1,3-二羟基-2-(羟基甲基)蒽醌 | 478-08-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1,3-二羟基-2-(羟基甲基)蒽醌
• 中文别名: 芦西定；光泽汀
• 英文名称: 1,3-dihydroxy-2-hydroxymethyl-9,10-anthraquinone
• 英文别名: lucidin；1,3-dihydroxy-2-(hydroxymethyl)anthracene-9,10-dione
• CAS: 478-08-0
• 化学式: C₁₅H₁₀O₅
• 分子量: 270.241
• InChiKey: AMIDUPFSOUCLQB-UHFFFAOYSA-N

物化性质

• 熔点：
  >330℃
• 沸点：
  333.35°C (rough estimate)
• 密度：
  1.592±0.06 g/cm3 (20 ºC 760 Torr)
• 溶解度：
  溶于二甲基亚砜
• 解离常数：
  pKa= 8.11 (20 °C, water)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

ADMET

毒理性

• 致癌性证据

评估：在实验动物中，茜草根（Rubia tinctorum）的致癌性证据有限。总体评估：茜草根（Rubia tinctorum）的致癌性对人不可分类（第3组）。/茜草根（Rubia tinctorum）/

Evaluation: There is limited evidence in experimental animals for the carcinogenicity of madder root (Rubia tinctorum). Overall evaluation: Madder root (Rubia tinctorum) is not classifiable as to its carcinogenicity to humans (Group 3). /Madder root (Rubia tinctorum)/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

神经毒素 - 其他中枢神经系统神经毒素

Neurotoxin - Other CNS neurotoxin

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 解毒与急救

基本治疗：建立专利气道。如有必要，进行吸痰。观察呼吸不足的迹象，如有需要，协助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，如有必要进行治疗……。监测休克，如有必要进行治疗……。预见并处理癫痫发作……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用生理盐水连续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的干呕反射且不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

高级治疗：对于无意识、严重肺水肿或呼吸停止的患者，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。监测心率和必要时治疗心律失常。 ... 开始静脉输液，使用D5W/SRP：“保持开放”，最低流量/。如果出现低血容量的迹象，使用乳酸钠林格氏液。注意液体过载的迹象。考虑使用药物治疗肺水肿。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象。用地西泮（安定）治疗癫痫。使用丙美卡因氢氯化物协助眼部冲洗。/毒药A和B/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

人类暴露研究/迄今为止报告的最大爆发发生在阿富汗西北部赫拉特省的古兰区，靠近苏联边境。...据估计，疫情影响了大约35,000人，分布在98个村庄。对受影响村庄的7,200名居民进行检查，发现22.6%有疾病证据，其中15%情况严重。因此，估计大约有8,000人患有这种疾病，包括5,000人严重受影响。所有年龄组的人都受到影响，但46%的受试者年龄在14岁以下。然而，在2岁以下的儿童中没有发现疾病的迹象。关于从14个肝脏活检和8个尸检中获得的病理材料的详细报告已经完成.../尽管/没有指出症状发作和活检/尸检之间的时间间隔。病理发现具有特征性，从具有特征性静脉闭塞的急性疾病到非门脉性肝硬化，这在上述22例中有5例观察到。疫情被归因于小麦的大规模污染，小麦是主要粮食作物，在连续两年干旱之后，与Heliotropium popovii H. Riedl subsp. gillianum H. Riedl的种子混合，这种植物在小麦作物中大量生长。这些种子含有吡咯烷生物碱，两个实验室报告的浓度分别为7.2和13.2-14.9 g/kg，主要被识别为heliotrine的N-氧化物（74%）...，还有一两种其他与lasiocarpine性质相似的化合物。来自几个村庄的小麦样本平均每千克含有40颗种子，即重量的0.03%。据估计，成年人每天至少消耗700克面粉，含有大约2毫克生物碱（基于种子分析的平均值）。/吡咯烷生物碱/

