(-)-Catechin
(Synonyms: (-)-儿茶素; (-)-Cianidanol; (-)-Catechuic acid) 目录号 : GC40842
A diastereoisomer of catechin
Cas No.:18829-70-4
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
(-)-Catechin is a diastereoisomer of catechin having a trans 2S,3R configuration at the chiral center. Catechins, in general, are polyphenolic flavonoids that can be isolated from a variety of natural sources including tea leaves, grape seeds, and the wood and bark of trees such as acacia and mahogany. Catechins are potent antioxidants that inhibit the free radical-induced oxidation of isolated LDL by AAPH . Catechins and other related procyanidin compounds have antitumor activity when tested in a two-stage mouse epidermal carcinoma model employing topical application.
| Cas No. | 18829-70-4 | SDF | |
| 别名 | (-)-儿茶素; (-)-Cianidanol; (-)-Catechuic acid | ||
| Canonical SMILES | OC1=CC2=C(C[C@@H](O)[C@H](C3=CC=C(O)C(O)=C3)O2)C(O)=C1 | ||
| 分子式 | C15H14O6 | 分子量 | 290.3 |
| 溶解度 | DMF: 25 mg/ml,DMSO: 15 mg/ml,Ethanol: 5 mg/ml,PBS (pH 7.2): 1 mg/ml | 储存条件 | Store at 2-8°C,protect from light |
| 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 | 3.4447 mL | 17.2236 mL | 34.4471 mL |
| 5 mM | 0.6889 mL | 3.4447 mL | 6.8894 mL |
| 10 mM | 0.3445 mL | 1.7224 mL | 3.4447 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。
Catechin prodrugs and analogs: a new array of chemical entities with improved pharmacological and pharmacokinetic properties
Nat Prod Rep 2013 Oct 11;30(11):1438-54.PMID:24056761DOI:10.1039/c3np70038k.
Extensive research on tea catechins, mainly (-)-epigallocatechin gallate, has shown numerous health promoting effects. However, various clinical studies demonstrated several issues associated with tea catechins which account for their poor systemic bioavailability. In order to improve pharmacological activity and bioavailability of natural tea catechins, two major strategies have been adopted to date which include synthesizing catechin analogs/prodrugs and the development of novel drug delivery systems. In this review, we provide a detailed account of novel synthetic analogs/prodrugs as well as novel drug delivery approaches used for natural tea catechins to make them therapeutically potent drug-like molecules.
Green Tea Catechins: Their Use in Treating and Preventing Infectious Diseases
Biomed Res Int 2018 Jul 17;2018:9105261.PMID:30105263DOI:10.1155/2018/9105261.
Green tea is one of the most popular drinks consumed worldwide. Produced mainly in Asian countries from the leaves of the Camellia sinensis plant, the potential health benefits have been widely studied. Recently, researchers have studied the ability of green tea to eradicate infectious agents and the ability to actually prevent infections. The important components in green tea that show antimicrobial properties are the catechins. The four main catechins that occur in green tea are (-)-epicatechin (EC), (-)-epicatechin-3-gallate (ECG), (-)-epigallocatechin (EGC), and (-)-epigallocatechin-3-gallate (EGCG). Of these catechins, EGCG and EGC are found in the highest amounts in green tea and have been the subject of most of the studies. These catechins have been shown to demonstrate a variety of antimicrobial properties, both to organisms affected and in mechanisms used. Consumption of green tea has been shown to distribute these compounds and/or their metabolites throughout the body, which allows for not only the possibility of treatment of infections but also the prevention of infections.
Function of Green Tea Catechins in the Brain: Epigallocatechin Gallate and its Metabolites
Int J Mol Sci 2019 Jul 25;20(15):3630.PMID:31349535DOI:10.3390/ijms20153630.
