View source for Chemistry:Deoxycholic acid

{{Short description|Bile acid}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 443682689
| Name = Deoxycholic acid
| ImageFile = Deoxycholic acid.svg
| ImageSize = 230px
| ImageAlt = Skeletal formula of deoxycholic acid
| ImageFile1 = Deoxycholic acid 3D ball.png
| ImageSize1 = 230px
| ImageAlt1 = Ball-and-stick model of deoxycholic acid
| ImageFile2 = Sample of Sodium deoxycholate.jpg
| ImageSize2 = 180px
| ImageAlt2 = White powder in a stoppered glass vial
| IUPACName = 3α,12α-Dihydroxy-5β-cholan-24-oic acid
| SystematicName = (4''R'')-4-[(1''R'',3a''S'',3b''R'',5a''R'',7''R'',9a''S'',9b''S'',11''S'',11a''R'')-7,11-Dihydroxy-9a,11a-dimethylhexadecahydro-1''H''-cyclopenta[''a'']phenanthren-1-yl]pentanoic acid
| OtherNames = Deoxycholate
| Section1 = {{Chembox Identifiers
| IUPHAR_ligand = 610
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 005990WHZZ
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 406393
| InChI = 1/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1
| InChIKey = KXGVEGMKQFWNSR-LLQZFEROBK
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KXGVEGMKQFWNSR-LLQZFEROSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 83-44-3
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 193196
| PubChem = 222528
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28834
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB07690
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C04483
| 3DMet = B05128
| SMILES = C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
}}
| Section2 = {{Chembox Properties
|C=24|H=40|O=4
|   MolarMass =
|   Density =
|   MeltingPtC = 174-176
| pKa = 6.58<ref name="hand">{{Cite book | vauthors = Lide DR | year = 1998 | title = Handbook of Chemistry and Physics | edition = 87 | location = Boca Raton, FL | publisher = CRC Press | isbn = 978-0-8493-0594-8 | page = 1287 }}</ref>
| Solubility = 0.024%<ref>{{cite web | title = Deoxycholic acid | url = http://www.sigmaaldrich.com/etc/medialib/docs/Sigma/Product_Information_Sheet/d2510pis.Par.0001.File.tmp/d2510pis.pdf | work = Sigma Aldrich | access-date = 2013-10-10 | archive-date = 2020-06-06 | archive-url = https://web.archive.org/web/20200606005659/http://www.sigmaaldrich.com/etc/medialib/docs/Sigma/Product_Information_Sheet/d2510pis.Par.0001.File.tmp/d2510pis.pdf | url-status = dead }}</ref>
| MagSus = -272.0·10<sup>−6</sup> cm<sup>3</sup>/mol
  }}
| Section6 = {{Chembox Pharmacology
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| Legal_US = Rx-only
| Legal_US_comment = <ref name="Kybella FDA label">{{cite web | title=Kybella- deoxycholic acid injection, solution | website=DailyMed | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=fe431ed4-ea6f-4e99-b4bc-ec25ae7b8553 | access-date=20 June 2021 | archive-date=24 June 2021 | archive-url=https://web.archive.org/web/20210624200813/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=fe431ed4-ea6f-4e99-b4bc-ec25ae7b8553 | url-status=live }}</ref>
| Legal_EU = Rx-only
| Legal_EU_comment = <ref>{{cite web | title = Active substance: deoxycholic acid | publisher = [[Organization:European Medicines Agency|European Medicines Agency]] (EMA) | date = 10 December 2020 | url = https://www.ema.europa.eu/documents/psusa/deoxycholic-acid-list-nationally-authorised-medicinal-products-psusa/00010525/202004_en.pdf | access-date = 23 January 2021 | archive-date = 28 August 2021 | archive-url = https://web.archive.org/web/20210828055034/https://www.ema.europa.eu/en/documents/psusa/deoxycholic-acid-list-nationally-authorised-medicinal-products-psusa/00010525/202004_en.pdf | url-status = live }}</ref>
| Legal_UN =
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| Pregnancy_AU = B1
| Pregnancy_AU_comment = <ref name="Belkyra AU label">{{cite web | title=Belkyra (deoxycholic acid solution for injection) Product Information | website=TGA | url=https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2016-PI-02296-1 | format=PDF | access-date=23 June 2021 | archive-date=25 June 2021 | archive-url=https://web.archive.org/web/20210625022041/https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2016-PI-02296-1 | url-status=live }}</ref>
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{{Infobox drug
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<!-- Clinical data -->
| pronounce         =
| tradename         = Kybella, Belkyra
| Drugs.com         = {{drugs.com|monograph|deoxycholic-acid}}
| MedlinePlus       =
| licence_EU        = <!-- EMA uses INN (or special INN_EMA) -->
| DailyMedID        = Deoxycholic_acid
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}}

