DL-Sulforaphane

Names

[ Name ]:
DL-Sulforaphane

[Synonym ]:
UNII:41684WL1GL
1-isothiocyanato-4-methylsulfinylbutane
MFCD00198068
1-Isothiocyanato-4-(methylsulfinyl)butane
SULFORAPHANE, (±)-
4-Isothiocyanatobutyl methyl sulfoxide
4-Methylsulfinylbutyl isothiocyanate
1-Isothiocyanato-4-[(R)-methylsulfinyl]butane
4-(Methylsulfinyl)butyl isothiocyanate
1-Isothiocyanato-4-(methylsulfinyl)-butane
Butane, 1-isothiocyanato-4-[(R)-(1R)-methylsulfinyl]-
Butane, 1-isothiocyanato-4-(methylsulfinyl)-
(R)-sulforaphane
DL-Sulforaphane
(R)-1-isothiocyanato-4-(methylsulfinyl)butane
Sulforaphane
(-)-Sulforaphane
L-Sulforaphane
4-isothiocyanatobutyl methyl (R)-sulfoxide
(R)-1-Isothiocyanato-4-(methylsulfinyl)butane,4-Methylsulfinylbutyl isothiocyanate
D,L-Sulforaphane
SCN4SO&1
Sulforafan

Biological Activity

[Description]:

Sulforaphane is an isothiocyanate present naturally in widely consumed vegetables; has shown anticancer and cardioprotective activities.

[Related Catalog]:

Signaling Pathways >> Cell Cycle/DNA Damage >> HDAC

Signaling Pathways >> Epigenetics >> HDAC

Natural Products >> Others

Research Areas >> Cancer

Research Areas >> Cardiovascular Disease

[Target]

HDAC

[In Vitro]

Sulforaphane induces a cell cycle arrest in a dose-dependent manner, followed by cell death. This sulforaphane-induced cell cycle arrest was correlated with an increased expression of cyclins A and B1. Sulforaphane induces cell death via an apoptotic process. Sulforaphane inhibits the reinitiation of growth and diminishes cellular viability in quiescent colon carcinoma cells (HT29) and has a lower toxicity on differentiated CaCo2 cells[1]. Pre-treatment of H9c2 rat myoblasts with sulforaphane decreases the apoptotic cell number and the expression of pro-apoptotic proteins (Bax, caspase-3 and cytochrome c), as well as the doxorubicin-induced increase in mitochondrial membrane potential. Furthermore, sulforaphane increases the mRNA and protein expression of heme oxygenase-1, which consequently reduces the levels of reactive oxygen species (ROS, measured using MitoSOX Red reagent) in the mitochondria which are induced by doxorubicin[2].

[In Vivo]

Sulforaphane can block the formation of ammary tumors in Sprague-Dawley rats treated with single doses of 9,10-dimethyl-1,2-benzanthracene. Administration of sulforaphane reduces the incidence, multiplicity, and weights and delays the development of the mammary tumors evoked by a single dose of DMBA in female Sprague-Dawley rats[3].

[Cell Assay]

HT29 cells are seeded at low density (5×104 cells/mL) in 35- or 120-mm diameter Primaria dishes in standard medium containing 5% FCS. One day after seeding, medium is changed, and HT29 cells are treated with sulforaphane (0-30 μM). An equivalent amount of the solvent (ethanol) is added to control cells (0.2% final concentration). Drug effect on cellular viability is evaluated using the MTT assay[1].

[Animal admin]

Rats: At age 47, 48, 49, 50, and 51 days, each animal receives by gavage either 0.5 mL of Emulphor EL-620 alone or the specified doses (75, 100, or 150 μM daily) of sulforaphane or compound 2, 3, or 4 in 0.5 mL of Emulphor EL-620. On day 50, 3 hr after administration of the vehicle or protector, all rats also receive an intragastric instillation of 8.0 mg of DMBA dissolved in 1.0 mL of sesame oil. This dose of DMBA is selected to produce a substantial tumor incidence, but not one so high as to overwhelm a potential chemoprotective effect. The animals are examined once weekly for the appearance and location of palpable tumors. At age 202 days, i.e., 152 days after carcinogen administration, all animals are euthanized with ether and weighed. The tumors are separated from fat and connective tissue by dissection, weighed, and fixed in buffered 10% formalin. All tumors are identified microscopically by examination of stained sections[3].

[References]

[1]. Gamet-Payrastre L, et al. Sulforaphane, a naturally occurring isothiocyanate, induces cell cycle arrest and apoptosis in HT29 human colon cancer cells. Cancer Res. 2000 Mar 1;60(5):1426-33.

[2]. Li B, et al. Sulforaphane prevents doxorubicin-induced oxidative stress and cell death in rat H9c2 cells. Int J Mol Med. 2015 Jul;36(1):53-64.

[3]. Zhang Y, et al. Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornylisothiocyanates. Proc Natl Acad Sci U S A. 1994 Apr 12;91(8):3147-50.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
368.2±25.0 °C at 760 mmHg

[ Molecular Formula ]:
C₆H₁₁NOS₂

[ Molecular Weight ]:
177.288

[ Flash Point ]:
176.5±23.2 °C

[ Exact Mass ]:
177.028198

[ PSA ]:
80.73000

[ LogP ]:
0.23

[ Vapour Pressure ]:
0.0±0.8 mmHg at 25°C

[ Index of Refraction ]:
1.567

[ Storage condition ]:
−20°C

[ Water Solubility ]:
DMSO: 40 mg/mL, soluble

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;half-mask respirator (US);multi-purpose combination respirator cartridge (US)

[ Hazard Codes ]:
Xn

[ Safety Phrases ]:
S23-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2930909090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2930909090

[ Summary ]:
2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Novel Nrf2 activators from microbial transformation products inhibit blood-retinal barrier permeability in rabbits.

Br. J. Pharmacol. 172(5) , 1237-49, (2015)

Nuclear factor erythroid 2-related factor 2 (Nrf2) is a redox-sensitive transcription factor that binds to antioxidant response elements located in the promoter region of genes encoding many antioxida...

Sulforaphane reduces molecular response to hypoxia in ovarian tumor cells independently of their resistance to chemotherapy.

Int. J. Oncol. 47 , 51-60, (2015)

One of the recently emerging anticancer strategies is the use of natural dietary compounds, such as sulforaphane, a cancer-chemopreventive isothiocyanate found in broccoli. Based on the growing eviden...

A phase II study of sulforaphane-rich broccoli sprout extracts in men with recurrent prostate cancer.

Invest. New Drugs 33(2) , 480-9, (2015)

Diets high in cruciferous vegetables are associated with lower risk of incidence of prostate cancer, including aggressive forms of this disease. Human intervention studies with cruciferous vegetable-r...