{{위키데이터 속성 추적}}
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477002603
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Liponic Acid Structural Formula V.2.svg
| ImageFile1 = Lipoic-acid-3D-vdW.png
| ImageFile2 = File:Lipoic-acid-from-xtal-3D-bs-17.png
| IUPACName = (''R'')-5-(1,2-dithiolan-3-yl)pentanoic acid
| OtherNames = α-lipoic acid,</br>alpha lipoic acid,</br>thioctic acid,</br>6,8-dithiooctanoic acid
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 4822
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5886
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C16241
| InChI = 1/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1
| InChIKey = AGBQKNBQESQNJD-SSDOTTSWBZ
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 134342
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = AGBQKNBQESQNJD-SSDOTTSWSA-N
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1 = 1200-22-2
| CASNo1_Comment = (''R'')
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 1077-28-7
| CASNo_Comment = (racemate)
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1= VLL71EBS9Z
| UNII1_Comment = (''R'')
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 73Y7P0K73Y
| UNII_Comment = (racemate)
| PubChem = 6112
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00166
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 30314
| SMILES = O=C(O)CCCC[C@H]1SSCC1
| MeSHName = Lipoic+acid

 }}
|Section2={{Chembox Properties
| C=8 | H=14 | O=2 | S=2
| Appearance = 노란색 바늘 모양의 결정
| Solubility = 아주 약간 용해됨(0.24 g/L)<ref name="pubmed">{{웹 인용|url= https://pubchem.ncbi.nlm.nih.gov/compound/thioctic_acid#section=Physical-Description|title=Lipoic Acid |author=<!--Not stated--> |website=Pubmed |publisher=NCBI |access-date=October 18, 2018 }}</ref>
| SolubleOther = 용해됨
| Solvent = ethanol 50 mg/mL
| Density =
| MeltingPtC = 60-62
| BoilingPtC = 
 }}
|Section7={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
 }}
|Section6={{Chembox Pharmacology
| ATCCode_prefix = A16
| ATCCode_suffix = AX01
| Bioavail = 30% (oral)<ref>{{저널 인용|last1= Teichert |first1= J |last2= Hermann |first2= R |last3= Ruus |first3= P |last4= Preiss |first4= R |title= Plasma kinetics, metabolism, and urinary excretion of alpha-lipoic acid following oral administration in healthy volunteers |journal= [[The Journal of Clinical Pharmacology]] |volume= 43 |issue= 11 |pages= 1257–67 |date= November 2003 |pmid= 14551180 |doi= 10.1177/0091270003258654 |s2cid= 30589232 }}</ref>
 }}
|Section8={{Chembox Related
| OtherCompounds = [[리포아마이드]],</br>[[아스파라거스산]]
 }}
}}

'''리포산'''({{llang|en|lipoic acid}}, '''LA''')은 [[카프릴산]](옥탄산)으로부터 파생된 [[유기 황 화합물]]이다.<ref name="lpi">{{웹 인용|url=https://lpi.oregonstate.edu/mic/dietary-factors/lipoic-acid|title=Lipoic acid|date=1 January 2019|publisher=Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis|access-date=5 November 2019}}</ref> '''α-리포산'''({{llang|en|α-lipoic acid}}, '''ALA'''), '''싸이옥트산'''({{llang|en|thioctic acid}})이라고도 한다. 리포산은 동물에서 정상적으로 만들어지며, [[호기성 대사]]에 필수적이다. 또한 제조되어 [[항산화제]]로 판매되는 일부 국가에서는 [[식이 보충제]]로 사용되며, 다른 국가에서는 [[의약품]]으로도 사용된다.<ref name=lpi/>

== 질병 ==

=== 복합 말론산 메틸말론산 산성뇨증(CMAMMA) ===
ACSF3 결핍으로 인한 대사성 질환[[복합 말론산 메틸말론산 산성뇨증]](CMAMMA)에서는 리포산 생합성의 전구체 반응인 미토콘드리아 지방산 합성(mtFASII)이 손상됩니다.<ref>{{저널 인용|제목=Combined malonic and methylmalonic aciduria due to ACSF3 mutations: Benign clinical course in an unselected cohort|저널=Journal of Inherited Metabolic Disease|성=Levtova|이름=Alina|성2=Waters|이름2=Paula J.|url=https://onlinelibrary.wiley.com/doi/10.1002/jimd.12032|날짜=2019-01|권=42|호=1|쪽=107–116|언어=en|doi=10.1002/jimd.12032|issn=0141-8955|성3=Buhas|이름3=Daniela|성4=Lévesque|이름4=Sébastien|성5=Auray‐Blais|이름5=Christiane|성6=Clarke|이름6=Joe T.R.|성7=Laframboise|이름7=Rachel|성8=Maranda|이름8=Bruno|성9=Mitchell|이름9=Grant A.}}</ref><ref name=":0">{{저널 인용|제목=The emerging role of the mitochondrial fatty-acid synthase (mtFASII) in the regulation of energy metabolism|저널=Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids|성=Wehbe|이름=Zeinab|성2=Behringer|이름2=Sidney|url=https://linkinghub.elsevier.com/retrieve/pii/S1388198119301349|날짜=2019-11|권=1864|호=11|쪽=1629–1643|언어=en|doi=10.1016/j.bbalip.2019.07.012|성3=Alatibi|이름3=Khaled|성4=Watkins|이름4=David|성5=Rosenblatt|이름5=David|성6=Spiekerkoetter|이름6=Ute|성7=Tucci|이름7=Sara}}</ref> 그 결과 [[피루브산 탈수소효소 복합체]](PDC) 및 [[알파-케토글루타르산 탈수소효소 복합체|α-케토글루타레이트 탈수소효소 복합체]](α-KGDH)와 같은 중요한 미토콘드리아 효소의 [[번역 후 변형|리포일화]] 정도가 감소합니다.<ref name=":0" /> 리포산을 보충한다고 해서 미토콘드리아 기능이 회복되지는 않습니다.<ref>{{저널 인용|제목=Mitochondrial fatty acid synthesis and respiration|저널=Biochimica et Biophysica Acta (BBA) - Bioenergetics|성=Hiltunen|이름=J. Kalervo|성2=Autio|이름2=Kaija J.|url=https://linkinghub.elsevier.com/retrieve/pii/S000527281000112X|날짜=2010-06|권=1797|호=6-7|쪽=1195–1202|언어=en|doi=10.1016/j.bbabio.2010.03.006|성3=Schonauer|이름3=Melissa S.|성4=Kursu|이름4=V.A. Samuli|성5=Dieckmann|이름5=Carol L.|성6=Kastaniotis|이름6=Alexander J.}}</ref><ref name=":0" />   

== 같이 보기 ==
* [[보조 인자]]
* [[리포아마이드]]

== 각주 ==
{{각주}}

{{효소 보조 인자}}
{{항산화제}}
{{식사 보충물}}
{{기타 소화관 및 대사산물}}

[[분류:산화 방지제]]
[[분류:카복실산]]
[[분류:보조 인자]]
[[분류:유기 이황화물]]
[[분류:다이사이올레인]]
[[분류:항노화 물질]]