'''Deoxycholic acid''' is a [[Chemistry:Bile acid|bile acid]]. Deoxycholic acid is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. The two primary bile acids secreted by the liver are [[Chemistry:Cholic acid|cholic acid]] and [[Chemistry:Chenodeoxycholic acid|chenodeoxycholic acid]]. Bacteria metabolize chenodeoxycholic acid into the secondary bile acid [[Chemistry:Lithocholic acid|lithocholic acid]], and they metabolize cholic acid into deoxycholic acid. There are additional secondary bile acids, such as [[Chemistry:Ursodeoxycholic acid|ursodeoxycholic acid]]. Deoxycholic acid is soluble in [[Chemistry:Ethanol|alcohol]] and [[Chemistry:Acetic acid|acetic acid]]. When pure, it exists in a white to off-white crystalline powder form.

Deoxycholic acid is available as a generic medication in the United States as of April 2021, sold under the brand name '''Kybella''' among others.<ref>{{cite web | title=Deoxycholic acid: FDA-Approved Drugs | website=U.S. [[Organization:Food and Drug Administration|Food and Drug Administration]] (FDA) | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=212296 | access-date=19 June 2021 | archive-date=24 June 2021 | archive-url=https://web.archive.org/web/20210624200338/https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=212296 | url-status=live }}</ref>

==Applications==

Deoxycholic acid has been used since its discovery in various fields of human medicine. In the [[Medicine:Human body|human body]] deoxycholic acid is used in the emulsification of [[Chemistry:Fat|fat]]s for absorption in the [[Chemistry:Intestine|intestine]]. It has, in some countries (including Switzerland) been licensed as an emulsifier in food industry,<ref>{{cite journal | vauthors = Streuli H, etal | date = 1992 | journal = SLMB – Schweizer Lebensmittelbuch | title = Chapter 58 | volume = 4 | issue = 3 }}</ref> but it is no longer common. Outside the body it is used in experimental basis of [[Chemistry:Cholagogue|cholagogue]]s and is also in use to prevent and dissolve [[Medicine:Gallstone|gallstone]]s.{{cn|date=March 2022}}

In research deoxycholic acid is used as a mild detergent for the isolation of membrane associated proteins. The [[Chemistry:Critical micelle concentration|critical micelle concentration]] for deoxycholic acid is approximately 2.4–4 mM.<ref name="Neugebauer_1990">{{cite book | vauthors = Neugebauer JM | chapter = Detergents: An overview | title = Guide to Protein Purification | series = Methods in Enzymology | volume = 182 | pages = 239–53 | date = 1990 | publisher = Academic Press | pmid = 2314239 | doi = 10.1016/0076-6879(90)82020-3 | isbn = 9780121820831 }}</ref>

Sodium deoxycholate, the sodium salt of deoxycholic acid, is often used as a biological detergent to lyse cells and solubilise cellular and membrane components.<ref>{{cite web | url = http://www.nzp.co.nz/products.php?cid=2&pid=251 | archive-url = https://web.archive.org/web/20120207094016/http://www.nzp.co.nz/products.php?cid=2&pid=251 | archive-date = 7 February 2012 | title = Sodium deoxycholate | work = nzp.co.nz }}</ref> Sodium deoxycholate mixed with [[Chemistry:Phosphatidylcholine|phosphatidylcholine]], is used in [[Unsolved:Mesotherapy|mesotherapy]] injections to produce lipolysis, and has been used as an alternative to surgical excision in the treatment of lipomas.<ref name="pmid21824545">{{cite journal | vauthors = Duncan D, Rotunda AM | title = Injectable therapies for localized fat loss: state of the art | journal = Clinics in Plastic Surgery | volume = 38 | issue = 3 | pages = 489–501, vii | date = July 2011 | pmid = 21824545 | doi = 10.1016/j.cps.2011.02.005 }}</ref>

