DIHYDROTHIOCTIC ACID

Details

Stereochemistry	RACEMIC
Molecular Formula	C8H16O2S2
Molecular Weight	208.341
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CCCCC(S)CCS

InChI

InChIKey=IZFHEQBZOYJLPK-UHFFFAOYSA-N

InChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10)

HIDE SMILES / InChI

Molecular Formula	C8H16O2S2
Molecular Weight	208.341
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Approval Year

PubMed

Title	Date	PubMed
Activity of alpha-lipoic acid in the protection against oxidative stress in skin.	2001	11225200
Effects of vitamin E and alpha-lipoic acid on skeletal muscle contractile properties.	2001 Apr	11247943
Thiols can either enhance or suppress DNA damage induction by catecholestrogens.	2001 Jan 1	11134896
Sulfur-centered radical formation from the antioxidant dihydrolipoic acid.	2001 Nov 16	11546802
alpha-Lipoic acid prevents the development of glucose-induced insulin resistance in 3T3-L1 adipocytes and accelerates the decline in immunoreactive insulin during cell incubation.	2001 Sep	11555840
Modulation of microphthalmia-associated transcription factor gene expression alters skin pigmentation.	2002 Dec	12485436
Avidin: a natural bridge for quantum dot-antibody conjugates.	2002 Jun 5	12033868
Zinc is a potent inhibitor of thiol oxidoreductase activity and stimulates reactive oxygen species production by lipoamide dehydrogenase.	2002 Mar 22	11744691
Alpha lipoic acid inhibits T cell migration into the spinal cord and suppresses and treats experimental autoimmune encephalomyelitis.	2002 Oct	12458042
Preventing superoxide formation in epineurial arterioles of the sciatic nerve from diabetic rats restores endothelium-dependent vasodilation.	2003 Jan	12653215
Reactive oxygen species are involved in the stimulation of the mitochondrial permeability transition by dihydrolipoate.	2003 Jan 1	12473377
Hemoprotein-mediated reduction of nitrated DNA bases in the presence of reducing agents.	2003 Jan 15	12521607
Biological and dietary antioxidants protect against DNA nitration induced by reaction of hypochlorous acid with nitrite.	2003 Jul 1	12801519
Dihydrolipoic acid lowers the redox activity of transition metal ions but does not remove them from the active site of enzymes.	2004	15035828
Lipoic acid pretreatment attenuates ferric chloride-induced seizures in the rat.	2004 Aug 6	15246849
Lipoic acid as a potential therapy for chronic diseases associated with oxidative stress.	2004 May	15134511
Protein thiol modifications visualized in vivo.	2004 Nov	15502869
Alpha lipoic acid inhibits human T-cell migration: implications for multiple sclerosis.	2004 Nov 1	15389837
[Lipoic acid: characteristics and therapeutic application].	2005	16407792
Fluoroimmunoassays using antibody-conjugated quantum dots.	2005	15923672
Thermodynamics of the As(III)-thiol interaction: arsenite and monomethylarsenite complexes with glutathione, dihydrolipoic acid, and other thiol ligands.	2005 Apr 18	15819584
Oxidative stress and the use of antioxidants in diabetes: linking basic science to clinical practice.	2005 Apr 29	15862133
Developmentally restricted genetic determinants of human arsenic metabolism: association between urinary methylated arsenic and CYT19 polymorphisms in children.	2005 Jun	15929903
Inhibition of gelatinase B (matrix metalloproteinase-9) by dihydrolipoic acid.	2005 Mar	15870844
alpha-Lipoic acid induces apoptosis in human colon cancer cells by increasing mitochondrial respiration with a concomitant O2-*-generation.	2005 Mar	15843897
Synthesis of compact multidentate ligands to prepare stable hydrophilic quantum dot fluorophores.	2005 Mar 23	15771523
Photophysical properties of biologically compatible CdSe quantum dot structures.	2005 May 26	16852208
Capping of CdSe-ZnS quantum dots with DHLA and subsequent conjugation with proteins.	2006	17406409
Stimulation of membrane permeability transition by alpha-lipoic acid and its biochemical characteristics.	2006	17405408
Cellular disulfide-reducing capacity: an integrated measure of cell redox capacity.	2006 Jun 16	16650819
Size series of small indium arsenide-zinc selenide core-shell nanocrystals and their application to in vivo imaging.	2006 Mar 1	16492023
Alpha-lipoic acid exhibits anti-amyloidogenicity for beta-amyloid fibrils in vitro.	2006 Mar 24	16460684
Optical molecular imaging for systems biology: from molecule to organism.	2006 Oct	16850295
Genetic and chemical rescue of the Saccharomyces cerevisiae phenotype induced by mitochondrial DNA polymerase mutations associated with progressive external ophthalmoplegia in humans.	2006 Oct 1	16940310
Effects of lipoic acid and dihydrolipoic acid on 4-aminophenol-mediated erythrocytic toxicity in vitro.	2006 Sep	16930295
Lipoic acid as a novel treatment for Alzheimer's disease and related dementias.	2007 Jan	16989905

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 21:07:41 GMT 2023` Edited by `admin` on `Fri Dec 15 21:07:41 GMT 2023`
Record UNII	7NV2KHU5JA
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

DIHYDROTHIOCTIC ACID

Common Name

English

(±)-DIHYDRO-.ALPHA.-LIPOIC ACID

Common Name

English

OCTANOIC ACID, 6,8-DIMERCAPTO-

Common Name

English

THIOCTIC ACID, DIHYDRO-

Common Name

English

DIHYDROLIPOIC ACID

Common Name

English

Code System Code Type Description

DRUG BANK

DB03760