S-lipoate
1,2-dithiolane-3-pentanoic acid, (S)-
Identification
| Name | S-lipoate |
| IUPAC | 5-[(3S)-dithiolan-3-yl]pentanoic acid |
| CAS Number | 1077-27-6 |
| FDA UNII | J2Y905FQ57 |
| Molecular Formula | C8 H14 O2 S2 |
| Molecular Weight | 206.32798000 |
| MDL Number | MFCD01863481 |
| Nikkaji Number | J231.967E |
| Beilstein | 0081852 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 362.50 °C. @ 760.00 mm Hg (est) |
| Flash Point | 343.00 °F. TCC ( 173.00 °C. ) (est) |
| logP (o/w) | 2.160 (est) |
| Soluble in | water, 126.6 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | information only not used for fragrances or flavors |
| Recommendation for S-lipoate usage levels up to | not for fragrance use. |
| Recommendation for S-lipoate flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
5-[(3S)-
dithiolan-3-yl]pentanoic acid
5-[(3S)-1,2-
dithiolan-3-yl]pentanoic acid
(S)-1,2-
dithiolane-3-pentanoic acid
1,2-
dithiolane-3-pentanoic acid, (S)-
(S)-
lipoic acid
(S)-(-)-
lipoic acid
S-(-)-alpha-
lipoic acid
(-)-
thioctic acid
(S)-
thioctic acid
L-
thioctic acid
thioctic acid L-form
thioctic acid laevo-form
PubMed:
R-α lipoic acid γ-cyclodextrin complex increases energy expenditure: a 4-month feeding study in mice.
PubMed:
Lipoic acid prevents fructose-induced changes in liver carbohydrate metabolism: role of oxidative stress.
PubMed:
Lipoic acid prevents liver metabolic changes induced by administration of a fructose-rich diet.
PubMed:
Age and gender dependent bioavailability of R- and R,S-α-lipoic acid: a pilot study.
PubMed:
Kinetic resolution of alpha-lipoic acid via enzymatic differentiation of a remote stereocenter.
PubMed:
Coenzyme Q(10) and alpha-lipoic acid supplementation in diabetic rats: conduction velocity distributions.
PubMed:
(r)-, but not (s)-alpha lipoic acid stimulates deficient brain pyruvate dehydrogenase complex in vascular dementia, but not in Alzheimer dementia.
PubMed:
Effect of single and combined supply of glutamine, glycine, N-acetylcysteine, and R,S-alpha-lipoic acid on glutathione content of myelomonocytic cells.
PubMed:
Purification, characterization, and cDNA cloning of lipoate-activating enzyme from bovine liver.
PubMed:
Engagement of the insulin-sensitive pathway in the stimulation of glucose transport by alpha-lipoic acid in 3T3-L1 adipocytes.
PubMed:
Inhibition of L-homocysteic acid and buthionine sulphoximine-mediated neurotoxicity in rat embryonic neuronal cultures with alpha-lipoic acid enantiomers.
PubMed:
Enantioselective high-performance liquid chromatography assay of (+)R- and (-)S-alpha-lipoic acid in human plasma.
PubMed:
Cytosolic and mitochondrial systems for NADH- and NADPH-dependent reduction of alpha-lipoic acid.
PubMed:
Stereospecific effects of R-lipoic acid on buthionine sulfoximine-induced cataract formation in newborn rats.
PubMed:
Antioxidant inhibition of skin inflammation induced by reactive oxidants: evaluation of the redox couple dihydrolipoate/lipoate.
PubMed:
2-ketoacid dehydrogenase complexes of Escherichia coli: stereospecificities of the three components for (R)-lipoate.
PubMed:
[Kinetics of 35S-lipoate binding in vitro by plasma proteins and formed elements of the blood].
PubMed:
Studies of energy-linked reactions. Net synthesis of adenosine triphosphate by isolated adenosine triphosphate synthase preparations: a role for lipoic acid and unsaturated fatty acids.