Deoxycholates and bile acid derivatives in general are actively being studied as structures for incorporation in nanotechnology.<ref>{{cite journal|pmc=6236364|doi=10.3390/60100047|title=A Simple Method for Synthesis of Active Esters of Isonicotinic and Picolinic Acids|journal=Molecules|volume=6|issue=12|pages=47–51|year=2001| vauthors = Christensen JB |citeseerx=10.1.1.362.1034|doi-access=free}}</ref>  They also have found application in microlithography as photoresistant components.<ref>{{cite journal | vauthors = Kim JB, Lee BW, Yun HJ, Kwon YG |title=193-nm Photoresists Based on Norbornene Copolymers with Derivatives of Bile Acid |journal=Chemistry Letters |volume=29 |issue=4 |pages=414–15 |year=2000 |doi=10.1246/cl.2000.414 }}</ref>

In the United States, deoxycholic acid, under the brand name Kybella, is approved by the [[Organization:Food and Drug Administration|Food and Drug Administration]] for reducing moderate-to-severe fat below the chin.<ref name="Kybella FDA label" /><ref name=FDA>{{cite web | url = https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm444978.htm | title = FDA approves treatment for fat below the chin | date = April 29, 2015 | publisher = [[Organization:Food and Drug Administration|Food and Drug Administration]] | access-date = December 16, 2019 | archive-date = May 1, 2015 | archive-url = https://web.archive.org/web/20150501175027/https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm444978.htm | url-status = dead }}</ref> When injected into [[Medicine:Submental triangle|submental]] fat, deoxycholic acid helps destroy (adipocytes) fat cells, which are metabolized by the body over the course of several months.<ref name=FDA/> Kybella is produced by Kythera Biopharmaceuticals.<ref>{{cite web |url=http://www.kythera.com/products/atx-101/ |title=ATX-101 – Kythera Biopharmaceuticals |publisher=Kythera.com |date=2014-06-20 |access-date=2016-11-02 |archive-date=2016-10-31 |archive-url=https://web.archive.org/web/20161031185613/http://kythera.com/products/atx-101/ |url-status=live }}</ref><ref name="cnn">{{cite web |vauthors=Christensen J |url=http://www.cnn.com/2015/04/30/health/chin-fat-drug-fda-approval/ |title=Double chin begone: It's an FDA yes for fat buster |publisher=CNN |date=2015-05-01 |access-date=2016-11-02 |archive-date=2016-10-31 |archive-url=https://web.archive.org/web/20161031193029/http://www.cnn.com/2015/04/30/health/chin-fat-drug-fda-approval |url-status=live }}</ref>

== Research in immunology ==

Its function as a detergent and isolating agent for membrane proteins also suits it for production of outer membrane protein (OMP) vaccines such as MenB, a Norwegian vaccine developed in the early 1990s.<ref name="pmid1812438">{{cite journal | vauthors = Fredriksen JH, Rosenqvist E, Wedege E, Bryn K, Bjune G, Frøholm LO, Lindbak AK, Møgster B, Namork E, Rye U | display-authors = 6 | title = Production, characterization and control of MenB-vaccine "Folkehelsa": an outer membrane vesicle vaccine against group B meningococcal disease | journal = NIPH Annals | volume = 14 | issue = 2 | pages = 67–79; discussion 79–80 | date = December 1991 | pmid = 1812438 }}</ref> The [[Chemistry:MeNZB|MeNZB]] vaccine was produced using the same method.<ref>{{cite web | url = http://www.scoop.co.nz/stories/GE0506/S00048.htm | title = MeNZB – Use science not opinion! | work = scoop.co.nz | date = 10 June 2005 | access-date = 12 April 2011 | archive-date = 27 April 2021 | archive-url = https://web.archive.org/web/20210427174121/https://www.scoop.co.nz/stories/GE0506/S00048.htm | url-status = live }}</ref>

