Erucic acid
(Synonyms: 芥酸) 目录号 : GC38694
A 22-
Cas No.:112-86-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >85.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
13(Z)-
1.Borg, K.Physiopathological effects of rapeseed oil: A reviewActa Med. Scand. Suppl.5855-13(1975) 2.Hulan, H.W., Kramer, J.K.G., Mahadevan, S., et al.Relationship between erucic acid and myocardial changes in male ratsLipids119-15(1975) 3.Astorg, P.O.Heart lipidosis induced by short-term feeding of cis- or trans-docosenoic acids in weanling or 7-week-old ratsAnn. Nutr. Metab.25(4)201-207(1981) 4.Cravatt, B.F., Prospero-Garcia, O., Siuzdak, G., et al.Chemical characterization of a family of brain lipids that induce sleepScience268(5216)1506-1509(1995)
| Cas No. | 112-86-7 | SDF | |
| 别名 | 芥酸 | ||
| Canonical SMILES | CCCCCCCC/C=C\CCCCCCCCCCCC(O)=O | ||
| 分子式 | C22H42O2 | 分子量 | 338.57 |
| 溶解度 | DMSO: ≥ 100 mg/mL (295.36 mM); Water: < 0.1 mg/mL (insoluble) | 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 | 2.9536 mL | 14.768 mL | 29.536 mL |
| 5 mM | 0.5907 mL | 2.9536 mL | 5.9072 mL |
| 10 mM | 0.2954 mL | 1.4768 mL | 2.9536 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。
Erucic acid, a nutritional PPARδ-ligand may influence Huntington's disease pathogenesis
Metab Brain Dis 2020 Jan;35(1):1-9.PMID:31625071DOI:10.1007/s11011-019-00500-6.
Increasing recent evidence suggests a key role of oligodendroglial injury and demyelination in the pathophysiology of Huntington's Disease (HD) and the transcription factor PPARδ is critical for oligodendroglial regeneration and myelination. PPARδ directly involves in the pathogenesis of HD and treatment with a brain-permeable PPARδ-agonist (KD3010) alleviates its severity in mice. Erucic acid (EA) is also a PPARδ-ligand ω9 fatty acid which is highly consumed in Asian countries through ingesting cruciferous vegetables such as rapeseed (Brassica napus) and indian mustard (Brassica juncea). EA is also an ingredient of Lorenzo's oil employed in the medical treatment of adrenoleukodystrophy and can be converted to nervonic acid, a component of myelin. HD pathogenesis also involves oxidative and inflammatory injury and EA exerts antioxidative and antiinflammatory efficacies including inhibition of thrombin and elastase. Consumption of rapeseed, indian mustard, and Canola oils (containing EA) improves cognitive parameters in animal models, as well as treatment with pure EA. Moreover, erucamide, an endogenous EA-amide derivative regulating angiogenesis and water balance, exerts antidepressive and anxiolytic effects in mice. Hitherto, no study has investigated the therapeutic potential of EA in HD and we believe that it strongly merits to be studied in animal models of HD as a potential therapeutic.
Could dietary Erucic acid lower risk of brain tumors? An epidemiological look to Chinese population with implications for prevention and treatment
Metab Brain Dis 2022 Dec;37(8):2643-2651.PMID:35704146DOI:10.1007/s11011-022-01022-4.
Erucic acid, an omega-9 monounsaturated fatty acid present in Brassicaceae plants (rapeseed and mustard oils) is highly consumed by the Chinese population and according to several global survey studies, its highest levels are encountered in the Chinese women's milk. Erucic acid is an activating ligand of the transcription factor PPARδ and an inhibitor of the transcriptional activity of PPARγ, which drive tumorigenesis of glioblastomas and medulloblastomas. In this theoretical review, we propose that Erucic acid in diet may associate with the risk of brain tumors. High grade brain tumors including medulloblastomas in children and glioblastomas in adults have devastating consequences for human health and the latter tumors are practically incurable. CONCORD-3 epidemiological study recently published in 2021 revealed a low ratio of medulloblastomas in the pediatric age group and also a low ratio of glioblastomas in adults in the Chinese population. It is certain that such profound differences can not be attributed to a single genetic factor or a single nurture pattern. It is very likely that multiple hereditary, nutritional and environmental factors are responsible for these lower ratios; yet here we propose that Erucic acid may be one of the contributing factors. If future epidemiological studies and animal models show antitumor activity of Erucic acid regarding brain neoplasias, it can be utilized as a preventive strategy for populations possessing very high risks to develop brain tumors such as those harbouring hereditary syndromes increasing the vulnerability to develop such malignancies.
