Talk:Fatty acid

Circular links

'Medium-chain fatty acid' and 'Long-chain fatty acid' both currently redirect to 'Fatty acid', so there are two circular links in the section on 'Length of free fatty acid chains'. I'm going to remove these two links.

Bmordue (talk) 12:29, 15 June 2013 (UTC)

Untitled

In the unsaturated section, there is the following item:

Omega-3 or Ω-3 : The first double bond is the third carbon-carbon bond counting from the end of the chain most distant from the carboxyl group. The next

It appears that most of a sentance is missing. I checked history and it has been this way since the distinction between delta and omega terminology was introduced, with no indication of what should go there. Can anyone correct this, or is "The next" unintentional?

Kutulu 19:17, 26 Apr 2005 (UTC)

For fatty acid. How much percentage of fatty acid in edible oil for human consumption? — Preceding unsigned comment added by Sg logistics (talk • contribs) 12:14, 17 October 2012 (UTC)

Muscles prefer fatty acids over glucose?

"Free fatty acids are an important source of fuel for many tissues since they can yield relatively large quantities of ATP. Many cell types can use either glucose or fatty acids for this purpose. However, heart and skeletal muscle prefer fatty acids. On the other hand, the brain cannot use fatty acids as a source of fuel, relying instead on glucose, or on ketone bodies produced by the liver from fatty acid metabolism during starvation, or periods of low carbohydrate intake."

I doubt it. This should be fact-checked. Lantoka 11:43, 6 April 2006 (UTC)

From Tom Brody's "Nutritional Biochemistry" 2nd ed., p. 195:\

Fatty acids are the major fuel of muscle at all times. Creatine phosphate is important only during the early stages of exercise (i.e., during sudden bursts of work). Glycogen tends to become depleted during exercise of moderate duration. With this depletion, the importance of gluconeogenesis as a source of glucose increases. During prolonged exercise, FFAs supply most of the energy requirements of muscle. Ketone bodies, which are made by the liver, are also used as fuel by exercising muscle, but their contribution is quite small compared with fatty acids.

(My emphasis) --Slashme 13:41, 7 April 2006 (UTC)

Really? Wow, everything else I've read on Wikipedia suggests to the contrary. The marathon article talks about runners "hitting a wall" when glycogen levels are depleted because the body has to switch to metabolizing fat (fatty acids). The common practice of football players and other athletes eating lots of pastas and other foods high in carbohydrates also supports this. And also, the article on the Krebs Cycle talks about how fatty acids are metabolized by the liver and other body parts into glucose before being used by cells to generate ATP:

"In fat catabolism, triglycerides are hydrolyzed to break them into fatty acids and glycerol. In the liver the glycerol can be converted into glucose via dihydroxyacetone phosphate and glyceraldehyde-3-phosphate by way of gluconeogenesis. In many tissues, especially heart tissue, fatty acids are broken down through a process known as beta oxidation which results in acetyl-CoA which can be used in the citric acid cycle. Sometimes beta oxidation can yield propionyl CoA which can result in further glucose production by gluconeogenesis in liver."

And here, from Exercise Physiology, 5th ed., p84:

Dietary carbohydrate intake takes on additional importance for individuals involved in a significant amount of physical activity on the job or in exercise training and sports competition. Stored muscle glycogen becomes the prime energy contributor under circumstances of inadequate oxygen supply to active muscles. In addition to this anaerobic role of carbohydrates, stored glycogen (and blood glucose) provides substantial energy during intense aerobic exercise.

The last claim in that quote is citation 21 in that book, coming from Coggan AR, Coyle EF. Carbohydrate ingestion during prolonged exercise: effects on metabolism and performance. Exerc Sport Sci Rev 1991:19:1.

Perhaps I'm misunderstanding something... please elaborate on your claim so that we can figure this out. =) Lantoka 08:12, 9 April 2006 (UTC)

We seem to agree to a large extent here. Athletes can continue on glycogen for quite a while, until the stores run out. Because glycogen produces glucose, that's a faster source of energy than FFA oxidation. This readily available energy can be extended by "carbo-loading" but there's a limit to how much glycogen the liver will store. After a while (typically about 30 minutes), you start liberating your fat deposits, and during prolonged exercise, the Krebs cycle in your muscle mitochondria runs almost exclusively on Acetyl-CoA from beta-oxidation of fat.