Deoxycholic acid binds and activates the membrane enzyme NAPE-PLD, which catalyzes the release of the endogenous cannabinoid [[Chemistry:Anandamide|anandamide]] and other N-acylethanolamines. These bioactive signaling molecules play important roles in several physiological pathways including stress and [[Medicine:Pain|pain]] response, [[Medicine:Appetite|appetite]], and [[Biology:Life expectancy|lifespan]].<ref name="Garau">{{cite journal | vauthors = Magotti P, Bauer I, Igarashi M, Babagoli M, Marotta R, Piomelli D, Garau G | title = Structure of human N-acylphosphatidylethanolamine-hydrolyzing phospholipase D: regulation of fatty acid ethanolamide biosynthesis by bile acids | journal = Structure | volume = 23 | issue = 3 | pages = 598–604 | date = March 2015 | pmid = 25684574 | pmc = 4351732 | doi = 10.1016/j.str.2014.12.018 }}</ref>

Some publications point towards the effect of deoxycholic acid as an [[Biology:Immunostimulant|immunostimulant]]<ref>{{cite journal | vauthors = Vlček B | title = Potentiation of the immune response with DCA | language = Czech | journal = Prakt. Lekar | volume = 52 | pages = 326–30 | date = 1972 }}</ref><ref>Chyle M., Chyle P.: ''Regulation of the immune response with DCA'' (Czech, engl. summary), Sbornik lek. 84, 212–18 (1982)</ref> of the [[Biology:Innate immune system|innate immune system]], activating its main actors, the [[Biology:Macrophage|macrophage]]s. According to these publications, a sufficient amount of deoxycholic acid in the human body would correspond with a good immune reaction of the non-specific immune system. Clinical studies conducted in the 1970s and 1980s confirm the expectation that deoxycholic acid is involved in the natural healing processes of local [[Medicine:Inflammation|inflammation]]s,<ref>{{cite journal | vauthors = Vlček B | date = 1972 | title = Deoxycholic acid as a potential cancerostatic and antiviral factor | pages = 145–47 | journal = Advances in Antimicrobial and Antineoplastic Chemotherapy | volume = II | issue = 1 | publisher = Urban & Schwarzenberg | location = München }}</ref><ref>{{cite conference | vauthors = Chyle M, Chyle P, Dolezal V | publisher = Institute f. Hygiene and Epidemiology, Prag | title = Deoxycholic acid – Therapy of viral infections and a toxicological inquiry | conference = 2nd Symp. on Prevention and Treatment of Viral Infections | location = Bechyne Castle | date = 1988 | page = 56 }}</ref> different types of [[Medicine:Herpes|herpes]],<ref name="pmid1182754">{{cite journal | vauthors = Chýle M, Chýle P | title = [Deoxycholic acid in the therapy of herpes labialis (author's transl)] | language = Czech | journal = Casopis Lekaru Ceskych | volume = 114 | issue = 40 | pages = 1226–9 | date = October 1975 | pmid = 1182754 | doi =  }}</ref><ref>{{cite journal | vauthors = Bradna J, ((Poliklinik, Kutna Hora)) | title = Treatment of herpes zoster with deoxycholic acid | language = Czech | journal = Rehabilitacia | location = Bratislava | volume = 16 | pages = 77–86 | date = 1983 }}</ref> and possibly [[Medicine:Cancer|cancer]].<ref>{{cite journal | vauthors = Vlcek B, Reif A, Budský F | title = Toxicity of deoxycholate at pH below 7.3 as a potential cancerostatic property | journal = Experientia | volume = 26 | issue = 7 | pages = 776–8 | year = 1970 | pmid = 5431154 | doi = 10.1007/BF02232545 | s2cid = 26829935 }}</ref><ref name="pmid4398280">{{cite journal | vauthors = Vlcek B, Reif A, Seidlová B | title = Evidence of the participation of deoxycholate in cancer immunity | journal = Zeitschrift für Naturforschung B | volume = 26 | issue = 5 | pages = 419–24 | date = May 1971 | pmid = 4398280 | doi = 10.1515/znb-1971-0509 | doi-access = free }}</ref>

