(S)-lipoic acid
Basic information
- CAS
1077-27-6- Standard SMILES
O=C(O)CCCC[C@H]1CCSS1- InChIKey
AGBQKNBQESQNJD-ZETCQYMHSA-N- Molecular formula
- C8H14O2S2
- Average molar mass
- 206.3 g/mol
- Monoisotopic mass
- 206.04352203
Overview
(S)-lipoic acid is the (S)-enantiomer of lipoic acid. Not found in nature, it may exert detrimental effects on biosystems. It is a lipoic acid, a member of dithiolanes, a heterocyclic fatty acid and a thia fatty acid. It is functionally related to an octanoic acid. It is an enantiomer of a (R)-lipoic acid.
Names & identifiers
- Preferred name
- (S)-lipoic acid
- IUPAC
- 5-[(3S)-dithiolan-3-yl]pentanoic acid
- English name
- 5-[(3S)-Dithiolan-3-yl]pentanoic acid
- Molecular formula
- C8H14O2S2
- Molecular weight
- 206.33
Names & synonyms
1077-27-6(S)-lipoic acid5-[(3S)-dithiolan-3-yl]pentanoic acid(S)-Thioctic Acid(-)-Thioctic Acid(S)-(-)-lipoic acidThioctic acid l-formL-6-thioctic acid5-[(3S)-1,2-dithiolan-3-yl]pentanoic acidL-6,8-thioctic acidS-LipoateThioctic acid, (-)-
Show more names
S(-)-a-Lipoic acidLIPOATES-LipoicS-LipoicAcidL-THIOCTIC ACID(S)-(-)-Thioctic acid(S)-6,8-Thioctic acid(S)-(-)-α-Lipoic AcidS- LIPOICACID (L-LIPOIC ACID)(S)-(?)-α -Lipoic acid
L-1,2-dithiolane 3-valeric acids-(-)-alpha-lipoic acidUNII-J2Y905FQ57(S)-1,2-Dithiolane-3-pentanoic acidESLIPOIC ACID1,2-Dithiolane-3-pentanoic acid, (3S)-J2Y905FQ57CHEBI:43796
Database identifiers
- CAS
1077-27-6、1200-22-2- PubChem CID
- 445125
- DTXSID
DTXSID40904735- ChEMBL
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 87.9 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 150
Experimental & physicochemical properties
LogP2.1
Solubility
Insoluble
2.24e-01 g/L
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 47 °C · 47 °C
- alpha
- 23 · D23 -113° (c = 1.88 in benzene)
- Boiling point
- 362.5 · 362.5±11.0 °C(Predicted)
- Density
- 1.218 · 1.218±0.06 g/cm3(Predicted)
- refractive index
- -114 ° · -114 ° (C=1, EtOH)
- storage temp.
- -20 °C · -20°C
- solubility
- Chloroform (Slightly, Heated), Methanol (Slightly)
- form
- Solid
- pka
- 4.75 · 4.75±0.10(Predicted)
- color
- Pale Yellow to Light Yellow
- Merck
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 3
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Pharmacology
Pharmacodynamics
Lipoic acid (or α-lipoic acid) is able to pass the blood-brain barrier and is putatively used for detoxification of mercury attached to the brain cells. It can mobilise bound mercury into the blood stream as it is a mercaptan (sulfur compound which readily binds to the mercury). In the blood stream, another chelator such as dimercaptosuccinic acid (DMSA) or methylsulfonylmethane (MSM) is used to transfer mercury safely into the urine for excretion. Since DMSA cannot cross the blood-brain barrier, both lipoic acid and DMSA tend to be used together. It is hypothesized that this treatment-along with carnitine, dimethylglycine (DMG), Vitamin B6, folic acid, and magnesium—could be used to treat autism and amalgam poisoning. In this hypothesis, the reason why autism is difficult to treat is that mercury is attached to the brain cells and most medicines and vitamin supplements do not penetrate the blood-brain barrier. However, α-lipoic acid and perhaps vitamin B12 could making it possible for other chelators to remove mercury safely out of the body and could perhaps one day be used as a treatment for autism. Because lipoic acid is related to cellular uptake of glucose and it is both soluble in water and fat, it is being used for treatment in diabetes. It may be helpful for people with Alzheimer's disease or Parkinson's disease.
Mechanism of Action
Lipoic Acid is generally involved in oxidative decarboxylations of keto acids and is presented as a growth factor for some organisms. Lipoic acid exists as two enantiomers, the R-enantiomer and the S-enantiomer. Normally only the R-enantiomer of an amino acid is biologically active, but for lipoic acid the S-enantiomer assists in the reduction of the R-enantiomer when a racemic mixture is given. Some recent studies have suggested that the S-enantiomer in fact has an inhibiting effect on the R-enantiomer, reducing its biological activity substantially and actually adding to oxidative stress rather than reducing it. Furthermore, the S-enantiomer has been found to reduce the expression of GLUT-4s in cells, responsible for glucose uptake, and hence reduce insulin sensitivity.
Cellular LocationsCytoplasm
Metabolite Pathways3-Phosphoglycerate dehydrogenase deficiency
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