As for the bit about glucose being formed from fat oxidation: That is a relatively minor pathway; it's just the last 3 carbons from odd-numbered fatty acids and the glycerol backbone of the triglyceride that go that way. The rest goes straight to acetyl-CoA that feeds the krebs cycle. The body can't make glucose from the main chains of fatty acids.

Then there's the question of what your muscles run on during normal, non-strenuous activity (sitting upright and walking around the office, for example). I'm not really sure. Can anyone clarify this? How much does the balance between carbs and fat in your diet affect this? --Slashme 11:19, 11 April 2006 (UTC)

In answer to your last question, I believe that muscles simply use aerobic respiration for normal activity, keeping enough ATP on hand in the cell to sustain normal activity. Other pathways come into play during different types of strenuous exercise. Sudden bursts of energy (to throw a punch or to swing a golf club, for example) simply come from manufactured ATP on hand in the muscle, which is regenerated through aerobic respiration after muscle contraction. Sustained power (such as sprinting and playing on the line in football) first uses existing ATP, then uses the phosphate group from phosphocreatine to recharge ADP. This is why some weight lifters take creatine supplements. Strenuous exertion over a period of more than 4-8 seconds brings lactic acid fermentation into play, which will exhaust the muscle once too much lactate has built up. Less strenuous exertion over a long period of time (more than 2-4 minutes) will call on normal aerobic respiration (Krebs Cycle and oxidative phosphorylation) to sustain the activity, and people who do extensive aerobic exercise have made this pathway very efficient.

But anyway, back to the original discussion. From research I've done, it looks like muscles keep a reserve of glycogen, fatty acids, and amino acids on hand. Once those reserves are exhausted, the muscle cell can then draw on glucose and amino acids released from hepatocytes in the liver and fatty acids released from adipocytes to power aerobic reactions. For anaerobic reactions, glycolysis must take place, and only carbohydrates (glucose, glycogen) can be used.

So, during short and strenuous exercise, carbohydrates are going to be the "perferred" source of energy. But what about during light and moderate exercise? Research I've done indicates that about 10% of that energy comes from proteins, 30% comes from carbohydrates, and 60% comes from fats. Which makes your original statement, that skeletal muscle perfers fatty acids, true.

Thanks for your responses! This discussion piqued my curiosity and, as a result, has increased my knowledge of nutrition and human physiology, so that I may better contribute to other articles on the subject. Lantoka 02:29, 12 April 2006 (UTC)

Excellent! I have also learned something here. It's this kind of thing that makes me happy to be a Wikipedian. --Slashme 07:37, 12 April 2006 (UTC)

Shape of fatty acids

The statements that "a chain has many cis bonds, it becomes quite curved" and that "Alpha-linolenic acid, with three double bonds, forms a hooked shape." seem misleading. As long as fatty acids have at least one C-C single bonds along their chain, they can assume an infinite number of conformations, only a subset of which are consistent with these statements. For example the structure of Alpha-linolenic acid drawn in its article is not hooked but straight. It all depends on the free rotation around the C-C single bonds.

It seems more correct to mention that cis bonds, by introducing kinks in the chain, decrease the conformational freedom of fatty acids. The effect of this is that in restricted environments, such as when fatty acids are part of a phospholipid in a lipid bilayer, or triglicerides in lipid droplets, cis bonds limit the ability of fatty acids to be closely packed and therefore could affect the melting temperature of the membrane or of the fat. --InfoCan 16:12, 26 May 2006 (UTC)

You are correct that the double bonds don't entirely prevent straight conformations, but they certainly cause bent, curved, or hooked conformations to be favored. I've made made a few changes to the text to clarify this (hopefully) and I added some of the text that you wrote. (In the future, you can be bold and make the changes yourself, if you like.) --Ed (Edgar181) 18:31, 26 May 2006 (UTC)

@Edgar181: Do you have a source for this statement? It seems to be "folk science". Logically there should be little difference between the shapes of fatty acids with (say) 18 carbons and zero or one double bond, cis or trans. The unsaturated molecule has 17 degrees of freedom due to rotations about the single bonds, with low energy barriers. Each double bond removes one degree of freedom; but even the most saturated acid (with 8 double bonds) still has enough freedom to assume a mostly straight or highly bent shape. --Jorge Stolfi (talk) 08:49, 19 August 2020 (UTC)

Acetic and butyric acids?

