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S6317

L-Sulforaphane

Name: <SC>L</SC>-Sulforaphane
Brand: SIGMA

≥95% (HPLC), oil

Synonym(s):

(R)-1-Isothiocyanato-4-(methylsulfinyl)butane, 4-Methylsulfinylbutyl isothiocyanate

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About This Item

Empirical Formula (Hill Notation):

C₆H₁₁NOS₂

CAS Number:

142825-10-3

Molecular Weight:

177.29

MDL number:

MFCD09039283

UNSPSC Code:

12352200

PubChem Substance ID:

24724618

NACRES:

NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

oil

optical activity

[α]/D -70 to -90°, c = 1.0 in chloroform-d

color

light yellow

solubility

DMSO: >5 mg/mL

storage temp.

−20°C

SMILES string

CS(=O)CCCCN=C=S

InChI

1S/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3/t10-/m1/s1

InChI key

SUVMJBTUFCVSAD-SNVBAGLBSA-N

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Application

L-Sulforaphane was used to study Nrf2-mediated signaling in mouse primary preadipocytes⁶ and murine macrophage RAW 264.7 cell line.⁷

Biochem/physiol Actions

L-Sulforaphane is a potent, selective inducer of phase II detoxification enzymes with anticarcinogenic properties. Organosulfur compound found in cruciferous vegetables, including broccoli.

Sulforaphane is an anti-cancer, anti-microbial and anti-diabetic compound found in cruciferous vegetables.^3,4 It induces the production of detoxifying enzymes such as quinone reductase and glutathione S-transferase that cause xenobiotic transformation. Sulforaphane also increases the transcription of tumor suppressor proteins and inhibits histone deacetylases. It modulates inflammatory responses by suppressing the LPS-mediated expression of iNOS, COX-2, IL-1β and TNF-α.^3,5

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Pharmacological characterization of memoquin, a multi-target compound for the treatment of Alzheimer's disease.

Valeria Capurro et al.

PloS one, 8(2), e56870-e56870 (2013-02-27)

Alzheimer's disease (AD) is characterized by progressive loss of cognitive function, dementia and altered behavior. Over 30 million people worldwide suffer from AD and available therapies are still palliative rather than curative. Recently, Memoquin (MQ), a quinone-bearing polyamine compound, has

Neuroprotective potential of isothiocyanates in an in vitro model of neuroinflammation.

Tiziana Latronico et al.

Inflammopharmacology, 29(2), 561-571 (2020-11-17)

Isothiocyanates (ITCs), present as glucosinolate precursors in cruciferous vegetables, have shown anti-inflammatory, antioxidant and anticarcinogenic activities. Here, we compared the effects of three different ITCs on ROS production and on the expression of matrix metalloproteinase (MMP)-2 and -9, which represent

The NRF2-LOC344887 signaling axis suppresses pulmonary fibrosis.

Pengfei Liu et al.

Redox biology, 38, 101766-101766 (2020-10-31)

Idiopathic pulmonary fibrosis (IPF) is a progressive and irreversible disease characterized by an increase in differentiation of fibroblasts to myofibroblasts and excessive accumulation of extracellular matrix in lung tissue. Pharmacological activation of NRF2 has proved to be a valuable antifibrotic

Tobacco Smoke and Inhaled Drugs Alter Expression and Activity of Multidrug Resistance-Associated Protein-1 (MRP1) in Human Distal Lung Epithelial Cells in vitro.

Mohammed Ali Selo et al.

Frontiers in bioengineering and biotechnology, 8, 1030-1030 (2020-10-06)

Multidrug resistance-associated protein-1 (MRP1/ABCC1) is highly expressed in human lung tissues. Recent studies suggest that it significantly affects the pulmonary disposition of its substrates, both after pulmonary and systemic administration. To better understand the molecular mechanisms involved, we studied the

Tolvaptan activates the Nrf2/HO-1 antioxidant pathway through PERK phosphorylation.

Tamami Fujiki et al.

Scientific reports, 9(1), 9245-9245 (2019-06-27)

Tolvaptan, a vasopressin type 2 receptor antagonist initially developed to increase free-water diuresis, has been approved for the treatment of autosomal dominant polycystic kidney disease in multiple countries. Furthermore, tolvaptan has been shown to improve the renal functions in rodent

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