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间位叶蝉散 | 64-00-6

中文名称
间位叶蝉散
中文别名
甲基氨基甲酸间异丙苯基酯虫草灵
英文名称
3-isopropylphenyl methylcarbamate
英文别名
3-Isopropylphenyl-N-methylcarbamat;m-Isopropyl-phenyl-N-methylcarbamat;m-Cumenyl methylcarbamate;(3-propan-2-ylphenyl) N-methylcarbamate
间位叶蝉散化学式
CAS
64-00-6
化学式
C11H15NO2
mdl
——
分子量
193.246
InChiKey
GYKXQTKSWLAUIT-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:
    53°C
  • 沸点:
    329.46°C (rough estimate)
  • 密度:
    1.0945 (rough estimate)
  • 溶解度:
    可溶于乙腈(少许)、DMSO(少许)、甲醇(少许)
  • 物理描述:
    Pure white solid without appreciable odor. Used as an insecticide to protect cotton, fruit, vegetables and field crops. Not registered as a pesticide in the U.S. (EPA, 1998)
  • 颜色/状态:
    White crystalline solid
  • 气味:
    Odorless
  • 蒸汽压力:
    4.4X10-3 mm Hg at 25 °C /Estimated/
  • 稳定性/保质期:

    This cmpd is stable to heat, light, & hydrolysis under normal conditions.

  • 分解:
    When heated to decomposition it emits toxic fumes of /nitrogen oxides/.

计算性质

  • 辛醇/水分配系数(LogP):
    2.6
  • 重原子数:
    14
  • 可旋转键数:
    3
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.36
  • 拓扑面积:
    38.3
  • 氢给体数:
    1
  • 氢受体数:
    2

