪便中可提取的极性代谢物和水分溶性代谢物更为丰富。
48 hr after oral admin, 90% was excreted by mice. Pretreatment of mice with 3-methylcholanthrene slightly incr initial rate of 7,12-DMBA elimination, but after 48 hr amt of residual 7,12-DMBA was the same as that in the nonpretreated mice. Ethyl acetate extractable polar metabolites and water-sol metabolites were more abundant in urine and feces of pretreated mice than in nonpretreated ones.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
两小时后,注射7,12-二甲基苯并(a)蒽(DMBA)后,亚马逊食蚊鱼全身都有DMBA,除了大脑和卵巢。在4个部位有增强的沉积,包括心脏房室和腹膜巨噬细胞、肝脏和外分泌胰腺。DMBA在注射后78小时内被网状内皮巨噬细胞摄取,然后消失。在肝脏和胰腺细胞中看到的放射性标记的积累和消失可能代表了化合物的代谢模式。在注射后400小时,几乎没有剩余的DMBA。标记在分泌牙齿珐琅质的成釉细胞中积累。没有观察到脾脏对DMBA的优先代谢。
Two hr after ip injection, 7,12-dimethylbenz(a)anthracene (DMBA) was present throughout the body of Amazon mollies, except in brain and ovary. There was an enhanced deposition at 4 sites, in macrophages of atrium of heart and peritoneum, liver, and exocrine pancreas. DMBA was taken up by reticuloendothelial macrophages for 78 hr after injection, then it was lost. Accumulation and disapperance of radioactive label seen in liver and pancreatic cells probably represented pattern of metab of compd. By 400 hr after injection there was little DMBA remaining. Label accumulated in ameloblasts, which secrete the enamel capping of the teeth. No preferential metab of DMBA by spleen was observed.
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • 危险品标志:
    C,T
  • 安全说明:
    S36/37,S45,S53,S60,S61,S62
  • 危险类别码:
    R22
  • WGK Germany:
    3
  • 海关编码:
    29029090
  • RTECS号:
    DP4500000
  • 包装等级:
    III
  • 危险类别:
    6.1(b)
  • 危险品运输编号:
    UN 3077 9/PG 3
  • 储存条件:
    本品应密封保存。

SDS

SDS:2bec0017e9f420af4e9e7f10897f8b9c
查看

模块 1. 化学品
1.1 产品标识符
: 7,12-二甲基苯并[a]蒽
产品名称
1.2 鉴别的其他方法
1,4-Dimethyl-2,3-benzophenanthrene
DMBA
9,10-Dimethyl-1,2-benzanthracene
1.3 有关的确定了的物质或混合物的用途和建议不适合的用途
仅用于研发。不作为药品、家庭或其它用途。

模块 2. 危险性概述
2.1 GHS-分类
急性毒性, 经口 (类别 4)
皮肤刺激 (类别 3)
致癌性 (类别 1B)
2.2 GHS 标记要素,包括预防性的陈述
象形图
警示词 危险
危险申明
H302 吞咽有害。
H316 引起轻微皮肤刺激。
H350 可能致癌。
警告申明
预防措施
P201 在使用前获取特别指示。
P202 在读懂所有安全防范措施之前切勿操作。
P264 操作后彻底清洁皮肤。
P270 使用本产品时不要进食、饮水或吸烟。
P281 使用所需的个人防护设备。
事故响应
P301 + P312 如果吞咽并觉不适: 立即呼叫解毒中心或就医。
P308 + P313 如接触到或有疑虑:求医/ 就诊。
P330 漱口。
P332 + P313 如觉皮肤刺激:求医/就诊。
安全储存
P405 存放处须加锁。
废弃处置
P501 将内容物/ 容器处理到得到批准的废物处理厂。
只限于专业使用者。
2.3 其它危害物 - 无

模块 3. 成分/组成信息
3.1 物 质
: 1,4-Dimethyl-2,3-benzophenanthrene
别名
DMBA
9,10-Dimethyl-1,2-benzanthracene
: C20H16
分子式
: 256.34 g/mol
分子量
组分 浓度或浓度范围
7,12-Dimethylbenz[a]anthracene
<=100%
化学文摘登记号(CAS 57-97-6
No.) 200-359-5
EC-编号

