Record Information
Version1.0
Creation date2010-04-08 22:06:12 UTC
Update date2019-11-26 02:59:58 UTC
Primary IDFDB004339
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namealpha-Lipoic acid
DescriptionLipoate, also known as lipoic acid or 6,8-thioctate, belongs to lipoic acids and derivatives class of compounds. Those are compounds containing a lipoic acid moiety (or a derivative thereof), which consists of a pentanoic acid (or derivative) attached to the C3 carbon atom of a 1,2-dithiolane ring. Lipoate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Lipoate can be synthesized from octanoic acid. Lipoate can also be synthesized into lipoamide and lipoyl-AMP. Lipoate can be found in broccoli and spinach, which makes lipoate a potential biomarker for the consumption of these food products. Lipoate may be a unique E.coli metabolite. Lipoate is a non-carcinogenic (not listed by IARC) potentially toxic compound.
CAS Number62-46-4
Structure
Thumb
Synonyms
SynonymSource
1,2-Dithiolane-3-pentanoic acidChEBI
1,2-Dithiolane-3-valeric acidChEBI
5-(1,2-Dithiolan-3-yl)valeric acidChEBI
5-(Dithiolan-3-yl)valeric acidChEBI
5-[3-(1,2-Dithiolanyl)]pentanoic acidChEBI
6,8-Thioctic acidChEBI
6,8-Thiotic acidChEBI
6-Thioctic acidChEBI
6-Thiotic acidChEBI
Acetate-replacing factorChEBI
alpha-Lipoic acidChEBI
alpha-LiponsaeureChEBI
BiletanChEBI
Liponic acidChEBI
ThioctansaeureChEBI
Thioctic acidChEBI
ThioctsaeureChEBI
ThioktsaeureChEBI
Lipoic acidKegg
DL-alpha-Lipoic acidKegg
DL-Thioctic acidKegg
ThiotominKegg
1,2-Dithiolane-3-pentanoateGenerator
1,2-Dithiolane-3-valerateGenerator
5-(1,2-Dithiolan-3-yl)valerateGenerator
5-(Dithiolan-3-yl)valerateGenerator
5-[3-(1,2-Dithiolanyl)]pentanoateGenerator
6,8-ThioctateGenerator
6,8-ThiotateGenerator
6-ThioctateGenerator
6-ThiotateGenerator
Acetic acid-replacing factorGenerator
a-LipoateGenerator
a-Lipoic acidGenerator
alpha-LipoateGenerator
Α-lipoateGenerator
Α-lipoic acidGenerator
a-LiponsaeureGenerator
Α-liponsaeureGenerator
LiponateGenerator
ThioctateGenerator
DL-a-LipoateGenerator
DL-a-Lipoic acidGenerator
DL-alpha-LipoateGenerator
DL-Α-lipoateGenerator
DL-Α-lipoic acidGenerator
DL-ThioctateGenerator
(R)-LipoateGenerator
Alpha LipogammaMeSH
Alpha Liponsaure sofotecMeSH
Alpha-LipogammaMeSH
Alpha-Lippon alMeSH
AlphaLipogammaMeSH
AlphaflamMeSH
Generosan brand OF thioctic acidMeSH
JuthiacMeSH
Liponsaure-ratiopharmMeSH
LiponsaureratiopharmMeSH
Merck dura brand OF thioctic acidMeSH
Pleomix Alpha NMeSH
Pleomix-Alpha NMeSH
Rosen brand OF thioctic acidMeSH
Thiogamma oralMeSH
TromliponMeSH
Trommsdorgg brand OF thioctic acidMeSH
Viatris brand OF thioctic acid tromethamineMeSH
alpha Lipoic acidMeSH
alpha-Liponsaure von CTMeSH
AlphaLiponaure heumannMeSH
AlphaLiponsaure von CTMeSH
biomo LiponMeSH
Esparma brand OF thioctic acidMeSH
Acid, alpha-lipoicMeSH
Alpha Lipon stadaMeSH
Alpha Lippon alMeSH
AlphaLipon stadaMeSH
AlphaLiponsaure sofotecMeSH
AlphaLippon alMeSH
Hexal brand OF thioctic acidMeSH
Injekt, thiogammaMeSH
Liponsaure ratiopharmMeSH
Pleomix AlphaMeSH
Stadapharm brand OF thioctic acidMeSH
Thioctacide TMeSH
