3H-1,2-dithiole-3-thione
 
Notes:
None found
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CAS Number: 534-25-8Picture of molecule3D/inchi
FDA UNII: WT2QF220RR
Nikkaji Web: J150.687K
MDL: MFCD00961788
XlogP3-AA: 1.20 (est)
Molecular Weight: 134.24394000
Formula: C3 H2 S3
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Category: natural substances and extractives
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 water, 3957 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Carbosynth
For experimental / research use only.
3H-1,2-Dithiole-3-thione
Santa Cruz Biotechnology
For experimental / research use only.
3H-1,2-Dithiole-3-thione 98%
Sigma-Aldrich: Sigma
For experimental / research use only.
D3T ≥98% (NMR)
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for 3H-1,2-dithiole-3-thione usage levels up to:
 not for fragrance use.
 
Recommendation for 3H-1,2-dithiole-3-thione flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
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EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 68296
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: nwg
 dithiole-3-thione
Chemidplus: 0000534258
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References:
 dithiole-3-thione
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 68296
Pubchem (cas): 534-25-8
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
HMDB (The Human Metabolome Database): HMDB35702
FooDB: FDB014422
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 garlic
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Synonyms:
 dithiole-3-thione
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Articles:
PubMed: Pharmacogenomics of Chemically Distinct Classes of Keap1-Nrf2 Activators Identify Common and Unique Gene, Protein, and Pathway Responses In Vivo.
PubMed: Pharmacological activation of the Nrf2 pathway by 3H-1, 2-dithiole-3-thione is neuroprotective in a mouse model of Alzheimer disease.
PubMed: 3H-1,2-Dithiole-3-thione as a novel therapeutic agent for the treatment of ischemic stroke through Nrf2 defense pathway.
PubMed: Protective effect of 3H-1, 2-dithiole-3-thione on cellular model of Alzheimer's disease involves Nrf2/ARE signaling pathway.
PubMed: 3H-1,2-dithiole-3-thione protects retinal pigment epithelium cells against Ultra-violet radiation via activation of Akt-mTORC1-dependent Nrf2-HO-1 signaling.
PubMed: Ethanol preconditioning of rat cerebellar cultures targets NMDA receptors to the synapse and enhances peroxiredoxin 2 expression.
PubMed: 3H-1,2-dithiole-3-thione as a novel therapeutic agent for the treatment of experimental autoimmune encephalomyelitis.
PubMed: Pharmacological induction of ferritin prevents osteoblastic transformation of smooth muscle cells.
PubMed: Tea Catechins Protect Goat Skeletal Muscle against H₂O₂-Induced Oxidative Stress by Modulating Expression of Phase 2 Antioxidant Enzymes.
PubMed: Hydrolysis-Sensitive Dithiolethione Prodrug Micelles.
PubMed: Searching phase II enzymes inducers, from Michael acceptor-[1,2]dithiolethione hybrids, as cancer chemopreventive agents.
PubMed: Hydrogen sulfide protects against myocardial ischemia and reperfusion injury by activating AMP-activated protein kinase to restore autophagic flux.
PubMed: A cardioprotective insight of the cystathionine γ-lyase/hydrogen sulfide pathway.
PubMed: Induction of complementary function reductase enzymes in colon cancer cells by dithiole-3-thione versus sodium selenite.
PubMed: Hydrogen sulfide protects blood-brain barrier integrity following cerebral ischemia.
PubMed: A serendipitous one-step conversion of 3H-1,2-dithiole-3-thione to (E)-3-[1-(alkylthio)alkylidene]-3H-1,2-dithiole: an experimental and theoretical study.
PubMed: Differential mechanisms underlying neuroprotection of hydrogen sulfide donors against oxidative stress.
PubMed: Involvement of the Nrf2-proteasome pathway in the endoplasmic reticulum stress response in pancreatic β-cells.
PubMed: Differential effects of cystathionine-γ-lyase-dependent vasodilatory H2S in periadventitial vasoregulation of rat and mouse aortas.
PubMed: The antioxidant 3H-1,2-dithiole-3-thione potentiates advanced glycation end-product-induced oxidative stress in SH-SY5Y cells.
PubMed: The lipid peroxidation by-product 4-hydroxy-2-nonenal (4-HNE) induces insulin resistance in skeletal muscle through both carbonyl and oxidative stress.
PubMed: Effects of potential dietary inhibitors of endogenous DNA damage on mutagenesis and lipid peroxidation in lacZ mice.
