cis-9,10-Methyleneoctadecanoic Acid
(Synonyms: 顺式9,10-亚甲基十八烷酸) 目录号 : GC40343
A cyclopropane fatty acid
Cas No.:4675-61-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
cis-9,10-Methyleneoctadecanoic acid is a cyclopropane fatty acid that has been found in bacteria and the digestive gland of P. globosa. It is a component of S. aureus cell membranes and levels decrease upon treatment with carvacrol. cis-9,10-Methyleneoctadecanoic acid is secreted by H. pylori and enhances histamine- and dibutyryl cAMP-stimulated acid secretion in isolated guinea pig parietal cells. It also activates protein kinase C (PKC) in a calcium-dependent manner.
| Cas No. | 4675-61-0 | SDF | |
| 别名 | 顺式9,10-亚甲基十八烷酸 | ||
| Canonical SMILES | OC(CCCCCCC[C@H](C1)[C@H]1CCCCCCCC)=O | ||
| 分子式 | C19H36O2 | 分子量 | 296.5 |
| 溶解度 | Chloroform: Soluble,Ethanol: Soluble,Methanol: Soluble | 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 | 3.3727 mL | 16.8634 mL | 33.7268 mL |
| 5 mM | 0.6745 mL | 3.3727 mL | 6.7454 mL |
| 10 mM | 0.3373 mL | 1.6863 mL | 3.3727 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。
The Helicobacter pylori fatty acid cis-9,10-Methyleneoctadecanoic Acid stimulates protein kinase C and increases DNA synthesis of gastric HM02 cells
Br J Cancer 1998 Jun;77(11):1852-6.PMID:9667658DOI:10.1038/bjc.1998.308.
Protein kinase C (PKC) has been implicated in the control of epithelial proliferative activity and in the process of malignant transformation. Helicobacter pylori (H.p.) infection is associated with increased gastric epithelial cell proliferation and has been linked with gastric carcinoma. In the present study, we report that the H.p. fatty acid cis-9,10-Methyleneoctadecanoic Acid (MOA) directly activates PKC (Ka 3.3 microM). The effect of MOA upon PKC activation was Ca2+ dependent but did not require phosphatidylserine as phospholipid cofactor. MOA increased the stimulatory effect of phosphatidylserine at low Ca2+ (1 microM) concentrations. These findings indicate that MOA interacts at the phospholipid- and the diacylglycerol-binding domain to elicit PKC activation. Treatment of gastric mucous cells HM02 caused translocation of PKC from the cytosol to the nuclear, mitochondrial and membrane fraction. Furthermore, MOA stimulated [3H]thymidine incorporation into the DNA of HM02 cells. Our results show that the H.p. fatty acid MOA activates PKC and increases DNA synthesis in gastric epithelial cells.
A model for the prediction of antimicrobial resistance in Escherichia coli based on a comparative evaluation of fatty acid profiles
Diagn Microbiol Infect Dis 2020 Mar;96(3):114966.PMID:31948696DOI:10.1016/j.diagmicrobio.2019.114966.
Antimicrobial resistance is a threat to agricultural production and public health. In this proof-of-concept study, we investigated predicting antimicrobial sensitive/resistant (S/R) phenotypes and host sources of Escherichia coli (n = 128) based on differential fatty acid abundance. Myristic (14:0), pentadecanoic acid (15:0), palmitic (16:0), elaidic (18:19) and steric acid (18:0) were significantly different (α = 0.05) using a two-way ANOVA for predicting nalidixic acid, ciprofloxacin, aztreonam, cefatoxime, and ceftazidime S/R phenotypes. Additionally, analyses of palmitoleic (16:1), palmitic acid (16:0), methyl palmitate (i-17:0), and cis-9,10-Methyleneoctadecanoic Acid (19:0Δ) showed these markers were significantly different (α = 0.05) between isolates obtained from cattle and raccoons. S/R phenotype prediction for the above antibiotics or host source, based on linear regression models of fatty acid abundance, were made using a replicated-randomized subsampling and modeling approach. This model predicted S/R phenotype with 79% and 81% accuracy for nalidixic acid and ciprofloxacin, respectively. The isolate host source was predicted with 63% accuracy.
Raman spectroscopy as a tool for tracking cyclopropane fatty acids in genetically engineered Saccharomyces cerevisiae
Analyst 2019 Jan 28;144(3):901-912.PMID:30207333DOI:10.1039/c8an01477a.
