1,2,3-Trimethoxybenzene
(Synonyms: 1,2,3-三甲氧基苯) 目录号 : GC61729
1,2,3-三甲氧基苯（1,2,3-Trimethoxybenzene），也称为甲基丁香醇或连苯三酚三甲醚，是苯甲醚类化合物的一员。苯甲醚是含有甲氧基苯或其衍生物的有机化合物。1,2,3-三甲氧基苯微溶于水（在水中），是一种极弱碱性（基本呈中性）的化合物。茶叶中含有 1,2,3-三甲氧基苯，这使得 1,2,3-三甲氧基苯成为食品消费的潜在生物标志物。
Cas No.:634-36-6
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
1,2,3-Trimethoxybenzene is a member of the class of compounds known as anisoles. 1,2,3-Trimethoxybenzene can be found in tea, which makes 1,2,3-trimethoxybenzene a potential biomarker for the consumption of this food product.
[1]. Zheng Li, et al. Cleavage of ethers and demethylation of lignin in acidic concentrated lithium bromide (ACLB) solution.
| Cas No. | 634-36-6 | SDF | |
| 别名 | 1,2,3-三甲氧基苯 | ||
| Canonical SMILES | COC1=C(OC)C(OC)=CC=C1 | ||
| 分子式 | C9H12O3 | 分子量 | 168.19 |
| 溶解度 | DMSO : 100 mg/mL (594.57 mM; Need ultrasonic) | 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 | 5.9457 mL | 29.7283 mL | 59.4566 mL |
| 5 mM | 1.1891 mL | 5.9457 mL | 11.8913 mL |
| 10 mM | 0.5946 mL | 2.9728 mL | 5.9457 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。
AlCl3-Catalyzed Cascade Reactions of 1,2,3-Trimethoxybenzene and Adipoyl Chloride: Spectroscopic Investigations and Density Functional Theory Studies
ACS Omega 2022 Oct 14;7(43):38882-38893.PMID:36340161DOI:10.1021/acsomega.2c04612.
The reaction of 1,2,3-Trimethoxybenzene with adipoyl chloride in the presence of AlCl3 gave two isomeric cyclopentene derivatives, 1,6-bis(2,3,4-trimethoxyphenyl)hexane-1,6-dione, and two demethylation products of aryl methyl ethers. The cyclopentene derivatives including unconjugated or conjugated enones are products formed in a cascade reaction resulting from first the Friedel-Crafts acylation reaction and then aldol condensation. All compounds were optimized by density functional theory calculated using two functional levels, B3LYP and M06-2X, with the 6-311+G(d,p) basis set. The structural properties were established, natural bond orbital analysis of donor-acceptor interactions was carried out, and charges on the atoms and quantum chemical reactivity identifiers were determined to compare the strength of the intramolecular hydrogen bonds formed and their stabilities. To compare the experimental 1H and 13C NMR chemical shifts with the calculated values, NMR chemical shift calculations were carried out using the gauge-invariant atomic orbital method.
Dynamic changes in the aroma profile of Qingzhuan tea during its manufacture
Food Chem 2022 May 1;375:131847.PMID:34942497DOI:10.1016/j.foodchem.2021.131847.
Changes in key odorants and aroma profiles of Qingzhuan tea (QZT) during its manufacture were determined using headspace solid-phase microextraction gas chromatography-mass spectrometry/olfactometry. An aroma profile was constructed to illustrate sensory changes during manufacture. The characteristic aroma of QZT was aged fragrance, which was mostly developed during pile fermentation and was enhanced during the aging and drying stages. Using volatile compounds found in the raw materials, sun-dried green tea and QZT finished product were compared by orthogonal partial least square-discriminant analysis. Among 108 detected volatiles, 19 were significantly upregulated and 15 were downregulated. (E)-β-Ionone, (E,Z)-2,6-nonadienal, 1-octen-3-one, (E,E)-2,4-heptadienal, (E,E)-2,4-nonadienal, safranal, (E)-2-nonenal, α-ionone, and 1,2,3-Trimethoxybenzene were found to be significant contributors to the aged QZT fragrance, reflecting their high odor-activity values and aroma intensities. Finally, the metabolic transformation of key aroma-active compounds was systematically analyzed. This study provided a theoretical basis for improving the processing and quality of QZT.
Trimethoprim: kinetic and mechanistic considerations in photochemical environmental fate and AOP treatment
Water Res 2012 Mar 15;46(4):1327-36.PMID:22244271DOI:10.1016/j.watres.2011.12.052.