模块 4. 急救措施
4.1 必要的急救措施描述
一般的建议
请教医生。 向到现场的医生出示此安全技术说明书。
吸入
如果吸入,请将患者移到新鲜空气处。 如呼吸停止,进行人工呼吸。 请教医生。
皮肤接触
用肥皂和大量的水冲洗。 请教医生。
眼睛接触
用水冲洗眼睛作为预防措施。
食入
切勿给失去知觉者通过口喂任何东西。 用水漱口。 请教医生。
4.2 主要症状和影响,急性和迟发效应
4.3 及时的医疗处理和所需的特殊处理的说明和指示
无数据资料

模块 5. 消防措施
5.1 灭火介质
灭火方法及灭火剂
用水雾,抗乙醇泡沫,干粉或二氧化碳灭火。
5.2 源于此物质或混合物的特别的危害
碳氧化物
5.3 给消防员的建议
如必要的话,戴自给式呼吸器去救火。
5.4 进一步信息
无数据资料

模块 6. 泄露应急处理
6.1 作业人员防护措施、防护装备和应急处置程序
使用个人防护用品。 避免粉尘生成。 避免吸入蒸气、烟雾或气体。 保证充分的通风。
人员疏散到安全区域。 避免吸入粉尘。
6.2 环境保护措施
如能确保安全,可采取措施防止进一步的泄漏或溢出。 不要让产品进入下水道。
6.3 泄漏化学品的收容、清除方法及所使用的处置材料
收集和处置时不要产生粉尘。 扫掉和铲掉。 放入合适的封闭的容器中待处理。
6.4 参考其他部分
丢弃处理请参阅第13节。

模块 7. 操作处置与储存
7.1 安全操作的注意事项
避免接触皮肤和眼睛。 避免形成粉尘和气溶胶。避免曝露:使用前需要获得专门的指导。
在有粉尘生成的地方,提供合适的排风设备。一般性的防火保护措施。
7.2 安全储存的条件,包括任何不兼容性
贮存在阴凉处。 使容器保持密闭,储存在干燥通风处。
7.3 特定用途
无数据资料

模块 8. 接触控制和个体防护
8.1 容许浓度
最高容许浓度
没有已知的国家规定的暴露极限。
8.2 暴露控制
适当的技术控制
根据良好的工业卫生和安全规范进行操作。 休息前和工作结束时洗手。
个体防护设备
眼/面保护
带有防护边罩的安全眼镜符合 EN166要求请使用经官方标准如NIOSH (美国) 或 EN 166(欧盟)
检测与批准的设备防护眼部。
皮肤保护
戴手套取 手套在使用前必须受检查。
请使用合适的方法脱除手套(不要接触手套外部表面),避免任何皮肤部位接触此产品.
使用后请将被污染过的手套根据相关法律法规和有效的实验室规章程序谨慎处理. 请清洗并吹干双手
所选择的保护手套必须符合EU的89/686/EEC规定和从它衍生出来的EN 376标准。
完全接触
物料: 丁腈橡胶
最小的层厚度 0.11 mm
溶剂渗透时间: 480 min
测试过的物质Dermatril® (KCL 740 / Z677272, 规格 M)
飞溅保护
物料: 丁腈橡胶
最小的层厚度 0.11 mm
溶剂渗透时间: 480 min
测试过的物质Dermatril® (KCL 740 / Z677272, 规格 M)
, 测试方法 EN374
如果以溶剂形式应用或与其它物质混合应用,或在不同于EN
374规定的条件下应用,请与EC批准的手套的供应商联系。
这个推荐只是建议性的,并且务必让熟悉我们客户计划使用的特定情况的工业卫生学专家评估确认才可.
这不应该解释为在提供对任何特定使用情况方法的批准.
身体保护
全套防化学试剂工作服, 防护设备的类型必须根据特定工作场所中的危险物的浓度和数量来选择。
呼吸系统防护
如危险性评测显示需要使用空气净化的防毒面具,请使用全面罩式多功能微粒防毒面具N100型(US
)或P3型(EN
143)防毒面具筒作为工程控制的候补。如果防毒面具是保护的唯一方式,则使用全面罩式送风防毒
面具。 呼吸器使用经过测试并通过政府标准如NIOSH(US)或CEN(EU)的呼吸器和零件。