/HUMAN EXPOSURE STUDIES/ The largest outbreak reported to date occurred in the Gulran district of Herat Province in northwest Afghanistan, close to the border of the USSR. ...The outbreak, was estimated to have affected a population of approximately 35,000 in 98 villages. Examination of 7,200 inhabitants of the affected villages showed evidence of disease in 22.6%, which was more serious in 15%. Thus, it was estimated that approximately 8,000 subjects suffered from the disease including 5,000 who were seriously affected. All age groups were affected, but 46% of subjects were below 14 years of age. However, no sign of disease was found in children below 2 years of age. A detailed report concerning the pathological material obtained from 14 liver biopsies and 8 autopsies was made... /although/ the time interval between the onset of symptoms and the biopsy/autopsy was not indicated. Pathological findings were characteristic, ranging from acute disease with characteristic veno-occlusion to non-portal cirrhosis, which was observed in 5 of the above 22 cases. The outbreak was ascribed to massive contamination of wheat, the staple food crop, following 2 years of drought, with the seeds of Heliotropium popovii H. Riedl subsp. gillianum H. Riedl, which had been growing profusely among the wheat crop. The seeds contained pyrrolizidine alkaloids at concentrations reported by 2 laboratories to be 7.2 and 13.2-14.9 g/kg, identified mainly as the N-oxide of heliotrine (74%)..., and one or two other compounds similar in character to lasiocarpine. Samples of wheat from several villages contained an average of 40 seeds/kg, i.e., 0.03% by weight. It was estimated that an adult consumed at least 700 g flour/day, containing approximately 2 mg alkaloid (based on a mean of the seed analyses). /Pyrrolizidine alkaloids/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• WGK Germany：
  3
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P201,P202,P264,P270,P280,P301+P312+P330,P308+P313,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H302,H350
• 储存条件：
  -20°C

制备方法与用途

生物活性方面，Lucidin（NSC 30546）是一种存在于茜草中的天然成分，能够诱导细菌和哺乳动物细胞发生突变。

反应信息

• 作为反应物：
  描述：

  1,3-二羟基-2-(羟基甲基)蒽醌 在 sodium hydroxide 、 silver(l) oxide 作用下， 生成 茜草酸
  参考文献：
  名称：

  Ayyangar; Venkataraman, Journal Of Scientific and Industrial Research, 1956, vol. 15 B, p. 359,361,362

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-二乙酰氧基-2-溴甲基蒽醌 在 乙醇 、 sodium acetate 作用下， 生成 1,3-二羟基-2-(羟基甲基)蒽醌
  参考文献：
  名称：

  Joshi et al., Journal Of Scientific and Industrial Research, 1955, vol. 14 B, p. 87,92

  摘要：

  DOI：

文献信息

• [EN] PHENOL GLYCOSIDES AND THEIR USE IN THE TREATMENT OF UROLITHIASIS<br/>[FR] GLYCOSIDES PHÉNOLIQUES ET LEUR UTILISATION DANS LE TRAITEMENT DE L'UROLITHIASE
  申请人：POLITECHNIKA WROCLAWSKA

  公开号：WO2017007346A1

  公开（公告）日：2017-01-12

  The present invention relates to novel derivatives of polyphenol glycoside or polyalcohols of formula (1), wherein R1, R2, R3 is selected from the group consisting of H, OH, C(O)R4, C(0) OR4, 0 (Gly H3)n, wherein n = 0 1, 2, 3, and R4 is selected from the group consisting of H, alkyl, and Gly is a mono- or disaccharide residue. The present invention also relates to novel derivatives of glycoside polyphenols or polyalcohols, as pharmaceutical composition comprising a novel polyphenol glycoside or polyalcohols and the use of novel polyphenol glycoside or polyalcohols for the treatment of urolithiasis.

  本发明涉及公式（1）的新型多酚糖苷或多醇衍生物，其中R1、R2、R3选自H、OH、C（O）R4、C（0）OR4、0（Gly H3）n的群组，其中n = 0、1、2、3，R4选自H、烷基，Gly是单糖或二糖残基。本发明还涉及糖苷多酚或多醇的新型衍生物，以及包括新型多酚糖苷或多醇的药物组合物，以及新型多酚糖苷或多醇用于治疗尿结石的用途。
• Identification of Adducts Formed by Reaction of Purine Bases with a Mutagenic Anthraquinone, Lucidin: Mechanism of Mutagenicity by Anthraquinones Occurring in Rubiaceae Plants.
  作者：Yoko KAWASAKI、Yukihiro GODA、Hiroshi NOGUCHI、Takashi YAMADA

  DOI：10.1248/cpb.42.1971

  日期：——

  A mutagenic anthraquinone, lucidin (1), occurring in Rubiaceae plants, reacted with nucleic bases under physiological conditions to form adducts. The order of the reactivity is as follows: adenine > guanine >> pyrimidine bases approximately 0. By spectroscopic analyses, the isolated purine base adducts were identified as condensed reactants at the benzylic position of 1 with a nitrogen atom of a purine

  发生在茜草科植物中的一种诱变的蒽醌，lucidin（1）在生理条件下与核酸碱基反应形成加合物。反应的顺序如下：腺嘌呤>鸟嘌呤>嘧啶碱基大约为0。通过光谱分析，分离出的嘌呤碱基加合物被鉴定为在1的苄基位置与嘌呤碱基的氮原子的缩合反应物。结果表明形成外亚甲基化合物作为亲电子中间体的可能性很大。
• Biosynthesis of anthraquinones and related compounds in Galium mollugo cell suspension cultures
  作者：Kenichiro Inoue、Yoshinori Shiobara、Hidekazu Nayeshiro、Hiroyuki Inouye、Graham Wilson、Meinhart H. Zenk

