3,4,5-Trimethoxycinnamic acid
(Synonyms: 3,4,5-三甲氧基肉桂酸) 目录号 : GC33703
3,4,5-Trimethoxycinnamic acid (TMCA) is one of the constituents of Polygalae Radix and may exert anti-seizure activity by acting at the GABAA/BZ receptor complex.
Cas No.:90-50-6 ; 20329-98-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
3,4,5-Trimethoxycinnamic acid (TMCA) is one of the constituents of Polygalae Radix and may exert anti-seizure activity by acting at the GABAA/BZ receptor complex.
TMCA decreased the locomotor activity in mice, prolonged total sleep time, and reduced sleep latency induced by pentobarbital. TMCA also increased the total sleep time and non-rapid eye movement (NREM) sleep. It alters sleep architecture through GABAAergic systyems[1]. TMCA exhibits anti-stress actions by the suppression of norepinephrine (NE) content in locus coeruleus (LC) induced by corticotrophin-releasing hormone (CRH)[2].
[1] Lee CI, et al. Arch Pharm Res. 2013, 36(10):1244-51. [2] Kawashima K, et al. Biol Pharm Bull. 2004, 27(8):1317-9.
| Cas No. | 90-50-6 ; 20329-98-0 | SDF | |
| 别名 | 3,4,5-三甲氧基肉桂酸 | ||
| Canonical SMILES | COC1=C(OC)C(OC)=CC(/C=C/C(O)=O)=C1 | ||
| 分子式 | C12H14O5 | 分子量 | 238.24 |
| 溶解度 | Soluble in DMSO | 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 | 4.1974 mL | 20.9872 mL | 41.9745 mL |
| 5 mM | 0.8395 mL | 4.1974 mL | 8.3949 mL |
| 10 mM | 0.4197 mL | 2.0987 mL | 4.1974 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。
Research progress in the biological activities of 3,4,5-Trimethoxycinnamic acid (TMCA) derivatives
Eur J Med Chem 2019 Jul 1;173:213-227.PMID:31009908DOI:10.1016/j.ejmech.2019.04.009.
TMCA (3,4,5-Trimethoxycinnamic acid) ester and amide are privileged structural scaffolds in drug discovery which are widely distributed in natural products and consequently produced diverse therapeutically relevant pharmacological functions. Owing to the potential of TMCA ester and amide analogues as therapeutic agents, researches on chemical syntheses and modifications have been carried out to drug-like candidates with broad range of medicinal properties such as antitumor, antiviral, CNS (central nervous system) agents, antimicrobial, anti-inflammatory and hematologic agents for a long time. At the same time, SAR (structure-activity relationship) studies have draw greater attention among medicinal chemists, and many of the lead compounds were derived for various disease targets. However, there is an urgent need for the medicinal chemists to further exploit the precursor in developing chemical entities with promising bioactivity and druggability. This review concisely summarizes the synthesis and biological activity for TMCA ester and amide analogues. It also comprehensively reveals the relationship of significant biological activities along with SAR studies.
Bacterial degradation of 3,4,5-Trimethoxycinnamic acid with production of methanol
J Bacteriol 1981 Aug;147(2):471-6.PMID:7263612DOI:10.1128/jb.147.2.471-476.1981.
When grown on 3,4,5-Trimethoxycinnamic acid, a strain of Pseudomonas putida oxidized this compound and also 3,4,5-trimethoxybenzoic, 3,5-dimethoxy-4-hydroxybenzoic (syringic), and 3,4-dihydroxy-5-methoxybenzoic (3-O-methylgallic) acids, but 3,5-dimethoxy-4-hydroxycinnamic and other acids bearing structural resemblances to the growth substrate were oxidized only slowly. These results indicate that two carbon atoms of the side chain of 3,4,5-trimethoxycinnamate were released before oxidative demethylation occurred to give the ring-fission substrate, 3-O-methylgallate. Oxidation of 3,4,5-trimethoxycinnamate by intact cells gave equimolar amounts of methanol, which was derived from the methoxyl group of 3-O-methylgallate. The tricarboxylic acids, 4-carboxy-2-keto-3-hexenedioic and 4-carboxy-4-hydroxy-2-ketoadipic acids, were shown to be formed by the action of a cell extract upon 3-O-methylgallate; therefore, methanol was released either during or immediately after fission of the benzene nucleus. Cell extracts, prepared from several independent soil isolates after growth on 3,4,5-trimethoxy derivatives of benzoic, cinnamic, and beta-phenylpropionic acids, rapidly oxidized 3-O-methylgallate without added cofactors. It is concluded that the reactions investigated serve generally as a source of methanol in nature.