Should acetic and butyric acids be listed as saturated fatty acids when the intro says that fatty acids are generally understood to have 8 carbons or more? --InfoCan 16:18, 26 May 2006 (UTC)

Normally they would not be considered fatty acids. I've removed them from the saturated examples. ChemGardener 16:39, 26 May 2006 (UTC)

cis/trans

Wouldn't it make more sense to write: "A cis configuration means that the two hydrogens are on the same side of the double bond" and "A trans configuration, by contrast, means that the next two hydrogen atoms are bound to opposite sides of the double bond"?

• The terms refer to position of arbitrary groups, not just hydrogens. Here (and in alkenes) the two groups are the two parts of the carbon chain separated by the double bond.--Jorge Stolfi (talk) 08:53, 19 August 2020 (UTC)

Typo?

"Changes in the levels and balance of these fatty acids due to a typical Western diet rich in omega-6 and poor in omega-9 fatty acids is alleged to be associated with depression and behavioral change, including violence."

Shouldn't this be:

"Changes in the levels and balance of these fatty acids due to a typical Western diet rich in omega-6 and poor in omega-3 fatty acids is alleged to be associated with depression and behavioral change, including violence."

Chain?

Hi - excuse my ignorance about fatty acids, but I'm trying to resolve/understand all the links to Chain and I see there's a reference in the first sentence of this article but I'm not sure what it means. If if refers to chain as a sequence of molecules, it should be a link to Chain (sequence) --Mortice 23:11, 31 October 2006 (UTC)

Classification by Length?

I have been investigating coconut oil and in the process found that while most articles and discussions mention saturation they do not discuss length and I do not have sufficient knowledge to judge the validity or siginificance of this ommission. There seems to be some rising debate about the relative value of long- versus medium-chain fatty acids. Here is the article that put length on my radar: https://www.westonaprice.org/knowyourfats/skinny.html#fatty

If the length of fatty acids is a significant factor then this article should include some mention of it and even if it is not significant it might be helpful to know why not. Donberg68 23:13, 23 February 2007 (UTC)

There have been several studies done showing that the different-length unsaturated fats have different properties w.r.t. forming atherosclerotic plaque. But results have been mixed and there's no consensus in the field.

Weston-price is not a high-quality source for a science cite. They do get some things right, but many of their claims are both controversial and either unsourced or sourced to other Weston-price articles. Mary Enig and Sally Fannon have some real gifts in terms of putting difficult scientific material into popular language. But one should always check their claims against the authorative literature before relying on it.

David.Throop 14:09, 11 November 2007 (UTC)

Vitamin E

Who cares about vitamin E in oils anyway? From this table, I see that the more polyunsaturated oils generally have more vitamin E. They need more refining and thus aren't that rich in vitamin E after all. Also, they require more antioxidants (like Vitamin E) for your body to use them. Liquid vegetable oils are always refined and deprived of their nutrients once they reach the supermarket (besides olive oil) and if they're highly polyunsaturated (which all liquid vegetable oils are besides olive oil, nut oil, avocado oil, tea seed oil and maybe some others), they'll have significant amounts of trans fats. Also, of the oils, the one with the most vitamin E is palm oil (wheat germ oil isn't commonly in the supermarket, just used as a supplement). I also bet unrefined/virgin/extra virgin olive oil would be high on the common oil list. When unrefined oils are used as supplements, that's a whole different story (unrefined wheat germ oil is packed with Vitamin E).