ADMET

代谢
当老鼠暴露于标记的UC-10854时,形成了标记的(14)C二氧化碳。在大鼠肝脏微粒体与UC-10854一同孵化,并且存在还原型烟酰胺腺嘌呤二核苷酸磷酸NADPH)的情况下,观察到了3-(1-羟基-1-甲基乙基)苯甲基氨基甲酸酯和3-异丙基N-羟甲基氨基甲酸酯。还发现了几种未识别的化合物。
When rats were exposed to labeled UC-10854, labeled (14)C-carbon dioxide was formed. After incubation of rat liver microsomes with UC-10854 in the presence of reduced nicotinamide--adenine dinucleotide phosphate (NADPH), 3-(1-hydroxy-1-methylethyl)phenyl methylcarbamate & 3-isopropyl N-hydroxymethylcarbamate were observed. Several unidentified compounds were also found.
来源:Hazardous Substances Data Bank (HSDB)
代谢
使用UC-10854标记的(14)C-CH3和(14)C-C=O进行的研究表明,处理过的家蝇中产生了来自这两种物质的(14)C-二氧化碳。家蝇还将这种物质解为相应的
Studies conducted with UC-10854 labeled (14)C-CH3 & (14)C-C=O showed that (14)C-carbon dioxide arose from both in treated houseflies. Houseflies also hydrolyzed this material to the corresponding phenol.
来源:Hazardous Substances Data Bank (HSDB)
代谢
在用UC-10854处理豆科植物后,除了几种未识别的化合物外,还发现了羟基丙基和N-羟甲基类似物。
After treatment of bean plants with UC-10854, in addition to several unidentified compounds, the hydroxypropyl & N-hydroxymethyl analogs were found.
来源:Hazardous Substances Data Bank (HSDB)
代谢
异丙威的间位异构体(m-异丙基苯基-N-甲基氨基甲酸酯)对动物的毒性要远大于其对位异构体...或许其更高的毒性是由于其通过侧链氧化代谢产生(1-羟基-1-甲基乙基)苯基甲基氨基甲酸酯,这也是一种胆碱酯酶抑制剂
The meta-isomer of isoprocarb (m-isopropylphenyl N-methylcarbamate) is much more toxic to animals /than the ortho-isomer/ ... Perhaps its higher toxicity is due to its metabolism by side chain oxidation to yield (1-hydroxy-1-methylethyl)phenyl methylcarbamate, which is also a cholinesterase inhibitor.
来源:Hazardous Substances Data Bank (HSDB)
代谢
甲酰胺通过肝脏酶促解;降解产物通过肾脏和肝脏排出。
The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 毒性总结
m-Cumenyl甲基氨基甲酸盐是一种胆碱酯酶乙酰胆碱酯酶(AChE)抑制剂氨基甲酸酯通过与胆碱酯酶的活性位点进行基甲酰化,形成不稳定的复合物。这种抑制作用是可逆的。胆碱酯酶抑制剂抑制乙酰胆碱酯酶的作用。由于其基本功能,干扰乙酰胆碱酯酶作用的化学物质是强效的神经毒素,即使在低剂量下也会导致过度流涎和流泪。在较高剂量的暴露下,头痛、流涎、恶心、呕吐、腹痛和腹泻通常是显著的症状。乙酰胆碱酯酶分解神经递质乙酰胆碱,后者在神经和肌肉接头处释放,以允许肌肉或器官放松。乙酰胆碱酯酶抑制的结果是乙酰胆碱积聚并继续发挥作用,使得任何神经冲动持续传递,肌肉收缩不会停止。
m-Cumenyl methylcarbamate is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop.
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 致癌物分类
对人类不具有致癌性(未被国际癌症研究机构IARC列名)。
No indication of carcinogenicity to humans (not listed by IARC).
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 健康影响
