Monounsaturated fat

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In biochemistry and nutrition, monounsaturated fatty acids (abbreviated MUFAs, or more plainly monounsaturated fats) are fatty acids that have one double bond in the fatty acid chain with all of the remainder carbon atoms being single-bonded. By contrast, polyunsaturated fatty acids (PUFAs) have more than one double bond.

Molecular description[edit]

Fatty acids are long-chained molecules having an alkyl group at one end and a carboxylic acid group at the other end. Fatty acid viscosity (thickness) and melting temperature increases with decreasing number of double bonds; therefore, monounsaturated fatty acids have a higher melting point than polyunsaturated fatty acids (more double bonds) and a lower melting point than saturated fatty acids (no double bonds). Monounsaturated fatty acids are liquids at room temperature and semisolid or solid when refrigerated resulting in a isotopic lattice structure.

Common monounsaturated fatty acids are palmitoleic acid (16:1 n−7), cis-vaccenic acid (18:1 n−7) and oleic acid (18:1 n−9). Palmitoleic acid has 16 carbon atoms with the first double bond occurring 7 carbon atoms away from the methyl group (and 9 carbons from the carboxyl end). It can be lengthened to the 18-carbon cis-vaccenic acid. Oleic acid has 18 carbon atoms with the first double bond occurring 9 carbon atoms away from the carboxylic acid group. The illustrations below show a molecule of oleic acid in Lewis formula and as a space-filling model.

Oleic acid's skeletal formula Oleic acid's space-filling structure

List of monounsaturated fats[edit]

Common name Lipid name Chemical name
Myristoleic acid 14:1 (n-5) cis-Tetradec-9-enoic acid
Palmitoleic acid 16:1 (n-7) cis-Hexadec-9-enoic acid
cis-Vaccenic acid 18:1 (n-7) cis-Octadec-11-enoic acid
Vaccenic acid 18:1 (n-7) trans-Octadec-11-enoic acid
Paullinic acid 20:1 (n-7) cis-13-Eicosenoic acid
Oleic acid 18:1 (n-9) cis-Octadec-9-enoic acid
Elaidic acid (trans-oleic acid) 18:1 (n-9) trans-Octadec-9-enoic acid
11-Eicosenoic acid (gondoic acid) 20:1 (n-9) cis-Eicos-11-enoic acid
Erucic acid 22:1 (n-9) cis-Tetracos-15-enoic acid
Brassidic acid 22:1 (n-9) trans-Tetracos-15-enoic acid
Nervonic acid 24:1 (n-9) cis-Tetracos-15-enoic acid
Sapienic acid 16:1 (n-10) cis-6-Hexadecenoic acid
Gadoleic acid 20:1 (n-11) cis-9-Icosenoic acid
Petroselinic acid 18:1 (n-12) cis-Octadec-6-enoic acid

Health[edit]

Monounsaturated fats protect against cardiovascular disease by providing more membrane fluidity than saturated fats, but they are more vulnerable to lipid peroxidation (rancidity). The large scale KANWU study found that increasing monounsaturated fat and decreasing saturated fat intake could improve insulin sensitivity, but only when the overall fat intake of the diet was low.[1] However, some monounsaturated fatty acids (in the same way as saturated fats) may promote insulin resistance, whereas polyunsaturated fatty acids may be protective against insulin resistance.[2][3] Studies have shown that substituting dietary monounsaturated fat for saturated fat is associated with increased daily physical activity and resting energy expenditure. More physical activity was associated with a higher-oleic acid diet than one of a palmitic acid diet. From the study, it is shown that more monounsaturated fats lead to less anger and irritability.[4]

Foods containing monounsaturated fats reduce low-density lipoprotein (LDL) cholesterol,[5] while possibly increasing high-density lipoprotein (HDL) cholesterol.[6]

Levels of oleic acid along with other monounsaturated fatty acids in red blood cell membranes were positively associated with breast cancer risk. The saturation index (SI) of the same membranes was inversely associated with breast cancer risk. Monounsaturated fats and low SI in erythrocyte membranes are predictors of postmenopausal breast cancer. Both of these variables depend on the activity of the enzyme delta-9 desaturase (Δ9-d).[7]

In children, consumption of monounsaturated oils is associated with healthier serum lipid profiles.[8]

The Mediterranean diet is one heavily influenced by monounsaturated fats. People in Mediterranean countries consume more total fat than Northern European countries, but most of the fat is in the form of monounsaturated fatty acids from olive oil and omega-3 fatty acids from fish, vegetables, and certain meats like lamb, while consumption of saturated fat is minimal in comparison. A 2017 review found evidence that the practice of a Mediterranean diet could lead to a decreased risk of cardiovascular diseases, overall cancer incidence, neurodegenerative diseases, diabetes, and early death.[9] A 2018 review showed that the practice of the Mediterranean diet may improve overall health status, such as reduced risk of non-communicable diseases, reduced total costs of living, and reduced costs for national healthcare.[10]