 —Preceding unsigned comment added by Press olive, win oil (talk • contribs) 20:57, 11 January 2008 (UTC) 

Status of very short-chain compounds as fatty acids

There's a little inconsistency on Wikipedia about whether certain short-chain compounds are considered fatty acids. This mainspace omits anything shorter than butyric acid from the table of saturated fatty acids, but language in a later section vaguely implies that formic and acetic acids are fatty acids. The Short chain fatty acid article includes acetic and propionic acids, but not formic. Meanwhile, the Acetic acid article implies that acetic acid is a fatty acid, the Propionic acid article states that propionic acid is not a fatty acid, and the Formic acid article is silent on the subject. Is there a chemist in the house? --Belgrano (talk) 20:13, 18 January 2008 (UTC)

From History page

I edited this article sectn. to maintain the sentence structure down thru the list; The option (dear editors) would be 1) to use a verb commensurate w/the subj. 2) to say Butyric ACID, Cpr. ACID, etc.) —Preceding unsigned comment added by Dsnow75 (talk • contribs) 23:10, 6 March 2008 (UTC)

Long Chain Fatty Acids in Foods

Does anyone know what foods are rich in long chain fatty acids? Thanks. —Preceding unsigned comment added by Interestedperson (talk • contribs) 01:15, 18 June 2008 (UTC)

I'd actually like to see examples of short, medium, long and very long chain fatty acids. I've been researching studies done on nutrition over the last 30 years and they mention these but do not go any further in identifying them. deepsack (talk) —Preceding undated comment added 19:44, 3 July 2012 (UTC)

Fixed Vandalism

Someone wrote "Josh is a fatty acid", replaced the headline text. fixed. If someone can revert to before the vandalism, even better as I havent tried the revert feature before. --94.193.135.142 (talk) 20:04, 13 November 2009 (UTC)

Info about the nomenclature.....

• https://scholar.google.com.hk/scholar?hl=en&q=allintitle%3A+fatty+acid+nomenclature&btnG=Search&as_sdt=2000&as_ylo=&as_vis=0
• https://scholar.google.com.hk/scholar?hl=en&q=allintitle%3A+fatty+acids+nomenclature&btnG=Search&as_sdt=2000&as_ylo=&as_vis=0

--222.67.208.221 (talk) 04:47, 19 May 2010 (UTC)

• https://scholar.google.com.hk/scholar?as_q=IUPAC+fatty&num=10&btnG=Search+Scholar&as_epq=&as_oq=&as_eq=&as_occt=title&as_sauthors=&as_publication=&as_ylo=&as_yhi=&as_sdt=1.&as_sdtp=on&as_sdts=5&hl=en

--222.67.208.221 (talk) 05:58, 19 May 2010 (UTC)

• https://old.iupac.org/publications/books/seriestitles/nomenclature.html#organic

--222.67.208.221 (talk) 06:03, 19 May 2010 (UTC)

• https://www.chem.qmul.ac.uk/iupac/bibliog/blue.html#NOC
• https://www.chem.qmul.ac.uk/iupac/bibliog/blue.html#guide

--222.67.208.221 (talk) 06:10, 19 May 2010 (UTC)

Fatty acid catabolism

There needs to be a section describing how Fatty acids are broken down to produce energy. ScienceApe (talk) 17:16, 14 August 2013 (UTC)

Omega numbering error in Figure

Omega numbering showed in the figure is wrong. The farest carbon atom (from the carboxyl group) should be numbered as ω (as used in ω-hydroxy acids), the second to last carbon should be numbered as ω−1, the third to last atom should be numbered as ω−2, and so on. When the position of a double bond is specified, the lowest locant (corresponding to two involved carbons) must be stated. Thus, a ω−3 fatty acid presents a C=C bond linking carbons ω−3 and ω−2. Differences between carbon atoms ω and ω−1 can be easily inferred from the literature: -Å. Ellin, S. V. Jakobsson, J. B. Schenkman, S. Orrenius, "Cytochrome P450K of rat kidney cortex microsomes: Its Involvement in fatty acid ω- and (ω-1)-hydroxylation", Arc. Biochem. Biophys. 1972, 150 (1), 64-71. DOI: 10.1016/0003-9861(72)90010-0 -K. J. Wahle, W. R. Hare, S. M. Paterson, "Aspects of ω- and (ω- 1)-Oxidation of Fatty Acids by Microsomal Preparations from Sheep Liver", Biochem. Soc. Trans. 1978, 6, 1158-1159. DOI: 10.1042/bst0061158 -R. A. Prough, R. T. Okita, L. L. Fan, B. S. S. Masters, "The measurement of ω- and ω-1 hydroxylation of fatty acids by mixed-function oxidase systems", Meth. Enzymology 1978, 52, 318-324. DOI: 10.1016/S0076-6879(78)52034-X -M. Okamoto, R. Miura, T. Yamano, M. Fujioka, "Formation of ω- and (ω-1)-hydroxyfatty acids and plausible formation of ketofatty acid from microsomal phospholipids", J. Biochem. 1981, 89, 955-962. -Y. Miura, "ω- and (ω-1)-hydroxylation of 1-dodecanol by frog liver microsomes", Lipids 1981, 16, 721-725. DOI: 10.1007/BF02535338 -A. S. Muerhoff, D. Williams, N. O. Reich, C. A. CaJacob, P. R. Ortiz de Montellano, B. S. Siler Masters, "Prostaglandin and fatty acid ω- and (ω-1)-oxidation in rabbit lung. Acetylenic fatty acid mechanism-based inactivators as specific Inhibitors", J. Biol. Chem. 1984, 259, 4136-4141.

