Monounsaturated Fat: History
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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.

  • monounsaturated fatty
  • fatty acids
  • double bond

1. Molecular Description

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 an 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.

1.1. List of Monounsaturated Fats

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

2. Health

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. It also may reduce the social and economic costs of diet-related illnesses.[10]

3. Sources

Monounsaturated fats are found in animal flesh such as red meat, whole milk products, nuts, and high fat fruits such as olives and avocados. Algal oil is about 92% monounsaturated fat.[11] Olive oil is about 75% monounsaturated fat.[12] The high oleic variety sunflower oil contains at least 70% monounsaturated fat.[13] Canola oil and cashews are both about 58% monounsaturated fat. Tallow (beef fat) is about 50% monounsaturated fat.[14] and lard is about 40% monounsaturated fat. Other sources include hazelnut, 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.[15]

Fat composition in different foods
Food Saturated Mono-
unsaturated		 Poly-
unsaturated
As weight percent (%) of total fat
Cooking oils
Algal oil[16] 04 92 04
Canola[17] 08 64 28
Coconut oil 87 13 00
Corn oil 13 24 59
Cottonseed oil[17] 27 19 54
Olive oil[18] 14 73 11
Palm kernel oil[17] 86 12 02
Palm oil[17] 51 39 10
Peanut oil[19] 17 46 32
Rice bran oil 25 38 37
Safflower oil, high oleic[20] 06 75 14
Safflower oil, linoleic[17][21] 06 14 75
Soybean oil 15 24 58
Sunflower oil[22] 11 20 69
Mustard oil 11 59 21
Dairy products
Butterfat[17] 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[23] 66 26 05
Meats
Beef 33 38 05
Ground sirloin 38 44 04
Pork chop 35 44 08
Ham 35 49 16
Chicken breast 99 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[24] 33 55 11
Dressing, blue cheese 16 54 25
Dressing, light Italian 14 24 58
Other
Egg yolk fat[25] 36 44 16
Avocado[26] 16 71 13
Unless else specified in boxes, then reference is:[27]
* 3% is trans fats

The content is sourced from: https://handwiki.org/wiki/Chemistry:Monounsaturated_fat

