Undecanoic acid
(Synonyms: 十一烷酸,Undecanoate; Hendecanoic acid) 目录号 : GC38246
An eleven carbon SFA
Cas No.:112-37-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Undecanoic acid is a saturated fatty acid containing eleven carbons (C11:0). It is cytotoxic to certain filamentous fungi and is used to study fungal mechanisms of resistance.1,2 Undecanoic acid is also used to acylate larger molecules.3
1.Brito-Madurro, A.G., Cuadros-Orellana, S., Martinez-Rossi, N.M., et al.Undecanoic acid resistance in filamentous fungi: Identification and linkage mapping of the Aspergillus nidulans udaA geneJ. Gen. Appl. Microbiol.51(1)47-49(2005) 2.Paiao, F.G., Segato, F., Cursino-Santos, J.R., et al.Analysis of Trichophyton rubrum gene expression in response to cytotoxic drugsFEMS Microbiol Lett.271(2)180-186(2007) 3.Bogatcheva, E., Dubuisson, T., Protopopova, M., et al.Chemical modification of capuramycins to enhance antibacterial activityJ. Antimicrob. Chemother.66(3)578-587(2011)
| Cas No. | 112-37-8 | SDF | |
| 别名 | 十一烷酸,Undecanoate; Hendecanoic acid | ||
| Canonical SMILES | CCCCCCCCCCC(=O)O | ||
| 分子式 | C11H22O2 | 分子量 | 186.29 |
| 溶解度 | DMF: 25 mg/ml,DMSO: 10 mg/ml,DMSO:PBS(pH7.2) (1:1): 0.25 mg/ml,Ethanol: 25 mg/ml | 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 | 5.368 mL | 26.8399 mL | 53.6797 mL |
| 5 mM | 1.0736 mL | 5.368 mL | 10.7359 mL |
| 10 mM | 0.5368 mL | 2.684 mL | 5.368 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。
Reassessing the Use of Undecanoic acid as a Therapeutic Strategy for Treating Fungal Infections
Mycopathologia 2021 Jun;186(3):327-340.PMID:33835367DOI:10.1007/s11046-021-00550-4.
Treating fungal infections is challenging and frequently requires long-term courses of antifungal drugs. Considering the limited number of existing antifungal drugs, it is crucial to evaluate the possibility of repositioning drugs with antifungal properties and to revisit older antifungals for applications in combined therapy, which could widen the range of therapeutic possibilities. Undecanoic acid is a saturated medium-chain fatty acid with known antifungal effects; however, its antifungal properties have not been extensively explored. Recent advances indicate that the toxic effect of Undecanoic acid involves modulation of fungal metabolism through its effects on the expression of fungal genes that are critical for virulence. Additionally, Undecanoic acid is suitable for chemical modification and might be useful in synergic therapies. This review highlights the use of Undecanoic acid in antifungal treatments, reinforcing its known activity against dermatophytes. Specifically, in Trichophyton rubrum, against which the activity of Undecanoic acid has been most widely studied, Undecanoic acid elicits profound effects on pivotal processes in the cell wall, membrane assembly, lipid metabolism, pathogenesis, and even mRNA processing. Considering the known antifungal activities and associated mechanisms of Undecanoic acid, its potential use in combination therapy, and the ability to modify the parent compound structure, Undecanoic acid shows promise as a novel therapeutic against fungal infections.
Biting deterrency of Undecanoic acid and dodecanoic acid ester analogs against Aedes aegypti
Pest Manag Sci 2021 Aug;77(8):3737-3743.PMID:32648638DOI:10.1002/ps.5994.
Background: Mosquitoes remain one of the most significant threats to the health of humans throughout the world. This study was designed to evaluate the biting deterrent effects of a series of ester analogs of Undecanoic acid (C:11:0) and dodecanoic acid (C:12:0) against Aedes aegypti (L), (Diptera: Culicidae), the yellow fever mosquito, using Klun and Debboun (K&D) and Ali and Khan (A&K) bioassay systems. Results: In the K&D bioassays, C:11:0 esters methyl undecanoate, propyl undecanoate, butyl undecanoate, and pentyl undecanoate, and the C:12:0 esters methyl dodecanoate, ethyl dodecanoate, propyl dodecanoate, octyl dodecanoate, and dodecyl dodecanoate were most active. All of these esters were as effective as N,N-diethyl-m-toluamide (DEET) and as effective as the parent acids Undecanoic acid and dodecanoic acid with biting deterrence index values ranging from 0.80 to 0.99. In the in vitro A&K bioassay Undecanoic acid with a minimum effective dose (MED) of 3.125 μg cm-2 was the most active compound and showed higher activity than DEET (MED of 25 μg cm-2 ). The most active synthetic analog was butyl undecanoate with a MED of 12.5 μg cm-2 . The next most active analogs are the methyl ester analogs methyl undecanoate and methyl dodecanoate, both with MED values of 25 μg cm-2 . Conclusion: Fatty acid synthetic esters and structural analogs are a promising source of new mosquito repelling compounds and should be investigated further. Published 2020. This article is a U.S. Government work and is in the public domain in the USA.
