View source for Olestra

{{Short description|Fat substitute}}
{{use mdy dates |date=February 2021}}
{{Infobox drug| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 
| IUPAC_name = 
| image = Olestra.svg
| width =
| image2 = Olestra stereo animation.gif
| caption = '''Top''': Generic 2D structure of olestra, where R = H or fatty acid group, C(O)C<sub>''n''</sub>H<sub>''m''</sub><br />'''Bottom''': Stereoscopic animation of a representative olestra molecule with 8 unsaturated fatty acid groups
<!-- Clinical data -->
| tradename = Olean
| Drugs.com = 
| legal_US = otc
| pregnancy_US = 
<!-- Identifiers -->
| DrugBank = 
| ChEBI_Ref = 
| ChEBI = 
| CAS_number_Ref = <ref>{{cite web |title=CompTox Chemicals Dashboard |url=https://comptox.epa.gov/dashboard/chemical/details/DTXSID2021078 |archive-url=https://web.archive.org/web/20230511004830/https://comptox.epa.gov/dashboard/chemical/details/DTXSID2021078 |url-status=dead |archive-date=May 11, 2023 |website=comptox.epa.gov}}</ref>
| CAS_number = 121854-29-3
| PubChem = 
| ChemSpiderID_Ref = 
| ChemSpiderID = none
| NIAID_ChemDB =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6742Y30KGK
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| ChEMBL_Ref = 
| ChEMBL = 
| ATC_prefix =
| ATC_suffix = 
<!-- Chemical data -->
| chemical_formula = {{Chem|C|''n''+12 | H|2''n''+22 | O|13}} (where fatty acids are saturated)
| molecular_weight = Variable
| SMILES = 
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}}

'''Olestra''' (also known by its brand name '''Olean''') is a [[fat substitute]] [[food additive]] that adds no metabolizable calories  to products. It has been used in the preparation of otherwise high-fat foods, thereby lowering or eliminating their fat content. 

The [[Food and Drug Administration]] (FDA) approved olestra for use in the US as a replacement for fats and oils in prepackaged ready-to-eat snacks in 1996,<ref name="AccessData" /> concluding that such use "meets the safety standard for food additives, reasonable certainty of no harm".<ref name="FedReg" />{{rp|46399}} In the early 2000s, olestra lost popularity due to supposed side effects and is largely phased out, but products containing the ingredient are available in some countries.{{Citation needed|date=May 2022}} As of 2024, no products using olestra are sold in the United States.{{cn|date=September 2024}}

== Commercialization ==
Olestra was discovered accidentally by [[Procter & Gamble]] (P&G) researchers F. Mattson and R. Volpenhein in 1968 while researching fats that could be more easily digested by premature infants.<ref name="Nestle_2013"/>{{rp|340}} In 1971, P&G met with the [[Food and Drug Administration]] (FDA) to examine what sort of testing would be required to introduce olestra as a [[food additive]].<ref name="Nestle_2013"/>{{rp|341}}

During the following tests, P&G noticed a decline in blood [[cholesterol]] levels as a side effect of olestra replacing natural dietary fats. Following this potentially lucrative possibility, in 1975, P&G filed a new request with the FDA to use olestra as a "drug", specifically to lower cholesterol levels.<ref name="Nestle_2013"/>{{rp|341}} The lengthy series of studies that followed failed, however, to demonstrate the 15% reduction required by the FDA to be approved as a treatment. Further work on Olestra languished.

