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Chemical Structure| 506-32-1 Chemical Structure| 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

Application In Synthesis of Arachidonic acid

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 506-32-1 ]

[ 506-32-1 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 506-32-1 ]
  • [ 41598-07-6 ]
  • [ 363-24-6 ]
  • [ 551-11-1 ]
  • 2
  • [ 506-32-1 ]
  • [ 41598-07-6 ]
  • [ 363-24-6 ]
  • [ 551-11-1 ]
  • 12-hydroxy-heptadecatrienoic acid [ No CAS ]
  • 3
  • [ 506-32-1 ]
  • [ 2002-24-6 ]
  • [ 94421-68-8 ]
  • 4
  • [ 506-32-1 ]
  • [ 27757-86-4 ]
  • (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid (thiophen-3-ylmethyl)-amide [ No CAS ]
 

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