Talk:Stearic acid

Complete oxidation (title added)
What is the complete oxidation of stearic acid? —The preceding unsigned comment was added by 195.194.252.14 (talk • contribs).
 * Carbon dioxide and water. If you're asking for the balanced equation, do your own homework. —Keenan Pepper 02:23, 8 August 2006 (UTC)
 * Amen to that comment, Keenan. Goldy496 (talk) 23:49, 2 February 2008 (UTC)

Where are the carbon atoms? (title added)
If CH3(CH2)16COOH is the formula, then where is the carbon in the picture? All I see are oxygen and hydrogen. Subversive 4 July 2005 04:04 (UTC)


 * The carbon is never shown in this kind of pictures. Xatufan
 * The points connecting the various line segments are understood to be carbon —The preceding unsigned comment was added by 129.24.141.230 (talk • contribs).
 * In organic chemistry, it becomes a nuisance to draw out dozens of C's. Instead, they are represent by lines connecting them and they are assumed to have an appropriate number of Hydrogens attached to each vertex.71.168.113.85 00:31, 3 April 2007 (UTC)

Reaction with water (title added)
What is the equation for its reaction with water? —The preceding unsigned comment was added by 203.173.2.13 (talk • contribs).
 * Do your own homework. —Keenan Pepper 02:23, 8 August 2006 (UTC)

Conversion in the human body (title added)
I've heard that the human body converts stearic acid to oleic acid for processing, which is why cocoa butter (high in stearic acid) isn't as unhealthy as other kinds of saturated fats. Is this true? Anyone know more about this? Frankg 18:34, 10 February 2006 (UTC)
 * That's interesting. I'll look it up. —Keenan Pepper 02:23, 8 August 2006 (UTC)
 * I added a section based on an isotope study I found. How's that? —Keenan Pepper 03:07, 8 August 2006 (UTC)
 * Definitely; thanks for digging that up! Frankg 20:36, 8 August 2006 (UTC)

Desaturation (title added)
How conduct the desaturation of stearic acid ? —The preceding unsigned comment was added by Grzybowski (talk • contribs).

Gelatin?
Would it be accurate to say that calcium stearate and magnesium stearate serve some of the same purposes as gelatin? A package of breath mints had calcium stearate in its list of ingredients (but no gelatin), while other brands such as Altoids do list gelatin. -- Gyrofrog (talk) 02:04, 7 December 2006 (UTC)

Freezing point
Someone wrote: FreezingPt=35.1 °C in the infobox. This does not show up in the infobox, as it is not a standard item. Also, I find it a bit strange that it's so far from the melting point (69.6 °C). If this is correct, we need to put it in the article somehow, with a reference. --Slashme 07:55, 1 October 2007 (UTC)

Trans Fatty Acid/Stearic Acid clarification and link
It would be helpfull if this page stated that hydrogenated vegitable oils are commonly known as Trans Fatty Acids and make a link to the Trans Fatty Acids page. This page missleads one to beleive that the hydrogenation of vegitable oils creates the same stearic acid that occurs in nature, when naturally occuring Stearic Acid has studies that suggest it lowers heart disease and is good for human ingestion, while Trans Fatty Acids have studies that suggest the opposite. 206.166.230.226 (talk) 18:59, 7 February 2008 (UTC)

even though its an old and apparently ignored statement, the above is utterly false. the only possible truth might come from measurement of commercial, relatively poorly prepared quantities of hydrogenated oils. Hydrogenation of the mono or polyunsaturated carbon number equivalent vegetable fatty acids produces a chemically indistinguishable molecule to stearic acid. even mildly modern and enormously widespread industrial techniques produce absurdly high purity and are a key factor in the widespread utilization of all alkane (saturated) fatty acids of any arbitrary length, since they cannot always be supplied in the quantities needed, or with special chemistry (eg branched) from the natural saturated phosphodiesters and glycerides. put more succintly: the purity is high enough that you have to start considering *other culprits* (purity levels *almost* semiconductor grade)67.165.123.62 (talk) 01:43, 22 December 2022 (UTC)

