• Title/Summary/Keyword: fatty acid derivatives

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Study on the Synthsis and Characteristics of Lipophilic Derivatives of β-Sitosterol (β-시토스테롤의 지용성 치환체의 합성 및 특성에 관한 연구)

  • Chung, Dae-won;Cho, Young Tai
    • Applied Chemistry for Engineering
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    • v.17 no.4
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    • pp.375-380
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    • 2006
  • In the paper, lipophilic derivatives of $\beta$-sitosterol, which are known to have a potential to reduce blood cholesterol level, were synthesized by the esterification of $\beta$-sitosterol and fatty acids. When the esterification reactions using stearic acid, oleic acid or linoleic acid as fatty acids were carried out in the presence of an acidic catalyst, the reaction for unsaturated fatty acids such as oleic acid and linoleic acid afforded a significant amount of side products which may be produced by oxidation of unsaturated groups. On the other hand, esterification reactions in the presence of dehydrating agents and a basic catalyst gave pure products regardless of the nature of fatty acids. The solubilities of lipophilic derivatives of $\beta$-sitostero to organic solvents and edible oil were observed to increase as the degree of unsaturation of fatty acids increases.

Synthesis of Some Phosphated Fatty acyl Derivatives of Mannitol and Their Evaluation

  • Jain, Sanjay;Tripathi, Meena;R.K.Uppadhyay;D.V.Kohli
    • Archives of Pharmacal Research
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    • v.12 no.4
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    • pp.233-235
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    • 1989
  • Sodium salts of phosphated capric and myristic acyl derivatives of mannitol were prepared and evaluated for surface activity, foam characteristics and emulsifying properties. Triacyl mannitols of cappric and myristic acid have better emulsifying property than the corresponding di and monocompounds.

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Conjugated Linoleic Acid Changes fatty Acid Composition by Decreasing Monounsaturated fatty Acids in Rabbits and Hep G2 Cells

  • Nam, Kisun
    • Journal of Nutrition and Health
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    • v.30 no.4
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    • pp.442-450
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    • 1997
  • Conjugated dienoic derivatives of linoleic acid(CLA) are a mixture of positional and geometric isomers of linoleic acid(LA). We previously found that CLA changes the fatty acid profile in chicken eggs and serum by decreasing monounsaturated fatty acids. Studies were conducted to explore the effects of CLA on fatty acid composition. Rabbits were fed a semisynthetic diet with or without CLA(0.5g CLA/rabbit/day) for 22 weeks. Compared to the control, rabbits fed CLA had significantly lower monounsaturated fatty acid levels(palmitoleic acid Cl6 : 1 by 50% and oleic acid Cl8 : 1, by 20%) in plasma lipids. We found similar differences in fatty acid composition in the liver and the aorta. The inhibitory effect of CLA on $\Delta$9 desaturation was confirmed in a human hepatoma cell line, Hep G2. CLA significantly decreased $\Delta$9 desaturation in 4-5 hours as shown by an increase in the ratio of Cl6 : 0 to C 16 1, This is apparently due to a decrease in $\Delta$9 desaturase(stearoyl-CoA desaturase, SCD) activity ; it was decreased more than 50%. These results, along with our previous findings, indicate that CLA is an inhibitor of $\Delta$9 desaturase in the liver.

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Ligand Design of 5,5'-Diphenylimidazolidine-2,4-dione Analogues as A New Class of Potent Inhibitors of Fatty Acid Amide Hydrolase (새로운 Fatty Acid Amide Hydrolase 저해제로서 5,5'-Diphenylimidazolidine-2,4-dione 유도체의 리간드 설계)

  • Cho, Jong-Un;Soung, Min-Gyu;Sung, Nack-Do
    • Applied Biological Chemistry
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    • v.51 no.2
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    • pp.119-123
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    • 2008
  • 3D-QSARs (3 dimensional quantitative structrue-activity relationships) on the inhibition activities of 3-substituted-5,5'-diphenylimidazolidine-2,4-dione derivatives (1-22) against FAAH (fatty acid amide hydrolase) were studied quantitatively using CoMFA (comparative molecular field analysis) and CoMSIA (comparative molecular similarity indice analysis) methods. The statistical results of the CoMFA 1A and CoMSIA 2F model are better predictability and fitness. And also, the designed X=I, Y=$N_{2}^{+}$-substituent (P1: $Pred.pI_{50}$=6.55), according to the contour maps with information of the two models, showed the most inhibition activity against FAAH.