PubMed: Stabilization of Nrf2 protein by D3T provides protection against ethanol-induced apoptosis in PC12 cells.
PubMed: Modulation of thiol homeostasis induced by H2S-releasing aspirin.
PubMed: HPLC determination of novel dithiolethione containing drugs and its application for in vivo studies in rats.
PubMed: Cruciferous nutraceutical 3H-1,2-dithiole-3-thione protects human primary astrocytes against neurocytotoxicity elicited by MPTP, MPP(+), 6-OHDA, HNE and acrolein.
PubMed: Cruciferous dithiolethione-mediated coordinated induction of total cellular and mitochondrial antioxidants and phase 2 enzymes in human primary cardiomyocytes: cytoprotection against oxidative/electrophilic stress and doxorubicin toxicity.
PubMed: Chemical genomics of cancer chemopreventive dithiolethiones.
PubMed: Upregulation of cellular glutathione by 3H-1,2-dithiole-3-thione as a possible treatment strategy for protecting against acrolein-induced neurocytotoxicity.
PubMed: Dithiolethiones for cancer chemoprevention: where do we stand?
PubMed: Induction of sulfiredoxin expression and reduction of peroxiredoxin hyperoxidation by the neuroprotective Nrf2 activator 3H-1,2-dithiole-3-thione.
PubMed: Nrf2-mediated transcriptional induction of antioxidant response in mouse embryos exposed to ethanol in vivo: implications for the prevention of fetal alcohol spectrum disorders.
PubMed: Renal protection by 3H-1,2-dithiole-3-thione against cisplatin through the Nrf2-antioxidant pathway.
PubMed: Nuclear factor E2-related factor 2-dependent myocardiac cytoprotection against oxidative and electrophilic stress.
PubMed: Antioxidants and phase 2 enzymes in macrophages: regulation by Nrf2 signaling and protection against oxidative and electrophilic stress.
PubMed: New sulfurated derivatives of valproic acid with enhanced histone deacetylase inhibitory activity.
PubMed: Potent induction of total cellular GSH and NQO1 as well as mitochondrial GSH by 3H-1,2-dithiole-3-thione in SH-SY5Y neuroblastoma cells and primary human neurons: protection against neurocytotoxicity elicited by dopamine, 6-hydroxydopamine, 4-hydroxy-2-nonenal, or hydrogen peroxide.
PubMed: In situ real-time chemiluminescence imaging of reactive oxygen species formation from cardiomyocytes.
PubMed: The hydrogen sulphide-releasing derivative of diclofenac protects against ischaemia-reperfusion injury in the isolated rabbit heart.
PubMed: The neuroprotective potential of phase II enzyme inducer on motor neuron survival in traumatic spinal cord injury in vitro.
PubMed: The highly expressed and inducible endogenous NAD(P)H:quinone oxidoreductase 1 in cardiovascular cells acts as a potential superoxide scavenger.
PubMed: Generation of superoxide from reaction of 3H-1,2-dithiole-3-thione with thiols: implications for dithiolethione chemoprotection.
PubMed: Induction of Nrf2-regulated genes by 3H-1, 2-dithiole-3-thione through the ERK signaling pathway in murine keratinocytes.
PubMed: Effect of S-diclofenac, a novel hydrogen sulfide releasing derivative, on carrageenan-induced hindpaw oedema formation in the rat.
PubMed: Tissue specific increase of the catalytic subunits of the 26S proteasome by indirect antioxidant dithiolethione in mice: enhanced activity for degradation of abnormal protein.
PubMed: Upregulation of endogenous glutathione system by 3H-1,2-dithiole-3-thione in pancreatic RINm5F beta-cells as a novel strategy for protecting against oxidative beta-cell injury.
PubMed: Glutathione and glutathione-linked enzymes in normal human aortic smooth muscle cells: chemical inducibility and protection against reactive oxygen and nitrogen species-induced injury.
PubMed: In vivo modulation of the Parkinsonian phenotype by Nrf2.
PubMed: Antioxidants and phase 2 enzymes in cardiomyocytes: Chemical inducibility and chemoprotection against oxidant and simulated ischemia-reperfusion injury.
PubMed: Nrf2-mediated induction of cytoprotective enzymes by 15-deoxy-Delta12,14-prostaglandin J2 is attenuated by alkenal/one oxidoreductase.
PubMed: Nrf2 controls bone marrow stromal cell susceptibility to oxidative and electrophilic stress.