Over the last three decades, green tea has been studied for its beneficial effects, including anti-cancer, anti-obesity, anti-diabetes, anti-inflammatory, and neuroprotective effects. At present, a number of studies that have employed animal, human and cell cultures support the potential neuroprotective effects of green tea catechins against neurological disorders. However, the concentration of (-)-epigallocatechin gallate (EGCG) in systemic circulation is very low and EGCG disappears within several hours. EGCG undergoes microbial degradation in the small intestine and later in the large intestine, resulting in the formation of various microbial ring-fission metabolites which are detectable in the plasma and urine as free and conjugated forms. Recently, in vitro experiments suggested that EGCG and its metabolites could reach the brain parenchyma through the blood-brain barrier and induce neuritogenesis. These results suggest that metabolites of EGCG may play an important role, alongside the beneficial activities of EGCG, in reducing neurodegenerative diseases. In this review, we discuss the function of EGCG and its microbial ring-fission metabolites in the brain in suppressing brain dysfunction. Other possible actions of EGCG metabolites will also be discussed.
Catechin glucosides: occurrence, synthesis, and stability
J Agric Food Chem 2010 Feb 24;58(4):2138-49.PMID:20112905DOI:10.1021/jf9034095.
Catechins are flavonoids with suggested health benefits, but are unstable during storage, processing and, after ingestion, during gut transit. We hypothesized that catechin glucosides, which occur in various plants, could be more stable than unsubstituted catechin, and additionally be deglucosylated in the gut and so act to deliver catechin in a form able to be absorbed. (+)-Catechin O-glucosides from various sources have been used in the course of this investigation. (+)-Catechin 3'-O-beta-D-glucopyranoside (C3'G), (+)-Catechin 5-O-beta-D-glucopyranoside (C5G), and (+)-Catechin 3-O-beta-D-glucopyranoside (C3G) were chemically synthesized. (+)-Catechin 4'-O-beta-D-glucopyranoside (C4'G) and (+)-Catechin 7-O-beta-D-glucopyranoside (C7G) were prepared enzymically using preparations from lentil and barley. In general, but with some exceptions, the (+)-Catechin glucosides were more stable between pH 4 and 8 than (+)-Catechin, with C3'G exhibiting greatest stability. The intestinal metabolism of (+)-Catechin and all (+)-Catechin glucosides in the gut was determined by perfusion of rat intestine in vivo. C3'G and C5G were extensively deglycosylated in the gut, and C3'G showed greatest apparent "absorption" as calculated by the difference between effluent and influent. The results show the potential of catechin glucosides, especially C3'G, as more stable prescursors of catechin.
Catechin transformation as influenced by aluminum
J Agric Food Chem 2006 Jan 11;54(1):212-8.PMID:16390201DOI:10.1021/jf051926z.
Polyphenols (catechins) are vital biomolecules in tea plants (Camellia sinensis), which are well-known as typical Al accumulators. However, the interaction between Al and catechin remains obscured. The objective of the present study was to investigate the effect of Al on the transformation of (+)-Catechin. Solutions with OH/Al molar ratios of 2.5 (pH 5.5) and 3.0 (pH 7.0) prepared at Al/catechin molar ratios (R) of 0, 0.2, 0.4, 0.6, 0.8, and 1.0 were aged for 7 and 30 days, respectively. The precipitates were collected and examined by wet chemistry, X-ray diffraction, transmission electron microscopy, electron spin resonance (ESR), cross-polarization magic angle (CPMAS) 13C nuclear magnetic resonance (13C NMR) analyses, and Fourier transformation infrared absorption spectrometry (FT-IR). The weight of the precipitates increased with increasing Al/catechin molar ratios and with prolonged aging. The molar ratios of Al/catechin in the precipitates increased with increasing initial Al/catechin molar ratios and were close to the initial solution Al/catechin molar ratios. The chemical analysis and spectroscopic studies indicated that Al was bonded with catechin, forming a 1:1 type complex. The reaction of crystalline catechin with Al resulted in the formation of X-ray noncrystalline precipitates. The solid-state CPMAS 13C NMR spectra of the precipitates show the change in chemical shifts of catechin as a result of catechin complexation with Al. The FT-IR spectra of the Al-catechin precipitates also show the loss of absorption bands of several functional groups compared with catechin. The FT-IR data substantiate this reasoning. The ESR spectra of the precipitates show a single symmetrical line devoid of any fine splitting, indicating the presence of free radicals of semiquinones, which are commonly present in humified materials.