trans-Cinnamaldehyde
(Synonyms: 桂皮醛) 目录号 : GC39729
Cinnamaldehyde is a flavonoid that is naturally synthesized by the shikimate pathway. Its supplementation can improve glucose and lipid homeostasis in diabetic animals; a TRPA1 agonist.
Cas No.:14371-10-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Cinnamaldehyde is a flavonoid that is naturally synthesized by the shikimate pathway. Its supplementation can improve glucose and lipid homeostasis in diabetic animals; a TRPA1 agonist.
Cinnamaldehyde (40 μM) could enhance the expression of hormone-sensitive lipase (HSL), and suppress the expression of perilipin and glycerol-3-phosphate dehydrogenase as well as reduce adipocyte genes expression of peroxisome proliferator-activated receptor (PPAR)-γ and CCAAT/enhancer-binding protein-α (CEBP-α) in 3T3-L1 pre-adipocytes. It also increases expression of PPARδ and PPARγ as well as its targeted genes such as aP2 and CD36 in 3T3-L1 differentiated adipocytes. Cinnamaldehyde (40 μM) treatment increases GLUT4 expression via activating peroxisome proliferator-activated receptor γ coactivator 1α (PGC-1α) and triggering its downstream effector myocyte enhancer factors 2 (MEF2) in C2C12 cells. Its treatment regulates oxidative metabolism through increasing expressions of 5'-adenosine monophosphate-activated protein kinase (AMPK), NAD+-dependent deacetylases sirtuin 1, PGC-1α and cytochrome C as well as improving PPARα and PPARβ/δ expression, which contributes to mitochondrial biogenesis. However, cinnamaldehyde is demonstrated to inhibit mitochondrial metabolism by reducing basal and chemically-induced peak myotube oxidative metabolism in C2C12 cells[1]. Cinnamaldehyde exerts cytotoxic effects on human leukemia K562 cells by inducing apoptosis and synergizing the cytotoxicity of CIK cells against K562 cells[3].
Cinnamaldehyde exhibits glucolipid lowering effects in diabetic animals by increasing glucose uptake and improving insulin sensitivity in adipose and skeletal muscle tissues, improving glycogen synthesis in liver, restoring pancreatic islets dysfunction, slowing gastric emptying rates, and improving diabetic renal and brain disorders. Cinnamaldehyde exerts these effects through its action on multiple signaling pathways, including PPARs, AMPK, PI3K/IRS-1, RBP4-GLUT4, and ERK/JNK/p38MAPK, TRPA1-ghrelin and Nrf2 pathways. In addition, cinnamaldehyde seems to regulate the activities of PTP1B and α-amylase. Oral administration of cinnamaldehyde ranging from 20mg/kg to 40 mg/kg per day for a duration lasting from 21 to 60 days results in a significant improvement in the levels of blood glucose and glycosylated hemoglobin (HbA1C) as well as insulin sensitivity in STZ-induced diabetic rats. Cinnamaldehyde is not stable in the body, with the possibility of metabolizing into cinnamic acid and transforming into cinnamyl alcohol. Excessive doses of cinnamaldehyde may generate the toxic response. In human, 3% cinnamaldehyde may cause skin irritation. Cinnamaldehyde is demonstrated to decrease serum IL-1β and inhibit inflammatory gene expression (COX-2, MCP-1, TNF-α, and IL-6) in WAT of HFD insulted male Swiss albino mice and C57BLKS db/db mice, while increased expression of Cpt1a protects against pro-inflammatory adipokines release and promotes fatty acid oxidation, which contributes to an improvement in insulin resistance[1].
