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Lipoic acid (PC000503)

Record Information
Version1.0
Creation date2015-10-09 22:30:58 UTC
Update date2017-01-19 02:36:26 UTC
FoodComEx IDPC000503
FoodDB RecordFDB022631
Chemical Information
NameLipoic acid
DescriptionA vitamin-like antioxidant that acts as a free-radical scavenger. Alpha-lipoic acid is also known as thioctic acid. It is a naturally occurring compound that is synthesized by both plants and animals. Lipoic acid contains two thiol groups which may be either oxidized or reduced. The reduced form is known as dihydrolipoic acid (DHLA). Lipoic acid (Delta E= -0.288) is therefore capable of thiol-disulfide exchange, giving it antioxidant activity. Lipoate is a critical cofactor for aerobic metabolism, participating in the transfer of acyl or methylamine groups via the 2-Oxoacid dehydrogenase (2-OADH) or alpha-ketoglutarate dehydrogenase complex. This enzyme catalyzes the conversion of alpha-ketoglutarate to succinyl CoA. This activity results in the catabolism of the branched chain amino acids (leucine, isoleucine and valine). Lipoic acid also participates in the glycine cleavage system(GCV). The glycine cleavage system is a multi-enzyme complex that catalyzes the oxidation of glycine to form 5,10 methylene tetrahydrofolate, an important cofactor in nucleic acid synthesis. Since Lipoic acid is an essential cofactor for many enzyme complexes, it is essential for aerobic life as we know it. This system is used by many organisms and plays a crucial role in the photosynthetic carbon cycle. Lipoic acid was first postulated to be an effective antioxidant when it was found it prevented vitamin C and vitamin E deficiency. It is able to scavenge reactive oxygen species and reduce other metabolites, such as glutathione or vitamins, maintaining a healthy cellular redox state. Lipoic acid has been shown in cell culture experiments to increase cellular uptake of glucose by recruiting the glucose transporter GLUT4 to the cell membrane, suggesting its use in diabetes. Studies of rat aging have suggested that the use of L-carnitine and lipoic acid results in improved memory performance and delayed structural mitochondrial decay. As a result, it may be helpful for people with Alzheimer's disease or Parkinson's disease. -- Wikipedia [HMDB]
CAS Number1200-22-2
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(+-)-1,2-Dithiolane-3-pentanoatehmdb
(+-)-1,2-Dithiolane-3-pentanoic acidhmdb
(+-)-1,2-Dithiolane-3-valeratehmdb
(+-)-1,2-Dithiolane-3-valeric acidhmdb
(+)-alpha-Lipoatehmdb
(+)-alpha-Lipoic acidhmdb
(R)-1,2-Dithiolane-3-pentanoatehmdb
(R)-1,2-Dithiolane-3-pentanoic acidhmdb
(RS)-alpha-Lipoatehmdb
(RS)-alpha-Lipoic acidhmdb
(RS)-Lipoatehmdb
(RS)-Lipoic acidhmdb
(S)-(−)-lipoic acidHMDB
(S)-1,2-Dithiolane-3-pentanoic acidHMDB
(S)-alpha-Lipoic acidHMDB
1,2-Dithiolane-3-pentanoatehmdb
1,2-Dithiolane-3-pentanoic acidhmdb
1,2-Dithiolane-3-valeratehmdb
1,2-Dithiolane-3-valeric acidhmdb
1,2-Dithiolane-3R-pentanoatehmdb
1,2-Dithiolane-3R-pentanoic acidhmdb
5-(1,2-Dithiolan-3-yl)pentanoatehmdb
5-(1,2-Dithiolan-3-yl)pentanoic acidhmdb
5-(1,2-Dithiolan-3-yl)valeratehmdb
5-(1,2-Dithiolan-3-yl)valeric acidhmdb
5-(Dithiolan-3-yl)valeratehmdb
5-(Dithiolan-3-yl)valeric acidhmdb
5-[3-(1,2-dithiolanyl)]pentanoatehmdb
5-[3-(1,2-dithiolanyl)]pentanoic acidhmdb
6-Thioctatehmdb
6-Thioctic acidhmdb
6-Thiotatehmdb
6-Thiotic acidhmdb
6,8-Dithiooctanoatehmdb
6,8-Dithiooctanoic acidhmdb
6,8-Thioctatehmdb
6,8-Thioctic acidhmdb
6,8-Thiotatehmdb
6,8-Thiotic acidhmdb
acetate replacing factorhmdb
Acetate-replacing factorhmdb
alpha Lipoatehmdb
alpha Lipoic acidhmdb
alpha-Liponatehmdb
alpha-Liponic acidhmdb
alpha-Liponsaeurehmdb
Biletanhmdb
delta-[3-(1,2-dithiacyclopentyl)]pentanoatehmdb
delta-[3-(1,2-dithiacyclopentyl)]pentanoic acidhmdb
DL-1,2-Dithiolane 3-valeratehmdb
DL-1,2-Dithiolane 3-valeric acidhmdb
DL-6-Thioctatehmdb
DL-6-Thioctic acidhmdb
DL-6,8-Dithiooctanoatehmdb
DL-6,8-Dithiooctanoic acidhmdb
DL-6,8-Thioctatehmdb
DL-6,8-Thioctic acidhmdb
DL-alpha-Lipoatehmdb
DL-alpha-Lipoic acidhmdb
dl-Lipoatehmdb
dl-Lipoic acidhmdb
dl-Thioctatehmdb
dl-Thioctic acidhmdb
DL-Thioctic acid > 98%hmdb
Heparliponhmdb
L-1,2-Dithiolane 3-valeric acidHMDB
L-6-Thioctic acidHMDB
L-6,8-Thioctic acidHMDB
Liphmdb
Lipoatehmdb
Lipoic acidhmdb
liponatehmdb
liponic acidhmdb
Liposanhmdb
Lipothionhmdb
Protogen Ahmdb
Pyruvate oxidation factorhmdb
R-Lipoatehmdb
R-Lipoic acidhmdb
Rac-lipoatehmdb
Rac-lipoic acidhmdb
S-LAHMDB
SLAHMDB
Thioctacidhmdb
Thioctanhmdb
Thioctatehmdb
Thioctic acidhmdb
Thioctic acid d-formhmdb
Thioctic acid dl-formhmdb
Thioctic acid L-formHMDB
Thioctidasehmdb
Thioctsanhmdb
Thioktsaeurehmdb
Thiooctanoatehmdb
Thiooctanoic acidhmdb
Tioctacidhmdb
Tioctanhmdb
Tioctidasihmdb
Tioctidasi acetate replacing factorhmdb
Chemical FormulaC8H14O2S2
IUPAC name5-[(3R)-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)/t7-/m1/s1
InChI KeyAGBQKNBQESQNJD-SSDOTTSWSA-N
Isomeric SMILESOC(=O)CCCC[C@@H]1CCSS1
Average Molecular Weight206.326
Monoisotopic Molecular Weight206.043521072
Chemical Taxonomy
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 1 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci H452