PubMed: Structure-activity relationships in the induction of Phase II enzymes by derivatives of 3H-1,2-dithiole-3-thione in rats.
PubMed: Synthesis of 1,3-dithiin dithioortho esters from the reaction of Fischer carbenes and 3H-1,2-dithiole-3-thiones.
PubMed: 3H-1,2-dithiole-3-thione targets nuclear factor kappaB to block expression of inducible nitric-oxide synthase, prevents hypotension, and improves survival in endotoxemic rats.
PubMed: Identification of novel transcriptional networks in response to treatment with the anticarcinogen 3H-1,2-dithiole-3-thione.
PubMed: Differential roles of 3H-1,2-dithiole-3-thione-induced glutathione, glutathione S-transferase and aldose reductase in protecting against 4-hydroxy-2-nonenal toxicity in cultured cardiomyocytes.
PubMed: Role of Nrf2 signaling in regulation of antioxidants and phase 2 enzymes in cardiac fibroblasts: protection against reactive oxygen and nitrogen species-induced cell injury.
PubMed: Protecting against peroxynitrite-mediated cytotoxicity in vascular smooth muscle cells via upregulating endogenous glutathione biosynthesis by 3H-1,2-dithiole-3-thione.
PubMed: Oltipraz, 3H-1,2-dithiole-3-thione, and sulforaphane induce overlapping and protective antioxidant responses in murine microglial cells.
PubMed: [Anethole dithiolethione: an antioxidant agent against tenotoxicity induced by fluoroquinolones].
PubMed: In vitro-in vivo antifungal evaluation and structure-activity relationships of 3H-1,2-dithiole-3-thione derivatives.
PubMed: Induction of phase II enzymes by 3H-1,2-dithiole-3-thione: dose-response study in rats.
PubMed: Effects of 3H-1,2-dithiole-3-thione, 1,4-phenylenebis(methylene)selenocyanate, and selenium-enriched yeast individually and in combination on benzo[a]pyrene-induced mutagenesis in oral tissue and esophagus in lacZ mice.
PubMed: Induction of endogenous glutathione by the chemoprotective agent, 3H-1,2-dithiole-3-thione, in human neuroblastoma SH-SY5Y cells affords protection against peroxynitrite-induced cytotoxicity.
PubMed: The role of chemically induced glutathione and glutathione S-transferase in protecting against 4-hydroxy-2-nonenal-mediated cytotoxicity in vascular smooth muscle cells.
PubMed: Induction of cellular glutathione and glutathione S-transferase by 3H-1,2-dithiole-3-thione in rat aortic smooth muscle A10 cells: protection against acrolein-induced toxicity.
PubMed: Modulation of gene expression by cancer chemopreventive dithiolethiones through the Keap1-Nrf2 pathway. Identification of novel gene clusters for cell survival.
PubMed: Protection of retinal pigment epithelial cells from oxidative damage by oltipraz, a cancer chemopreventive agent.
PubMed: Cell-based studies reveal differences in glutathione S-transferase induction between oltipraz and tert-butylhydroquinone.
PubMed: Induction of cellular glutathione-linked enzymes and catalase by the unique chemoprotective agent, 3H-1,2-dithiole-3-thione in rat cardiomyocytes affords protection against oxidative cell injury.
PubMed: Enhanced expression of the transcription factor Nrf2 by cancer chemopreventive agents: role of antioxidant response element-like sequences in the nrf2 promoter.
PubMed: Chemical induction of cellular antioxidants affords marked protection against oxidative injury in vascular smooth muscle cells.
PubMed: Role of transcription factor Nrf2 in the induction of hepatic phase 2 and antioxidative enzymes in vivo by the cancer chemoprotective agent, 3H-1, 2-dimethiole-3-thione.
PubMed: Chemoprotective 3H-1,2-dithiole-3-thione induces antioxidant genes in vivo.
PubMed: Transcriptional activation of the UDP-glucuronosyltransferase 1A7 gene in rat liver by aryl hydrocarbon receptor ligands and oltipraz.
PubMed: Evidence for thiol-dependent production of oxygen radicals by 4-methyl-5-pyrazinyl-3H-1,2-dithiole-3-thione (oltipraz) and 3H-1,2-dithiole-3-thione: possible relevance to the anticarcinogenic properties of 1,2-dithiole-3-thiones.
PubMed: Regulation of phase 2 enzyme induction by oltipraz and other dithiolethiones.
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