1-Isothiocyanato-6-(methylsulfinyl)-hexane

Product Name1-Isothiocyanato-6-(methylsulfinyl)-hexane
CAS4430-35-7
MFC8H15NOS2
MW205.34
EINECS
MOL FileMol File

Chemical Properties

Boiling point	385.9±25.0 °C(Predicted)
Density	1.12±0.1 g/cm3(Predicted)
storage temp.	Refrigerator, under inert atmosphere
solubility	Chloroform (Sparingly), Methanol (Slightly)
form	Oil
color	Colourless to Pale Yellow
LogP	0.959 (est)

Usage And Synthesis

Description

6-Methylsulfinylhexyl isothiocyanate (6-MSITC) is an isothiocyanate that has been found in wasabi (W. japonica) and has diverse biological activities. It inhibits nitric oxide (NO) production in mouse peritoneal exudate macrophages when used at a concentration of 5 μM. It inhibits aggregation of isolated human platelets induced by arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607; IC₅₀ = 21.9 μM). 6-MSITC reduces cell survival in a panel of breast, brain, colon, lung, ovarian, renal, and prostate cancer cell lines (mean IC₅₀ = 43.7 μM). In vivo, 6-MSITC (5 mg/kg twice weekly) reduces apoptosis of substantia nigral dopaminergic neurons and motor dysfunction in a mouse model of Parkinson''s disease induced by 6-OHDA . 6-MSITC also reduces the number of lung metastases in a B16/F10 murine melanoma model.

Uses

6-(Methylsulfinyl)hexyl isothiocyanate derived from Wasabia japonica was discovered as an inhibitor of glycogen synthase kinase-3β.

Definition

ChEBI: 1-isothiocyanato-6-(methylsulfinyl)hexane is a sulfoxide.

in vivo

Hesperin (6-Methylsulfinylhexyl isothiocyanate, 6-MSITC) activates Nrf2 and induces phase II enzyme genes but this induction is absent in Nrf2-null mice, suggesting that Hesperin is a potential activator of the Nrf2/ARE-dependent detoxification pathway. To determine whether Hesperin ameliorates hepatic steatosis and iron accumulation, wild-type and Nrf2-null mice are fed the following diets for 12 weeks: 1) control diet, 2) high-fat diet (HFD), 3) HFD plus Hesperin (10 mg/kg/day ip), 4) HFD for 6 weeks followed by an iron-supplemented HFD for 6 weeks (HFD/Iron), 5) HFD/Iron plus Hesperin. The HFD increased hepatic triglycerides in both genotypes and Hesperin suppress increased hepatic triglycerides in wild-type mice but do not reduce these triglycerides in Nrf2-null mice^[1].

References

[1] TOSHIRO NOSHITA . Anti-nitric oxide production activity of isothiocyanates correlates with their polar surface area rather than their lipophilicity[J]. European Journal of Medicinal Chemistry, 2009, 44 12: Pages 4931-4936. DOI: 10.1016/j.ejmech.2009.08.005
[2] YASUJIRO MORIMITSU . Antiplatelet and anticancer isothiocyanates in Japanese domestic horseradish, Wasabi[J]. Mechanisms of Ageing and Development, 2000, 116 2: Pages 125-134. DOI: 10.1016/s0047-6374(00)00114-7
[3] TAKAHIRO NOMURA PHD . Selective sensitivity to wasabi-derived 6-(methylsulfinyl)hexyl isothiocyanate of human breast cancer and melanoma cell lines studied in vitro[J]. Cancer Epidemiology, 2005, 29 2: Pages 155-160. DOI: 10.1016/j.cdp.2004.07.010
[4] FABIANA MORRONI . Neuroprotection by 6-(methylsulfinyl)hexyl isothiocyanate in a 6-hydroxydopamine mouse model of Parkinsons disease[J]. Brain Research, 2014, 1589: Pages 93-104. DOI: 10.1016/j.brainres.2014.09.033
[5] YOKO FUKE PHD . Preventive effect of oral administration of 6-(methylsulfinyl)hexyl isothiocyanate derived from wasabi (Wasabia japonica Matsum) against pulmonary metastasis of B16-BL6 mouse melanoma cells[J]. Cancer Epidemiology, 2006, 30 2: Pages 174-179. DOI: 10.1016/j.cdp.2005.10.005

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