模块 9. 理化特性
9.1 基本的理化特性的信息
a) 外观与性状
形状: 粉末
颜色: 淡黄
b) 气味
无数据资料
c) 气味阈值
无数据资料
d) pH值
无数据资料
e) 熔点/凝固点
熔点/凝固点: 122 - 123 °C - lit.
f) 沸点、初沸点和沸程
无数据资料
g) 闪点
无数据资料
h) 蒸发速率
无数据资料
i) 易燃性(固体,气体)
无数据资料
j) 高的/低的燃烧性或爆炸性限度 无数据资料
k) 蒸气压
无数据资料
l) 蒸汽密度
无数据资料
m) 密度/相对密度
无数据资料
n) 水溶性
无数据资料
o) n-辛醇/水分配系数
无数据资料
p) 自燃温度
无数据资料
q) 分解温度
无数据资料
r) 粘度
无数据资料

模块 10. 稳定性和反应活性
10.1 反应性
无数据资料
10.2 稳定性
无数据资料
10.3 危险反应
无数据资料
10.4 应避免的条件
无数据资料
10.5 不相容的物质
强氧化剂
10.6 危险的分解产物
其它分解产物 - 无数据资料

模块 11. 毒理学资料
11.1 毒理学影响的信息
急性毒性
半数致死剂量 (LD50) 经口 - 大鼠 - 327 mg/kg
皮肤刺激或腐蚀
皮肤 - 小鼠 - 轻度的皮肤刺激
眼睛刺激或腐蚀
无数据资料
呼吸道或皮肤过敏
无数据资料
生殖细胞致突变性
实验室测试表明由诱变效应
致癌性
该产品是或包含被IARC, ACGIH, EPA, 和 NTP 列为可能是致癌物的组分
可能的人类致癌物
IARC:
此产品中没有大于或等于 0。1%含量的组分被 IARC鉴别为可能的或肯定的人类致癌物。
生殖毒性
实验室试验表明有畸胎生成效应
特异性靶器官系统毒性(一次接触)
无数据资料
特异性靶器官系统毒性(反复接触)
无数据资料
吸入危险
无数据资料
潜在的健康影响
吸入 吸入可能有害。 可能引起呼吸道刺激。
摄入 误吞对人体有害。
皮肤 通过皮肤吸收可能有害。 可能引起皮肤刺激。
眼睛 可能引起眼睛刺激。
附加说明
化学物质毒性作用登记: CW3850000

模块 12. 生态学资料
12.1 生态毒性
无数据资料
12.2 持久性和降解性
无数据资料
12.3 潜在的生物累积性
无数据资料
12.4 土壤中的迁移性
无数据资料
12.5 PBT 和 vPvB的结果评价
无数据资料
12.6 其它不良影响
无数据资料

模块 13. 废弃处置
13.1 废物处理方法
产品
将剩余的和不可回收的溶液交给有许可证的公司处理。
联系专业的拥有废弃物处理执照的机构来处理此物质。
与易燃溶剂相溶或者相混合,在备有燃烧后处理和洗刷作用的化学焚化炉中燃烧
受污染的容器和包装
按未用产品处置。

模块 14. 运输信息
14.1 联合国危险货物编号
欧洲陆运危规: - 国际海运危规: - 国际空运危规: -
14.2 联合国运输名称
欧洲陆运危规: 非危险货物
国际海运危规: 非危险货物
国际空运危规: 非危险货物
14.3 运输危险类别
欧洲陆运危规: - 国际海运危规: - 国际空运危规: -
14.4 包裹组
欧洲陆运危规: - 国际海运危规: - 国际空运危规: -
14.5 环境危险
欧洲陆运危规: 否 国际海运危规 国际空运危规: 否
海洋污染物(是/否): 否
14.6 对使用者的特别提醒
无数据资料


模块 15 - 法规信息
N/A


模块16 - 其他信息
N/A


制备方法与用途

用途

9,10-二甲基-1,2-苯并蒽是一种蒽类衍生物,可用作生化试剂。

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

点击查看最新优质反应信息

文献信息

  • Pheromone content of azinphosmethyl-susceptible and -resistant obliquebanded leafrollers (Lepidoptera: Tortricidae) as a function of time of day and female age
    作者:Ashraf M. El-Sayed、R.M. Trimble
    DOI:10.4039/ent134331-3
    日期:2002.6
    Abstract