==Research in cancer==
Deoxycholate and other secondary bile acids cause DNA damage.<ref>{{cite journal | vauthors = Bernstein H, Bernstein C, Payne CM, Dvorakova K, Garewal H | title = Bile acids as carcinogens in human gastrointestinal cancers | journal = Mutation Research | volume = 589 | issue = 1 | pages = 47–65 | date = January 2005 | pmid = 15652226 | doi = 10.1016/j.mrrev.2004.08.001 }}</ref>  Secondary bile acids increase intracellular production of reactive oxygen and reactive nitrogen species resulting in increased oxidative stress and DNA damage.<ref>{{cite journal | vauthors = Tsuei J, Chau T, Mills D, Wan YJ | title = Bile acid dysregulation, gut dysbiosis, and gastrointestinal cancer | journal = Experimental Biology and Medicine | volume = 239 | issue = 11 | pages = 1489–504 | date = November 2014 | pmid = 24951470 | pmc = 4357421 | doi = 10.1177/1535370214538743 }}</ref><ref>{{cite journal | vauthors = Ajouz H, Mukherji D, Shamseddine A | title = Secondary bile acids: an underrecognized cause of colon cancer | journal = World Journal of Surgical Oncology | volume = 12 | issue = 1 | pages = 164 | date = May 2014 | pmid = 24884764 | pmc = 4041630 | doi = 10.1186/1477-7819-12-164 | doi-access = free }}</ref> As shown in the figure below, deoxycholate added to the diet of mice increased the level of [[Chemistry:8-Oxo-2'-deoxyguanosine|8-oxo-dG]], an oxidative DNA damage, in the colonic epithelium of mice.  When the level of deoxycholate-induced DNA damage is high, DNA repair enzymes that ordinarily reverse DNA damage may not be able to keep up.{{cn|date=March 2022}}

DNA damage has frequently been proposed as a major cause of cancer.<ref name="pmid373122">{{cite journal | vauthors = Ames BN | title = Identifying environmental chemicals causing mutations and cancer | journal = Science | volume = 204 | issue = 4393 | pages = 587–93 | date = May 1979 | pmid = 373122 | doi = 10.1126/science.373122 | bibcode = 1979Sci...204..587A }}</ref><ref>{{cite journal | vauthors = Tudek B, Winczura A, Janik J, Siomek A, Foksinski M, Oliński R | title = Involvement of oxidatively damaged DNA and repair in cancer development and aging | journal = American Journal of Translational Research | volume = 2 | issue = 3 | pages = 254–84 | date = May 2010 | pmid = 20589166 | pmc = 2892402 }}</ref>  DNA damage can give rise to cancer by causing mutations.{{cn|date=March 2022}}

When deoxycholate was added to the food of mice so that their feces contained deoxycholate at about the same level present in feces of human on a high fat diet, 45% to 56% of the mice developed colon cancer over the next 10 months, while none of the mice on a diet without deoxycholate developed cancer.<ref name=Prasad /><ref>{{cite journal | vauthors = Bernstein C, Holubec H, Bhattacharyya AK, Nguyen H, Payne CM, Zaitlin B, Bernstein H | title = Carcinogenicity of deoxycholate, a secondary bile acid | journal = Archives of Toxicology | volume = 85 | issue = 8 | pages = 863–71 | date = August 2011 | pmid = 21267546 | pmc = 3149672 | doi = 10.1007/s00204-011-0648-7 }}</ref>  Thus, exposure of the colon to deoxycholate may cause cancer in mice. However, this same study reported that, when [[Chemistry:Chlorogenic acid|chlorogenic acid]] was added to the diet alongside deoxycholate, only 18% of the mice developed colon cancer. Chlorogenic acid is a component of common foods and beverages; coffee contains an average of 53.8&nbsp;mg chlorogenic acid per 100 ml.<ref>{{cite journal | vauthors = Jeon JS, Kim HT, Jeong IH, Hong SR, Oh MS, Yoon MH, Shim JH, Jeong JH, Abd El-Aty AM | title = Contents of chlorogenic acids and caffeine in various coffee-related products | journal = Journal of Advanced Research | volume = 17 | pages = 85–94 | date = May 2019 | pmid = 31193351 | pmc = 6526205 | doi = 10.1016/j.jare.2019.01.002 }}</ref> Therefore, to consume the level of chlorogenic acid used in the study, a human on a "standard" 2000-calorie daily diet (416 g/d; 250g carbs, 100g protein, 66g fat) would need to consume roughly 55 mL of coffee each day, or just under 2 fluid ounces.

