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Chemical Structure| 506-32-1 Chemical Structure| 506-32-1

Structure of Arachidonic acid
CAS No.: 506-32-1

Chemical Structure| 506-32-1

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Arachidonic Acid is an unsaturated, essential fatty acid. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is formed by the synthesis from dietary linoleic acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes.

Synonyms: Immunocytophyt; Eicosatetraenoic acid (all cis-5,8,11,14); C20:4 (all cis-5,8,11,14) Fatty acid

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Lee, Jin ; Park, Hyun-Ah ; Shin, Kyung-Chul ; Park, Jin-Byung ; Oh, Deok-Kun ;

Abstract: Resolvin D5 (RvD5), 7S,17S-dihydroxy-4Z,8E,10Z,13Z,15E,19Z-docosahexaenoic acid (DHA) is a specialized pro-resolving mediator (SPM) generated in human macrophages. It is implicated in the resolution of inflammation and synthesized using an inefficient chem. process. Here, DHA-enriched oil hydrolyzate was prepared from oils by lipase with resin treatment and solvent extraction The reaction factors on the biotransformation of oil hydrolyzate into RvD5 were optimized using Escherichia coli expressing arachidonate double-oxygenating 15S-lipoxygenase. After optimization, the cells converted 5.0 mM (1.64 g/L) DHA in oil hydrolyzate into 4.0 mM (1.44 g/L) RvD5 in a bioreactor for 3.0 h, which was 15-fold higher than that in a flask before optimization, and RvD5 with a purity of > 97% was prepared from reaction solution by treatments of resins. This is the first trial for the production of C22-dihydroxy fatty acid using a bioreactor. This study will contribute to the large-scale production of SPMs from oils.

Keywords: Lipoxygenase ; Resolvin D5 ; Docosahexaenoic acid-enriched oil hydrolysate ; Biotransformation ; Bioreactor

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Lee, Hyejin ; Yoon, Hye-Ran ;

Abstract: We developed and validated a fast, sensitive, and accurate anal. method using ultra high-pressure liquid chromatog.-electrospray ionization tandem mass spectrometry (UHPLC-ESI-MS/MS) for simultaneous extraction and quantification of 5 targeted omega fatty acids on human dried serum spots. MS/MS was performed with multiple reaction monitoring (MRM) mode under neg. electrospray ionization. We targeted omega fatty acids which are likely to have a pos. effect on various inflammatory reactions such as asthma, chronic obstructive pulmonary diseases and rheumatoid arthritis. If applicable, it is necessary to determine them as asthma biomarkers for intervention and public health. The coefficient of determination (r2) of calibration curve exhibited a good linear relationship between 0.9942 and 0.9963 in a range of 0.05-5μg mL-1. The anal. method was validated with excellent sensitivity (limit of detection; 0.005-0.01μg mL-1, limit of quantification; 0.03-0.1μg mL) that allows targeted analyses of omega fatty acids. We obtained the recoveries of 92.6 to 110.4% (RSD, 0.2-9.6%) for intraday and 92.6 to 107.6% (RSD, 1.4-7.0%) for interday. Clin. correlation between the healthy subjects and asthmatic patients sera was evaluated with the ratio of omega-3/omega-6 fatty acids. The developed method combines the advantages of easy handling dried filter paper and UHPLC-MS/MS for effectiveness of extraction and analyses step. We evaluated the validation for the quantification and applicability of human serum as a possible role of asthma biomarkers.

Keywords: Omega fatty acids ; Dried human serum spot ; UHPLC-MS ; MS ; Negative ionization ; Asthma

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Hyejin Lee ; Hye-Ran Yoon ;