急性暴露于胆碱酯酶抑制剂可能会导致胆碱能危象,表现为严重的恶心/呕吐、流涎、出汗、心动过缓、低血压、崩溃和抽搐。肌肉无力可能性增加,如果呼吸肌肉受累,可能导致死亡。在运动神经积累的乙酰胆碱会导致神经肌肉接头处烟碱表达的过度刺激。当这种情况发生时,可以看到肌肉无力、疲劳、肌肉痉挛、肌肉跳动和麻痹的症状。当自主神经节有乙酰胆碱积累时,这会导致交感系统中烟碱表达的过度刺激。与此相关的症状是高血压和低血糖。由于乙酰胆碱积累,中枢神经系统中烟碱乙酰胆碱受体的过度刺激会导致焦虑、头痛、抽搐、共济失调、呼吸和循环抑制、震颤、全身无力,甚至可能昏迷。当由于乙酰胆碱过多而在毒蕈碱乙酰胆碱受体上表现出毒蕈碱过度刺激时,可能会出现视力障碍、胸部紧绷、由于支气管收缩引起的喘息、支气管分泌物增加、唾液分泌增加、流泪、出汗、肠蠕动和排尿的症状。长期高(>10年)暴露会导致神经心理学后果,包括感知和视动处理方面的障碍(A15321)。
Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (A15321).
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 暴露途径
吸入 (L793);口服 (L793);皮肤给药 (L793)
Inhalation (L793) ; oral (L793); dermal (L793)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 症状
与有机化合物一样,症状和体征基于过度的胆碱能刺激。与有机中毒不同,氨基甲酸酯中毒的持续时间往往较短,因为神经组织乙酰胆碱酯酶的抑制作用是可逆的,而且氨基甲酸酯的代谢速度更快。肌肉无力、眩晕、出汗和轻微的身体不适是常见的早期症状。头痛、流涎、恶心、呕吐、腹痛和腹泻在较高暴露平时常常很明显。瞳孔收缩伴有视力模糊、不协调、肌肉抽搐和言语不清的情况也有报道。(L795)
As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (L795)
来源:Toxin and Toxin Target Database (T3DB)
吸收、分配和排泄
关于通过吸入或口服途径暴露后,氨基甲酸盐在哺乳动物的各种器官和组织中的分布,目前可用的信息很少。据报道含有残留物的器官包括肝脏、肾脏、大脑、脂肪和肌肉。在大鼠中,半衰期约为3-8小时。似乎氨基甲酸盐通过尿液在人体中的排泄也很迅速,而且人体的代谢途径与大鼠相同。/氨基甲酸酯类杀虫剂/
Little information is available on the distribution of carbamates in the various organs and tissues in mammals following exposure by inhalation or the oral route. The organs in which residues have been reported are the liver, kidneys, brain, fat, and muscle. The half-life in the rat is of the order of 3-8 hr. It seems that the excretion of carbamates via urine is also rapid in man, and that the metabolic pathways in man are the same as those in the rat. /Carbamate pesticides/
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
活体研究表明,氨基甲酸酯在通过胃肠道的正常传输过程中几乎被完全吸收。在老鼠体内,所有氨基甲酸酯都迅速分布到组织和器官中。氨基甲酸酯的渗透半衰期从8-17分钟不等。在动物体内,氨基甲酸酯的氧化通常,但不总是,导致解毒。氧化代谢通常导致极性更大、溶性更高的产物,这些产物比母体化合物更容易通过尿液和粪便排出体外。/氨基甲酸酯类杀虫剂/
In vivo studies have shown that carbamates are almost completely absorbed during normal transit through the gastrointestinal tract. ...In mice, all carbamates were rapidly distributed to the tissues and organs. The half-life values of penetration ranged from 8-17 min for carbamates. ...In animals, oxidation of carbamates often, but not always, results in detoxification. Oxidative metabolism generally leads to products of greater polarity and water solubility, and these can be more readily eliminated through the urine and feces than the parent compound. /Carbamate pesticides/
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • 危险等级:
    6.1(a)
  • 包装等级:
    I
  • 危险类别:
    6.1(a)
  • 危险品运输编号:
    UN 2757