In 1984, the FDA allowed [[Kellogg Company|Kellogg]] to claim publicly that their high-fiber [[breakfast cereal]]s were effective in reducing the risk of [[cancer]]. P&G immediately started another test series that lasted three years. When these tests were completed, P&G filed for approval as a food additive for up to 35% replacement of fats in home cooking and 75% in commercial uses.<ref name="Nestle_2013"/>{{rp|341}}

One of the main concerns the FDA had about olestra was it might encourage consumers to eat more of the "[[food guide pyramid|top of the pyramid]]" foods because of the perception of its being healthier. This could result in consumers engaging in over-consumption, thinking the addition of olestra would remove negative consequences.<ref name="Nestle_2013"/>{{rp|339–40}} In light of this possibility, approving it as an additive would have meant consumers would be consuming a food with a relatively high amount of an additive, whose long-term health effects were not documented. This made the FDA particularly hesitant to approve the product, as well as the side effects, such as [[diarrhea]], and concern for the loss of fat-soluble vitamins.<ref name="Nestle_2013"/>{{rp|340}} In August 1990, P&G narrowed their focus to "savory snacks", [[potato chip]]s, [[tortilla chip]]s, [[cracker (food)|cracker]]s and similar foods.

By this point, the original patents were approaching their 1995 expiration. P&G lobbied for an extension, which they received in December 1993. This extension lasted until 25 January 1996.<ref name="History"/> With pressure from P&G, the approval was finally granted on 24 January, one day before the patent expired, automatically extending the patent by two years.<ref name="History"/>

At the time of the 1996 ruling, FDA concluded that, "to avoid being misbranded... olestra-containing foods would need to bear a label statement to inform consumers about possible effects of olestra on the gastrointestinal system. The label statement also would clarify that the added vitamins were present to compensate for any nutritional effects of olestra, rather than to provide enhanced [[nutritional value]]".<ref name="FedReg"/>{{rp|46364}} The FDA later removed the label requirement saying that the "current label does not accurately communicate information to consumers".<ref name="FedReg"/>{{rp|46387}} The FDA also agreed with P&G that the "label statement could be misleading and cause consumers of olestra to attribute serious problems to olestra when this was unlikely to be the case".<ref name="FedReg"/>{{rp|46397}}

=== Discontinued products ===
Olestra was approved by the Food and Drug Administration for use as a food additive in 1996 and was initially used in potato chips under the [[WOW brand]] by [[Frito Lay]]. In 1998, the first year olestra products were marketed nationally after the FDA's Food Advisory Committee confirmed a judgment it made two years earlier, sales were over $400 million.<ref name="Nestle_2013" />{{rp|338}} By 2000, though, sales slowed to $200 million. P&G abandoned attempts to widen the uses of olestra and sold off its [[Cincinnati]]-based factory to [[Twin Rivers Technologies]] in February 2002.<ref name="History" /> The WOW chips were rebranded to "Lay's Light" in 2004<ref>{{Cite web|date=2006-01-04|title=Frito-Lay Target of Olestra Lawsuit|url=https://www.consumeraffairs.com/news04/2006/01/cspi_olestra.html |access-date=2021-05-12|website=[[Consumer Affairs]]|language=en}}</ref> and were discontinued by 2016.<ref>{{Cite web| vauthors = Winderl AM |date=2016-04-08|title=5 Sneaky Ingredients In Food That Can Cause Diarrhea|url=https://www.self.com/story/5-sneaky-ingredients-in-food-that-can-cause-diarrhea |access-date=2021-05-12|website=SELF|publisher=[[Condé Nast]]|language=en-US}}</ref>

[[Pringles]] Light potato crisps, manufactured by [[Kellogg Company|Kellogg's]] (though at one time a P&G product), used Olean-brand olestra before being discontinued in 2015.<ref>{{Cite web|date=2015-09-01|title=@flybrook Sorry for the disappointment! Our Fat Free Pringles have been discontinued. We'll let the team know you would like them back!|url=https://twitter.com/pringles/status/638732581710757888 |access-date=2021-05-12|website=[[Pringles]]|language=en|via=[[Twitter]]}}</ref>

== Side effects ==
Starting in 1996, an FDA-mandated health warning label reads "This Product Contains Olestra. Olestra may cause [[abdomen|abdominal]] [[cramp]]ing and [[Diarrhea|loose stools]]. Olestra inhibits the absorption of some vitamins and other nutrients. Vitamins [[Vitamin A|A]], [[Vitamin D|D]], [[Vitamin E|E]], and [[Vitamin K|K]] have been added".<ref name="FDA_1996"/>

These symptoms, normally occurring only by excessive consumption in a short period of time, are known as [[steatorrhea]] and are caused by an excess of fat in stool.