A Sensitive Determination of Plasma Free Fatty Acids Following Tert-butyldimethylsilyl Derivatization using Gas Chromatography-Mass Spectrometry for Screening of Fatty Acid Oxidation Disorders (지방산대사이상질환 스크리닝을 위한 TBDMS 유도체화 후 GC-MS를 이용한 혈장 중 유리지방산의 분석)

  • Yoon, Hye-Ran;Thapa, Maheshwor
    • Journal of The Korean Society of Inherited Metabolic disease
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    • v.17 no.2
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    • pp.39-47
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    • 2017
  • Purpose: A sensitive gas chromatography mass spectrometry (GC-MS) method was developed for screening of fatty acid oxidation disorders. Methods: The assay utilized a simple protein precipitation with sulfosalicylic acid followed by tert-butyl dimethylsilyl (TBDMS) derivatization of hydroxyl functional group by N-tert-butyldimethylsilyl-N-methyltrifluoroacetamide (MTBSTFA). Results: Calibration curves of spiked pooled plasma showed a linear relationship in the range of 0.01 ng -2 mg with correlation coefficient value greater than 0.98. Limits of detection (LOD) and limits of quantification (LOQ) were found in the range of 0.9-8.8 ng and 9-88 ng, respectively. Conclusion: The new developed method might be useful for a rapid, sensitive screening of inherited fatty acid oxidation disorders. In addition, the method expected to be one of the alternative method for screening newborns of metabolic disorders in the laboratories where expensive MS/MS is unavailable.

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Chemical Modification of Rupestonic Acid and Preliminarily In Vitro Antiviral Activity Against Influenza A3 and B Viruses

  • Yong, Jian-Ping;Aisa, Haji Akber
    • Bulletin of the Korean Chemical Society
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    • v.32 no.4
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    • pp.1293-1297
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    • 2011
  • To improve the biological activities of rupestonic acid, 21 new rupestonic acid fatty ester derivatives (2a-2h) and aromatic ester derivatives (2i-2u) were synthesized and preliminarily evaluated for their anti-influenza activity in vitro by the national center for drug screening of China, using the Oseltamivir and Ribavirin as reference drugs. The results showed that 2l ($IC_{50}=0.5{\mu}mol/L$) exhibited potent anti-influenza $A_3$ viral activity among the synthesized compounds and was 10-fold more potent than that of the reference drug Oseltamivir ($IC_{50}=5.1{\mu}mol/L$).

Chemical Investigation of the Sea Cucumber Stichopus japonicus

  • Shinde, Pramod B.;Dang, Hung The;Li, Huayue;Hong, Jong-Ki;Shin, Sook;Jung, Jee-H.
    • Natural Product Sciences
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    • v.14 no.1
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    • pp.12-15
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    • 2008
  • A chemical investigation of the polar extract of the sea cucumber Stichopus japonicus, collected from Jeju Island, Korea, has led to isolation of five new fatty acid derivatives (1, 4 - 7) along with known compounds (2 - 3, 8 - 14). Their structures were elucidated by a combination of MS and NMR spectroscopy.

The Photo-reproducibility and Stability of Long Chain Fatty Acid Containing Azobenzene (아조벤젠을 함유한 장쇄 지방산의 광재현성과 안정성에 관한 연구)

  • Par, Keun-Ho;Park, Tae-Gone
    • Journal of the Korean Applied Science and Technology
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    • v.12 no.1
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    • pp.109-114
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    • 1995
  • The Synthesis of long chain fatty acid containing azobenzene and $(C_{n}-Azo)$ was optimized, starting from p-(p'-hydroxy phenyl azo)-benzoic acid and the product of reaction containing azobenzene chromophores was investigated by ultraviolet spectrophotometery in chloroform solvent at the various temperature. In addition, Reversibility and stability of azo compounds have been measured by means of Ultraviolet and the structure of these compound were ascertained by means of FT-IR and NMR. Recrystallization of reaction product in the solvent results the experimental yield obtained about 62.93% p-(p'-octadecyloxy phenyl azo)-benzoic acid. Long chain azobenzene derivatives in chloroform solution are induced photoisomerization by u. v. and visible light irradiation. The solution of long chain fatty acids$(C_{n}-Azo)$ containing azobenzene are possible of being applied to functional molecular devices such as photomemory and light switching.

DERIVATIZATION OF FATTY ACIDS WITH 2-BROMOACETYLTRIPHENYLENE FOR HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY

  • Ryu, Jae-Ha;Park, Man-Ki
    • Analytical Science and Technology
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    • v.6 no.4
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    • pp.411-415
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    • 1993
  • A method for UV labeling of fatty acids with 2-bromoacetyltriphenylene using 18-crown-6-ether as a catalyst is described. The procedure is rapid, simple, quantitative and applicable to the HPLC analysis of fatty acids with UV detector. They have high molar absorptivity and their detection limit was about 1ng level. Nine derivatives of saturated fatty acid($C_{12}-C_{22}$) were separated on reverse-phase column(${\mu}$-Bondapak C-18) using acetonitrile-water gradient.

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