7,10-dihydroxy-8(E)-Octadecenoic Acid
目录号 : GC48769
An antibacterial hydroxy fatty acid
Cas No.:131021-99-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
7,10-dihydroxy-8(E)-Octadecenoic acid is a hydroxy fatty acid and metabolite of oleic acid that is produced by P. aeruginosa from vegetable oils.1 It is active against the food-borne pathogenic bacteria S. aureus, S. typhimurium, L. monocytogenes, B. subtilis, and E. coli (MIC50s = 31.3, 125, 125, 62.5, and 250 µg/ml, respectively), as well as the plant pathogenic bacteria Erwinia, R. solanacearum, C. glutamicum, and P. syringae (MIC90s = 125, 125, 250, and 500 µg/ml, respectively).2,1
1.Sohn, H.-R., Bae, J.-H., Hou, C.T., et al.Antibacterial activity of a 7,10-dihydroxy-8(E)-octadecenoic acid against plant pathogenic bacteriaEnzyme Microb. Technol.53(3)152-153(2013) 2.Chen, K.Y., Kim, I.H., Hou, C.T., et al.Monoacylglycerol of 7,10-dihydroxy-8(E)-octadecenoic acid enhances antibacterial activities against food-borne bacteriaJ. Agric. Food Chem.67(29)8191-8196(2019)
| Cas No. | 131021-99-3 | SDF | |
| Canonical SMILES | CCCCCCCCC(O)/C=C/C(O)CCCCCC(O)=O | ||
| 分子式 | C18H34O4 | 分子量 | 314.5 |
| 溶解度 | DMF: 15 mg/ml,DMSO: 20 mg/ml,Ethanol: 100 mg/ml,PBS (pH 7.2): 0.25 mg/ml | 储存条件 | -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 | 3.1797 mL | 15.8983 mL | 31.7965 mL |
| 5 mM | 0.6359 mL | 3.1797 mL | 6.3593 mL |
| 10 mM | 0.318 mL | 1.5898 mL | 3.1797 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。
Production of 7,10-dihydroxy-8(E)-Octadecenoic Acid using cell-free supernatant of Pseudomonas aeruginosa
Enzyme Microb Technol 2021 Oct;150:109892.PMID:34489045DOI:10.1016/j.enzmictec.2021.109892.
Cell-free synthesis has been adopted in the bioconversion process due to its known advantages, such as fast production rate, high product content, and no substrate/product inhibition effect. In this study, the cell-free supernatant of Pseudomonas aeruginosa was used to improve the production of 7,10-dihydroxy-8(E)-Octadecenoic Acid (DOD) from oleic acid. DOD production using cell-free supernatant demonstrated reduction in bioconversion duration and higher product concentration than conventional method using whole cell culture. The maximum DOD concentration (6.41 g/L) was obtained after 36 h of biotransformation using 1 % v/v oleic acid as a substrate with a productivity of 0.178 g/L/h and a yield of 74.8 %. DOD concentration, productivity, and yield using cell-free supernatant were 2.12, 7.12, and 2.22 times higher, respectively, than using the conventional whole cell culture method. Of the carbon and nitrogen sources used in pre-culture, galactose and sodium glutamate along with diammonium phosphate were found to be the most effective for DOD production. An incubation temperature of 27 °C and pH 8.0 were found to be most favorable for DOD production. In addition, sodium dodecyl sulfate polyacrylamide gel electrophoresis analysis demonstrated the presence of enzymes related to DOD production in the cell-free supernatant, which was substantiated by performing DOD production experiment using the supernatant enzymes extracted from protein gel bands with oleic acid as a substrate. To the best of our knowledge, this is the first report on DOD production using a cell-free supernatant and verifying the existence of the relevant enzymes in the cell-free supernatant. Compared to whole cell process, cell-free DOD production holds several advantages, including higher DOD productivity which could be beneficial for large-scale production.
Production of 7,10,12-trihydroxy-8(E)-octadecenoic acid from ricinoleic acid by Pseudomonas aeruginosa KNU-2B
Biotechnol Lett 2020 Aug;42(8):1547-1558.PMID:32246345DOI:10.1007/s10529-020-02883-4.