In humans, higher levels of colonic deoxycholate are associated with higher frequencies of colon cancer.  As an example, the fecal deoxycholate concentrations in African Americans (who eat a relatively high fat diet) is more than five times higher than fecal deoxycholate of Native Africans in South Africa (who eat a low fat diet).<ref>{{cite journal | vauthors = Ou J, DeLany JP, Zhang M, Sharma S, O'Keefe SJ | title = Association between low colonic short-chain fatty acids and high bile acids in high colon cancer risk populations | journal = Nutrition and Cancer | volume = 64 | issue = 1 | pages = 34–40 | year = 2012 | pmid = 22136517 | pmc = 6844083 | doi = 10.1080/01635581.2012.630164 }}</ref>  Male African Americans have a high incidence of colon cancer of 72 per 100,000,<ref>{{cite web | publisher = American Cancer Society | url = http://www.cancer.org/Research/CancerFactsFigures/cancer-facts-figures-2009 | title = Cancer Facts and Figures | date = 2009 | access-date = 2015-04-07 | archive-date = 2012-09-13 | archive-url = https://web.archive.org/web/20120913232938/http://www.cancer.org/Research/CancerFactsFigures/cancer-facts-figures-2009 | url-status = live }}</ref> while Native Africans in South Africa have a low incidence rate of colon cancer of less than 1 per 100,000,<ref>{{cite journal | vauthors = O'Keefe SJ, Kidd M, Espitalier-Noel G, Owira P | title = Rarity of colon cancer in Africans is associated with low animal product consumption, not fiber | journal = The American Journal of Gastroenterology | volume = 94 | issue = 5 | pages = 1373–80 | date = May 1999 | doi = 10.1111/j.1572-0241.1999.01089.x | pmid = 10235221 | s2cid = 6402410 }}</ref> a more than 72-fold difference in rates of colon cancer.

A prospective human study investigating the relationship between microbial metabolites and cancer found a strong correlation between circulating deoxycholic acid and [[Medicine:Colorectal cancer|colorectal cancer]] risk in women.<ref>Erikka Loftfield, PhD, MPH, Roni T Falk, MS, Joshua N Sampson, PhD, Wen-Yi Huang, PhD, Autumn Hullings, MPH, Gwen Murphy, PhD, MPH, Stephanie J Weinstein, PhD, Demetrius Albanes, MD, Neal D Freedman, PhD, MPH, Rashmi Sinha, PhD, Prospective Associations of Circulating Bile Acids and Short-Chain Fatty Acids with Incident Colorectal Cancer, JNCI Cancer Spectrum, 2022;, pkac027, https://doi.org/10.1093/jncics/pkac027 {{Webarchive|url=https://web.archive.org/web/20220702225333/https://academic.oup.com/jncics/article/6/3/pkac027/6555997 |date=2022-07-02 }}</ref>

