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

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

Uses

Used in Pharmaceutical Industry:
Anethole trithione is used as a therapeutic agent for promoting liver health and function. It is particularly beneficial for patients suffering from hepatitis and other liver-related conditions. Anethole trithione aids in the reduction of liver portal pressure, elimination of liver congestion, and improvement of overall liver function.
Used in Hepatoprotective Applications:
Anethole trithione serves as a hepatoprotective agent, helping to protect the liver from damage and promoting the recovery of liver cells. It is used to alleviate symptoms associated with hepatitis lesions and to support the activation of liver cells, contributing to the overall improvement and recovery of liver function.
Used in Detoxification Processes:
Due to its ability to enhance liver glutathione levels and the activity of various liver enzymes, Anethole trithione is used in detoxification processes. It helps the liver to effectively eliminate toxins and maintain optimal health.
Used in Digestive Health:
As a secretory choleretic drug, Anethole trithione is used to increase bile secretion, which is essential for the digestion and absorption of fats. This application makes it a valuable component in the treatment of various digestive health issues related to fat metabolism and absorption.

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

• 831-30-1 5-(p-methoxyphenyl)dithia<1,2>cyclopenten-3-one 
• 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 

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 
• 1820-42-4 bis(4-chlorophenyl)acetylene 
• 81385-69-5 4,5-bis(4-chlorophenyl)-3H-1,2-dithiol-3-one 
• 77654-93-4 α-(diethylamino-4 methyl-5 dithiole-1,3 ylidene-2) p-methoxy thioacetophenone 
• 17835-44-8 4,5-diphenyl-3H-1,2-dithiol-3-one 
• 77655-00-6 α-(dimethylamino-4 phenyl-5 dithiole-1,3 ylidene-2) p-methoxy thioacetophenone 
• 77655-06-2 dimethylamino-2 p-methoxyphenyl-5 phenyl-3 trithia-1,6,6aλ⁴ pentalene 

Relevant articles and documents

Gallic acid hydrogen sulfide derivative and preparation method and medical application thereof

The invention discloses a gallic acid hydrogen sulfide derivative and a preparation method and medical application thereof. The general formula of the gallic acid hydrogen sulfide derivative is A-Y-X,and A is gallic acid; Y is -C (O) O-, -C (O) NH-, -C (O) OC (O)-, -C (O) NHCH2 C (O)- or is absent, and when Y is absent, the compound is A-X; X is a moiety capable of releasing hydrogen sulfide alone or in combination with A. Compared with gallic acid and existing classic non-steroidal anti-inflammatory drugs, the gallic acid hydrogen sulfide derivative has the advantages that the anti-inflammatory activity is equivalent or enhanced, the side effects of gastrointestinal tracts and cardiovascular diseases are weakened, and the gallic acid hydrogen sulfide derivative has high anti-tumor activity and good cardiovascular and neuroprotective effects.

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.

Method for synthesizing 1,2-disulfide-3-thioketone derivative by using copper to catalyze

The invention relates to a method for synthesizing 1,2-disulfide-3-thioketone derivative by copper-catalyzed propargylamine sulfur cyclization, and the method comprises the following steps: N, N-dimethyl-3-phenyl propyl-2-alkynyl-1-amine is taken as a substrate, cuprous chloride, cuprous bromide or cuprous iodide is added into the substrate to serve as a catalyst, potassium phosphate, sodium bicarbonate or sodium acetate is taken as an alkali, elemental sulfur is taken as a sulfur source, stirring reaction is performed in a solvent for 12 hours at the temperature of 100-120 DEG C. The elemental sulfur is used as the sulfur source, and the method has the advantages of simple and easily available raw materials, simple reaction operation, relatively mild conditions, wide substrate universality, relatively high yield and good functional group compatibility.

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.