Microbial production of hydroxy fatty acids (HFAs) was widely studied because of important biological properties of HFAs. Among microorganisms producing HFAs, Pseudomonas aeruginosa PR3 was well known to produce various HFAs from different unsaturated fatty acids. Recently, a new variant species of P. aeruginosa PR3 was isolated and characterized, showing improved efficiency for producing 7,10-dihydroxy-8(E)-Octadecenoic Acid from oleic acid. In this study, we report the production of 7,10,12-trihydroxy-8(E)-octadecenoic acid (TOD) from ricinoleic acid by the newly isolated P. aeruginosa KNU-2B. TOD was efficiently produced from ricinoleic acid by KNU-2B with the maximum conversion yield of 56.7% under the optimum reaction conditions of pH 8.0 and 48-h incubation at 27 °C, 150 rpm. Under optimized reaction conditions, maximum TOD production reached 340.3 mg/100 mL of the culture. However, requirement of nutritional factors by KNU-2B for production of TOD were considerably different from those by PR3 strain.
Monoacylglycerol of 7,10-Dihydroxy-8( E)-octadecenoic Acid Enhances Antibacterial Activities against Food-Borne Bacteria
J Agric Food Chem 2019 Jul 24;67(29):8191-8196.PMID:31282662DOI:10.1021/acs.jafc.9b03063.
Conversion of free fatty acids into monoacylglycerol gives rise to new structural properties, particularly amphipathic property. Therefore, monoacylglycerols are widely used in pharmaceutical and food industries and are also reported to facilitate better absorption into the human body. A functional fatty acid when transformed into a monoacylglycerol will possibly conserve both the original functionality and amphipathic property. The compound 7,10-dihydroxy-8(E)-Octadecenoic Acid (DOD) was generated from oleic acid by Pseudomonas aeruginosa PR3 and was known to contain antimicrobial activities against a broad range of food-borne and plant pathogenic bacteria. Here, we attempted to convert DOD into its monoacylglycerol form using lipase for producing an amphipathic antibacterial agent. Consequently, the monoacylglycerol of DOD (DOD-MAG) was successfully produced by coincubating DOD, glycerol, and lipase at 30 °C. The maximum conversion yield reached 70% after 12 h of incubation. Antibacterial activity of DOD-MAG was enhanced by 8 times from the original activity of DOD against food-borne bacteria.
alpha-Glucosidase inhibitory activities of 10-hydroxy-8(E)-octadecenoic acid: an intermediate of bioconversion of oleic acid to 7,10-dihydroxy-8(E)-Octadecenoic Acid
N Biotechnol 2010 Sep 30;27(4):419-23.PMID:20385262DOI:10.1016/j.nbt.2010.04.002.
Microbial conversion of unsaturated fatty acids often leads to special changes in their product structures and in biological potential. In our continuous effort to screen natural products for their antimicrobial and enzyme inhibitor activities, we found that 10-hydroxy-8(E)-octadecenoic acid (HOD) exhibited strong anti-alpha-glucosidase (EC 3.2.1.20) activity. HOD is an intermediate in the bioconversion of oleic acid to 7,10-dihydroxy-8(E)-Octadecenoic Acid (DOD) by a bacterial isolate, Pseudomonas aeruginosa (PR3). Diabetes mellitus is the most serious, chronic metabolic disorder characterized by defect in insulin secretion and action, which can lead to damage blood vessels and nerves. We analyzed the inhibitory activity of HOD and the commercially available antidiabetic remedy, acarbose. We found that HOD exhibited a better inhibition (IC(50) 0.07+/-0.12) on alpha-glucosidase as compared to acarbose (IC(50) 0.42+/-0.1). HOD showed competitive inhibition against yeast alpha-glucosidase. Our study is the first report on anti-alpha-glucosidase activity of HOD and could be helpful to develop medicinal preparation or functional food for diabetes and related symptoms.
Antibacterial activity of a 7,10-dihydroxy-8(E)-Octadecenoic Acid against plant pathogenic bacteria
Enzyme Microb Technol 2013 Aug 15;53(3):152-3.PMID:23830454DOI:10.1016/j.enzmictec.2013.02.009.
7,10-dihydroxy-8(E)-Octadecenoic Acid (DOD), one of hydroxy fatty acids, was successfully produced from oleic acid and natural vegetable oils containing oleic acid by a bacterial strain Pseudomonas aeruginosa (PR3). However, biological properties of DOD remained unknown so far. In this study, as a trial to determine the biological properties of DOD molecule, antibacterial activities of DOD against plant pathogenic bacteria were determined qualitatively and quantitatively. DOD presented strong antibacterial activities against all the bacterial strains tested with MIC value being in the range of 125-1000μg/ml and there was no sensitivity preference detected between Gram-positive and Gram-negative strains.