Sources[edit]

Monounsaturated fats are found in animal flesh such as red meat, whole milk products, nuts, and high fat fruits such as olives and avocados. Olive oil is about 75% monounsaturated fat.[11] The high oleic variety sunflower oil contains as much as 85% monounsaturated fat.[citation needed] Canola oil and cashews are both about 58% monounsaturated fat.[citation needed] Tallow (beef fat) is about 50% monounsaturated fat.[12] and lard is about 40% monounsaturated fat.[citation needed] Other sources include avocado oil, macadamia nut oil, grapeseed oil, groundnut oil (peanut oil), sesame oil, corn oil, popcorn, whole grain wheat, cereal, oatmeal, almond oil, sunflower oil, hemp oil, and tea-oil Camellia.[13]

Fat composition in different foods
Fat composition in foods.png
Food Saturated Mono-
unsaturated
Poly-
unsaturated
As weight percent (%) of total fat
Cooking oils
Canola oil 08 64 28
Coconut oil 87 13 00
Corn oil 13 24 59
Cottonseed oil[14] 27 19 54
Olive oil[15] 14 73 11
Palm kernel oil[14] 86 12 02
Palm oil[14] 51 39 10
Peanut oil[16] 17 46 32
Rice bran oil 25 38 37
Safflower oil, high oleic[17] 06 75 14
Safflower oil, linoleic[14][18] 06 14 75
Soybean oil 15 24 58
Sunflower oil[19] 11 20 69
Mustard oil 11 59 21
Dairy products
Butterfat[14] 66 30 04
Cheese, regular 64 29 03
Cheese, light 60 30 00
Ice cream, gourmet 62 29 04
Ice cream, light 62 29 04
Milk, whole 62 28 04
Milk, 2% 62 30 00
*Whipping cream[20] 66 26 05
Meats
Beef 33 38 05
Ground sirloin 38 44 04
Pork chop 35 44 08
Ham 35 49 16
Chicken breast 29 34 21
Chicken 34 23 30
Turkey breast 30 20 30
Turkey drumstick 32 22 30
Fish, orange roughy 23 15 46
Salmon 28 33 28
Hot dog, beef 42 48 05
Hot dog, turkey 28 40 22
Burger, fast food 36 44 06
Cheeseburger, fast food 43 40 07
Breaded chicken sandwich 20 39 32
Grilled chicken sandwich 26 42 20
Sausage, Polish 37 46 11
Sausage, turkey 28 40 22
Pizza, sausage 41 32 20
Pizza, cheese 60 28 05
Nuts
Almonds dry roasted 09 65 21
Cashews dry roasted 20 59 17
Macadamia dry roasted 15 79 02
Peanut dry roasted 14 50 31
Pecans dry roasted 08 62 25
Flaxseeds, ground 08 23 65
Sesame seeds 14 38 44
Soybeans 14 22 57
Sunflower seeds 11 19 66
Walnuts dry roasted 09 23 63
Sweets and baked goods
Candy, chocolate bar 59 33 03
Candy, fruit chews 14 44 38
Cookie, oatmeal raisin 22 47 27
Cookie, chocolate chip 35 42 18
Cake, yellow 60 25 10
Pastry, Danish 50 31 14
Fats added during cooking or at the table
Butter, stick 63 29 03
Butter, whipped 62 29 04
Margarine, stick 18 39 39
Margarine, tub 16 33 49
Margarine, light tub 19 46 33
Lard 39 45 11
Shortening 25 45 26
Chicken fat 30 45 21
Beef fat 41 43 03
Goose fat[21] 33 55 11
Dressing, blue cheese 16 54 25
Dressing, light Italian 14 24 58
Other
Egg yolk fat[22] 36 44 16
Avocado[23] 16 71 13
Unless else specified in boxes, then reference is:[24]
* 3% is trans fats

See also[edit]

References[edit]