Synthesis and evaluation of a series of 3,4,5-Trimethoxycinnamic acid derivatives as potential antinarcotic agents
Chem Biol Drug Des 2013 Mar;81(3):389-98.PMID:23121934DOI:10.1111/cbdd.12087.
A series of 3,4,5-Trimethoxycinnamic acid derivatives was prepared and evaluated for antinarcotic effects on morphine dependence in mice and binding affinities on serotonergic receptors. The key synthetic strategies involve generation of ketones 6-7, esters 9-12 through condensation reaction, and amides 13-19 via coupling reaction using 1-hydroxybenzotriazole/ethyl(dimethylaminopropryl)carbodiimide system in high yield. We found that the naloxone-induced morphine withdrawal syndrome was significantly suppressed by new synthetic 3,4,5-Trimethoxycinnamic acid derivatives (20 mg/kg/day). Most of 3,4,5-Trimethoxycinnamic acid derivatives were found to have high affinity to 5-HT(1A) receptor. The naloxone-induced morphine withdrawal syndrome was attenuated by (+)8-OH-DPAT (0.1 mg/kg/day, i.p.), a 5-HT(1A) receptor agonist. In cortical neuronal cells, (+)8-OH-DPAT (1 μM) produced an elevation of the pERK 1/2 expression, and the elevated pERK levels were inhibited by WAY 100635, a 5-HT(1A) receptor-specific antagonist. Interestingly, the pERK levels were increased by the 3,4,5-Trimethoxycinnamic acid derivatives and the derivatives-mediated changes in pERK levels were blocked by the WAY 100635. These results suggested that new synthetic 3,4,5-Trimethoxycinnamic acid derivatives have a potential antinarcotic effect through acting as a 5-HT(1A) receptor agonist in mice.
3,4,5-Trimethoxycinnamin acid ameliorates restraint stress-induced anxiety and depression
Neurosci Lett 2015 Jan 12;585:54-9.PMID:25445378DOI:10.1016/j.neulet.2014.11.016.
The present study investigated whether 3,4,5-Trimethoxycinnamic acid (TMCA) treatment ameliorated restraint stress-provoked anxiety- and depression-like behaviors in mice. Fourteen consecutive days of restraint stress produced anxiety- and depression-like behaviors, including reduced time and frequency in the open arms of the elevated plus maze (EPM), as well as enhanced immobility times in the forced swim test (FST). However, TMCA (50 mg/kg) treatment ameliorated this effect; mice showed increased time and frequency of visits in the open arms of the EPM and showed reduced immobility in the FST. In parallel with the behavioral data, long-lasting stimulation of ΔFosB in the nucleus accumbens shell subregion was exhibited in response to TMCA. Furthermore, a reduction in expression of SC1, a target of ΔFosB, in the nucleus accumbens of mice subjected to restraint stress was significantly reversed by TMCA (50 mg/kg) treatment. Collectively, these results suggest that TMCA treatment might provide a therapeutic strategy for treatment of anxiety and depression.
3,4,5-Trimethoxycinnamic acid, one of the constituents of Polygalae Radix exerts anti-seizure effects by modulating GABAAergic systems in mice
J Pharmacol Sci 2016 May;131(1):1-5.PMID:26260747DOI:10.1016/j.jphs.2015.07.021.
Polygalae Radix is an important medicinal plant that is widely used in most of Africa. 3,4,5-Trimethoxycinnamic acid (TMCA) is one of the constituents of Polygalae Radix. Until now, the mechanisms involved in the anti-seizure property of TMCA are still unclear. We examined the anti-seizure effect of TMCA. TMCA administered at doses of 5, 10 and 20 mg/kg and evaluated anti-seizure effects by maximal electroshock (MES) and pentylenetetrazol (PTZ) models in mice. TMCA administered at doses of 10 and 20 mg/kg significantly reduced the incidence of MES-induced tonic hindlimb extension (THE). TMCA significantly delayed the onset of myoclonic jerks (MJ), and decreased the seizure severity and mortality compared with the vehicle-treated animals in PTZ seizure model. TMCA 10 and 20 mg/kg treated groups also did not determined generalized clonic seizures (GCS). Pretreatment with a GABAA/benzodiazepine (BZ) receptor antagonist flumazenil blocked the anti-seizure effects of TMCA. These data support the further investigation of TMCA as a GABAA/BZ receptor agonist for anti-seizure therapy.