The FDA removed the warning requirement in 2003, as it had "conducted a scientific review of several post-market studies submitted by P&G, as well as adverse event reports submitted by P&G and the [[Center for Science in the Public Interest]]. The FDA concluded the label statement was no longer warranted".<ref name="FDA_2003"/> The FDA also agreed with P&G that the "label statement could be misleading and cause consumers of olestra to attribute serious problems to olestra when this [was] unlikely to be the case".<ref name="FedReg"/>{{rp|46397}}

When removing the olestra warning label requirement, the FDA cited a six-week P&G study of more than 3000 people showing the olestra-eating group experienced only a small increase in [[Defecation|bowel movement frequency]] compared to the control group.<ref name="Label" />  The FDA concluded that "subjects eating olestra-containing chips were no more likely to report having had loose stools, abdominal cramps, or any other GI symptom compared to subjects eating an equivalent amount of [potato] chips".<ref name="FedReg"/>{{rp|46372}}

In addition to the effects of the health warnings on public acceptance of the product, olestra might not have lived up to consumer expectations of speedy results. If consumers believed that they could eat more to compensate for the fat calories "saved", olestra would not be an effective way to improve overall diet.<ref name="Nestle_2013"/>{{rp|353}} The manufacturers claim that the authentic taste and feel of olestra offsets this tendency,<ref name="Olestra_FAQ"/> and some studies have shown that people who consume foods with olestra don't eat more to offset the loss in calories.<ref name="Bray_1995"/> P&G conducted publicity campaigns to highlight olestra's benefits, including working directly with the health-care community.<ref name="Nestle_2013"/>{{rp|351}}

Olestra is prohibited from sale in many markets, including the European Union and Canada.<ref name="Peale_2000"/><ref name="healthyandhot"/>

Consumption of olestra may encourage rats to eat too much of foods containing regular fats, due to the learning of an incorrect association between fat intake and calories. Rats that were fed regular potato chips as well as chips cooked with olestra gained more weight when subsequently eating a high-fat diet than rats that received just regular chips.<ref name="Swithers_2011"/>

== Chemistry ==
[[Triglyceride]]s, the energy-yielding dietary [[fat]]s, consist of three [[fatty acid]]s bonded in the form of [[ester]]s to a [[glycerol]] backbone. Olestra uses [[sucrose]] as the backbone in place of glycerol, and it can form esters with up to eight fatty acids.<ref name="Orna_1993"/> Olestra is a mixture of hexa-, hepta-, and octa-esters of sucrose with various long chain fatty acids.  The resulting radial arrangement is too large and irregular to move through the intestinal wall and be absorbed into the bloodstream. Olestra has the same taste and [[mouthfeel]] as fat, but it passes through the [[gastrointestinal tract]] undigested without contributing calories or nutritive value to the diet.<ref>{{cite web | url=https://www.mentalfloss.com/article/619261/olestra-fat-free-snack-controversy-1990s | title=May Cause Anal Leakage: The Olestra Fat-Free Snack Controversy of the 1990s | date=April 9, 2020 }}</ref>

From a mechanical point of view, scientists were able to manipulate the compound in such a way that it could be used in place of cooking oils in the preparation of many types of food.<ref name="Nestle_2013"/>{{rp|340}}

Since it contains fatty acid [[functional group]]s, olestra is able to dissolve lipid-soluble [[vitamin]]s, such as [[vitamin D]], [[vitamin E]], [[vitamin K]], and [[vitamin A]], along with [[carotenoid]]s. Fat-soluble nutrients consumed with olestra products are excreted with the undigested olestra molecules. To counteract this loss of nutrients, products made with olestra are fortified with oil-soluble vitamins.<ref name="CSPINET"/>

