Multi-Functional Products from Palm oil
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Dr. Hanaa M. Soliman proposes using palm oil as a source for palmitic acid to synthesize new heterocyclic compounds with potential biological activities. The document discusses the preparation of various heterocyclic systems like triazoles, thiadiazoles, thiadiazines appended to a palmitic acid residue. These amphiphilic compounds could have applications as pharmaceuticals, food additives, emulsifiers, and more. Testing showed some synthesized compounds had inhibition of bacterial growth. The document concludes by thanking professors who provided support and acknowledges natural compounds could also be modified with palmitic acid to create multi-functional products composed entirely of natural sources.
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Multi-Functional Products from Palm oil
- 1. Dr.Hanaa M. Soliman National Research Centre Multi-Functional Products from Palm oil
- 2. Chemist_hanaa@hotmail.com 1. Introduction 2. Preparation of hetero cyclic compounds 5. Acknowledgment 3. Preparation of amphiphilic radical capture 4. Conclusion
- 4. Chemist_hanaa@hotmail.com Hot Tip Fatty acids have been reported for their various biological applications such as antimicrobial, antifungal, Pesticidal activities. Palmitic acid found to comprise 21–30% (molar) of human adipose tissue,(fat is loose). Heterocyclic compounds are well known by their pharmaceutical importance. Derivatives of triazoles, thiadiazoles and thiadiazines have played an important role in the medicinal chemistry. Where they possess broad-spectrum antimicrobial activity. Also they have been studied for a number of pathological conditions such as inflammation, pain, and hypertension. Thus they can be used as antibacterial, antimycobacterial , antifungal, antioxidant, and antidepressant agents.
- 5. Chemist_hanaa@hotmail.com Palm oil can be used as a non expensive source for pure palmitic acid hexadecanoic acid (it can easily extracted by a new simple technique), which appended to triazole, thiadiazole and thiadiazine nucleus, in order to combine the beneficial effects of both of hetero cyclic nucleus and fatty acid in a new single structure of a certain biological activity on human health. .
- 6. Moreover these compounds are expected to have several advantages over the parent heterocyclic one, where they can easily penetrate the lipoprotein cell membrane, they may be stored in liver and skin as a lipid component that can be used whenever they needed, also the toxicity and side effects of this new compounds may be reduced by the presence of the long chain fatty acid residue which circulate the hetero nucleus Chemist_hanaa@hotmail.com
- 8. Chemist_hanaa@hotmail.com Palmetic acid is a suitable starting material for the synthesis of a variety of heterocyclic systems pendent to a long chain fatty acid residue of biological potency. Synthesis of phenyl isothiocyanate CH3(CH2)14COOH N H H N H N O S 4A 4B R N H H N N O SH RR = CH3(CH2)14
- 9. Chemist_hanaa@hotmail.com Synthesis of triazole thiadiazole derivatives 4 H2SO4KOH 65A5B N H H N H N O S NN S N H Ph NN N SH Ph NHN N S Ph R R R R R = CH3(CH2)14