[1] Zhu R, et al. Pharmacol Res. 2017, 122:78-89. [2] Tamura Y, et al. J Nutr Sci Vitaminol (Tokyo). 2012, 58(1):9-13. [3] Zhang JH, et al. Acta Pharmacol Sin. 2010, 31(7):861-6.
| Cas No. | 14371-10-9 | SDF | |
| 别名 | 桂皮醛 | ||
| Canonical SMILES | O=C/C=C/C1=CC=CC=C1.[E] | ||
| 分子式 | C9H8O | 分子量 | 132.16 |
| 溶解度 | DMSO : 50mg/mL | 储存条件 | Store at -20°C, stored under nitrogen |
| 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 | 7.5666 mL | 37.8329 mL | 75.6659 mL |
| 5 mM | 1.5133 mL | 7.5666 mL | 15.1332 mL |
| 10 mM | 0.7567 mL | 3.7833 mL | 7.5666 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。
trans-Cinnamaldehyde Eluting Porous Silicon Microparticles Mitigate Cariogenic Biofilms
Pharmaceutics 2022 Jul 7;14(7):1428.PMID:35890323DOI:10.3390/pharmaceutics14071428.
Dental caries, a preventable disease, is caused by highly-adherent, acid-producing biofilms composed of bacteria and yeasts. Current caries-preventive approaches are ineffective in controlling biofilm development. Recent studies demonstrate definite advantages in using natural compounds such as trans-Cinnamaldehyde in thwarting biofilm assembly, and yet, the remarkable difficulty in delivering such hydrophobic bioactive molecules prevents further development. To address this critical challenge, we have developed an innovative platform composed of components with a proven track record of safety. We fabricated and thoroughly characterised porous silicon (pSi) microparticles to carry and deliver the natural phenyl propanoid trans-Cinnamaldehyde (TC). We investigated its effects on preventing the development of cross-kingdom biofilms (Streptococcus mutans and Candida albicans), typical of dental caries found in children. The prepared pSi microparticles were roughly cubic in structure with 70-75% porosity, to which the TC (pSi-TC) was loaded with about 45% efficiency. The pSi-TC particles exhibited a controlled release of the cargo over a 14-day period. Notably, pSi-TC significantly inhibited biofilms, specifically downregulating the glucan synthesis pathways, leading to reduced adhesion to the substrate. Acid production, a vital virulent trait for caries development, was also hindered by pSi-TC. This pioneering study highlights the potential to develop the novel pSi-TC as a dental caries-preventive material.
trans-Cinnamaldehyde suppresses microtubule detyrosination and alleviates cardiac hypertrophy
Eur J Pharmacol 2022 Jan 5;914:174687.PMID:34883072DOI:10.1016/j.ejphar.2021.174687.
Background: trans-Cinnamaldehyde (TCA) is a main compound of Cinnamomum cassia, used in traditional Chinese medicine to treat many ailments. Increasing evidence has demonstrated the therapeutic effects of TCA in cardiovascular diseases. Purpose: The present study aimed to determine whether TCA exerts antihypertrophic effects in vitro and in vivo and to elucidate the underlying mechanisms of these effects. Methods: Neonatal rat cardiac myocytes (NRCMs) and adult mouse cardiac myocytes (AMCMs) were treated with 50 μΜ phenylephrine (PE) for 48 h. Tubulin detyrosination, store-operated Ca2+ entry (SOCE), stromal interaction molecule-1 (STIM1)/Orai1 translocation, and calcineurin/nuclear factor of activated T-cells (NFAT) signaling pathways were analyzed in NRCMs. Meanwhile, tubulin detyrosination, junctophilin-2, T-tubule distribution pattern, Ca2+ handling, and sarcomere shortening were observed in AMCMs. Male C57BL/6 mice were stimulated with PE (70 mg/kg per day) with or without TCA treatment for 2 weeks. Cardiac hypertrophy and tubulin detyrosination were also assessed. Results: TCA was confirmed to alleviate cardiac hypertrophy induced by PE stimulation in vitro and in vivo. PE-induced cardiac hypertrophy was associated with excessive tubulin detyrosination and overexpression of vasohibin 1 (VASH1) and small vasohibin binding protein (SVBP), two key proteins responsible for tubulin detyrosination. These effects were largely blocked by TCA administration. PE treatment also enhanced SOCE with massive translocation of STIM1 and Orai1, Ca2+ mishandling, reduced sarcomere shortening, junctophilin-2, and T-tubule redistribution, all of which were significantly ameliorated by TCA administration. Conclusion: Our study indicated that the therapeutic effects of TCA against cardiac hypertrophy may be associated with its ability to reduce tubulin detyrosination.
