Apocholic acid

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| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 426288097

| Reference =[http://www.sigmaaldrich.com/catalog/ProductDetail.do?N4=260142 |ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC Apocholic acid]{{dead link|date=October 2016 |bot=InternetArchiveBot |fix-attempted=yes }} at Sigma-Aldrich

| ImageFile =Apocholic acid.svg

| ImageSize =

| IUPACName = 3α,12α-Dihydroxy-5β-chol-8(14)-en-24-oic acid

| SystematicName = (4R)-4-[(1R,5aR,7R,9aS,9bR,11S,11aR)-7,11-Dihydroxy-9a,11a-dimethyl-2,3,4,5,5a,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid

| OtherNames = 3α,12α-Dihydroxy-5β,8(14)-cholen-24-oic acid; 5β,8(14)-Cholen-24-oic acid-3α,12α-diol

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo =641-81-6

| CASNo2_Ref = {{cascite|correct|CAS}}

| CASNo2 = 63949-02-0

| CASNo2_Comment = (sodium apocholate)

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = MZW7515V5Z

| UNII2 = U2L03X5GY0

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2_Comment = (sodium apocholate)

| PubChem =101818

| SMILES =C[C@H](CCC(O)=O)[C@@]1([H])CCC2=C3CC[C@]4([H])C[C@H](O)CC[C@]4(C)C3C[C@H](O)[C@@]21C

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 91993

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = XWJTYEGVQBFZHI-IMPNNSMHSA-N

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI =1S/C24H38O4/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/h14-16,18,20-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,18-,20+,21+,23+,24-/m1/s1

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|Section2={{Chembox Properties

| C=24 | H=38 | O=4

| Appearance =

| Density =

| MeltingPtC = 175 to 176

| MeltingPt_notes =

| BoilingPt =

| Solubility =

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|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

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Apocholic acid is an unsaturated bile acid first characterized in the 1920s.{{cite journal |author1=Boedecker, F. |author2=Volk, H. | title = Unsaturated bile acids. III. Relations of apocholic acid, dihydroxycholenic acid (m. 260) and cholic acid to desoxycholic acid | journal = Berichte der Deutschen Chemischen Gesellschaft B | year = 1922 | volume = 55 | pages = 2302–2309|doi=10.1002/cber.19220550810 }} It has questionable carcinogenic activity as experimentally, sarcomas were induced in mice with injection of deoxycholic acid. {{cite journal |title=Carcinogenic activity of apocholic acid |volume = 190|issue = 4780|pages = 1007–8|last=Lacassagne |first=A |journal=Nature |date=June 10, 1961 |pmid = 13831121|doi = 10.1038/1901007a0|bibcode = 1961Natur.190.1007L| s2cid=4175440 }}

The salts and esters of apocholic acid are known as apocholates.{{cn|date=March 2022}}

:File:Sodium apocholate.svg{{clear-left}}