    The effect of time of day and age on the amounts and ratios of four pheromone compounds [(Z)-11-tetradecenyl acetate (Z11-14:Ac), (E)-11-tetradecenyl acetate (E11-14:Ac), (Z)-11-tetradecenol (Z11-14:OH), and (Z)-11-tetradecenal (Z11-14:Al)] was compared in azinphosmethyl-susceptible (susceptible) and -resistant (resistant) female obliquebanded leafrollers, Choristoneura rosaceana (Harris). The amounts of all four pheromone compounds varied during the hour before and five hours after the onset of scotophase. The glands of resistant females contained approximately one half the amount of Z11-14:Ac and Z11-14:OH as the glands of susceptible females during the second and third hours of scotophase, and between 50 and 70% as much Z11-14:Al as the glands of susceptible females during the hour before and second to fourth hours of scotophase. The glands of susceptible and resistant females contained similar amounts of E11-14:Ac. The relative amounts of each of the four pheromone compounds were affected by time of day but not by resistance status. There was a negative linear relationship between the amounts of each of the four compounds and female age in both types of females. The amounts of Z11-14:Ac and E11-14:Ac declined at similar rates with age in susceptible and resistant females; the amounts of Z11-14:OH and Z11-14:Al declined more rapidly with age in susceptible than in resistant females. The relative amounts of the four compounds were not affected by female age. Temporal variation in the relative amounts of pheromone in susceptible and resistant C. rosaceana may be associated with similar variation in the emission of pheromone and corresponding temporal variation in the relative attractiveness of the two types of females.