- 10. Chemist_hanaa@hotmail.com MeI/EtOH 5 7 8 R NN N SH Ph R NN N SMe Ph R NN N NHNH2 Ph NH2NH2 R = CH3(CH2)14 Triazoles are usually used as antifungal, antiasthma and allergic drugs
- 11. Chemist_hanaa@hotmail.com Thaiadiazoles can be used in antibiotic preparations, antimicrobial,antiinflammatory, anticancer, anti convulsant, antidepressant, antioxidant, and radio protective. EtO N N H Ar O Cl 13 9 a b C6H5-Clp C6H5-CH3p 13 Ar N N S N H N O Ar 4 N H H N H N O S R R COOEt 15 a b C6H6 C6H5-Cl-p Ar15 C6H5-CH3-pd Ph-HN N N H Ar O Cl 10 NN SN H N O Ar R CONHPh 16 R' N N H Ar O Cl11 NN S N H N O Ar R COR' a b C6H6 C6H5-Br-m Ar16 C6H5-CH3-pc R' CH3 CH3 CH3 PhPhd R = CH3(CH2)14
- 12. Chemist_hanaa@hotmail.com Thiadiazines arteriosclerosis treatment, antiprotozoal, antibacterial, and antifungal 4 N H H N H N O S R R = CH3(CH2)14 N H N S R' H N Ph O R R' Br O 22 21 a b OCH2CH3 CH3 22 R' Ar Br O 17 N H N S Ar H N Ph O 20 a b C6H5-Cl-p C6H5-CH3-p Ar c C6H6 20 R Cl CN N H N S H N Ph NC 26 23R
- 13. Chemist_hanaa@hotmail.com oxadiazolethione, thiadiazolthione KOH / EtOH N H NH S O SK O N NH S 28 HCl / EtOHH2SO4 / ice S N NH S 29 NH NH2 O 2 CS2 27 R R RR R = CH3(CH2)14
- 14. Chemist_hanaa@hotmail.com Cl OEt O N H NH Cl O O O N NH O O N N OH N H NH2 O 2 30 31A 31B R RR R R = CH3(CH2)14 Oxadiazole can be used as muscle relaxants, antibacterial anti- inflammatory and antifungal
- 15. Chemist_hanaa@hotmail.com O N NH X 28 or 31 H2N Y N N NH Y N N N XHY R R R 32A, 33A 32B, 33B a b O S X33 X a b C6H5-CH3-p Ar c C6H6 C6H6 C6H5-CH3-pd S S O O X32 Y= NH2, Ar R = CH3(CH2)14
- 17. Chemist_hanaa@hotmail.com O N NH O 31 N N N O O 38 NH2 OH O R R NH2 OH O N O NN O 39 R NH2 NH2 NHN NN 40 R R = CH3(CH2)14
- 18. Chemist_hanaa@hotmail.com NH O 2 N H N N NH2 NH2 NH2 S 41 NH2 Hg(OAc)2 R R N N N N CN C17H35 CN O N(CH3)2 C17H35 42 R N H N N N O CH349 CH3 OEt O O 47 R 51 Ar Br O 50 a b C6H6 C6H5-Cl-p Ar51 C6H5-CH3-pd N N N R N Ar 48 N H N N N O 54 NC OEt O NH2 R52 R = CH3(CH2)14
- 19. Chemist_hanaa@hotmail.com N N NH NH2 N N NH N2NO2 41 55 HNO3 NaNO2 CN CN R R N N N N N CN NH2R 57 N N N N N NH261 N NH2 CN R CN CN H2N NC 58 62 N N N N N NH2 N N N NH2 NH2 R H2N NH2 O N N N N N N N NH2 NH2 R H2N NH2 O N N N N N NH2 NH2 N OH N N N N N N NH2 HN 65 NH2OH 64 R R 63 R = CH3(CH2)14
- 20. Chemist_hanaa@hotmail.com N N NH NH2 N N NH N2NO2 41 55 HNO3 NaNO2 R R H3C R' OO N N N N N R' CH3 O 68 a b OCH2CH3 CH3 68 R R 55 R N N N N O R' R'73 a b CH3 R' H 73 OO R' R' Ar CN O N N N N N CN Ar 76 74 a b C6H5-CH3-p Ar C6H6 76 R R = CH3(CH2)14
- 21. Diazoles are used for preventing the nephrotoxicity induced by cisplatin Chemist_hanaa@hotmail.com N N CH3 O HO N N CH3 O O N H NH2 O 2 79A 79B R O EtO O RR N N CH3 O H3CO O R 81 R = CH3(CH2)14