==Factors affecting deoxycholate levels==
A number of factors, including diet, obesity, and exercise, affect the level of deoxycholate in the human colon.  When humans were switched from their usual diet to a meat, egg and cheese based diet for five days, deoxycholate in their feces increased by factors of 2 to 10 fold.<ref>{{cite journal | vauthors = David LA, Maurice CF, Carmody RN, Gootenberg DB, Button JE, Wolfe BE, Ling AV, Devlin AS, Varma Y, Fischbach MA, Biddinger SB, Dutton RJ, Turnbaugh PJ | display-authors = 6 | title = Diet rapidly and reproducibly alters the human gut microbiome | journal = Nature | volume = 505 | issue = 7484 | pages = 559–63 | date = January 2014 | pmid = 24336217 | pmc = 3957428 | doi = 10.1038/nature12820 | bibcode = 2014Natur.505..559D }}</ref>  Rats fed diets with 30% beef tallow (high fat) had almost 2-fold more deoxycholate in their feces than rats fed 5% beef tallow (low fat).<ref name=Han>{{cite journal | vauthors = Han Y, Haraguchi T, Iwanaga S, Tomotake H, Okazaki Y, Mineo S, Moriyama A, Inoue J, Kato N | display-authors = 6 | title = Consumption of some polyphenols reduces fecal deoxycholic acid and lithocholic acid, the secondary bile acids of risk factors of colon cancer | journal = Journal of Agricultural and Food Chemistry | volume = 57 | issue = 18 | pages = 8587–90 | date = September 2009 | pmid = 19711910 | doi = 10.1021/jf900393k }}</ref>  In the same study, adding the further dietary elements of [[Chemistry:Curcumin|curcumin]] or [[Chemistry:Caffeic acid|caffeic acid]] to the rats' high fat (30% beef tallow) diet reduced the deoxycholate in their feces to levels comparable to levels seen in the rats on a low fat diet.  Curcumin is a component of the spice turmeric, and caffeic acid is a component high in some fruits and spices.<ref>{{cite web |url=http://phenol-explorer.eu/contents/polyphenol/457 |title=Phenol-Explorer: Showing all foods in which the polyphenol Caffeic acid is found |publisher=Phenol-explorer.eu |access-date=2016-11-02 |archive-date=2017-10-19 |archive-url=https://web.archive.org/web/20171019135032/http://phenol-explorer.eu/contents/polyphenol/457 |url-status=live }}</ref>  Caffeic acid is also a digestive break-down product of chlorogenic acid, high in coffee and some fruits and vegetables.<ref>{{cite journal | vauthors = Clifford M | year = 1999 | title = Chlorogenic acids and other cinnamates – nature, occurrence and dietary burden | journal = J. Sci. Food Agric. | volume = 79 | issue = 3| pages = 362–72 | doi=10.1002/(sici)1097-0010(19990301)79:3<362::aid-jsfa256>3.0.co;2-d}}</ref>[[File:Colonic epithelium mouse without tumorigenesis (A) and with tumorigenesis (B). Brown shows 8-oxo-dG.jpg|thumb|277x277px|Colonic epithelium from a mouse not undergoing colonic tumorigenesis (A), and a mouse that is undergoing colonic tumorigenesis (B). Cell nuclei are stained dark blue with hematoxylin (for nucleic acid) and immunostained brown for 8-oxo-dG. The level of 8-oxo-dG was graded in the nuclei of colonic crypt cells on a scale of 0–4. Mice not undergoing tumorigenesis had crypt 8-oxo-dG at levels 0 to 2 (panel A shows level 1) while mice progressing to colonic tumors had 8-oxo-dG in colonic crypts at levels 3 to 4 (panel B shows level 4)  Tumorigenesis was induced by adding deoxycholate to the mouse diet to give a level of deoxycholate in the mouse colon similar to the level in the colon of humans on a high fat diet.<ref name="Prasad">{{cite journal | vauthors = Prasad AR, Prasad S, Nguyen H, Facista A, Lewis C, Zaitlin B, Bernstein H, Bernstein C | display-authors = 6 | title = Novel diet-related mouse model of colon cancer parallels human colon cancer | journal = World Journal of Gastrointestinal Oncology | volume = 6 | issue = 7 | pages = 225–43 | date = July 2014 | pmid = 25024814 | pmc = 4092339 | doi = 10.4251/wjgo.v6.i7.225 | doi-access = free }}</ref>  The images were made from original photomicrographs.|left]]In addition to fats, the type or amount of protein in the diet may also affect bile acid levels.  Switching from a diet with protein provided by casein to a diet with protein provided by salmon protein hydrolysate led to as much as a 6-fold increase in levels of bile acids in the blood plasma of rats.<ref>{{cite journal | vauthors = Liaset B, Hao Q, Jørgensen H, Hallenborg P, Du ZY, Ma T, Marschall HU, Kruhøffer M, Li R, Li Q, Yde CC, Criales G, Bertram HC, Mellgren G, Ofjord ES, Lock EJ, Espe M, Frøyland L, Madsen L, Kristiansen K | display-authors = 6 | title = Nutritional regulation of bile acid metabolism is associated with improved pathological characteristics of the metabolic syndrome | journal = The Journal of Biological Chemistry | volume = 286 | issue = 32 | pages = 28382–95 | date = August 2011 | pmid = 21680746 | pmc = 3151081 | doi = 10.1074/jbc.M111.234732 | doi-access = free }}</ref>  In humans, adding high protein to a high fat diet raised the level of deoxycholate in the plasma by almost 50%.<ref name="pmid19710199">{{cite journal | vauthors = Bortolotti M, Kreis R, Debard C, Cariou B, Faeh D, Chetiveaux M, Ith M, Vermathen P, Stefanoni N, Lê KA, Schneiter P, Krempf M, Vidal H, Boesch C, Tappy L | display-authors = 6 | title = High protein intake reduces intrahepatocellular lipid deposition in humans | journal = The American Journal of Clinical Nutrition | volume = 90 | issue = 4 | pages = 1002–10 | date = October 2009 | pmid = 19710199 | doi = 10.3945/ajcn.2008.27296 | doi-access = free }}</ref>