  1. ^ Vessby B, Uusitupa M, Hermansen K, Riccardi G, Rivellese AA, Tapsell LC, Nälsén C, Berglund L, Louheranta A, Rasmussen BM, Calvert GD, Maffetone A, Pedersen E, Gustafsson IB, Storlien LH (March 2001). "Substituting dietary saturated for monounsaturated fat impairs insulin sensitivity in healthy men and women: The KANWU Study". Diabetologia. 44 (3): 312–9. doi:10.1007/s001250051620. PMID 11317662.
  2. ^ Lovejoy JC (October 2002). "The influence of dietary fat on insulin resistance". Current Diabetes Reports. 2 (5): 435–40. doi:10.1007/s11892-002-0098-y. PMID 12643169.
  3. ^ Fukuchi S, Hamaguchi K, Seike M, Himeno K, Sakata T, Yoshimatsu H (June 2004). "Role of fatty acid composition in the development of metabolic disorders in sucrose-induced obese rats". Experimental Biology and Medicine. 229 (6): 486–93. doi:10.1177/153537020422900606. PMID 15169967.
  4. ^ Kien CL, Bunn JY, Tompkins CL, Dumas JA, Crain KI, Ebenstein DB, Koves TR, Muoio DM (April 2013). "Substituting dietary monounsaturated fat for saturated fat is associated with increased daily physical activity and resting energy expenditure and with changes in mood". The American Journal of Clinical Nutrition. 97 (4): 689–97. doi:10.3945/ajcn.112.051730. PMC 3607650. PMID 23446891.
  5. ^ "You Can Control Your Cholesterol: A Guide to Low-Cholesterol Living". MerckSource. Archived from the original on 2009-03-03. Retrieved 2018-01-02.
  6. ^ "Monounsaturated Fat". American Heart Association. Archived from the original on 2018-03-07. Retrieved 2018-04-19.
  7. ^ Pala V, Krogh V, Muti P, Chajès V, Riboli E, Micheli A, Saadatian M, Sieri S, Berrino F (July 2001). "Erythrocyte membrane fatty acids and subsequent breast cancer: a prospective Italian study". Journal of the National Cancer Institute. 93 (14): 1088–95. doi:10.1093/jnci/93.14.1088. PMID 11459870.
  8. ^ Sanchez-Bayle M, Gonzalez-Requejo A, Pelaez MJ, Morales MT, Asensio-Anton J, Anton-Pacheco E (February 2008). "A cross-sectional study of dietary habits and lipid profiles. The Rivas-Vaciamadrid study". European Journal of Pediatrics. 167 (2): 149–54. doi:10.1007/s00431-007-0439-6. PMID 17333272.
  9. ^ Dinu, M; Pagliai, G; Casini, A; Sofi, F (10 May 2017). "Mediterranean diet and multiple health outcomes: an umbrella review of meta-analyses of observational studies and randomised trials". European Journal of Clinical Nutrition. 72: 30–43. doi:10.1038/ejcn.2017.58. PMID 28488692.
  10. ^ Martinez-Lacoba, R; Pardo-Garcia, I; Amo-Saus, E; Escribano-Sotos, F (2018). "Mediterranean diet and health outcomes: a systematic meta-review". European Journal of Public Health. Advance articles. doi:10.1093/eurpub/cky113. PMID 29992229.
  11. ^ Abdullah MM, Jew S, Jones PJ (February 2017). "Health benefits and evaluation of healthcare cost savings if oils rich in monounsaturated fatty acids were substituted for conventional dietary oils in the United States". Nutrition Reviews. doi:10.1093/nutrit/nuw062. PMC 5914363. PMID 28158733.
  12. ^ Board on Agriculture and Renewable Resources Commission on Natural Resources and Food and Nutrition Board, Assembly of Life Sciences, National Research Council (1976). Fat content and composition of animal products: proceedings of a symposium, Washington, D.C., December 12-13, 1974. Washington: National Academy of Sciences. ISBN 978-0-309-02440-2. PMID 25032409.
  13. ^ Aizpurua-Olaizola O, Ormazabal M, Vallejo A, Olivares M, Navarro P, Etxebarria N, Usobiaga A (January 2015). "Optimization of supercritical fluid consecutive extractions of fatty acids and polyphenols from Vitis vinifera grape wastes". Journal of Food Science. 80 (1): E101–7. doi:10.1111/1750-3841.12715. PMID 25471637.
  14. ^ a b c d e Anderson. "Fatty acid composition of fats and oils" (PDF). UCCS. Retrieved April 8, 2017.
  15. ^ "NDL/FNIC Food Composition Database Home Page". Nal.usda.gov. Retrieved May 21, 2013.
  16. ^ USDA → Basic Report: 04042, Oil, peanut, salad or cooking Retrieved on January 16, 2015
  17. ^ nutritiondata.com → Oil, vegetable safflower, oleic Retrieved on April 10, 2017
  18. ^ nutritiondata.com → Oil, vegetable safflower, linoleic Retrieved on April 10, 2017
  19. ^ nutritiondata.com → Oil, vegetable, sunflower Retrieved on September 27, 2010
  20. ^ USDA Basic Report Cream, fluid, heavy whipping
  21. ^ "Nutrition And Health". The Goose Fat Information Service.
  22. ^ nutritiondata.com → Egg, yolk, raw, fresh Retrieved on August 24, 2009
  23. ^ "09038, Avocados, raw, California". National Nutrient Database for Standard Reference, Release 26. United States Department of Agriculture, Agricultural Research Service. Retrieved 14 August 2014.
  24. ^ "Feinberg School > Nutrition > Nutrition Fact Sheet: Lipids". Northwestern University. Archived from the original on 2011-07-20.

External links[edit]