Viatris brand OF thioctic acidMeSH
alpha Liponsaure von CTMeSH
AlphaVibolexMeSH
BiomoliponMeSH
Ratiopharm brand OF thioctic acidMeSH
Aliud brand OF thioctic acidMeSH
Alpha-Liponsaure sofotecMeSH
AzulipontMeSH
Illa brand OF thioctic acidMeSH
Illa brand OF thioctic acid tromethamineMeSH
MTW AlphaliponsaureMeSH
MTW Brand OF thioctic acidMeSH
Pharmacia brand OF thioctic acidMeSH
Pleomix-AlphaMeSH
PleomixAlphaMeSH
PleomixAlpha NMeSH
Q Pharm brand OF thioctic acidMeSH
Q-Pharm brand OF thioctic acidMeSH
Verla liponMeSH
Verla-liponMeSH
alpha Liponaure heumannMeSH
alpha VibolexMeSH
biomo-LiponMeSH
DuraliponMeSH
Alpha-Lipon stadaMeSH
Azupharma brand OF thioctic acidMeSH
FenintMeSH
Heumann brand OF thioctic acidMeSH
Juta brand OF thioctic acidMeSH
Lichtenstein brand OF thioctic acidMeSH
MTW-AlphaliponsaureMeSH
MTWAlphaliponsaureMeSH
NeuriumMeSH
Sofotec brand OF thioctic acidMeSH
ThioctacidMeSH
Thiogamma injektMeSH
Verla brand OF thioctic acidMeSH
VerlaLiponMeSH
Worwag brand OF thioctic acidMeSH
Worwag brand OF thioctic acid meglumineMeSH
alpha-Liponaure heumannMeSH
alpha-VibolexMeSH
biomo Brand OF thioctic acidMeSH
CT Arzneimittel brand OF thioctic acidMeSH
CT-Arzneimittel brand OF thioctic acidMeSH
Espa liponMeSH
Espa-liponMeSH
EspaliponMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
logP2.75ALOGPS
logP2.11ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)4.52ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity54.37 m³·mol⁻¹ChemAxon
Polarizability22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC8H14O2S2
IUPAC name5-(1,2-dithiolan-3-yl)pentanoic acid
InChI IdentifierInChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)
InChI KeyAGBQKNBQESQNJD-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CCCCC1CCSS1
Average Molecular Weight206.326
Monoisotopic Molecular Weight206.043521072
Classification
Description belongs to the class of organic compounds known as lipoic acids and derivatives. Lipoic acids and derivatives are compounds containing a lipoic acid moiety (or a derivative thereof), which consists of a pentanoic acid (or derivative) attached to the C3 carbon atom of a 1,2-dithiolane ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDithiolanes
Sub ClassLipoic acids and derivatives
Direct ParentLipoic acids and derivatives
Alternative Parents
Substituents
  • Lipoic_acid_derivative
  • Medium-chain fatty acid
  • Heterocyclic fatty acid
  • Thia fatty acid
  • Fatty acyl
  • Fatty acid
  • 1,2-dithiolane
  • Organic disulfide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0920000000-cf913d1d1afc04e5450cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bti-5910000000-294c510229247ef63f20JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bvi-9600000000-f8f54eb79c5d4d5bef48JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0920000000-5a823a30dd1fb434e5b1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kmu-1910000000-6f491a68afd82922e71bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-330e4766f82ed571497bJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDALPHA-LIPOIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).