lipids - unirio

http://www.unirio.br/analisedealimentos

Profa. dra. Édira Castello Branco de Andrade Gonçalves

Lipids


Lipids

http://caravel.sc.edu/2014/10/learning-organic-chemistry-reactions-as-a-nursing-student/


Lipids Fatty Acids

Satured Unsatured

Monounsatured Polyunsatured

Lauric acid Myristic acid Palmitic acid Stearic acid

Oleic acid (Omega-9)

Omega-6 Omega-3

Linoleic acid CLA GLA

Arachidonic acid

Linolenic acid EPA DHA


Lipids

http://ib.bioninja.com.au/standard-level/topic-2-molecular-biology/23-carbohydrates-and-lipids/types-of-fatty-acids.html

Fatty Acids


Lipids Fatty Acids


Lipids Esterification


Lipids

Pathways for triacylglyceride synthesis. Triacylglycerides (triglycerides) are synthesized by virtually all cells. The

major tissues for TAG synthesis are the small intestine, the liver, and adipocytes. Except for the intestine and adipocytes, TAG synthesis begins with glycerol.


Lipids

1. Fatty acyls

2. Glycerolipids (triglycerides)

3. Glycerophospholipids

4. Sphingolipids

5. Sterol lipids

6. Prenol lipids

7. Saccharolipids

8. Polyketides


Lipids

http://chemistry.tutorvista.com/biochemistry/types-of-lipids.html


Lipids

http://gk.queryhome.com/?qa=blob&qa_blobid=9149415162322332478 http://www.chemguide.co.uk/organicprops/alkenes/makemarg.gif

Reactions


Lipids Enzymatic Interesterification

http://www.wikiwand.com/en/Enzymatic_interesterification

Reactions


Lipids Reactions


Lipids

Reactions


Lipids

http://27.109.7.67:1111/econtent/lipids-I/phospholipids.php

Emulsification


Lipids

Lipid Digestion

Emulsification


Lipids

Vegan mayonnaise – Canola oil; water; ciclodextrina (αCD )

http://www.cyclochem.com/cyclochembio/research_e/049.html

Emulsification


Lipids

Reactions


Lipids

Structural schematic of the thermotropic and lyotropic mesophases formed by n-octyl β-D-glucopyranoside


Lipids

Reactions

Desirable or undesirable

? ?


Lipids

Saturated fatty acid – degradation - T > 200o C oxidation - T > 150o C

Unsaturated fatty acid – degradation - T > 180o C oxidation – T


Lipids

https://www.researchgate.net/figure/280389114_fig4_Fig-5-Integrated-scheme-for-lipid-oxidation-107

Integrated scheme for lipid oxidation


Lipids

Chemical and physical changes of oil due to heating

https://www.researchgate.net/figure/280389114_fig5_Fig-7-Chemical-and-physical-

changes-of-oil-due-to-heating-adapted-from-115


Lipids


Lipids Effect of heating/reheating of fats/oils, as used by Asian Indians, on trans fatty acid formation

Formation of trans fatty acids (TFA) occurs during frying/heating of fats/oil.•TFAs were estimated in 6 fats/oilsbefore/after heating/frying at 180°C and 220°C.•Heating/frying led to formation and increase in TFA in all fat/oil samples.•Heating/frying also increased the saturated fatty acids and

decreased cis-unsaturated fatty acids.•Guidelines for heating/re-frying of fats/oils by Asian Indians should be devised. Heating/frying and reuse of edible fats/oils induces

chemical changes such as formation of trans fatty acids (TFAs). The aim of this study was to investigate the effect of heating/frying on formation of TFAs in fats/oils. Using gas

chromatography with flame ionisation detector, TFA was estimated in six commonly used fat/oils in India (refined soybean oil, groundnut oil, olive oil, rapeseed oil, clarified

butter, partially hydrogenated vegetable oil), before and after subjecting them to heating/frying at 180°C and 220°C. All six fats/oils subjected to heating/frying demonstrated an increase in TFAs

(p<0.001), saturated fatty acids (p<0.001) and decrease in cis-unsaturated fatty acids (p<0.001). The absolute increase in TFA content of edible oils (after subjecting to heating/reheating) ranged

between 2.30±0.89g/100g and 4.5±1.43g/100g; amongst edible fats it ranged between 2.60±0.38g/100g and 5.96±1.94g/100g. There were no significant differences between the two

treatment groups (heating and frying; p=0.892). Considering the undesirable health effects of TFA, appropriate guidelines for heating/re-frying of edible fats/oils by Asian Indians should be devised.

Bhardwaj et al. 2016


Lipids

Mariutti & Bragagnolo 2017

Sodium chloride

preservation and

antimicrobial properties

enhancing flavor

water retention capacity

lipid oxidation

Influence of salt on lipid oxidation in meat and seafood products


Lipids

Autoxidation of linoleic acid

Photo-oxidation of oleic acid

Cholesterol oxidation



Lipids

Main cholesterol oxides formed by enzymatic and/or

non-enzymatic reactions. ROS: reactive oxygen

species, ENZ: enzyme.

Main mechanisms of lipid oxidation

acceleration by salt in meat and seafood



Lipids Acrylamide formation in vegetable oils and animal fats during heat treatment

The method of liquid chromatographic tandem mass spectrometry was utilized and modified to confirm and

quantify acrylamide in heating cooking oil and animal fat. Heating asparagine with various cooking oils and animal fat at 180 oC produced varying amounts of acrylamide.

