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[ CAS No. 6217-54-5 ] {[proInfo.proName]}

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Chemical Structure| 6217-54-5
Chemical Structure| 6217-54-5
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Quality Control of [ 6217-54-5 ]

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Product Citations

Product Citations      Expand+

Lee, Jin ; Park, Hyun-Ah ; Shin, Kyung-Chul , et al. DOI: PubMed ID:

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 ; DOI:

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 ; DOI:

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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Product Details of [ 6217-54-5 ]

CAS No. :6217-54-5 MDL No. :MFCD00065722
Formula : C22H32O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 328.49 Pubchem ID :-
Synonyms :
DHA;Cervonic acid;Doconexent;C22:6 (all cis-4,7,10,13,16,19) omega-3 Fatty acid;Docosahexaenoic acid (all cis-4,7,10,13,16,19)

Calculated chemistry of [ 6217-54-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.41
Num. rotatable bonds : 14
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 106.8
TPSA : 37.3 ?2

Pharmacokinetics

GI absorption : None
BBB permeant : None
P-gp substrate : None
CYP1A2 inhibitor : None
CYP2C19 inhibitor : None
CYP2C9 inhibitor : None
CYP2D6 inhibitor : None
CYP3A4 inhibitor : None
Log Kp (skin permeation) : None cm/s

Lipophilicity

Log Po/w (iLOGP) : None
Log Po/w (XLOGP3) : None
Log Po/w (WLOGP) : 6.55
Log Po/w (MLOGP) : None
Log Po/w (SILICOS-IT) : None
Consensus Log Po/w : None

Druglikeness

Lipinski : None
Ghose : None
Veber : None
Egan : None
Muegge : None
Bioavailability Score : None

Water Solubility

Log S (ESOL) : None
Solubility : None mg/ml ; None mol/l
Class : None
Log S (Ali) : None
Solubility : None mg/ml ; None mol/l
Class : None
Log S (SILICOS-IT) : None
Solubility : None mg/ml ; None mol/l
Class : None

Medicinal Chemistry

PAINS : None alert
Brenk : None alert
Leadlikeness : None
Synthetic accessibility : None

Safety of [ 6217-54-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P210-P261-P264-P271-P273-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P370+P378-P403+P233-P403+P235-P405-P501 UN#:N/A
Hazard Statements:H227-H315-H319-H335-H413 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6217-54-5 ]

* 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 [ 6217-54-5 ]

[ 6217-54-5 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 6217-54-5 ]
  • [ 255735-88-7 ]
  • [ 1204318-28-4 ]
YieldReaction ConditionsOperation in experiment
70% With triethylamine; HATU; In acetonitrile; at 0 - 20℃; Example 21; Preparation of N-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidopropyl)-2-hydroxybenzamide (14); To a solution of tert-butyl 2-aminopropylcarbamate (1.06 g, 6.09 mmol, prepared as previously described), DHA (2.0 g, 6.09 mmol) and Et3N (1.7 mL, 12.8 mmol) in CH3CN (40 mL) at 0° C. was added HATU (2.31 g, 6.09 mmol). The mixture was stirred (RT, 16 h) and concentrated under reduced pressure. The residue was diluted with brine (100 mL) and extracted with EA (2.x.100 mL). The combined organic layers were washed with saturated NaHCO3 (100 mL) and brine (100 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel, eluting with EA-PE (0-25percent) to afford tert-butyl 2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidopropylcarbamate (2.1 g, 70percent) as a light yellow oil. Mass calculated for C30H48N2O3=484.71; found: [M+H]+=485.6.
  • 2
  • [ 6217-54-5 ]
  • [ 2934-05-6 ]
  • [ 1224157-47-4 ]
  • 3
  • [ 6217-54-5 ]
  • [ 263162-13-6 ]
  • [ 1333067-38-1 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In acetonitrile; at 20℃; for 2h; <strong>[263162-13-6]tert-butyl 2-((2-aminoethyl)(methyl)amino)ethylcarbamate</strong> (430 mg, 1.98 mmol) was taken up in 10 mL of CH3CN along with (4Z,7Z,10Z,13Z,16Z,19Z)-docosa- 4,7,10,13,16,19-hexaenoic acid (DHA, 650 mg, 1.98 mmol), HATU (750 mg, 2.2 mmol) and DIEA (0.550 mL). The resulting reaction mixture was stirred at room temperature for 2 h and then diluted with EtOAc (40 mL). The organic layer was washed with brine, dried (Na2S04) and concentrated under reduced pressure. Purification by chromatography (95% CH2C12, 5% MeOH) afforded 400 mg of the Boc-protected intermediate. This material was taken up in 3 mL of 4 M HC1 in dioxane and allowed to stir at room temperature for 10 min. The reaction mixture was concentrated under reduced pressure to afford the HCl salt of (4Z,7Z, 10Z, 13Z, 16Z, 19Z)-N-(2-((2-aminoethyl)(methyl)amino)ethyl)docosa- 4,7,10,13,16,19-hexaenamide.
With N-ethyl-N,N-diisopropylamine; HATU; at 20℃; for 2h; <strong>[263162-13-6]tert-butyl 2-((2-aminoethyl)(methyl)amino)ethylcarbamate</strong> (430 mg, 1.98 mmol) was taken up in 10 mL of CH3CN along with (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19- hexaenoic acid (DHA, 650 mg, 1.98 mmol), HATU (750 mg, 2.2 mmol) and DIEA (0.550 mL). The resulting reaction mixture was stirred at room temperature for 2 h and then diluted with EtOAc (40 mL). The organic layer was washed with brine, dried (Na2S04) and concentrated under reduced pressure. Purification by chromatography (95% CH2CI2, 5% MeOH) afforded 400 mg of the Boc-protected intermediate. This material was taken up in 3 mL of 4 M HCl in dioxane and allowed to stir at room temperature for 10 min.
  • 4
  • [ 6217-54-5 ]
  • [ 22808-73-7 ]
  • (4Z,7Z,10Z,13Z,16Z,19Z)-N-((4-methoxycarbonyl)phenylsulfonyl)docosa-4,7,10,13,16,19-hexaenamide [ No CAS ]
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