== Applications ==
[[Procter & Gamble|P&G]] is marketing its sucrose ester products under the brand "Sefose" for use as an industrial lubricant and paint additive.<ref name="P&amp;G"/> Because Sefose is made by chemically combining sugar and vegetable oil, it releases no toxic fumes and could potentially become a safe and environmentally friendly replacement for [[petrochemical]]s in these applications.<ref name="Ballantyne_2009"/> It is currently used as a base for deck stains and a lubricant for small power tools, and there are plans to use it on larger machinery.<ref name="Ballantyne_2009b"/>

There is preliminary evidence that indicates that administration of olestra may accelerate the excretion of [[hydrophobic]] toxins, although there have been no randomized controlled clinical trials to establish the effectiveness of this potential treatment.<ref name="Klein_2015"/> Toxins that have been studied in conjunction with olestra treatment include [[Dioxins and dioxin-like compounds|dioxins]],<ref name="Geusau_2001"/> [[hexachlorobenzene]],<ref name="Jandacek_2005"/> and [[polychlorinated biphenyl]]s (PCBs).<ref name="Redgrave_2005"/><ref name="Jandacek_2014"/>

== References ==
{{Reflist| refs =

<ref name = "AccessData">{{cite web | url = https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=172.867 | title = 21CFR172.867: Olestra | work = Code of Federal Regulations | publisher = U.S. Food and Drug Administration }}</ref>

<ref name = "Ballantyne_2009">{{cite web | vauthors = Ballantyne C| title = Olestra makes a comeback – This time in paints and lubricants, not potato chips | website = 60-Second Science | publisher = Scientific American | date = 6 Apr 2009 | url = http://www.sciam.com/blog/60-second-science/post.cfm?id=olestra-makes-a-comeback-and-this-t-2009-04-06 | access-date = 2009-04-12 | archive-url = https://web.archive.org/web/20090410001022/http://www.sciam.com/blog/60-second-science/post.cfm?id=olestra-makes-a-comeback-and-this-t-2009-04-06 | archive-date = 10 April 2009 }}</ref>

<ref name = "Ballantyne_2009b">{{cite web | vauthors = Ballantyne C| title = New chemicals for eco-friendly paints and lubricants | website = 60-Second Science | publisher = Scientific American | date = 13 Apr 2009 | url = http://www.sciam.com/blog/60-second-science/post.cfm?id=new-chemicals-for-eco-friendly-pain-2009-04-13 | access-date = 2009-04-14 | archive-url = https://web.archive.org/web/20090415054312/http://www.sciam.com/blog/60-second-science/post.cfm?id=new-chemicals-for-eco-friendly-pain-2009-04-13 | archive-date = 15 April 2009 }}</ref>

<ref name = "Bray_1995">{{cite journal | vauthors = Bray GA, Sparti A, Windhauser MM | title = Effect of Two Weeks Fat Replacement by Olestra on Food Intake and Energy Metabolism | journal = FASEB J | date = March 1995 | volume = 9 | issue = 3 | pages = A439 }}</ref>

<ref name = "CSPINET">{{cite web |url=http://www.cspinet.org/olestra/11cons.html |title=The Problems With Olestra |archive-url=https://web.archive.org/web/20070702223802/http://www.cspinet.org/olestra/11cons.html |archive-date=2007-07-02 |work=Center for Science in the Public Interest }}</ref>

<ref name = "FDA_1996">{{cite web |url=http://www.fda.gov/bbs/topics/NEWS/NEW00524.html |title=FDA approves fat substitute, Olestra |access-date=December 6, 2006 |date=January 24, 1996 |work=FDA.gov |archive-url=https://web.archive.org/web/20090512155913/http://www.fda.gov/bbs/topics/NEWS/NEW00524.html |archive-date=May 12, 2009 }}</ref>

<ref name = "FDA_2003">{{cite web | url = https://www.fda.gov/bbs/topics/ANSWERS/2003/ANS01245.html | archive-url = https://web.archive.org/web/20090511171627/https://www.fda.gov/bbs/topics/ANSWERS/2003/ANS01245.html | archive-date = 11 May 2009 | title = FDA Changes Labeling Requirement for Olestra | website = [[Food and Drug Administration]] | access-date = October 12, 2007 }}</ref>

