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Merck

574215

D,L-Sulforaphane

≥98% (UPLC), liquid, phase II detoxifying enzymes inducer, Calbiochem®

Synonyme(s) :

D,L-Sulforaphane, 1-Isothiocyanato-4-(methylsulfinyl)butane, R,S-Sulforaphane

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A propos de cet article

Formule empirique (notation de Hill) :
C6H11NOS2
Numéro CAS:
4478-93-7
Poids moléculaire :
177.29
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00198068

Principaux documents

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Nom du produit

D,L-Sulforaphane, An isothiocyanate isolated from broccoli that acts as a potent inducer of phase II detoxifying enzymes in mouse tissues and murine hepatoma cells in culture.

SMILES string

[S](=O)(CCCCN=C=S)C

InChI

1S/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3

InChI key

SUVMJBTUFCVSAD-UHFFFAOYSA-N

assay

≥98% (UPLC)

form

liquid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, protect from light

color

slight yellow

solubility

ethanol: 10 mg/mL, DMSO: 20 mg/mL

shipped in

ambient

storage temp.

−20°C

Quality Level

100

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Catégories apparentées

General description

An isothiocyanate isolated from broccoli that acts as a potent inducer of phase II detoxifying enzymes in mouse tissues and murine hepatoma cells in culture. It has been shown to be an effective agent in prevention of chemically-induced mammary tumors in rats. It also inhibits the phase I cytochrome P450 isoenzymes 2E1 and IA2 which have been associated with the activation of carcinogens. The induction of phase II enzymes is mediated by mitogen-activated protein kinase (MAPK) pathway.

Biochem/physiol Actions

Cell permeable: no
Primary Target
Potent inducer of phase II detoxifying enzymes in mouse tissues and murine hepatoma cells in culture
Product does not compete with ATP.
Reversible: no

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze DMSO stock solutions (-20°C) and ethanol stock solutions (-70°C). DMSO stock solutions are stable for up to 3 months at -20°C and ethanol stock solutions are stable for up to 3 months at -70°C.

Other Notes

Gamet-Payrastre, L., et al. 2000. Cancer Res.60, 1426.
Yu, R., et al. 2000. J. Biol. Chem.275, 2322.
Yu, R., et al. 1999. J. Biol. Chem.274, 27545.
Barcelo, S., et al. 1998. Mutat. Res.402, 111.
Maheo, K., et al. 1997. Cancer Res.57, 3649.
Zhang, Y., et al. 1994. Proc. Natl. Acad. Sci. USA91, 3147.
Zhang, Y., et al. 1992. Proc. Natl. Acad. Sci. USA89, 2399.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Classe de stockage

10 - Combustible liquids

wgk

WGK 3

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Jessica Gasparello et al.
Nucleic acid therapeutics, 30(3), 164-174 (2020-02-19)
Sulforaphane (SFN) is one of most important dietary constituents of broccoli (Brassica oleracea) and other cruciferous vegetables, which have been reported to exhibit health benefits, including prevention and therapy of cancer, such as colorectal carcinoma (CRC). The objective of this
Amanda Swain et al.
Nature metabolism, 2(7), 594-602 (2020-07-23)
Following activation, macrophages undergo extensive metabolic rewiring1,2. Production of itaconate through the inducible enzyme IRG1 is a key hallmark of this process3. Itaconate inhibits succinate dehydrogenase4,5, has electrophilic properties6 and is associated with a change in cytokine production4. Here, we
Yuting Yan et al.
Cell death & disease, 12(10), 917-917 (2021-10-09)
We previously demonstrated that sulforaphane (SFN) inhibited autophagy leading to apoptosis in human non-small cell lung cancer (NSCLC) cells, but the underlying subcellular mechanisms were unknown. Hereby, high-performance liquid chromatography-tandem mass spectrometry uncovered that SFN regulated the production of lipoproteins
Eslam Mohamed et al.
Immunity, 52(4), 668-682 (2020-04-16)
The primary mechanisms supporting immunoregulatory polarization of myeloid cells upon infiltration into tumors remain largely unexplored. Elucidation of these signals could enable better strategies to restore protective anti-tumor immunity. Here, we investigated the role of the intrinsic activation of the

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