SDS

SDS:ecae6cee655035c93a75b690bd24d986
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制备方法与用途

类别:农药

  • 毒性分级:剧毒
  • 急性毒性(口服):
    • 大鼠 LD50:16 毫克/公斤
    • 小鼠 LD50:16 毫克/公斤
  • 可燃性危险特性:受热分解,产生有毒氧化氮气体
  • 储运特性:库房需通风、低温和干燥;与食品原料分开储存和运输
  • 灭火剂:砂土、干粉、泡沫

反应信息

  • 作为反应物:
    描述:
    间位叶蝉散 生成 3-isopropylphenyl (chlorosulfinyl)(methyl)carbamate
    参考文献:
    名称:
    N-Chlorosulfinylcarbamate esters
    摘要:
    N-氯磺酰基氨基甲酸酯是通过硫酰氯与卡巴酯酯反应制得的,该卡巴酯酯在氨基甲酸氮原子上具有一个未被取代的氢,最好在氯化氢受体的存在下进行。所得的N-氯磺酰基氨基甲酸酯是制备相对低哺乳动物毒性的杀虫剂的有用中间体。
    公开号:
    US04261897A1
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文献信息

  • Process for preparing N-[(phosphinyl)amino]thio- and N-[(phosphinyl)amino]t
    申请人:The Upjohn Company
    公开号:US04201733A1
    公开(公告)日:1980-05-06
    Some new phosphinic acid derivatives of aminothio methylcarbamates have been synthesized and tested as pesticides. The new compounds are active against insects, mites, and nematodes. The N-[(phosphinyl)amino]thio- and N-](phosphinothioyl)amino]thio-methylcarbamates are readily prepared by the general procedure of reacting a phosphinic acid amide with sulfur dichloride so as to obtain the corresponding N-(chlorothio)phosphinic acid amide which reactant will react with a methylcarbamate so as to produce the corresponding object compounds, the N-[(phosphinyl)amino]thio- and N-[(phosphinothioyl)-amino]thio-methylcarbamates of this invention. Various formulations for pesticidal use are described along with appropriate rates of application.
    已合成并测试了一些新的甲酸磷酸生物作为杀虫剂。这些新化合物对昆虫、螨和线虫具有活性。N-[(基)基]基和N-[(酰)基]甲酸酯可通过将磷酸酰胺与二氯化硫反应的一般程序轻松制备,从而获得相应的N-()磷酸酰胺,该反应物将与甲基氨基甲酸酯反应,从而产生本发明的相应化合物,即N-[(基)基]基和N-[(酰)基]甲酸酯。描述了用于杀虫剂使用的各种配方以及适当的施用速率。
  • N-[(phosphinyl or phosphinothioyl)amino]thio-methylcarbamates and
    申请人:The Upjohn Company
    公开号:US04208409A1
    公开(公告)日:1980-06-17
    Some new phosphinic acid derivatives of aminothio methylcarbamates have been synthesized and tested as pesticides. The new compounds are active against insects, mites, and nematodes. The N-[(phosphinyl)amino]thio- and N-[(phosphinothioyl)amino]thio- methylcarbamates are readily prepared by the general procedure of reacting a phosphinic acid amide with sulfur dichloride so as to obtain the corresponding N-(chlorothio)phosphinic acid amide which reactant will react with a methylcarbamate so as to produce the corresponding object compounds, the N-[(phosphinothioyl)amino]thio- methylcarbamates of this invention. Various formulations for pesticidal use are described along with appropriate rates of application.
    已合成并测试了一些新的甲酸磷酸酯衍生物作为杀虫剂。这些新化合物对昆虫、螨和线虫具有活性。N-[(基)基]-和N-[(酰)基]甲基氨基甲酸酯可通过将磷酸胺与二氯化硫反应的一般程序制备,从而获得相应的N-()磷酸胺,该反应物将与甲基氨基甲酸酯反应,从而产生本发明的相应化合物,即N-[(酰)基]甲基氨基甲酸酯。描述了用于杀虫剂使用的各种配方以及适当的施用速率。
  • N-[(phosphinyl) amino]thio- and
    申请人:The Upjohn Company
    公开号:US04081536A1
    公开(公告)日:1978-03-28
    Some new phosphinic acid derivatives of aminothio methylcarbamates have been synthesized and tested as pesticides. The new compounds are active against insects, mites, and nematodes. The N-[(phosphinyl)amino]thio- and N-[(phosphinothioyl)amino]thio- methylcarbamates are readily prepared by the general procedure of reacting a phosphinic acid amide with sulfur dichloride so as to obtain the corresponding N-(chlorothio)phosphinic acid amide which reactant will react with a methylcarbamate so as to produce the corresponding object compounds, the N-[phosphinyl)amino]thio- and N-[(phosphinothioyl)-amino]thio- methylcarbamates of this invention. Various formulations for pesticidal use are described along with appropriate rates of application.
    已合成并测试了一些新的磷酸酯类甲基氨基甲酸酯衍生物作为杀虫剂。这些新化合物对昆虫、螨和线虫具有活性。N-[(酰胺基)代]和N-[(酰基)胺基]甲基氨基甲酸酯可通过一般程序制备,即将磷酸酯酰胺与二氯化硫反应,从而获得相应的N-()磷酸酯酰胺,该反应物将与甲基氨基甲酸酯反应,从而产生本发明的相应化合物,即N-[(酰胺基)代]和N-[(酰基)胺基]甲基氨基甲酸酯。还描述了用于杀虫剂使用的各种配方以及适当的施用速率。
  • N-alkoxy- and N-aryloxysulfinylcarbamate esters
    申请人:The Reagents of the University of California
    公开号:US04263318A1
    公开(公告)日:1981-04-21
    A novel class of chemical compounds useful as pesticides consists of N-alkoxy- and N-aryloxysulfinylcarbamate esters. The preparation of these compounds and their formulation to control insects are exemplified.
    一种新型的化学化合物可用作杀虫剂,包括N-烷氧基和N-芳氧基磺酰基氨基甲酸酯。本文举例说明了这些化合物的制备方法以及它们的配制方法来控制昆虫。
  • N-Alkylsulfonyl-, N-arylsulfonyl-, and
    申请人:The Regents of the University of California
    公开号:US04308274A1
    公开(公告)日:1981-12-29
    A novel class of chemical compounds useful as pesticides consists of N-alkylsulfonyl-, N-arylsulfonyl-, and N-aminosulfonylaminosulfinylcarbamate esters. The preparation of these compounds and their formulation to control insects are exemplified.
    一种新型的化学化合物可用作杀虫剂,包括N-烷基磺酰基,N-芳基磺酰基和N-基磺酰基亚磺酰基氨基甲酸酯。本文举例说明这些化合物的制备以及它们的配方用于控制昆虫。
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同类化合物

