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S6317

Sigma-Aldrich

L-Sulforaphane

≥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

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

Storage Class Code

11 - Combustible Solids

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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Valeria Capurro et al.
PloS one, 8(2), e56870-e56870 (2013-02-27)
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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
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
Yongyong Hou et al.
Free radical biology & medicine, 52(2), 462-472 (2011-12-06)
Nuclear factor erythroid-derived factor 2-related factor 2 (Nrf2) is a cap-n-collar basic leucine zipper transcription factor that is involved in the cellular adaptive response to oxidative stress. Our previous study reported that targeted disruption of the Nrf2 gene in mice
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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