- 22. COMPOUNDS NO. Inhibition Zone Diameter (IZD) (mm/mg CompoundTested) Gram + ve Gram - ve Staphelococcus Epiderm Enterococus fesalis Enterobacter. cloacae Flavobacterium CONTROL 0.0 0.0 0.0 0.0 4 + ve ++ ve -------- +++ ve 5 +++ ve + ve + ve -------- 7 ++ ve +++ ve +++ ve +++ ve 15a ++ ve + ve + ve + ve 20a +++ ve +++ ve +++ ve + ve 26 ++ ve ++ ve +++ ve +++ ve 35 ++ ve -------- ++ ve -------- 36 -------- +++ ve ++ ve ++ ve 39 ++ ve + ve ++ ve +++ ve 46 ++ ve ++ ve ++ ve +++ ve 57 + ve +++ ve ++ ve + ve 61 +++ ve + ve -------- ++ ve 62 ++ ve +++ ve +++ ve ++ ve 65 -------- + ve + ve + ve 76 +++ ve +++ ve +++ ve +++ ve 81 ++ ve ++ ve ++ ve ++ ve Referances Vacomycin – rifampin Penicillin G Gentamycin – cephpalosporin – cefotaxime Imipenem Normal flora Natpathegen
- 24. Palmitic acid can also be appended to certain naturally occurring compounds, to produce a new compound of malti functions and composed of 100% natural products. Chemist_hanaa@hotmail.com
- 25. Chemist_hanaa@hotmail.com OH OH OH OH OH OH OH OH OH OHOH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH
- 26. OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH Chemist_hanaa@hotmail.com
- 27. Chemist_hanaa@hotmail.com 0 5 10 15 20 25 control TBHQ P-N inductiontime(h) oxidation stabilityoxidation stability
- 28. Total antioxidant activity (%) Chemist_hanaa@hotmail.com 80 85 90 95 100 105 110 0 10 20 30 40 50 60 Totalantioxidantactivity(%) time (h) N P-N BHT BHA
- 29. 0 10 20 30 40 50 60 70 80 90 100 0 5 10 15 20 25 30 35 40 45 DPPHscavengingactivity(%) Concentration (μg/mL) BHA N P-N BHT Chemist_hanaa@hotmail.com DPPH scavenging activity (%)
- 30. ABTS+ scavenging activity (%) 0 20 40 60 80 100 120 0 5 10 15 20 25 30 35 40 45 ABTS˙+scavengingactivity(%) Concentration (μg/mL) BHA P-N N BHT Chemist_hanaa@hotmail.com
- 31. Superoxide anion radical scavenging activity (%) Chemist_hanaa@hotmail.com 0 10 20 30 40 50 60 70 80 90 100 N-P N BHT BHA Superoxideanionradical(O˙̄2) scavengingactivity(%)
- 32. Hydrogen peroxide scavenging activity(%) Chemist_hanaa@hotmail.com 0 10 20 30 40 50 60 N P-N BHA BHT Hydrogenperoxidescavenging activity(%)
- 33. Ferrous ions (Fe2+) chelating activity (%) Chemist_hanaa@hotmail.com 0 10 20 30 40 50 60 70 80 N P_N BHT BHA Ferrousions(Fe2+)chelating activity(%)
- 35. This amphiphilic compound composed of 100% natural products, Thus it can be used as: Dietary supplements and diseases preventing Food additives in order to prevent oxidative degradation of foods. Hindrance of metal corrosion, vulcanization of rubber, and polymerization of fuels in the fouling of internal combustion engines Emulsifiers. Surfactants. Removal for heavy metals during water treatment. Chemist_hanaa@hotmail.com
- 37. Chemist_hanaa@hotmail.com I would like to express my respectful thanks and sincere gratitude to Prof. Dr. Shaker Arafaat , Prof. Dr. Amany Basuny, Prof. Dr. Ahmed Elsharkay and Prof. Dr. Magdy Al-egami Professors at Food Technology Research Institute, Agricultural Research Center, for their continuous and valuable help, fruitful criticism and encouragement during the execution of this work . The author wishes to express her most sincere gratitude and respectful thanks to Prof. Dr. Ferial Zaher, Prof. Dr. Yosef El-shatory, Prof. Dr. Mahmoud El-mallah, Prof. Dr. Hend El-noamany, Prof. Dr.Saadeya Mostafa and Prof. Dr. Omayma El kinawe Professors at National research centre, for their useful help, incessant effort, useful suggestion and valuable support.