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| Targets |
This compound is not a drug but a natural product with a broad spectrum of biological activities. Its mechanism of action for antimicrobial activity likely involves reaction with thiol groups in essential microbial proteins or disruption of cellular thiol homeostasis. It does not target a specific human receptor or enzyme. Its activity is primarily biocidal, targeting the cell membranes or metabolic pathways of bacteria, fungi, and invertebrates.
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| ln Vitro |
In vitro, (6-Isothiocyanatohexyl)(methyl)sulfane is active against the Gram-positive bacterium Bacillus subtilis and the fungus Trichophyton mentagrophytes, with a Minimum Inhibitory Concentration (MIC) of 25 microg/mL. It also exhibits anthelmintic activity against blue mussels (Mytilus edulis). It has potent antifouling activity when applied to polyvinyl chloride (PVC) panels at 50 micromol/cm2, effectively preventing the settlement of marine organisms. No specific EC₅0 for a target enzyme has been reported.
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| ln Vivo |
In vivo activity has been demonstrated only in the context of its antifouling properties. No therapeutic in vivo activity in animal disease models has been reported because it is a natural pesticide/repellent, not a drug. Its role in plants like wasabi is as a defense chemical against pests and pathogens. It is not administered systemically to mammals for disease treatment. Any potential systemic effects remain uncharacterized.
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| Enzyme Assay |
No standard cell-free enzyme or receptor binding assays are performed for this compound. As an alkylating agent, its reactivity can be studied using a biochemical assay involving the reaction with the thiol group of L-cysteine. The compound (0.1-10 mM) is incubated with L-cysteine (1 mM) in PBS (pH 7.4) at 25degC for 1 h. The formation of a dithiocarbamate adduct is monitored by UV-Vis spectroscopy or HPLC-MS. This method quantifies its electrophilic potential.
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| Cell Assay |
No standard cell viability assays are performed for therapeutic screening. MIC assays are used to assess its antibacterial and antifungal activity. For bacteria, a broth microdilution method is used. B. subtilis is grown in LB broth. Serial two-fold dilutions of the compound (0.39-100 ug/mL) are prepared in a 96-well plate. The bacterial suspension is added (5 × 10⁵ CFU/mL), and plates are incubated for 18-24 h at 37degC. MIC is the lowest concentration with no visible turbidity. For fungi, RPMI-1640 medium is used, incubated at 28degC for 48 h.
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| Animal Protocol |
No in vivo animal experiments have been conducted with this compound for therapeutic purposes. It has been tested for antifouling efficacy in immersion tests. PVC panels coated with the compound (50 micromol/cm2) are suspended in a marine environment or in tanks containing blue mussels (M. edulis). The number of settled organisms is counted over 4-8 weeks. For anthelmintic testing, the compound (0.1-100 mg/L) is added to seawater containing mussels, and mortality is assessed. No mammalian efficacy studies exist.
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| ADME/Pharmacokinetics |
The pharmacokinetics of (6-Isothiocyanatohexyl)(methyl)sulfane in mammals have not been studied. As a volatile, lipophilic isothiocyanate (logP ~3.0), it is expected to be rapidly absorbed from the gastrointestinal tract. It is likely conjugated with glutathione (GSH) via the action of glutathione S-transferases (GSTs) in the liver, forming a dithiocarbamate adduct, and is then metabolized via the mercapturic acid pathway. Oral bioavailability is predicted to be low due to rapid first-pass metabolism.
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| Toxicity/Toxicokinetics |
The toxicity of this compound in mammals is not well-documented. As an isothiocyanate, it can be a skin and mucous membrane irritant. No acute oral LD₅0 values in rats have been published. Based on its structure, it is predicted to be harmful if swallowed and a skin/eye irritant. It has been used as a food flavoring agent (wasabi) at very low concentrations and is generally recognized as safe (GRAS) for that purpose. Standard precautions: handle with gloves in a fume hood.
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| References | |
| Additional Infomation |
6-Methylthiohexyl isothiocyanate is an isothiocyanate with a hexane structure, wherein the two methyl hydrogens at the 1 and 6 positions are replaced by isothiocyanate and methylthio groups. It possesses various activities, including as an inhibitor of EC 4.1.1.17 (ornithine decarboxylase), an Arabidopsis metabolite, an antitumor agent, and a neuroprotective agent. It is an isothiocyanate and methyl sulfide derived from the hydride of hexane. 1-Isothiocyanate-6-(methylthio)hexane has been reported in wasabi (Sabia japonica) and Leptosphaeria maculans, and relevant data are available. It was isolated from wasabi (Wasabia japonica).
(6-Isothiocyanatohexyl)(methyl)sulfane is not a clinical drug and has no regulatory approvals. It is a natural product and research chemical used in antimicrobial and antifouling studies. It is also known by its common name, Lesquerellin. The compound is found in wasabi, where it contributes to its pungency and presumed health benefits. It is used as an analytical standard for flavor and fragrance analysis. It is typically stored at -20degC. No human clinical trials are associated with this compound. |
| Molecular Formula |
C₈H₁₅NS₂
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|---|---|
| Molecular Weight |
189.34
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| Exact Mass |
189.065
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| CAS # |
4430-39-1
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| PubChem CID |
165224
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| Appearance |
Colorless to light yellow viscous liquid
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| Density |
1g/cm3
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| Boiling Point |
284.6ºC at 760 mmHg
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| Flash Point |
125.9ºC
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| Index of Refraction |
1.522
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| LogP |
3.013
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
11
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| Complexity |
119
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CSCCCCCCN=C=S
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| InChi Key |
YIBXPFAXPUDDTK-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H15NS2/c1-11-7-5-3-2-4-6-9-8-10/h2-7H2,1H3
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| Chemical Name |
1-isothiocyanato-6-methylsulfanylhexane
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| Synonyms |
Lesquerellin; 6-Methylthiohexyl isothiocyanate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.2815 mL | 26.4075 mL | 52.8150 mL | |
| 5 mM | 1.0563 mL | 5.2815 mL | 10.5630 mL | |
| 10 mM | 0.5282 mL | 2.6408 mL | 5.2815 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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