(βS)-β-氨基-4-(4-羟基苯氧基)-3,5-二碘苯甲丙醇 (S,S)-邻甲苯基-DIPAMP (S)-(-)-7'-〔4(S)-(苄基)恶唑-2-基]-7-二(3,5-二-叔丁基苯基)膦基-2,2',3,3'-四氢-1,1-螺二氢茚 (S)-盐酸沙丁胺醇 (S)-3-(叔丁基)-4-(2,6-二甲氧基苯基)-2,3-二氢苯并[d][1,3]氧磷杂环戊二烯 (S)-2,2'-双[双(3,5-三氟甲基苯基)膦基]-4,4',6,6'-四甲氧基联苯 (S)-1-[3,5-双(三氟甲基)苯基]-3-[1-(二甲基氨基)-3-甲基丁烷-2-基]硫脲 (R)富马酸托特罗定 (R)-(-)-盐酸尼古地平 (R)-(-)-4,12-双(二苯基膦基)[2.2]对环芳烷(1,5环辛二烯)铑(I)四氟硼酸盐 (R)-(+)-7-双(3,5-二叔丁基苯基)膦基7''-[((6-甲基吡啶-2-基甲基)氨基]-2,2'',3,3''-四氢-1,1''-螺双茚满 (R)-(+)-7-双(3,5-二叔丁基苯基)膦基7''-[(4-叔丁基吡啶-2-基甲基)氨基]-2,2'',3,3''-四氢-1,1''-螺双茚满 (R)-(+)-7-双(3,5-二叔丁基苯基)膦基7''-[(3-甲基吡啶-2-基甲基)氨基]-2,2'',3,3''-四氢-1,1''-螺双茚满 (R)-(+)-4,7-双(3,5-二-叔丁基苯基)膦基-7“-[(吡啶-2-基甲基)氨基]-2,2”,3,3'-四氢1,1'-螺二茚满 (R)-3-(叔丁基)-4-(2,6-二苯氧基苯基)-2,3-二氢苯并[d][1,3]氧杂磷杂环戊烯 (R)-2-[((二苯基膦基)甲基]吡咯烷 (R)-1-[3,5-双(三氟甲基)苯基]-3-[1-(二甲基氨基)-3-甲基丁烷-2-基]硫脲 (N-(4-甲氧基苯基)-N-甲基-3-(1-哌啶基)丙-2-烯酰胺) (5-溴-2-羟基苯基)-4-氯苯甲酮 (5-溴-2-氯苯基)(4-羟基苯基)甲酮 (5-氧代-3-苯基-2,5-二氢-1,2,3,4-oxatriazol-3-鎓) (4S,5R)-4-甲基-5-苯基-1,2,3-氧代噻唑烷-2,2-二氧化物-3-羧酸叔丁酯 (4S,4''S)-2,2''-亚环戊基双[4,5-二氢-4-(苯甲基)恶唑] (4-溴苯基)-[2-氟-4-[6-[甲基(丙-2-烯基)氨基]己氧基]苯基]甲酮 (4-丁氧基苯甲基)三苯基溴化磷 (3aR,8aR)-(-)-4,4,8,8-四(3,5-二甲基苯基)四氢-2,2-二甲基-6-苯基-1,3-二氧戊环[4,5-e]二恶唑磷 (3aR,6aS)-5-氧代六氢环戊基[c]吡咯-2(1H)-羧酸酯 (2Z)-3-[[(4-氯苯基)氨基]-2-氰基丙烯酸乙酯 (2S,3S,5S)-5-(叔丁氧基甲酰氨基)-2-(N-5-噻唑基-甲氧羰基)氨基-1,6-二苯基-3-羟基己烷 (2S,2''S,3S,3''S)-3,3''-二叔丁基-4,4''-双(2,6-二甲氧基苯基)-2,2'',3,3''-四氢-2,2''-联苯并[d][1,3]氧杂磷杂戊环 (2S)-(-)-2-{[[[[3,5-双(氟代甲基)苯基]氨基]硫代甲基]氨基}-N-(二苯基甲基)-N,3,3-三甲基丁酰胺 (2S)-2-[[[[[((1S,2S)-2-氨基环己基]氨基]硫代甲基]氨基]-N-(二苯甲基)-N,3,3-三甲基丁酰胺 (2S)-2-[[[[[[((1R,2R)-2-氨基环己基]氨基]硫代甲基]氨基]-N-(二苯甲基)-N,3,3-三甲基丁酰胺 (2-硝基苯基)磷酸三酰胺 (2,6-二氯苯基)乙酰氯 (2,3-二甲氧基-5-甲基苯基)硼酸 (1S,2S,3S,5S)-5-叠氮基-3-(苯基甲氧基)-2-[(苯基甲氧基)甲基]环戊醇 (1S,2S,3R,5R)-2-(苄氧基)甲基-6-氧杂双环[3.1.0]己-3-醇 (1-(4-氟苯基)环丙基)甲胺盐酸盐 (1-(3-溴苯基)环丁基)甲胺盐酸盐 (1-(2-氯苯基)环丁基)甲胺盐酸盐 (1-(2-氟苯基)环丙基)甲胺盐酸盐 (1-(2,6-二氟苯基)环丙基)甲胺盐酸盐 (-)-去甲基西布曲明 龙蒿油 龙胆酸钠 龙胆酸叔丁酯 龙胆酸 龙胆紫-d6 龙胆紫