Abstract: Omega fatty acids play an important role as biomarkers of chronic inflammatory diseases such as asthma, chronic obstructive pulmonary disease, rheumatoid arthritis, and inflammatory bowel disease. The purpose of our study was to develop a new analytical method for the detection of omega fatty acids from dried serum spots. We developed an ultra-high performance liquid chromatography-electrospray ionization tandem mass spectrometry (UHPLC-ESI-MS/MS)-based method in the multiple reaction monitoring (MRM) mode with negative ionization. The detected MRM transitions for five omega fatty acids are as follow: α-linolenic acid (m/z=277.20→277.20), eicosapentaenoic acid (m/z=301.10→257.30), docosahexaenoic acid (m/z=327.00→283.15), arachidonic acid (m/z=303.20→259.25), and docosapentaenoic acid (m/z= 329.10→285.25). The calibration curve showed an excellent linearity within 0.1-2.5 μg/mL range (R2=0.9947~0.9994). The analytical methods howed excellent sensitivity (LOD: 0.005-0.01 μg/mL, LOQ: 0.03-0.1 μg/mL), which would allow for the targeted analyses of omega fatty acids. The recoveries of the omega fatty acid from the dried serum spots were 92.6%-110.4% (RSD: ±0.2%-9.6%) and the retention time was within 5 min. This improved method offers rapid and sensitive quantification of omega fatty acids on dried serum spots using a small volume of serum and is expected to be applied to various biological specimens.

Keywords: Omega fatty acid ; Dried serum spot ; Negative ionization ; UPLC-MS/MS ; Asthma

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Alternative Products

Product Details of Arachidonic acid

CAS No. :506-32-1
Formula : C20H32O2
M.W : 304.47
SMILES Code : CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(O)=O
Synonyms :
Immunocytophyt; Eicosatetraenoic acid (all cis-5,8,11,14); C20:4 (all cis-5,8,11,14) Fatty acid
MDL No. :MFCD00004417
InChI Key :YZXBAPSDXZZRGB-DOFZRALJSA-N
Pubchem ID :444899

Safety of Arachidonic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
A375 cells 30 µM 3 days Combination of IFNγ and AA induced A375 cell death via ferroptosis, which was specifically blocked by ferroptosis inhibitor Fer1. Cancer Cell. 2022 Apr 11;40(4):365-378. e6
THP-1 monocyte/macrophage cells 40 μM 24 hours To evaluate the effect of AA on PA-induced NLRP3 inflammasome activity, results showed AA inhibited IL-1β secretion and ASC speck formation. Cell Rep. 2024 Feb 27;43(2):113700.
Murine platelets 1 µM 4 h To investigate the effect of arachidonic acid on murine platelet apoptosis. Results showed that arachidonic acid induced apoptosis in murine platelets. Haematologica. 2012 Oct;97(10):1514-22
Human platelets 1-100 μM 10 min To investigate the effect of arachidonic acid on platelet apoptosis. Results showed that arachidonic acid dose-dependently increased mitochondrial membrane potential changes, indicating its induction of platelet apoptosis. Haematologica. 2012 Oct;97(10):1514-22
RAW 267.4 cells 50 μM 30 min To investigate the formation of TOG after arachidonic acid treatment. Results showed a significant increase in intracellular TOG levels after arachidonic acid treatment. Free Radic Biol Med. 2009 Oct 1;47(7):953-61
Mouse endometrial stromal cells 20 µM 3 h Arachidonic acid induces S100A6 expression in stromal cells via the COX2/PGI2/PPARδ pathway. Cells. 2024 Jan 23;13(3):206
Mouse endometrial epithelial cells 20 µM 3 h Lactate stimulates p-cPLA2 expression in epithelial cells, promoting arachidonic acid secretion. Cells. 2024 Jan 23;13(3):206
Monocyte-derived macrophages 50 µM 30 min Investigate the effect of AA on the transcriptome of IL-6-stimulated macrophages, showing AA inhibits IL-6-induced gene expression Mol Oncol. 2022 Sep;16(17):3146-3166
Monocyte-derived macrophages 50 µM 30 min Investigate the effect of AA on the transcriptome of IFNγ-stimulated macrophages, showing AA inhibits IFNγ-induced gene expression Mol Oncol. 2022 Sep;16(17):3146-3166
Monocyte-derived macrophages 50 µM 30 min Investigate the effect of AA on the transcriptome of IFNβ-stimulated macrophages, showing AA inhibits IFNβ-induced gene expression Mol Oncol. 2022 Sep;16(17):3146-3166

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.28mL

0.66mL

0.33mL

16.42mL

3.28mL

1.64mL

32.84mL

6.57mL

3.28mL

Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1
Protocol 2
The prepared working fluid is recommended to be prepared now and used up as soon as possible in a short period of time. The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1

References

 

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