<ref name = "FedReg">{{cite web |url=https://www.govinfo.gov/content/pkg/FR-2003-08-05/pdf/03-19508.pdf |via=govinfo.gov |work=[[Federal Register]] |page=46364 |date=2003-08-05 |title=Food Additives Permitted for Direct Addition to Food for Human Consumption; Olestra }}</ref>

<ref name = "Geusau_2001">{{cite journal | vauthors = Geusau A, Abraham K, Geissler K, Sator MO, Stingl G, Tschachler E | title = Severe 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) intoxication: clinical and laboratory effects | journal = Environmental Health Perspectives | volume = 109 | issue = 8 | pages = 865–869 | date = August 2001 | pmid = 11564625 | pmc = 1240417 | doi = 10.1289/ehp.01109865 | bibcode = 2001EnvHP.109..865G }}</ref>

<ref name = "healthyandhot">{{cite web |url=http://www.healthyandhot.com/everything_you_wanted_to_know_about_olestra.htm |title=Everything you wanted to know about Olestra |date=2007-08-23 |website=Healthy and Hot |access-date=31 March 2011 |archive-url=https://web.archive.org/web/20110711155739/http://www.healthyandhot.com/everything_you_wanted_to_know_about_olestra.htm |archive-date=11 July 2011}}</ref>

<ref name = "History">{{cite web |url=http://www.cspinet.org/olestra/history.html |title=A Brief History of Olestra |archive-url=https://web.archive.org/web/20031212173821/http://www.cspinet.org/olestra/history.html |work=[[Center for Science in the Public Interest]] |archive-date=2003-12-12 }}</ref>

<ref name = "Jandacek_2005">{{cite journal | vauthors = Jandacek RJ, Anderson N, Liu M, Zheng S, Yang Q, Tso P | title = Effects of yo-yo diet, caloric restriction, and olestra on tissue distribution of hexachlorobenzene | journal = American Journal of Physiology. Gastrointestinal and Liver Physiology | volume = 288 | issue = 2 | pages = G292–9 | date = February 2005 | pmid = 15513954 | doi = 10.1152/ajpgi.00285.2004| s2cid = 3218642 }}
*{{lay source |template=cite web |title=Olestra Could Be Antidote to Toxins |url=http://healthnews.uc.edu/publications/findings/?/466/1576/ |archive-url=https://web.archive.org/web/20060904081614/http://healthnews.uc.edu/publications/findings/?/466/1576/ |archive-date=2006-09-04 |website=University of Cincinnati Health News |date=February 2005}}</ref>

<ref name = "Jandacek_2014">{{cite journal | vauthors = Jandacek RJ, Heubi JE, Buckley DD, Khoury JC, Turner WE, Sjödin A, Olson JR, Shelton C, Helms K, Bailey TD, Carter S, Tso P, Pavuk M | display-authors = 6 | title = Reduction of the body burden of PCBs and DDE by dietary intervention in a randomized trial | journal = The Journal of Nutritional Biochemistry | volume = 25 | issue = 4 | pages = 483–8 | date = April 2014 | pmid = 24629911 | pmc = 3960503 | doi = 10.1016/j.jnutbio.2014.01.002 }}</ref>

<ref name = "Klein_2015">{{cite journal | vauthors = Klein AV, Kiat H | title = Detox diets for toxin elimination and weight management: a critical review of the evidence | journal = Journal of Human Nutrition and Dietetics | volume = 28 | issue = 6 | pages = 675–86 | date = December 2015 | pmid = 25522674 | doi = 10.1111/jhn.12286 }}</ref>