Obesity has been linked to cancer,<ref>{{cite journal | vauthors = Ungefroren H, Gieseler F, Fliedner S, Lehnert H | title = Obesity and cancer | journal = Hormone Molecular Biology and Clinical Investigation | volume = 21 | issue = 1 | pages = 5–15 | date = January 2015 | pmid = 25719336 | doi = 10.1515/hmbci-2014-0046 | s2cid = 207452705 }}</ref> and this link is in part through deoxycholate.<ref name=Bradlow>{{cite journal | vauthors = Bradlow HL | title = Obesity and the gut microbiome: pathophysiological aspects | journal = Hormone Molecular Biology and Clinical Investigation | volume = 17 | issue = 1 | pages = 53–61 | date = January 2014 | pmid = 25372730 | doi = 10.1515/hmbci-2013-0063 | s2cid = 22924768 }}</ref><ref>{{cite journal | vauthors = Devkota S, Turnbaugh PJ | title = Cancer: An acidic link | journal = Nature | volume = 499 | issue = 7456 | pages = 37–8 | date = July 2013 | pmid = 23803768 | doi = 10.1038/nature12404 | bibcode = 2013Natur.499...37D | s2cid = 12714870 }}</ref><ref>{{cite journal | vauthors = Ohtani N, Yoshimoto S, Hara E | title = Obesity and cancer: a gut microbial connection | journal = Cancer Research | volume = 74 | issue = 7 | pages = 1885–9 | date = April 2014 | pmid = 24638983 | doi = 10.1158/0008-5472.CAN-13-3501 | doi-access = free }}</ref>  In obese people, the relative proportion of Firmicutes (Gram-positive bacteria) in gut microbiota is increased resulting in greater conversion of the non-genotoxic primary bile acid, cholic acid, to carcinogenic deoxycholate.<ref name=Bradlow />

Exercise decreases deoxycholate in the colon.  Humans whose level of physical activity placed them in the top third had a 17% decrease in fecal bile acid concentration compared to those whose level of physical activity placed them in the lowest third.<ref>{{cite journal | vauthors = Wertheim BC, Martínez ME, Ashbeck EL, Roe DJ, Jacobs ET, Alberts DS, Thompson PA | title = Physical activity as a determinant of fecal bile acid levels | journal = Cancer Epidemiology, Biomarkers & Prevention | volume = 18 | issue = 5 | pages = 1591–8 | date = May 2009 | pmid = 19383885 | pmc = 2743306 | doi = 10.1158/1055-9965.EPI-08-1187 }}</ref>  Rats provided with an exercise wheel had a lower ratio of secondary bile acids to primary bile acids than sedentary rats in their feces.<ref>{{cite journal | vauthors = Hagio M, Matsumoto M, Yajima T, Hara H, Ishizuka S | title = Voluntary wheel running exercise and dietary lactose concomitantly reduce proportion of secondary bile acids in rat feces | journal = Journal of Applied Physiology | volume = 109 | issue = 3 | pages = 663–8 | date = September 2010 | pmid = 20616226 | doi = 10.1152/japplphysiol.00777.2009 | s2cid = 7982611 }}</ref>  There is a positive association of exercise and physical activity with cancer prevention, tolerance to cancer-directed therapies (radiation and chemotherapy), reduction in recurrence, and improvement in survival.<ref>{{cite journal | vauthors = Jeon JY, Meyerhardt JA | title = Exercise after cancer diagnosis: time to get moving | journal = Oncology | volume = 27 | issue = 6 | pages = 585–6, 588 | date = June 2013 | pmid = 23909074 }}</ref>

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== References ==
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{{Other dermatological preparations}}

{{DEFAULTSORT:Deoxycholic Acid}}
[[Category:Bile acids]]
[[Category:Cholanes]]

{{Sourceattribution|Deoxycholic acid}}