The acrylamide in the different cooking oils and animal fat using a constant amount of asparagine was measured.

Cooking oils were also examined for peroxide, anisidine and iodine values (or oxidation values). A direct correlation

was observed between oxidation values and acrylamide formation in different cooking oils. Significantly less

acrylamide was produced in saturated animal fat than in unsaturated cooking oil, with 366 ng/g in lard and 211 ng/g in ghee versus 2447 ng/g in soy oil, followed by palm olein

with 1442 ng/g

Correlation of acrylamide formation and oxidation values.

Daniali et al. 2016


Lipids Bai, Long, and David McClements. 2016. “Extending Emulsion Functionality: Post-Homogenization Modification of Droplet Properties.” Processes 4 (2). Multidisciplinary Digital Publishing Institute: 17. doi:10.3390/pr4020017. Bhardwaj, Swati, Santosh Jain Passi, Anoop Misra, Kamal K Pant, Khalid Anwar, R M Pandey, and Vikas Kardam. 2016. “Effect of Heating/reheating of Fats/oils, as Used by Asian Indians, on Trans Fatty Acid Formation.” Food Chemistry 212 (December): 663–70. doi:https://doi.org/10.1016/j.foodchem.2016.06.021. Courraud, J, C Charnay, J P Cristol, J Berger, and S Avallone. 2013. “In Vitro Lipid Peroxidation of Intestinal Bile Salt-Based Nanoemulsions: Potential Role of Antioxidants.” Free Radical Research 47 (12). IRD; UMR 204 NUTRIPASS, IRD/Montpellier2/Montpellier1 , Montpellier , France.: Informa Healthcare: 1076–87. doi:10.3109/10715762.2013.853877. Damodaran, Srinivasan, Kirk L Parkin, and Owen R Fennema. 2010. Quimica de Alimentos de Fennema. Edited by Artmed. Quimica de Alimentos de Fennema. 4thed. Porto Alegre. Daniali, G, S Jinap, P Hajeb, M Sanny, and C P Tan. 2016. “Acrylamide Formation in Vegetable Oils and Animal Fats during Heat Treatment.” Food Chemistry 212: 244–49. doi:http://dx.doi.org/10.1016/j.foodchem.2016.05.174. Édira Castelo Branco de Andrade. 2015. Análise de Alimentos - Uma Visão Química Da Nutrição. Edited by Varela. São Paulo. Estévez, M., and C. Luna. 2016. “Dietary Protein Oxidation: A Silent Threat to Human Health?” Critical Reviews in Food Science and Nutrition 57 (17): 00–00. doi:10.1080/10408398.2016.1165182. Ghorbani Gorji, Sara, Heather E Smyth, Mary Sharma, and Melissa Fitzgerald. 2016. “Lipid Oxidation in Mayonnaise and the Role of Natural Antioxidants: A Review.” Trends in Food Science and Technology. doi:10.1016/j.tifs.2016.08.002. Hartel, Richard W. 2013. “Advances in Food Crystallization.” Annual Review of Food Science and Technology 4 (1). Annual Reviews: 277–92. doi:10.1146/annurev-food-030212-182530. Hes, Marzanna. 2017. “Protein-Lipid Interactions in Different Meat Systems in the Presence of Natural Antioxidants - A Review.” Polish Journal of Food and Nutrition Sciences. doi:10.1515/pjfns-2016-0024.

References


Lipids Lee, Dong Ryeol, Ji Su Park, Il Hak Bae, Yan Lee, and B Moon Kim. 2016. “Liquid Crystal Nanoparticle Formulation as an Oral Drug Delivery System for Liver-Specific Distribution.” International Journal of Nanomedicine 11 (March). Dove Medical Press: 853–71. doi:10.2147/IJN.S97000. Maria Aliciane Fontenele Domingues, Ana Paula Badan Ribeiro, Theo Guenter Kieckbusch, Luiz Antonio Gioielli, Renato Grimaldi, Lisandro Pavie Cardoso and Lireny Aparecida Guaraldo Gonçalves (2015). Advances in Lipids Crystallization Technology, Advanced Topics in Crystallization, Prof. Yitzhak Mastai (Ed.), InTech, DOI: 10.5772/59767. Available from: https://www.intechopen.com/books/advanced-topics-in-crystallization/advances-in-lipids-crystallization-technology Mariutti, Lilian R.B., and Neura Bragagnolo. 2017. “Influence of Salt on Lipid Oxidation in Meat and Seafood Products: A Review.” Food Research International. doi:10.1016/j.foodres.2017.02.003. Sicari, Michela, Roberto Stevanato, Italo Ongaro, Roberto Zuliani, Giampietro Ravagnan, and Vittorio Lucchini. 2018. “Searching for an Absolute Kinetic Scale of Antioxidant Activity against Lipid Peroxidation.” Food Chemistry 239. doi:10.1016/j.foodchem.2017.06.139. Soumanou, Mohamed M, Marlène Pérignon, and Pierre Villeneuve. 2013. “Lipase‐catalyzed Interesterification Reactions for Human Milk Fat Substitutes Production: A Review.” European Journal of Lipid Science and Technology 115 (3). Wiley Online Library: 270–85. doi:10.1002/ejlt.201200084. Yildiz, Fatih. 2010. Advances in Food Biochemistry. CRC Press.

References

https://www.intechopen.com/books/advanced-topics-in-crystallization/advances-in-lipids-crystallization-technology















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