Trans-cinnamaldehyde-Biosurfactant Complex as a Potent Agent against Enterococcus faecalis Biofilms
Pharmaceutics 2022 Oct 31;14(11):2355.PMID:36365173DOI:10.3390/pharmaceutics14112355.
Enterococcus faecalis is an opportunistic microbial pathogen frequently associated with diverse infections, including those of the skin and teeth, as well as those from surgical wounds. It forms robust biofilms that are highly tolerant to most antimicrobials and first-line antibiotics. Therefore, investigating alternative strategies to eradicate its biofilms is a critical need. We recently demonstrated that trans-Cinnamaldehyde (TC) potently kills E. faecalis biofilm cells and prevents biofilm recovery, and yet, the extreme hydrophobicity of TC hampers clinical translation. Here, we report that a complex of TC with an FDA-approved biosurfactant (acidic sophorolipid/ASL) significantly reduces the bacterial viability and biomass of E. faecalis biofilms, compared to TC alone. A confocal laser-scanning microscopic analysis demonstrated that the TC-ASL treatment significantly decreased the biofilm thickness and volume. In conclusion, our study highlights the anti-biofilm potential of the newly developed TC-ASL.
trans-Cinnamaldehyde as a Novel Candidate to Overcome Bacterial Resistance: An Overview of In Vitro Studies
Antibiotics (Basel) 2023 Jan 27;12(2):254.PMID:36830165DOI:10.3390/antibiotics12020254.
The increasing of drug-resistant bacteria and the scanty availability of novel effective antibacterial agents represent alarming problems of the modern society, which stimulated researchers to investigate novel strategies to replace or assist synthetic antibiotics. A great deal of attention has been devoted over the years to essential oils that contain mixtures of volatile compounds and have been traditionally exploited as antimicrobial remedies. Among the essential oil phytochemicals, remarkable antimicrobial and antibiotic-potentiating activities have been highlighted for cinnamaldehyde, an α,β-unsaturated aldehyde, particularly abundant in the essential oils of Cinnamomum spp., and widely used as a food additive in industrial products. In line with this evidence, in the present study, an overview of the available literature has been carried out in order to define the bacterial sensitizing profile of cinnamaldehyde. In vitro studies displayed the ability of the substance to resensitize microbial strains to drugs and increase the efficacy of different antibiotics, especially cefotaxime, ciprofloxacin, and gentamicin; however, in vivo, and clinical trials are lacking. Based on the collected findings, cinnamaldehyde appears to be of interest as an adjuvant agent to overcome superbug infections and antibiotic resistance; however, future more in-dept studies and clinical investigations should be encouraged to clarify its efficacy and the mechanisms involved.
A review of cinnamaldehyde and its derivatives as antibacterial agents
Fitoterapia 2019 Nov;139:104405.PMID:31707126DOI:10.1016/j.fitote.2019.104405.
There is a continuing rise in the occurrence of multidrug-resistant bacterial infections. Antibiotic resistance to currently available antibiotics has become a global health issue leading to an urgent need for alternative antibacterial strategies. There has been a renewed interest in the development of antibacterial agents from natural sources, and trans-Cinnamaldehyde is an example of a naturally occurring compound that has received significant attention in recent years. trans-Cinnamaldehyde has been shown to possess substantial antimicrobial activity, as well as an array of other medicinal properties, and represents an intriguing hit compound from which a number of derivatives have been developed. In some cases, these derivatives have been shown to possess improved activity, not only compared to trans-Cinnamaldehyde but also to commonly used antibiotics. Therefore, understanding the antibacterial mechanisms of action that these compounds elicit is imperative in order to facilitate their development and the development of new antibacterial agents that could exploit similar mechanistic approaches. The purpose of this review is to provide an overview of current knowledge on the antibacterial activity and mechanisms of action of cinnamaldehyde and its derivatives, and to highlight significant contributions made in this research area. It is hoped that the findings presented in this work will aid the future development of new antibacterial agents.