 — Preceding unsigned comment added by 155.210.88.194 (talk) 14:32, 27 April 2016 (UTC) 

Assessment comment

The comment(s) below were originally left at Talk:Fatty acid/Comments, and are posted here for posterity. Following several discussions in past years, these subpages are now deprecated. The comments may be irrelevant or outdated; if so, please feel free to remove this section.

Rated "high" as high school/SAT biology content, part of biomolecules. - tameeria 23:45, 18 February 2007 (UTC)

Last edited at 23:45, 18 February 2007 (UTC). Substituted at 14:59, 29 April 2016 (UTC)

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Use as soap?

Fatty acids are incorporated into some soaps without further ado. Some discussion about this would be pertinent, beyond implying using such soaps may change our odours and make us indiscernible to some Animals. Since they are used in hands, it would also be interesting to discuss what effects might further ingestion have. — Preceding unsigned comment added by 4.35.92.11 (talk) 00:15, 28 March 2017 (UTC)

Added brief description of industrial applications, along with references. If it is appropriate for the scope of this article, perhaps other editors could help expand this section with a history of industrial uses or further description? Thank you, Laatu (talk) 15:36, 22 April 2018 (UTC)

Self assembly

It may be helpful to add a section about self-assembly of fatty acids into vesicles. Zackcohen55 (talk) 16:34, 22 February 2018 (UTC)Zack

Vast literature on fatty acids

According to Chemical Abstracts Service: references (519842)>refine "2000-" (318869)>refine "Review" (23583). Since the year 2000, many reviews appear daily on fatty acids. --Smokefoot (talk) 11:26, 6 August 2019 (UTC)

Free fatty acids

"Fatty acids are usually not found in organisms in their standalone form." This statement is incorrect as written. Free fatty acids are found in some species in large amounts, such as in algae.--Kermitchemist (talk) 13:20, 30 April 2021 (UTC)

Source?--Smokefoot (talk) 16:07, 30 April 2021 (UTC)

Ok. I put the source into the article, along with a tweak of the sentence to fix the problem. Hope I did it correctly.--Kermitchemist (talk) 20:03, 30 April 2021 (UTC)

Melioidosis infectious

What is melioidosis and treatment diagnosis 2409:4040:E04:715C:0:0:4D09:590F (talk) 20:27, 14 March 2022 (UTC)

"Calogen" listed at Redirects for discussion

The redirect Calogen has been listed at redirects for discussion to determine whether its use and function meets the redirect guidelines. Readers of this page are welcome to comment on this redirect at Wikipedia:Redirects for discussion/Log/2023 August 25 § Calogen until a consensus is reached. Mdewman6 (talk) 23:53, 25 August 2023 (UTC)

"Aromatic fatty acid" listed at Redirects for discussion

The redirect Aromatic fatty acid has been listed at redirects for discussion to determine whether its use and function meets the redirect guidelines. Readers of this page are welcome to comment on this redirect at Wikipedia:Redirects for discussion/Log/2023 September 7 § Aromatic fatty acid until a consensus is reached. Mdewman6 (talk) 22:15, 7 September 2023 (UTC)