Cyclopropane fatty acids (CFAs) are a group of lipids with unique physical and chemical properties between those of saturated and monounsaturated fatty acids. The distinctive physicochemical characteristics of CFAs (e.g. oxidative stability, self-polymerization at high temperatures, etc.) results from the presence of a cyclopropane ring within their structure making them highly useful in industrial applications. CFAs are present in several species of plants and bacteria and are typically detected with standard lipid profiling techniques, such as gas or liquid chromatography. In this work we investigated several strains of S. cerevisiae, genetically modified to introduce the production of CFAs, in comparison to control strain using confocal Raman spectroscopy (CRS). The aim of our work was to demonstrate the potential of CRS not only to detect changes introduced due to the CFAs presence, but also to track CFAs within the cells. We present for the first time Raman and IR spectra of CFA standard (cis-9,10-Methyleneoctadecanoic Acid), completed with quantum chemical calculations and band assignment. We identified marker bands of CFA (e.g. 2992, 1222, 942 cm-1) attributed to the vibrations of the cyclopropyl ring. Furthermore, we analysed lipid bodies (LBs) from modified and control yeast using CRS imaging and identified multiple changes in size, number and composition of LBs from engineered strains. We observed a significant reduction in the degree of unsaturation of LBs using the ratio of bands located at 1660 cm-1 (ν(C[double bond, length as m-dash]C)) and 1448 cm-1 (δ(CH2)) in the modified cell lines. In addition, we were able to detect the presence of CFAs in LBs, using the established marker bands. CRS shows tremendous potential as technique to identify CFAs in lipid bodies providing a new way to track lipid production in genetically modified single yeast cells.
Unusual cellular fatty acids and distinctive ultrastructure in a new spiral bacterium (Campylobacter pyloridis) from the human gastric mucosa
J Med Microbiol 1985 Apr;19(2):257-67.PMID:3981612DOI:10.1099/00222615-19-2-257.
Spiral bacteria, named Campylobacter pyloridis, were obtained from endoscopic biopsies of the gastric antrum of 14 patients with active chronic gastritis. Methyl esters of their cellular fatty acids were prepared by acid-catalysed transmethylation of whole cells. Their major fatty acids were tetradecanoic acid (14:0) and cis-9,10-Methyleneoctadecanoic Acid (19:0 delta), with a very small amount of hexadecanoic acid (16:0). This is markedly different from the fatty acids of other Campylobacter sp. whose major fatty acids are hexadecanoic, octadecenoic (18:1) and hexadecenoic acids (16:1). This is also different from other enterobacteria. Thin-section electronmicroscopy of gastric mucosal biopsies, and negative staining of cultured C. pyloridis, revealed features that differ from those of other campylobacters so far studied. C. pyloridis has a smooth not a rugose surface and multiple unipolar flagella of the sheathed type, each with a terminal bulb. Flagellar sheaths were in continuity with the unit membrane of the outer cell wall. The proposed species C. pyloridis does not belong among the spirochaetes and its DNA composition is incompatible with membership of the genera Spirillum or Vibrio but is compatible with Campylobacter. Thus C. pyloridis is either an atypical member of the genus Campylobacter, the limits of which may have to be redefined to accommodate the new species, or a representative of a new genus.
Effects of thiastearic acids on growth and on dihydrosterculic acid and other phospholipid fatty acyl groups of Leishmania promastigotes
Mol Biochem Parasitol 1989 Jun 1;35(1):57-66.PMID:2761573DOI:10.1016/0166-6851(89)90142-4.
Thiastearic acid positional isomers (8, 9, 10, 11) were examined for their ability to inhibit population growth and the biosynthesis of a phosphatidylethanolamine cyclopropane fatty acyl group, cis-9,10-Methyleneoctadecanoic Acid (dihydrosterculic acid), by promastigotes of Leishmania species. Thiastearic acids are candidate chemotherapeutic agents, since cyclopropane fatty acids are not formed by vertebrate cells. 8- and 10-thiastearic acids strongly inhibited the growth of strains containing the most dihydrosterculic acid (Leishmania tropica and Leishmania donovani; 25-35% phosphatidylethanolamine fatty acyl groups) and less strongly inhibited strains containing no dihydrosterculic acid (Leishmania major). The 11-thiastearic acid was less effective and 9-thiastearic acid ineffective. Strains containing 1-15% dihydrosterculic acid (L. donovani, Leishmania braziliensis, Leishmania aethiopica and Leishmania mexicana mexicana) were with few exceptions not inhibited by any of the isomers. All the thiastearic acid isomers caused a dose-dependent loss of dihydrosterculic acid. This was accompanied by a loss of phosphatidylethanolamine in the case of dihydrosterculic acid-rich leishmanial strains exposed to the 8- and 10-isomers. The 8- and 10-thiastearic acids also caused a loss of C18 unsaturated fatty acyl groups and increases in palmitic and stearic acids in the phosphatidylethanolamine and phosphatidylcholine of the dihydrosterculic acid-rich and dihydrosterculic acid-free leishmanial strains. 11-Thiastearic acid was much less effective and 9-thiastearic acid ineffective. These changes were not evident in those strins which contained 1-15% dihydrosterculic acid and whose growth was not inhibited by the thiastearic acid isomers. It is concluded that thiastearic acid isomers may inhibit both dihydrosterculic acid biosynthesis and fatty acid desaturation, with the 9-isomer having the highest specificity for dihydrosterculic acid biosynthesis. Population growth of promastigotes of Leishmania species in culture is not dependent upon dihydrosterculic acid biosynthesis but is dependent upon fatty acid desaturation.