References

  1. "Substituting dietary saturated for monounsaturated fat impairs insulin sensitivity in healthy men and women: The KANWU Study". Diabetologia 44 (3): 312–9. March 2001. doi:10.1007/s001250051620. PMID 11317662.  https://dx.doi.org/10.1007%2Fs001250051620
  2. "The influence of dietary fat on insulin resistance". Current Diabetes Reports 2 (5): 435–40. October 2002. doi:10.1007/s11892-002-0098-y. PMID 12643169.  https://dx.doi.org/10.1007%2Fs11892-002-0098-y
  3. "Role of fatty acid composition in the development of metabolic disorders in sucrose-induced obese rats". Experimental Biology and Medicine 229 (6): 486–93. June 2004. doi:10.1177/153537020422900606. PMID 15169967.  https://dx.doi.org/10.1177%2F153537020422900606
  4. "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. April 2013. doi:10.3945/ajcn.112.051730. PMID 23446891.  http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3607650
  5. "You Can Control Your Cholesterol: A Guide to Low-Cholesterol Living". MerckSource. http://www.mercksource.com/pp/us/cns/cns_krames_template.jspzQzpgzEzzSzppdocszSzuszSzcnszSzcontentzSzkrameszSz1292_01zPzhtm. 
  6. "Monounsaturated Fat". American Heart Association. https://healthyforgood.heart.org/Eat-smart/Articles/Monounsaturated-Fats. 
  7. "Erythrocyte membrane fatty acids and subsequent breast cancer: a prospective Italian study". Journal of the National Cancer Institute 93 (14): 1088–95. July 2001. doi:10.1093/jnci/93.14.1088. PMID 11459870.  https://dx.doi.org/10.1093%2Fjnci%2F93.14.1088
  8. "A cross-sectional study of dietary habits and lipid profiles. The Rivas-Vaciamadrid study". European Journal of Pediatrics 167 (2): 149–54. February 2008. doi:10.1007/s00431-007-0439-6. PMID 17333272.  https://dx.doi.org/10.1007%2Fs00431-007-0439-6
  9. "Mediterranean diet and multiple health outcomes: an umbrella review of meta-analyses of observational studies and randomised trials". European Journal of Clinical Nutrition 72 (1): 30–43. January 2018. doi:10.1038/ejcn.2017.58. PMID 28488692.  https://dx.doi.org/10.1038%2Fejcn.2017.58
  10. "Mediterranean diet and health outcomes: a systematic meta-review". European Journal of Public Health 28 (5): 955–961. October 2018. doi:10.1093/eurpub/cky113. PMID 29992229.  https://dx.doi.org/10.1093%2Feurpub%2Fcky113
  11. "Error: no |title= specified when using {{Cite web}}". https://www.thrivealgae.com/our-product/.
  12. "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 75 (3): 163–174. February 2017. doi:10.1093/nutrit/nuw062. PMID 28158733.  http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=5914363
  13. "A systematic review of high-oleic vegetable oil substitutions for other fats and oils on cardiovascular disease risk factors: implications for novel high-oleic soybean oils". Advances in Nutrition 6 (6): 674–93. November 2015. doi:10.3945/an.115.008979. PMID 26567193.  http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=4642420
  14. 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. https://www.ncbi.nlm.nih.gov/books/NBK216535/. 
  15. "Optimization of supercritical fluid consecutive extractions of fatty acids and polyphenols from Vitis vinifera grape wastes". Journal of Food Science 80 (1): E101-7. January 2015. doi:10.1111/1750-3841.12715. PMID 25471637.  https://dx.doi.org/10.1111%2F1750-3841.12715
  16. "Thrive Culinary Algae Oil". https://www.thrivealgae.com/our-product/. 
  17. "Fatty acid composition of fats and oils". Colorado Springs: University of Colorado, Department of Chemistry. http://www.uccs.edu/Documents/danderso/fats_oils.pdf. Retrieved April 8, 2017. 
  18. "NDL/FNIC Food Composition Database Home Page". United States Department of Agriculture, Agricultural Research Service. http://www.nal.usda.gov/fnic/foodcomp/search/. Retrieved May 21, 2013. 
  19. "Basic Report: 04042, Oil, peanut, salad or cooking". USDA. http://ndb.nal.usda.gov/ndb/foods/show/634?fg=Fats+and+Oils&man=&lfacet=&format=&count=&max=25&offset=&sort=&qlookup=. 
  20. "Oil, vegetable safflower, oleic". nutritiondata.com. Condé Nast. http://nutritiondata.self.com/facts/fats-and-oils/574/2. 
  21. "Oil, vegetable safflower, linoleic". nutritiondata.com. Condé Nast. http://nutritiondata.self.com/facts/fats-and-oils/573/2. 
  22. "Oil, vegetable, sunflower". nutritiondata.com. Condé Nast. http://nutritiondata.com/facts/fats-and-oils/572/2. 
  23. USDA Basic Report Cream, fluid, heavy whipping https://ndb.nal.usda.gov/ndb/foods/show/52?fgcd=&manu=&lfacet=&format=&count=&max=50&offset=&sort=default&order=asc&qlookup=cream+whipping&ds=
  24. "Nutrition And Health". The Goose Fat Information Service. http://www.goosefat.co.uk/page/nutrition-and-health. 
  25. "Egg, yolk, raw, fresh". nutritiondata.com. Condé Nast. http://www.nutritiondata.com/facts/dairy-and-egg-products/113/2. 
  26. "09038, Avocados, raw, California". National Nutrient Database for Standard Reference, Release 26. United States Department of Agriculture, Agricultural Research Service. http://ndb.nal.usda.gov/ndb/foods/show/2235. Retrieved 14 August 2014. 
  27. Nutrition > Nutrition Fact Sheet: Lipids". Northwestern University. Archived from the original on 2011-07-20. https://web.archive.org/web/20110720014201/nuinfo-proto4.northwestern.edu/nutrition/factsheets/lipids.html. " id="ref_27">"Feinberg School > Nutrition > Nutrition Fact Sheet: Lipids". Northwestern University. Archived from the original on 2011-07-20. https://web.archive.org/web/20110720014201/nuinfo-proto4.northwestern.edu/nutrition/factsheets/lipids.html. 
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