Can it be vegan?
The article states "Stearic acid is prepared by treating animal fat with water at a high pressure and temperature," but there are some vegan products that contain it, such as this one. Is it possible to produce without any animal products, as these product labels imply? Badagnani (talk) 18:45, 14 July 2008 (UTC)
 * The article says that stearic acid is present is some vegetable oils and that it can be "obtained from the hydrogenation of some unsaturated vegetable oils", so it certainly seems to be a possible ingredient in vegan foods. -- Ed (Edgar181) 19:07, 14 July 2008 (UTC)
 * Cocoa butter and shea are some well-known plant-based sources of stearic acid. Frankg (talk) 21:57, 14 July 2008 (UTC)

Kosher or halaal status
I removed the comment about stearic acid not necessarily being kosher or halaal. No ingredient can safely be assumed to be kosher or halaal unless certified as such by a registering authority. It doesn't matter whether it's lactose, steric acid or vitamin B12. We can't go adding this "disclaimer" to all our articles on chemical substances and food ingredients. --Slashme (talk) 06:32, 12 August 2008 (UTC)

A call today to Health Concerns concerning use of stearic acid in their proprietary Chinese medicinal herbal formulas resulted in their confirming that it is of plant source, particularly palm oil. (per their CEO Andrew Gaddeart). note by Tom Chi L.Ac. (NY) Dipl. Ac. (NCCAOM) —Preceding unsigned comment added by 71.169.42.220 (talk) 17:40, 10 June 2010 (UTC)

Allergic responses?
Though subject to further tests, I am virtually certain that I am severely allergic to either magnesium stearate and/or stearic acid (as a non-specialist, I am not altogether sure of the differences between these substances, and would appreciate clarification).

I have discussed the subject with an expert in this field, and his view is that allergic responses to magnesium stearate are probably frequent, but under-reported. Whilst the incidence of this allergic reaction in the population may be small, the resulting symptoms are particularly nasty.

It also occurs to me that patients diagnosed as allergic to particular pharmaceutical compounds may be allergic not to the compound itself but to the magnesium stearate used in tablet preparation.

According to ScienceLab.com, magnesium stearate is "hazaradous in case of ingestion", and "may be toxic to liver and skin".

Any comments gratefully received. Because I'm not sure of the chemical distinction, I'll post this comment under "magnesium stearate" as well as "stearic acid".--Vvmodel (talk) 15:46, 11 January 2009 (UTC)

in muscle cells stearic acid induced mitochondrial dysfunction associated with impaired insulin-induced glucose metabolism
Hirabara SM, Curi R, Maechler P.*

Saturated fatty acid-induced insulin resistance is associated with mitochondrial dysfunction in skeletal muscle cells.

J Cell Physiol. 2010 Jan;222(1):187-94

Abstract

Increased plasma levels of free fatty acids (FFA) occur in states of insulin resistance such as obesity and type 2 diabetes mellitus. These high levels of plasma FFA are proposed to play an important role for the development of insulin resistance but the mechanisms involved are still unclear. This study investigated the effects of saturated and unsaturated FFA on insulin sensitivity in parallel with mitochondrial function. C2C12 myotubes were treated for 24 h with 0.1 mM of saturated (palmitic and stearic) and unsaturated (oleic, linoleic, eicosapentaenoic, and docosahexaenoic) FFA. After this period, basal and insulin-stimulated glucose metabolism and mitochondrial function were evaluated. Saturated palmitic and '''stearic acids decreased insulin-induced glycogen synthesis, glucose oxidation, and lactate production. Basal glucose oxidation was also reduced. Palmitic and stearic acids impaired mitochondrial function as demonstrated by decrease of both mitochondrial hyperpolarization and ATP generation. These FFA also decreased Akt activation by insulin.''' As opposed to saturated FFA, unsaturated FFA did not impair glucose metabolism and mitochondrial function. Primary cultures of rat skeletal muscle cells exhibited similar responses to saturated FFA as compared to C2C12 cells. These results show that in muscle cells saturated FFA-induced mitochondrial dysfunction associated with impaired insulin-induced glucose metabolism.

