Citral
(Synonyms: 柠檬醛) 目录号 : GC39267
Citral (Geranialdehyde) is an α,β-unsaturated aldehyde present in the oils of several plants. It is an aroma compound used in perfumery for its citrus effect and is also used as a flavor and for fortifying lemon oil.
Cas No.:5392-40-5
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Citral (Geranialdehyde) is an α,β-unsaturated aldehyde present in the oils of several plants. It is an aroma compound used in perfumery for its citrus effect and is also used as a flavor and for fortifying lemon oil.
| Cas No. | 5392-40-5 | SDF | |
| 别名 | 柠檬醛 | ||
| Canonical SMILES | C/C(C)=C\CC/C(C)=C/C=O | ||
| 分子式 | C10H16O | 分子量 | 152.23 |
| 溶解度 | DMSO: ≥ 100 mg/mL (656.90 mM); Water: 1 mg/mL (6.57 mM; ultrasonic and warming and heat to 80°C) | 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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 6.569 mL | 32.845 mL | 65.6901 mL |
| 5 mM | 1.3138 mL | 6.569 mL | 13.138 mL |
| 10 mM | 0.6569 mL | 3.2845 mL | 6.569 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。
Citral induced apoptosis in MDA-MB-231 spheroid cells
BMC Complement Altern Med 2018 Feb 13;18(1):56.PMID:29433490DOI:10.1186/s12906-018-2115-y.
Background: Breast cancer remains a leading cause of death in women worldwide. Although breast cancer therapies have greatly advanced in recent years, many patients still develop tumour recurrence and metastasis, and eventually succumb to the disease due to chemoresistance. Citral has been reported to show cytotoxic effect on various cancer cell lines. However, the potential of Citral to specifically target the drug resistant breast cancer cells has not yet been tested, which was the focus of our current study. Methods: The cytotoxic activity of Citral was first tested on MDA-MB-231 cells in vitro by MTT assay. Subsequently, spheroids of MDA-MB-231 breast cancer cells were developed and treated with Citral at different concentrations. Doxorubicin, cisplatin and tamoxifen were used as positive controls to evaluate the drug resistance phenotype of MDA-MB-231 spheroids. In addition, apoptosis study was performed using AnnexinV/7AAD flowcytometry. Aldefluor assay was also carried out to examine whether Citral could inhibit the ALDH-positive population, while the potential mechanism of the effect of Citral was carried out by using quantitative real time- PCR followed by western blotting analysis. Results: Citral was able to inhibit the growth of the MDA-MB-231 spheroids when compared to a monolayer culture of MDA-MB-231 cells at a lower IC50 value. To confirm the inhibition of spheroid self-renewal capacity, the primary spheroids were then cultured to additional passages in the absence of Citral. A significant reduction in the number of secondary spheroids were formed, suggesting the reduction of self-renewal capacity of these aldehyde dehydrogenase positive (ALDH+) drug resistant spheroids. Moreover, the AnnexinV/7AAD results demonstrated that Citral induced both early and late apoptotic changes in a dose-dependent manner compared to the vehicle control. Furthermore, Citral treated spheroids showed lower cell renewal capacity compared to the vehicle control spheroids in the mammosphere formation assay. Gene expression studies using quantitative real time PCR and Western blotting assays showed that Citral was able to suppress the self-renewal capacity of spheroids and downregulate the Wnt/β-catenin pathway. Conclusion: The results suggest that Citral could be a potential new agent which can eliminate drug-resistant breast cancer cells in a spheroid model via inducing apoptosis.
Chemical Properties and Therapeutic Potential of Citral, a Monoterpene Isolated from Lemongrass
Med Chem 2021;17(1):2-12.PMID:31880247DOI:10.2174/1573406416666191227111106.
Background: Citral is one of the main components of lemongrass oil present at a concentration of 65-85% approximately and is generally separated by steam refining. It is an important component in the manufacturing of scents, citrus chemicals, cosmetics, food and pharmaceutical products. Objectives: This article aims at reviewing the published literature to highlight the metabolism, extraction strategies and therapeutic significance of Citral for improving the scope of its application in the food and pharma industry. Discussions: Apart from steam refining, there are other techniques like solvent extraction, supercritical fluid extraction and ultrasonication by which Citral can be extracted and the method of extraction defines its quality. It is an unstable molecule and undergoes rapid deterioration on exposure to air. Citral is biosynthesized by the plants through the 5 carbon precursor isopentenyl diphosphate (IPP) units utilizing two diverse biochemical pathways, acetate- mevalonate (acetate- MVA) pathway or 2C-methylerythritol-4-phosphate (MEP). Orally Citral was absolutely digested in the gastrointestinal tract and its metabolism leads to the discharge of metabolites which include a number of acids and a biliary glucuronide. There is no scientific evidence about the long term bioavailability of Citral in the body and it has no adverse effect on tissue related to its accumulation and delayed excretion. Citral exhibits various important therapeutic properties like antimicrobial, antioxidant, anticancer, anti-diabetic and anti-inflammatory. Conclusion: Citral is a potent biomolecule with various important biological activities and therapeutic implications. Strategies are required to increase the stability of Citral which could increase its applications.
pH-responsive Citral microcapsules with tannic acid-FeIII coordination complexes
Food Chem 2022 Dec 15;397:133715.PMID:35905617DOI:10.1016/j.foodchem.2022.133715.
