532-11-6

Basic information

• Product Name: Anethole trithione
• Synonyms: ANETHOLE TRITHIONE;5-(4-methoxyphenyl)-3h-1,2-dithiole-3-thione;5-(4-methoxyphenyl)-1,2-dithiole-3-thione;3-(p-anisy)trithione;3-(p-Methoxyphenyl)trithione;3-(p-Methoxyphenyl)-trithione;3H-1,2-Dithiole-3-thione, 5-(p-methoxyphenyl)-;5-(4-methoxyphenyl)-3h-2-dithiole-3-thione
• CAS NO: 532-11-6
• Molecular Formula: C₁₀H₈OS₃
• Molecular Weight: 240.36
• EINECS: 208-528-5
• Mol File: 532-11-6.mol
• Article Data: 24

Chemical Properties

• Melting Point: 111°
• Boiling Point: 353.09°C (rough estimate)
• Flash Point: 194.6 °C
• Appearance: Powder
• Density: 1.4406 (rough estimate)
• Vapor Pressure: 3.46E-06mmHg at 25°C
• Refractive Index: 1.5080 (estimate)
• Storage Temp.: 2-8°C
• Solubility: soluble in Chloroform
• CAS DataBase Reference: Anethole trithione(CAS DataBase Reference)
• NIST Chemistry Reference: Anethole trithione(532-11-6)
• EPA Substance Registry System: Anethole trithione(532-11-6)

Safety Data

• Hazardous Substances Data: 532-11-6(Hazardous Substances Data)

Usage

Description

Anise trisulfide, also known as bile vita, is a secretory choleretic drug, which can significantly enhance liver glutathione levels, significantly enhance glutamyl cysteine synthase, glutathione reductase and glutathione sulfur Transferase activity, reduce glutathione peroxidase activity, enhance liver cell viability, and increase bile secretion. Without increasing the burden on the liver, it can reduce liver portal pressure, eliminate liver congestion and other symptoms of hepatitis lesions, promote liver cell activation, and contribute to the improvement and recovery of liver function.

Originator

Sialor,Paladin Labs

Manufacturing Process

1 mol anethol (1-methoxy-4-propenyl-benzene) and 3 mol sulfur were heated in an open vessel to temperature 190°-200°C. H2S was removed at this temperature. On cooling the reaction mixture was getting solid. The solid product was recrystallizated from acetone or ethanol to give the orange-red needles of 5-(4-methoxyphenyl)-3H-1,2-dithiole-3-thione; MP 108.5°C.

Therapeutic Function

Salivation stimulant, Choleretic, Neuroprotective

Safety Profile

Poison by intramuscular route.Moderately toxic by ingestion and intraperitoneal routes.Experimental reproductive effects. When heated todecomposition it emits toxic fumes of SOx.

InChI:InChI=1/C10H8OS3/c1-11-8-4-2-7(3-5-8)9-6-10(12)14-13-9/h2-6H,1H3

Upstream product

• 100-09-4 4-methoxybenzoic acid 
• 10364-93-9 1-(4-methoxybenzoyl)-imidazole 
• 2881-83-6 ethyl 4-methoxybenzoylacetate 
• 768-60-5 4-methoxyphenylacetylen 
• 118968-67-5 1-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-4-methoxybenzene 
• 82203-83-6 1-(p-methoxyphenyl)-3,3,3-trifluoropropyne 
• 20365-71-3 methyl 3-hydroxy-3-(p-methoxyphenyl)-2-propenedithiolate 
• 104-46-1 anethole 
• 25679-28-1 cis-Anethole 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 75-15-0 carbon disulfide 
• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 
• 50849-98-4 3,3-dimercapto-1-(4-methoxy-phenyl)-propenone 
• 831-30-1 5-(p-methoxyphenyl)dithia<1,2>cyclopenten-3-one 

Downstream Products

• 5953-99-1 5-(4-methoxy-phenyl)-[1,2]dithiol-3-one oxime 
• 28955-46-6 3-ethylsulfanyl-5-(4-methoxy-phenyl)-[1,2]dithiolylium; iodide 
• 19652-13-2 5-amino-3-(4-methoxylphenyl)-1-phenyl-1H-pyrazole 
• 95876-30-5 3-(4-methoxy-phenyl)-5-methylsulfanyl-[1,2]dithiolylium; methyl sulfate 
• 32470-65-8 5-(4-Methoxyphenyl)-3-(methylthio)-1,2-dithiolium-iodid 
• 18274-81-2 desmethyl anethole trithione 
• 831-30-1 5-(p-methoxyphenyl)dithia<1,2>cyclopenten-3-one 
• 138990-87-1 3-bromomercapto-5-(4-methoxy-phenyl)-[1,2]dithiolylium; bromide 
• 100-63-0 phenylhydrazine 
• 13232-76-3 4,5-diphenyl-[1,2]dithiole-3-thione 
• 81385-79-7 5-Methyl-2,3,6-triphenylthieno<3,2-b>furan 
• 80608-91-9 2,3,5,6-Tetraphenylthieno<3,2-b>furan 
• 1134191-22-2 4-(5-thioxo-5H-1,2-dithiol-3-yl)phenyl 2-(4-(4-ethoxy-3-(5-methyl-4-oxo-7-propyl-1,4-dihydroimidazo[1,5-f][1,2,4]triazin-2-yl)phenylsulfonyl)piperazin-1-yl)acetate 

Relevant articles and documents

A novel H2S releasing-monastrol hybrid (MADTOH) inhibits L-type calcium channels

A new alleged monastrol-H2S releasing hybrid, named MADTOH, was designed based on the structure of monastrol (M) and 5-(4-hydroxyphenyl)-3H-1,2-dithiole-3-thione (ADTOH) and synthesized in 7.8% overall yield. MADTOH was shown to be an H2S donor under physiological conditions. In addition, the hybrid causes a decrease in global calcium transient in cardiomyocytes similar to nifedipine (NIFE), taken as a positive control. Whole-cell voltage-clamp showed that MADTOH decreases L-type Ca2+ current in isolated ventricular cardiomyocytes.

Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine-or H2O2-induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.

Copper-Catalyzed Tandem Sulfuration/Annulation of Propargylamines with Sulfur via C-N Bond Cleavage

Copper-catalyzed aerobic oxidative sulfuration and annulation of propargylamines with elemental sulfur is described. The tandem reaction involves C-N bond cleavage and the formation of multiple C-S bonds, affording 1,2-dithiole-3-thiones in good to excellent yields with good functional group tolerance.