Supplemental Content

Related citations

Acute effect of fatty acids on metabolism and mitochondrial coupling in skeletal muscle. [Biochim Biophys Acta. 2006]   Hirabara SM, Silveira LR, Alberici LC, Leandro CV, Lambertucci RH, Polimeno GC, Cury Boaventura MF, Procopio J, Vercesi AE, Curi R. Biochim Biophys Acta. 2006 Jan; 1757(1):57-66. Epub 2005 Dec 13.

Dimopoulos N, Watson M, Sakamoto K, Hundal HS.

Differential effects of palmitate and palmitoleate on insulin action and glucose utilization in rat L6 skeletal muscle cells. Biochem J. 2006 Nov 1; 399(3):473-81.

Hirabara SM, Silveira LR, Abdulkader F, Carvalho CR, Procopio J, Curi R.   Time-dependent effects of fatty acids on skeletal muscle metabolism. J Cell Physiol. 2007 Jan; 210(1):7-15.

Yuzefovych L, Wilson G, Rachek L.    Different effects of oleate vs. palmitate on mitochondrial function, apoptosis, and insulin signaling in L6 skeletal muscle cells: role of oxidative stress. Am J Physiol Endocrinol Metab. 2010 Dec; 299(6):E1096-105. Epub 2010 Sep 28.

Review Free fatty acids in obesity and type 2 diabetes: defining their role in the development of insulin resistance and beta-cell dysfunction. [Eur J Clin Invest. 2002]

Boden G, Shulman GI. Free fatty acids in obesity and type 2 diabetes: defining their role in the development of insulin resistance and beta-cell dysfunction. Eur J Clin Invest. 2002 Jun; 32 Suppl 3:14-23.

Full-text articles in the PubMed Central Database that cite the current articles.

Saturated fatty acid-induced insulin resistance is associated with mitochondrial dysfunction in skeletal muscle cells. J Cell Physiol. 2010 Jan ;222(1):187-94. PubMed

Influence of stearic acid on cholesterol metabolism relative to other long-chain fatty acids. Am J Clin Nutr. 1994 Dec ;60(6 Suppl):986S-990S. PubMed


 * Ocdnctx (talk) 01:50, 26 May 2011 (UTC)

Influence of stearic acid on cholesterol metabolism relative to other long-chain fatty acids
Grundy SM.

Am J Clin Nutr. 1994 Dec;60(6 Suppl):986S-990S. Influence of stearic acid on cholesterol metabolism relative to other long-chain fatty acids.

Free full text http://www.ajcn.org/cgi/pmidlookup?view=long&pmid=7977157

Abstract

Stearic acid is a long-chain saturated fatty acid. However, in contrast with other saturated fatty acids, stearic acid apparently does not raise serum cholesterol concentrations. Studies carried out three decades ago provided strong suggestive evidence that this was the case. More recent investigations that specifically compared stearic acid with other fatty acids in human studies have confirmed that stearic acid is not hypercholesterolemic. Stearic acid was shown not to raise low-density-lipoprotein cholesterol relative to oleic acid, which is known to be neutral in its effects on cholesterol concentrations. In contrast, palmitic acid, another long-chain saturated fatty acid, definitely raises cholesterol concentrations. For this reason, fats rich in stearic acid might be used in place of those high in palmitic acid in cholesterol-lowering diets.

Free full text http://www.ajcn.org/cgi/pmidlookup?view=long&pmid=7977157

Source

Department of Internal Medicine, University of Texas Southwestern Medical Center, Dallas.

Ocdnctx (talk) 15:52, 24 November 2011 (UTC)

"Stearic" vs "steric"?
The article currently has two different spellings: "stearic acid" and "steric acid". Is this intentional, or is it an error? Mister Sharkey (talk) 20:22, 22 September 2011 (UTC)
 * Steric and stearic have very different meaning, and steric was not meant there. Changed to stearic, thanks. Materialscientist (talk) 00:57, 23 September 2011 (UTC)

Ster is classical Greek for volume. It pertains to volume/density analysis, particularly of sea water. Another example is steradian for solid angles.220.244.141.217 (talk) 01:23, 14 September 2014 (UTC)

Stearic acid exerts a neutral cholesterolemic response in humans
Steinberg FM, Bearden MM, Keen CL.