Undecanoic acid, Lauric Acid, and N-Tridecanoic Acid Inhibit Escherichia coli Persistence and Biofilm Formation
J Microbiol Biotechnol 2021 Jan 28;31(1):130-136.PMID:33046677DOI:10.4014/jmb.2008.08027.
Persister cell formation and biofilms of pathogens are extensively involved in the development of chronic infectious diseases. Eradicating persister cells is challenging, owing to their tolerance to conventional antibiotics, which cannot kill cells in a metabolically dormant state. A high frequency of persisters in biofilms makes inactivating biofilm cells more difficult, because the biofilm matrix inhibits antibiotic penetration. Fatty acids may be promising candidates as antipersister or antibiofilm agents, because some fatty acids exhibit antimicrobial effects. We previously reported that fatty acid ethyl esters effectively inhibit Escherichia coli persister formation by regulating an antitoxin. In this study, we screened a fatty acid library consisting of 65 different fatty acid molecules for altered persister formation. We found that Undecanoic acid, lauric acid, and N-tridecanoic acid inhibited E. coli BW25113 persister cell formation by 25-, 58-, and 44-fold, respectively. Similarly, these fatty acids repressed persisters of enterohemorrhagic E. coli EDL933. These fatty acids were all medium-chain saturated forms. Furthermore, the fatty acids repressed Enterohemorrhagic E. coli (EHEC) biofilm formation (for example, by 8-fold for lauric acid) without having antimicrobial activity. This study demonstrates that medium-chain saturated fatty acids can serve as antipersister and antibiofilm agents that may be applied to treat bacterial infections.
Synergistic Effect of Quinic Acid Derived From Syzygium cumini and Undecanoic acid Against Candida spp. Biofilm and Virulence
Front Microbiol 2018 Nov 26;9:2835.PMID:30534118DOI:10.3389/fmicb.2018.02835.
In recent decades, fungal infections have incredibly increased with Candida genus as the major cause of morbidity and mortality in hospitalized and immunocompromised patients. Most of the Candida species are proficient in biofilm formation on implanted medical devices as well as human tissues. Biofilm related Candida infections are very difficult to treat using common antifungal agents owing to their increased drug resistance. To address these issues, the present study investigated the antibiofilm and antivirulent properties of Syzygium cumini derived quinic acid in combination with known antifungal compound Undecanoic acid. Initially, antibiofilm potential of S. cumini leaf extract was assessed and the active principles were identified through gas chromatography and mass spectrometry analysis. Among the compounds identified, quinic acid was one of the major compounds. The interaction between quinic acid and Undecanoic acid was found to be synergistic in the Fractional inhibitory concentration index (≤0.5). Results of in vitro assays and gene expression analysis suggested that the synergistic combinations of quinic acid and Undecanoic acid significantly inhibited virulence traits of Candida spp. such as the biofilm formation, yeast-to-hyphal transition, extracellular polymeric substances production, filamentation, secreted hydrolases production and ergosterol biosynthesis. In addition, result of in vivo studies using Caenorhabditis elegans demonstrated the non-toxic nature of QA-UDA combination and antivirulence effect against Candida spp. For the first time, synergistic antivirulence ability of quinic acid and Undecanoic acid was explored against Candida spp. Thus, results obtained from the present study suggest that combination of phytochemicals might be used an alternate therapeutic strategy for the prevention and treatment of biofilm associated Candida infection.
11-(Ethylthio)Undecanoic acid. A myristic acid analogue of altered hydrophobicity which is functional for peptide N-myristoylation with wheat germ and yeast acyltransferase
J Biol Chem 1988 Feb 15;263(5):2127-33.PMID:3123489doi
The covalent attachment of myristic acid to the NH2-terminal glycine residue of proteins is catalyzed by the enzyme myristoyl CoA:protein N-myristoyltransferase (NMT). Using synthetic octapeptide substrates we have identified and characterized an NMT activity in wheat germ lysates used for cell-free translation of exogenous mRNAs. C-12 and C-14 fatty acids are efficiently transferred to the peptides by this plant NMT, but C-10 and C-16 fatty acids are not. Glycine is required as the NH2-terminal residue: peptides with an NH2-terminal alanine were not substrates. Peptides with proline, aspartic acid, or tyrosine residues adjacent to the NH2-terminal glycine were also not myristoylated. Serine in the fifth position reduced the peptide's Km up to 4000-fold. We have chemically synthesized a sulfur analogue of myristate, 11-(ethylthio)Undecanoic acid. Its CoA ester is as good a substrate as myristoyl-CoA for both wheat germ and yeast NMT. Peptides linked to 11-(ethylthio)Undecanoic acid are less hydrophobic than the corresponding myristoylpeptides. 11-(Ethylthio)-undecanoic acid may, therefore, help define the role of myristic acid in targeting of acyl proteins within cells.