Erucic Acid-Both Sides of the Story: A Concise Review on Its Beneficial and Toxic Properties
Molecules 2023 Feb 17;28(4):1924.PMID:36838911DOI:10.3390/molecules28041924.
Erucic acid (EA) is monounsaturated fatty acid (22:1 n-9), synthesized in the seeds of many plants from the Brassicaceae family, with Brassica napus, B. rapa, or B. carinata considered as its richest source. As the compound has been blamed for the poisoning effect in Toxic Oil Syndrome, and some data indicated its cardiotoxicity to rats, EA has been for decades classified as toxic substance, the use of which should be avoided. However, the cardiac adverse effects of EA have not been confirmed in humans, and the experiments in animal models had many limitations. Thus, the aim of this review was to present the results of the so far published studies on both toxic, and pharmacological properties of EA, trying to answer the question on its future medicinal use. Despite the ambiguous and relatively small data on toxic and beneficial effects of EA it seems that the compound is worth investigating. Further research should be particularly directed at the verification EA toxicity, more in-depth studies on its neuroprotective and cytotoxic properties, but also its use in combination with other drugs, as well as its role as a drug carrier.
A review on neuropharmacological role of Erucic acid: an omega-9 fatty acid from edible oils
Nutr Neurosci 2022 May;25(5):1041-1055.PMID:33054628DOI:10.1080/1028415X.2020.1831262.
Neurodegenerative diseases (ND) are characterised by loss of neurons in the brain and spinal cord. For the normal functioning of the brain, divers group of fatty acids in the form of glycerophospholipids, glycerol ether lipids, cerebrosides, sulfatides, and gangliosides are essential. They are present abundantly in the nervous system and are actively involved in both the development and maintenance of the nervous system. A dietary deficiency of essential fatty acid during development results in hypomyelination state which affects various neuronal functions. Several studies suggested that age remains the primary risk factor for almost all neurodegenerative disorders. The potential contribution of these fatty acids in the progression of neurodegenerative disorders is indispensable. Erucic acid an omega 9 fatty acid, which is obtained from edible oils has proven to cause myocardial lipidosis, heart lesions and hepatic steatosis in animals therefore, its content in edible oils is restricted to certain levels by regulatory agencies. However, Erucic acid in the form of a mixture with oleic acid is often used as a dietary treatment for the management of adrenoleukodystrophy without any cardiotoxicity. Our literature search revealed that, Erucic acid reported to enhance cognitive function, interact with peroxisome proliferator activated receptors (PPARs), inhibit elastase and thrombin. In this review first we have attempted to describe the relationship between fatty acids and neurodegeneration followed by a description on the pharmacology of Erucic acid. The overall purpose of this review is to analyse toxic and beneficial neuropharmacological effects of Erucic acid.
A Review of Erucic acid Production in Brassicaceae Oilseeds: Progress and Prospects for the Genetic Engineering of High and Low-Erucic Acid Rapeseeds ( Brassica napus)
Front Plant Sci 2022 May 11;13:899076.PMID:35645989DOI:10.3389/fpls.2022.899076.
Erucic acid (C22:1, ω-9, EA) is a very-long-chain monounsaturated fatty acid (FA) that is an important oleochemical product with a wide range of uses in metallurgy, machinery, rubber, the chemical industry, and other fields because of its hydrophobicity and water resistance. EA is not easily digested and absorbed in the human body, and high-EA rapeseed (HEAR) oil often contains glucosinolates. Both glucosinolates and EA are detrimental to health and can lead to disease, which has resulted in strict guidelines by regulatory bodies on maximum EA contents in oils. Increasingly, researchers have attempted to enhance the EA content in Brassicaceae oilseeds to serve industrial applications while conversely reducing the EA content to ensure food safety. For the production of both LEAR and HEAR, biotechnology is likely to play a fundamental role. Elucidating the metabolic pathways of EA can help inform the improvement of Brassicaceae oilseeds through transgenic technology. In this paper, we introduce the industrial applications of HEAR oil and health benefits of low-EA rapeseed (LEAR) oil first, following which we review the biosynthetic pathways of EA, introduce the EA resources from plants, and focus on research related to the genetic engineering of EA in Brassicaceae oilseeds. In addition, the effects of the environment on EA production are addressed, and the safe cultivation of HEAR and LEAR is discussed. This paper supports further research into improving FAs in Brassicaceae oilseeds through transgenic technologies and molecular breeding techniques, thereby advancing the commercialization of transgenic products for better application in various fields.