Citral is one of the most important aromatic ingredients in foods and beverages for its distinct lemon-like odor. However, the fast evaporation and oxidation limit these applications. Herein, Citral microcapsules were constructed by tannic acid-FeIII coordination complexes (Citral@TA-FeIII). The morphologies, structure, Citral loading amount, pH responsiveness, oxidative stability and olfactory sensory evaluation were investigated. The obtained Citral@TA-FeIII microcapsules presented core-shell structure with the average size of 528.16 nm. Citral loading amount was 12.79 %. Citral release exhibited pH-responsiveness with a sustained release rate at neutral pH and a fast release under acidic condition. Citral microcapsules retained excellent sensory profile due to the antioxidant capsule shells. Citral@TA-FeIII microcapsules efficiently inhibited bacteria (S. aureus and E. coli) growth, and the performance is enhanced under acidic condition by Citral pH-responsive release. This work may open a new path for hydrophobic unsaturated aroma compounds encapsulation, widening their applications with multifunctionalities.
Citral mitigates inflammation of Caco-2 cells induced by Cronobacter sakazakii
Food Funct 2022 Mar 21;13(6):3540-3550.PMID:35253831DOI:10.1039/d2fo00098a.
The aim of this study was to explore the anti-inflammatory effect and mechanism of Citral in Cronobacter sakazakii-stimulated Caco-2 cells. Safe doses of Citral were first determined in Caco-2 cells. Then, the effect of Citral on the adhesion and invasion of C. sakazakii into Caco-2 cells and the translocation of C. sakazakii through Caco-2 monolayers were investigated. The release of nitric oxide (NO), interleukin (IL)-1β, IL-6, and TNF-α, transcription of inflammatory genes, and expression of proteins associated with inflammatory signaling pathways were determined. Subsequently, activation of caspase-3, -8, and -9 and apoptosis induced by C. sakazakii were assessed. The results showed that up to 10 μg mL-1 Citral had no cytotoxicity in Caco-2 cells. Citral protected Caco-2 cells by affecting the adhesion and invasion of C. sakazakii into Caco-2 cells and the translocation of C. sakazakii across Caco-2 monolayers. Additionally, inflammation induced by C. sakazakii was effectively inhibited by Citral via suppression of inflammatory factors that included NO, IL-1β, IL-6, and TNF-α, transcription of related genes, and expression of proteins associated with inflammatory signaling pathways. Moreover, the activation of caspase-3, -8, and -9, and apoptosis caused by C. sakazakii were suppressed by pretreatment with Citral. These findings suggest that Citral mitigates the inflammatory response of Caco-2 cells. Citral has the potential to prevent the inflammation of Caco-2 associated with C. sakazakii.
Citral modulates virulence factors in methicillin-resistant Staphylococcus aureus
Sci Rep 2021 Aug 13;11(1):16482.PMID:34389776DOI:10.1038/s41598-021-95971-y.
Methicillin-resistant Staphylococcus aureus (MRSA) is responsible for high morbidity and mortality rates. Citral has been studied in the pharmaceutical industry and has shown antimicrobial activity. This study aimed to analyze the antimicrobial activity of Citral in inhibiting biofilm formation and modulating virulence genes, with the ultimate goal of finding a strategy for treating infections caused by MRSA strains. Citral showed antimicrobial activity against MRSA isolates with minimum inhibitory concentration (MIC) values between 5 mg/mL (0.5%) and 40 mg/mL (4%), and minimum bactericidal concentration (MBC) values between 10 mg/mL (1%) and 40 mg/mL (4%). The sub-inhibitory dose was 2.5 mg/mL (0.25%). Citral, in an antibiogram, modulated synergistically, antagonistically, or indifferent to the different antibiotics tested. Prior to evaluating the antibiofilm effects of Citral, we classified the bacteria according to their biofilm production capacity. Citral showed greater efficacy in the initial stage, and there was a significant reduction in biofilm formation compared to the mature biofilm. qPCR was used to assess the modulation of virulence factor genes, and icaA underexpression was observed in isolates 20 and 48. For icaD, seg, and sei, an increase was observed in the expression of ATCC 33,591. No significant differences were found for eta and etb. Citral could be used as a supplement to conventional antibiotics for MRSA infections.