  DOI：10.1016/s0031-9422(00)80323-4

  日期：1984.1

  Abstract From Galium mollugo cell suspension cultures, 1,4-dihydroxy-3-prenyl-2-naphtholic acid methyl ester diglucoside was isolated along with anthraquinones and mollugin. Production of the diglucoside was much increased by administering 2-succinylbenzoate to the cultures. The incorporation of 2-succinylbenzoate into lucidin-3-primeveroside, mollugin and the diglucoside in the mode so far proposed

  摘要 从 Galium mollugo 细胞悬浮培养物中分离出 1,4-dihydroxy-3-prenyl-2-naphtholic acid 甲酯二葡糖苷以及蒽醌和 mollugin。通过向培养物中施用 2-琥珀酰苯甲酸酯，二葡糖苷的产量大大增加。通过向细胞培养物中施用 13C 标记的 2-琥珀酰苯甲酸酯，证实了 2-琥珀酰苯甲酸酯以迄今为止为红宝石蒽醌提出的模式掺入 lucidin-3-primeveroside、mollugin 和二葡糖苷中。
• Anthraquinones from Neonauclea calycina and Their Inhibitory Activity against DNA Topoisomerase II.
  作者：Hideki TOSA、Munekazu IINUMA、Fujio ASAI、Toshiyuki TANAKA、Hiroshi NOZAKI、Shougo IKEDA、Ken TSUTSUI、Kimiko TSUTSUI、Masashi YAMADA、Shiho FUJIMORI

  DOI：10.1248/bpb.21.641

  日期：——

  In a series of searches fot DNA topoisomerase II inhibitors from naturally occurring compounds, a wood extract of Neonauclea calycina MERR. (Rubiaceae) showed a moderate effect in vitro. Purification of the extract resulted in the isolation of seven known anthraquinones. The structures were characterized as damnacanthal, rubiadin 1-methyl ether, nordamnacanthal, morindone, damnacanthol, lucidin 3-O-primeveroside and morindone 6-O-primeveroside by spectral analysis, respectively. Damnacanthal and morindone showed an intensive inhibitory effect against topoisomerase II (IC50 : 20μg/ml and 21μg/ml).

  在一系列从天然化合物（Neonauclea calycina MERR 的木材提取物）中寻找 DNA 拓扑异构酶 II 抑制剂的过程中。 （茜草科）在体外表现出中等效果。提取物的纯化导致七种已知的蒽醌的分离。通过光谱分析，其结构分别为damacanthal、rubiadin 1-methyl ether、nordamnacanthal、morindone、damacanthol、lucidin 3-O-primeveroside和morindone 6-O-primeveroside。 Damnacanthal 和吗啉酮对拓扑异构酶 II 显示出强烈的抑制作用（IC50：20μg/ml 和 21μg/ml）。
• Degradation of lucidin: New insights into the fate of this natural pigment present in Dyer's madder ( Rubia tinctorum L.) during the extraction of textile artefacts
  作者：Lauren Ford、Christopher M. Rayner、Richard S. Blackburn

  DOI：10.1016/j.dyepig.2018.03.023

  日期：2018.7

  with 37% hydrochloric acid: methanol: water (2:1:1, v/v/v), but this solvent system hydrolyses dye glycosides and may also induce chemical reactions. One of the primary components in Dyers' madder (Rubia tinctorum L.) is lucidin primeveroside, but it is rarely seen in artefacts, nor is the corresponding aglycon lucidin. It has been demonstrated that the hydrochloric acid method causes hydrolysis of anthraquinone

  存在于不同茜草物种中的着色剂的复杂混合物可以提供有关使用哪种植物物种或技术对历史纺织人工制品的纤维进行染色的重要信息，因此，从纺织人工制品中提取和分析着色剂时，应尽可能多地获取这些信息。保留。历史悠久的纺织品通常使用37％的盐酸：甲醇：水（2：1：1，v / v / v）萃取，但是这种溶剂系统会水解染料糖苷，还可能引起化学反应。Dyers'madder（Rubia tinctorum）的主要成分之一L.）是lucidin primveroside，但在人工制品中很少见到，相应的糖苷配基糖苷也没有。已经证明，盐酸方法使蒽醌糖苷水解成它们的糖苷配基。在此证明，在这种酸性条件下，lucidin不稳定，并迅速降解为黄嘌呤嘌呤。HPLC，LC-MS和1 H NMR证实了这一点，这也提供了降解机理为逆醛醇缩过程的证据。