1,2-dithio-3-thioketone derivative synthesized by cyclizing of fluorine-sulfur removal of trifluoropropyne via copper catalyzing

The invention discloses a 1,2-dithio-3-thioketone derivative synthesized by cyclizing of fluorine-sulfur removal of trifluoropropyne via copper catalyzing. The 1,2-dithio-3-thioketone derivative is prepared by the following steps of using a 2-chloro-3,3,3-trifluoro-1 propene compound as a primer; adding cuprous bromide as a catalyst into the primer, using cesium carbonate as alkaline, using tetramethylethylenediamine as a ligand, using elemental sulfur as a sulfur source, and stirring to react for 12 hours in a N,N-dimethyl formamide solvent at the temperature of 120 DEG C; after reaction is finished, filtering a reaction liquid, extracting a filtrate twice by a saturated sodium chloride solution, reversely extracting once, separating to obtain an organic phase, and drying with anhydrous sodium sulfate; filtering again, and removing the solvent out of the filtrate by a rotary evaporator, so as to obtain the remaining matter; performing column chromatography separating on the remainingmatter by a silicon gel column, spraying by an elution solution, and collecting an effluent solution containing the target product; combining the effluent solution, concentrating under the vacuum condition, and removing the solvent, so as to obtain the target product. The 1,2-dithio-3-thioketone derivative has the advantages that the raw materials are simple and are easy to obtain, the preparationtechnology is novel and simple, the pollution is little, the energy consumption is low, and the yield rate is high.

Copper-Catalyzed Defluorinative Thioannulation of Trifluoropropynes for the Synthesis of 1,2-Dithiole-3-thiones

A simple and practical strategy for the preparation of 1,2-dithiole-3-thiones via copper-catalyzed defluorinative thioannulation of trifluoropropynes has been developed using elemental sulfur as the sole sulfur source. This reaction displays a wide substrate scope and high functional group tolerance to afford the corresponding S-heterocycles in moderate to good yields and features efficient construction of multiple C?S bonds through C?F bond cleavage of CF3 groups. (Figure presented.).

Convenient method for the synthesis of 5-(4-methoxyphenyl)-3H-1,2-dithiole-3-thione (ADT-OMe) and 5-(4-hydroxyphenyl)-3H-1,2-dithiol-3-thione (ADT-OH) using microwave irradiation

A convenient method is described for the rapid synthesis of 5-(4-methoxyphenyl)-3H-1,2-dithiole-3-thione (ADT-OMe) from anethole and elemental sulfur using microwave irradiation. Various reaction conditions were applied to reduce the reaction time from several hours to 10?min, resulting in an improvement in yield and overcoming the undesired by-product formation associated with conventional methods. 5-(4-Hydroxyphenyl)-3H-1,2-dithiol-3-thione (ADT-OH) was obtained by the deprotection of ADT-OMe using pyridine hydrochloride under microwave irradiation.

Synthesis of Amino-ADT Provides Access to Hydrolytically Stable Amide-Coupled Hydrogen Sulfide Releasing Drug Targets

As additional physiological functions of hydrogen sulfide (H2S) are discovered, developing practical methods for exogenous H2S delivery is important. In particular, nonsteroidal anti-inflammatory drugs (NSAIDs) functionalized with H2S-releasing anethole dithiolethione (ADT-OH) through ester bonds are being investigated for their combined anti-inflammatory and antioxidant potential. The chemical robustness of the connection between drug and H2S-delivery components, however, is a key and controllable linkage in these compounds. Because esters are susceptible to hydrolysis, particularly under acidic conditions such as stomach acid in oral drug delivery applications, we report here a simple synthesis of amino-ADT (ADT-NH2) and provide conditions for successful ADT-NH2 derivatization with the drugs naproxen and valproic acid. Using UV-vis spectroscopy and HPLC analysis, we demonstrate that amide-functionalized ADT derivatives are significantly more resistant to hydrolysis than ester-functionalized ADT derivatives.

Switching Selectivity of α-Enolic Dithioesters: One Pot Access to Functionalized 1,2- and 1,3-Dithioles

An operationally simple cascade protocol has been developed for the construction of 1,2- and 1,3-dithiole derivatives from α-enolic dithioesters. 1,2-Dithioles are achieved by the reaction of dithioesters with elemental sulfur in the presence of InCl3 under solvent-free conditions. 1,3-Dithioles have been constructed via DABCO mediated self-coupling of dithioesters in open air enabling the formation of two new C-S bonds and one ring in a single operation in contiguous fashion. The reactions proceeded smoothly affording the desired sulfur-rich heterocycles in good to excellent yields, exhibiting gram-scale ability and broad functional group tolerance utilizing easy to handle cheap and easily available reagents. The probable mechanisms for the formation of 1,2- and 1,3-dithioles from α-enolic dithioesters have been suggested.