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Key Documents

SML3554

Sigma-Aldrich

6-(Methylsulfinyl)hexyl isothiocyanate

≥98% (HPLC)

Synonym(s):

1-Isothiocyanato-6-(methylsulfinyl)hexane, 6-MITC, 6-MSITC, Hesperin

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About This Item

Empirical Formula (Hill Notation):
C8H15NOS2
CAS Number:
Molecular Weight:
205.34
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

oil

color

colorless to yellow

storage temp.

2-8°C

SMILES string

O=S(C)CCCCCCN=C=S

InChI

1S/C8H15NOS2/c1-12(10)7-5-3-2-4-6-9-8-11/h2-7H2,1H3

InChI key

XQZVZULJKVALRI-UHFFFAOYSA-N

Biochem/physiol Actions

6-(Methylsulfinyl)hexyl isothiocyanate (6-MITC) is a major bioactive compound in wasabi that exhibits antimicrobial, anti-inflammatory, antiplatelet, antioxidant and anticancer properties (mean log GI50 = −5.41 (3.9 μM) in a human cancer cell panel). 6-MITC concurrently induces autophagy and mitotic arrest, suppresses NF-κβ signaling by competitive inhibition of GSK-3β.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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6-(methylsulfinyl)hexyl isothiocyanate (6-MITC) from Wasabia japonica alleviates inflammatory bowel disease (IBD) by potential inhibition of glycogen synthase kinase 3 beta (GSK-3?)
Lohning A, Kidachi Y, Kamiie K, Sasaki K, Ryoyama K, Yamaguchi H
European Journal of Medicinal Chemistry, 216 (2021)
Akira Uruno et al.
Molecular and cellular biology, 40(6) (2020-01-15)
Nrf2 (NF-E2-related-factor 2) is a stress-responsive transcription factor that protects cells against oxidative stresses. To clarify whether Nrf2 prevents Alzheimer's disease (AD), AD model AppNL-G-F/NL-G-F knock-in (AppNLGF ) mice were studied in combination with genetic Nrf2 induction model Keap1FA/FA mice.

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