<ref name = "Label" >{{cite web | url = http://www.fritolay.com/assets/images/bigVault/lays-light-original_1__1_.gif | title = Nutrition Facts Label | work = Frito-Lay North America, Inc. a Division of PepsiCo. | archive-url = https://web.archive.org/web/20210511045305/http://3.bp.blogspot.com/-HiYVLmchXdY/UqN1PJxQLEI/AAAAAAAAAEQ/XyxhnjRxpY8/s1600/3.png | archive-date = 11 May 2021 }}</ref>

<ref name = "Nestle_2013">{{cite book | vauthors = Nestle M  | date = 2013 | edition = 10th | chapter = Chapter 15: Selling the Ultimate Techno-food: Olestra |title=Food Politics |publisher=University of California Press, Ltd. |location=London |isbn=978-0-520-27596-6 |chapter-url=https://books.google.com/books?id=qakwDwAAQBAJ&pg=PA339 }}</ref>

<ref name = "Olestra_FAQ">{{cite web | title=Olean Brand Olestra: Frequently Asked Questions | url=http://www.olean.com/default.asp?p=faq | archive-url = https://web.archive.org/web/20120307075206/http://www.olean.com/default.asp?p=faq | archive-date = 7 March 2012 | access-date=2012-04-16}}</ref>

<ref name = "Orna_1993">{{cite web | vauthors = Orna MV | title = Artificial fats, Simplesse, Olestra | url = http://chemmovies.unl.edu/chem_source_pdf/FOOD.pdf | work = Food and Chemistry | archive-url = https://web.archive.org/web/20110526045404/http://chemmovies.unl.edu/chem_source_pdf/FOOD.pdf | archive-date=2011-05-26 | publisher = [[University of Nebraska–Lincoln]] | date = 1993 | page = 29 }}</ref>

<ref name = "P&G">{{cite web | title = Sefose | publisher = P&G Chemicals | url = http://www.pgchemicals.com/products/sefose/ | archive-url = https://web.archive.org/web/20120509215938/http://www.pgchemicals.com/products/sefose/ | archive-date = 9 May 2012 | access-date = 20 August 2012 }}</ref>

<ref name = "Peale_2000">{{cite news |url=http://www.enquirer.com/editions/2000/06/23/fin_canadian_ban_adds_to.html |title=Canadian ban adds to woes for P&G's olestra | vauthors = Peale C |date=June 23, 2000 |work=The Cincinnati Enquirer |access-date=31 March 2011}}</ref>

<ref name = "Redgrave_2005">{{cite journal | vauthors = Redgrave TG, Wallace P, Jandacek RJ, Tso P | title = Treatment with a dietary fat substitute decreased Arochlor 1254 contamination in an obese diabetic male | journal = The Journal of Nutritional Biochemistry | volume = 16 | issue = 6 | pages = 383–4 | date = June 2005 | pmid = 15936651 | doi = 10.1016/j.jnutbio.2004.12.014 }}</ref>

<ref name = "Swithers_2011">{{cite journal | vauthors = Swithers SE, Ogden SB, Davidson TL | title = Fat substitutes promote weight gain in rats consuming high-fat diets | journal = Behavioral Neuroscience | volume = 125 | issue = 4 | pages = 512–8 | date = August 2011 | pmid = 21688890 | pmc = 3144274 | doi = 10.1037/a0024404 }}</ref>

}}

== External links ==
* [https://web.archive.org/web/20031212173821/http://www.cspinet.org/olestra/history.html History of olestra]
* [https://web.archive.org/web/20050930110154/http://www.chemcases.com/olestra/ "Case studies and the chemistry of olestra", Kennesaw State University]
* [http://www.consumeraffairs.com/news04/2006/01/cspi_olestra.html ''Consumer Affairs'' report on Frito-Lay litigation]
* [http://www.cspinet.org/olestra/ Center for Science in the Public Interest: Various articles on Olestra (1999–2006)] {{Webarchive|url=https://web.archive.org/web/20031204193230/http://www.cspinet.org/olestra/ |date=December 4, 2003 }}

{{Food Substitutes}}

[[Category:Fat substitutes]]
[[Category:Procter & Gamble]]