Thianthrene
(Synonyms: 噻蒽) 目录号 : GC68232Thianthrene 是一种含硫杂环化合物，是二硫因的衍生物。Thianthrene 可用于皮肤感染相关的研究，可干扰酶和核酸的功能。
Cas No.:92-85-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Thianthrene, a sulfur-containing heterocyclic compound, is a derivative of dithiin. Thianthrene can be used in the research of dermal infections, in which it interferes with enzyme and nucleic acid function[1].
[1]. Mitchell SC, et al. Fate of thianthrene in biological systems. Xenobiotica. 2017 Aug;47(8):731-740.
| Cas No. | 92-85-3 | SDF | Download SDF |
| 别名 | 噻蒽 | ||
| 分子式 | C12H8S2 | 分子量 | 216.32 |
| 溶解度 | 储存条件 | Store at -20°C | |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.6228 mL | 23.1139 mL | 46.2278 mL |
| 5 mM | 0.9246 mL | 4.6228 mL | 9.2456 mL |
| 10 mM | 0.4623 mL | 2.3114 mL | 4.6228 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Fate of Thianthrene in biological systems
Xenobiotica 2017 Aug;47(8):731-740.PMID:27560772DOI:10.1080/00498254.2016.1222107.
1. Thianthrene is a sulfur-containing tricyclic molecule distributed widely within the macrostructure of hydrocarbon fossil fuels. Identified nearly 150 years ago, its chemistry has been widely explored leading to insights into reaction mechanisms and radical ion formation. 2. It has been claimed to have therapeutic application in the treatment of dermal infections and to interfere with enzyme and nucleic acid function, but appears to have little toxicity. 3. Following its oral administration to the rat, the majority remained within the gastrointestinal tract. After three days, about 88% was detected in the combined excreta with the remainder still within the animal. It is readily taken up into fish from the surrounding aqueous environment and has been placed within the "bioaccumulative category" to be regarded with concern. 4. Mammalian metabolism appeared to be restricted to ring carbon oxidation and subsequent glucuronic acid conjugation. Small amounts of sulfoxide and disulfoxide were also formed. No ring degradation was evident. Microorganisms similarly undertook aromatic ring hydroxylation but were able also to rupture the ring system by attacking the carbon-sulfur linkages and thereby degrading the molecule.
Site-Selective Silylation of Arenes Mediated by Thianthrene S-Oxide
Org Lett 2020 Aug 21;22(16):6657-6661.PMID:32806161DOI:10.1021/acs.orglett.0c02458.
The Thianthrene S-oxide (TTSO)-mediated site-selective silylation of arenes has been realized via a thianthrenation/Pd-catalyzed silylation sequence. This method features a broad substrate scope and wide functional group tolerance under mild conditions and allows the synthesis of a set of (hetero)arylsilanes with operationally simple manipulations. The application and generality of the approach were further demonstrated by the late-stage functionalization of marketed drugs. This reaction also represents the first example of a Pd-catalyzed silylation reaction of aryl sulfonium salts.
Conformational mobility of thianthrene-5-oxide
J Org Chem 2005 Apr 29;70(9):3450-7.PMID:15844977DOI:10.1021/jo048802q.
[reaction: see text] Data on the apparent dipole moment of thianthrene-5-oxide (1) and (1)H NMR spectra in different solvents support the conformational mobility of 1, which flaps between two limit boat conformations with the sulfinyl group in pseudoequatorial and pseudoaxial positions, respectively. The conformational equilibrium of 1 occurs too fast for the (1)H NMR (500 MHz) time-scale even at -130 degrees C, and the equilibrium constant has not been determined. The apparent dipole moments of 1 in n-hexane and 1,4-dioxane and the (1)H NMR spectra of 1 and the model compounds cis- and trans-thianthrene-5,10-dioxides (2) and Thianthrene (5) in different solvents and at various temperatures confirm that the relative position of the conformational equilibrium of 1 is solvent-dependent, and more polar solvents favor the conformation with the sulfoxide group in the pseudoaxial position (1(')(ax)). Variable-temperature (1)H NMR spectra have established the interconversion barrier of trans-2 and confirmed that the conformational equilibrium of cis-2 is strongly displaced toward the conformation with both sulfinyl groups in the pseudoequatorial position. The (1)H NMR data support the transannular interaction of the functional groups in 1 and trans-2.
Thianthrene 5-oxide as a probe for the electronic character of oxygen-transfer reactions: re-interpretation of experiments required
J Org Chem 2001 Apr 20;66(8):2686-91.PMID:11304188DOI:10.1021/jo001474j.
The electronic character of oxidants, i.e., whether they attack substrates in an electrophilic or nucleophilic way, has extensively been investigated using Thianthrene 5-oxide (SSO) as probe. The SSO molecule has a sulfide group, which is attacked by electrophilic oxidants, and a sulfoxide moiety, which is oxidized by nucleophilic oxidants. This density-functional study has been carried out in order to gain insight into the origin of the chemo- and stereoselectivity of SSO oxidation. It has been found that the endo and exo stereoisomers of the Thianthrene oxides interconvert via ring-inversion with moderate energy barriers. Thus, the stereoselectivity of SSO oxidation has to be interpreted with caution. Furthermore, a topological electron-density analysis of Thianthrene 5-oxide reveals that there is an area of charge depletion at the sulfoxide group. The location of this area indicates that the attack of nucleophilic oxidants on SSO is sterically hindered. Therefore, the SSO probe makes oxidants such as dioxiranes appear to be more electrophilic than they actually are.
Fate of Thianthrene in rat
Xenobiotica 1998 Jan;28(1):93-101.PMID:9493322DOI:10.1080/004982598239786.
1. Radiolabelled Thianthrene was administered by gavage (200 mg/kg body weight) to the adult female Wistar rat following an overnight fast. 2. Faeces was the major route of excretion of radioactivity (62%) with substantial amounts still being voided during the third day (17%). Urinary elimination (26%) peaked during the second and third days and a small amount of radioactivity (7%) remained within the carcass after 4 days. Distribution studies showed that the majority of the compound remained within the gastrointestinal tract. 3. Metabolism was limited to ring hydroxylation with subsequent conjugate formation. Oxidation of the sulphur to form the monosulphoxide and disulphoxide derivatives also occurred. No evidence for cleavage of the ring structures was observed.