Trimethoprim (TMP), a bacteriostatic antibiotic, has recently been detected in wastewater and surface waters. In this study the sunlight mediated photochemical fate, and treatment using advanced oxidation and reduction (free radical) processes, have been investigated with respect to their effect on TMP. Photochemical fate, in the presence of humic acid, and advanced oxidation treatment both involve the hydroxyl radical (OH) as one of the reactive species of interest. Another reactive oxygen species, singlet oxygen (1O2), may also be important in the photochemical fate of TMP. The bimolecular reaction rate constants of TMP with 1O2 and OH were evaluated to be (3.2±0.2)×10(6) M(-1) s(-1) and 8.66×10(9) M(-1) s(-1), respectively. The reaction kinetics for the sub-structural moieties of TMP, 1,2,3-Trimethoxybenzene (TMBz) and 2,4-diaminoprimidine (DAP), was evaluated to facilitate an understanding of the loss mechanisms. For TMBz and DAP the reaction rate constants with 1O2 were <1.0×10(4) and (3.0±0.1)×10(6) M(-1) s(-1), while with OH they were 8.12×10(9) and 1.64×10(9) M(-1) s(-1), respectively. The data suggests that the 1O2 attacks the DAP and the OH radical attacks the TMBz moiety. However, for TMP, 1O2 and OH reactions accounted for only ∼19% and ∼6%, of its total photodegradation, respectively. Therefore, the reaction of TMP with excited state natural organic matter is postulated as a significant degradation pathway for the loss of TMP in sunlit waters containing natural organic matter. There was no effect of pH on the direct or indirect photolysis of TMP. To complete the study for reductive treatment processes, the solvated electron reaction rates for the destruction of TMP, TMBz and DAP were also evaluated. The absolute bimolecular reaction rates obtained were, (13.6±0.01)×10(9), (6.36±0.11)×10(7) and (10.1±0.01)×10(9) M(-1) s(-1), respectively.
Thermally assisted hydrolysis and methylation of purified tannins from plants
Anal Chem 2005 Sep 1;77(17):5604-14.PMID:16131072DOI:10.1021/ac050564r.
A collection of tannins extracted from various plant species was subjected to thermally assisted hydrolysis and methylation (THM) using tetramethylammonium hydroxide. The products obtained included 1,3,5-trimethoxybenzenes, derived from A rings of condensed tannins (CTs), and 1,2-dimethoxybenzene, 1,2,3-Trimethoxybenzene, and derivatives as major products from the B ring. 1,2,4-Tri- and two tetramethoxybenzenes were also detected in most analyses. Correlation analyses revealed that they were derived from the B ring, with 1,2,4-trimethoxybenzene being derived from a procyanidin (PC) B ring and 1,2,3,5-tetramethoxybenzene from a prodelphinidin (PD) ring. Tannins from species that contained both CT and hydrolyzable tannin (HT) produced mainly permethylated gallic acid moieties upon THM, and the products derived from CTs were less abundant. Most likely, the ester-bound HTs are more easily transmethylated than the cleavage and methylation of the C-C and C-O linked CTs. Statistical analyses of the THM products and 13C NMR data of the tannins showed good correlations between the B ring hydroxylation and the di- and trimethoxybenzenes observed. Using the ratio of the methyl esters of 3,4-dimethoxybenzoic acid and 3,4,5-trimethoxybenzoic acid only provided good correlations of the percent PC as well. Furthermore, the 1,3,5-trimethoxybenzenes may serve as good markers of tannins in plant, soil, sediment or other samples as analyzed by THM.
Synthesis of 3,3'-di-O-methyl ardimerin and exploration of its DNA binding properties
Org Lett 2014 Apr 18;16(8):2212-5.PMID:24712737DOI:10.1021/ol500725e.
The 3,3'-di-O-methyl derivative (15) of the bis-C-aryl glycoside natural product ardimerin (1) has been synthesized in 11 steps from 2,3,4,6-tetrabenzylglucose (2) and 1,2,3-Trimethoxybenzene (3). Key steps in the synthesis involve a Lewis acid mediated Friedel-Crafts type glycosylation and a Yamaguchi lactonization under Yonemitsu conditions. 3,3'-Di-O-methyl ardimerin aggregates in aqueous solutions at concentrations greater than 1 μM, and both UV and fluorescence binding studies indicate that 15 has a low affinity for duplex DNA.