Cocoa and chocolate flavonoids: implications for cardiovascular health.

J Am Diet Assoc. 2003 Feb;103(2):215-23.

Abstract

This paper offers a review of current scientific research regarding the potential cardiovascular health benefits of flavonoids found in cocoa and chocolate. Recent reports indicate that the main flavonoids found in cocoa, flavan-3-ols and their oligomeric derivatives, procyanidins, have a variety of beneficial actions, including antioxidant protection and modulation of vascular homeostasis. These findings are supported by similar research on other flavonoid-rich foods. Other constituents in cocoa and chocolate that may also influence cardiovascular health are briefly reviewed. The lipid content of chocolate is relatively high; however, one third of the lipid in cocoa butter is composed of the fat stearic acid, which exerts a neutral cholesterolemic response in humans. Cocoa and chocolate contribute to trace mineral intake, which is necessary for optimum functioning of all biologic systems and for vascular tone. Thus, multiple components in chocolate, particularly flavonoids, can contribute to the complex interplay of nutrition and health. Applications of this knowledge include recommendations by health professionals to encourage individuals to consume a wide range of phytochemical-rich foods, which can include dark chocolate in moderate amounts.

Source

Didactic Program in Dietetics, Department of Nutrition, University of California, Davis, CA, USA. fmsteinberg@ucdavis.edu

Ocdnctx (talk) 19:24, 25 November 2011 (UTC)

Stearic acid less damaging to health than other saturated fatty acids, but still damaging.
Other saturated fats have even worse effects on the blood cholesterol profile than stearic acid. But compared with unsaturated fatty acids (and presumably monosaturated fatty acids) stearic acid is less healthy.


 * As for stearic acid, the allegedly non-cholesterol-raising fat, while it appears to lower LDL-C relative to other SFAs, one analysis concluded that it raised LDL-C, lowered HDL-C, and increased the ratio of total to HDL cholesterol in comparison with unsaturated fatty acids.[13]


 * 13. Hunter JE, Zhang J, Kris-Etherton PM. Cardiovascular disease risk of dietary stearic acid compared with trans, other saturated, and unsaturated fatty acids: a systematic review. Am J Clin Nutr. 2010;91:46-63. Abstract [Full text:  http://ajcn.nutrition.org/content/91/1/46]

http://www.medscape.com/viewarticle/839360?nlid=76484_1521&src=wnl_edit_medp_wir&uac=70451CR&spon=17 — Preceding unsigned comment added by Ocdcntx (talk • contribs) 23:10, 17 February 2015 (UTC)

Solubility in water
Can anyone find 9.93 g/L (37 °C) in the fifth reference that is given? I can only find 0.1 grams per 100 milliliters on the page before. My edit was reverted. — Preceding unsigned comment added by 94.39.186.127 (talk) 22:48, 22 June 2015 (UTC)

Assessment comment
Substituted at 06:58, 30 April 2016 (UTC)

Classification as an Acid
A page about an acid should most certainly contain the pKa of said acid. I am shocked to find that this one doesn't. — Preceding unsigned comment added by 2600:100A:B01D:B45C:1CAB:AC19:F317:F4D5 (talk) 22:06, 3 August 2016 (UTC)

CAS report
get references (158663)>refine "2000-" (122813)>refine "Review" (272).

Top ranked review: Fat deposition, fatty acid composition and meat quality: A review Wood, J. D.; Enser, M.; Fisher, A. V.; Nute, G. R.; Sheard, P. R.; Richardson, R. I.; Hughes, S. I.; Whittington, F. M. Meat Science (2008), 78(4), 343-358. doi :10.1016/j.meatsci.2007.07.019. --Smokefoot (talk) 01:22, 6 August 2019 (UTC)

One two many carbons listed
The chemical formula given in the first sentence has one two many carbon atoms. The total number of carbons is 18, so instead of "C₁₈H₃₅CO₂H" it should be C₁7H₃₅CO₂H or C₁₈H₃₅O₂H Elsewhere in the article the empirical formula is listed correctly. From a Ph.D. chemist — Preceding unsigned comment added by 128.249.96.12 (talk) 23:40, 29 February 2020 (UTC)