    摘要 比较了一天中的时间和年龄对四种信息素化合物[(Z)-11-十四烯基乙酸酯(Z11-14:Ac)、(E)-11-十四烯基乙酸酯(E11-14:Ac)、(Z)-11-十四烯醇(Z11-14:OH)和 (Z)-11-十四烯醛(Z11-14:Al)]进行了比较。所有四种信息素化合物的含量在光照开始前一小时和光照开始后五小时内各不相同。在光斑期的第二和第三小时,抗性雌虫腺体中 Z11-14:Ac 和 Z11-14:OH 的含量约为易感雌虫腺体的一半;在光斑期开始前一小时和第二至第四小时,抗性雌虫腺体中 Z11-14:Al 的含量约为易感雌虫腺体的 50% 至 70%。易感雌虫和抗性雌虫腺体中的 E11-14:Ac 含量相似。四种信息素化合物的相对含量受一天中时间的影响,但不受抗性状态的影响。两种雌虫的四种化合物的含量与雌虫的年龄呈负线性关系。在易感雌性和抗性雌性中,Z11-14:Ac和E11-14:Ac的含量随年龄下降的速度相似;在易感雌性中,Z11-14:OH和Z11-14:Al的含量随年龄下降的速度比抗性雌性快。四种化合物的相对含量不受雌性年龄的影响。易感性和抗性蔷薇雌虫信息素相对含量的时间变化可能与信息素释放量的相似变化以及两种雌虫相对吸引力的相应时间变化有关。
  • Synthesis of Adducts Formed by Iodine Oxidation of Aromatic Hydrocarbons in the Presence of Deoxyribonucleosides and Nucleobases
    作者:Aaron A. Hanson、Eleanor G. Rogan、Ercole L. Cavalieri
    DOI:10.1021/tx980127q
    日期:1998.10.1
    hydrocarbons (PAH) undergo two main pathways of metabolic activation related to the initiation of tumors: one-electron oxidation to give radical cations and monooxygenation to yield bay-region diol epoxides. Synthesis of standard adducts is essential for identifying biologically formed adducts. Until recently, radical cation adducts were synthesized by oxidation of the PAH in an electrochemical apparatus
    多环芳烃(PAH)经历了与肿瘤发生有关的两种主要的代谢活化途径:单电子氧化产生自由基阳离子,单氧化产生海湾区域的二醇环氧化物。标准加合物的合成对于鉴定生物形成的加合物至关重要。直到最近,自由基阳离子加合物是在电化学装置中通过PAH的氧化来合成的,在许多有机化学实验室中尚不容易获得。我们已经开发了一种方便有效的方法,可以使用I2作为氧化剂来合成PAH-核苷加合物。苯并[a] py(BP),二苯并[a],1](DB [a,l] P)和7,12-二甲基苯并[a]蒽的加合物与脱氧鸟苷(dG),脱氧腺苷,鸟嘌呤(瓜)含或不含AgClO4的Me2SO或二甲基甲酰胺(DMF)中的腺嘌呤或腺嘌呤。例如,当在3当量的I2、5当量的dG和1当量的AgClO4存在下,将有效的致癌物BP溶解在DMF中时,45%的BP转化为BP-6-N7Gua。当在没有AgClO4的情况下将BP置于相同的反应条件下时,BP-6-N
  • De Novo Design of Selective Quadruplex–Duplex Junction Ligands and Structural Characterisation of Their Binding Mode: Targeting the G4 Hot‐Spot
    作者:Laura Díaz‐Casado、Israel Serrano‐Chacón、Laura Montalvillo‐Jiménez、Francisco Corzana、Agatha Bastida、Andrés G. Santana、Carlos González、Juan Luis Asensio
    DOI:10.1002/chem.202005026
    日期:2021.4.7
    Targeting the interface between DNA quadruplex and duplex regions by small molecules holds significant promise in both therapeutics and nanotechnology. Herein, a new pharmacophore is reported, which selectively binds with high affinity to quadruplex–duplex junctions, while presenting a poorer affinity for Gquadruplex or duplex DNA alone. Ligands complying with the reported pharmacophore exhibit a
    小分子靶向DNA四链体和双链体区域之间的界面在治疗学和纳米技术中都具有重大前景。本文报道了一种新的药效基团,它以高亲和力选择性结合四链体-双链体连接,而对单独的G-四链体或双链体DNA的亲和力较弱。符合报道的药效基团的配体对四链体-双链体连接具有显着的亲和力和选择性,包​​括在HIV-1 LTR-III序列中观察到的亲和力和选择性。四联体-双联体连接与该家族的配体之间的复合物的结构已通过NMR方法确定。根据这些数据,通过迄今为止在药物和生物化学中尚未开发的前所未有的相互作用模式,实现了这种结构基序对四链体-双链体连接的显着选择性:将苄基铵部分插入到部分暴露的G-tetrad中心,与双工。所述支架的进一步修饰以及其他片段为基因组G-四链体形成区域的选择性配体的开发开辟了道路。
  • Synthesis and structure determination of the adducts of the potent carcinogen 7,12-dimethylbenz[a]anthracene and deoxyribonucleosides formed by electrochemical oxidation: models for metabolic activation by one-electron oxidation
    作者:N. V. S. RamaKrishna、Ercole L. Cavalieri、E. G. Rogan、G. Dolnikowski、R. L. Cerny、M. L. Gross、H. Jeong、R. Jankowiak、G. J. Small
    DOI:10.1021/ja00031a047
    日期:1992.2
    Anodic oxidation of 7,12-dimethylbenz[a]anthracene (7,12-DMBA) in the presence of dG yields four adducts and one oxygenated derivative of 7,12-DMBA: 7-methylbenz[a]anthracene (MBA)-12-CH 2 -C8dG (13%), 7-MBA-12-CH 2 -N7Gua (55%), 12-MBA-7-CH 2 -N7Gua (12%), 7-MBA-12-CH 2 -C8Gua (10%), and 7,12-(CH 2 OH) 2 -BA (10%). The first three are primary products of the electrochemical reaction, whereas the last
    在 dG 存在下,7,12-二甲基苯并 [a] 蒽 (7,12-DMBA) 的阳极氧化产生四种加合物和一种 7,12-DMBA 的氧化衍生物:7-甲基苯并 [a] 蒽 (MBA)-12 -CH 2 -C8dG (13%), 7-MBA-12-CH 2 -N7Gua (55%), 12-MBA-7-CH 2 -N7Gua (12%), 7-MBA-12-CH 2 -C8Gua (10%) 和 7,12-(CH 2 OH) 2 -BA (10%)。前三个是电化学反应的初级产物,而后两个是次级产物
  • Effect of Ultraviolet Light on Polycyclic Hydrocarbons in Sterol Surface Film Systems
    作者:W. W. Davis、M. E. Krahl、G. H. A. Clowes
    DOI:10.1126/science.94.2448.519
    日期:1941.11.28
    2-benzanthracenes and other polycyclic hydrocarbons, when irradiated either in bulk aqueous suspensions or in the comparable excess phase under mixed surface films, were converted rapidly by ultraviolet light to photo-oxides. When held in two-dimensional solution or molecular association with sterols in mixed surface films at the air-water interface, the hydrocarbons were protected from such photodecomposition
    某些烷基-1,2-苯并蒽和其他多环烃,当在大量水悬浮液中或在混合表面膜下的相当过量相中照射时,会被紫外光迅速转化为光氧化物。当在二维溶液中或在气-水界面的混合表面膜中与甾醇分子缔合时,碳氢化合物不受这种光分解。在可以进行比较的一种情况下,光氧化伴随着烃与甾醇膜相互作用能力的丧失。
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