L-Sulforaphane

Names

[ Name ]:
L-Sulforaphane

[Synonym ]:
UNII:41684WL1GL
1-Isothiocyanato-4-(methylsulfinyl)butane
SULFORAPHANE, (±)-
4-Isothiocyanatobutyl methyl sulfoxide
4-Methylsulfinylbutyl isothiocyanate
1-Isothiocyanato-4-[(R)-methylsulfinyl]butane
4-(Methylsulfinyl)butyl isothiocyanate
Butane, 1-isothiocyanato-4-[(R)-(1R)-methylsulfinyl]-
Butane, 1-isothiocyanato-4-(methylsulfinyl)-
(R)-sulforaphane
MFCD09039283
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
SCN4SO&1

Biological Activity

[Description]:

(R)-Sulforaphane is a highly potent inducer of the Keap1/Nrf2/ARE pathway. (R)-Sulforaphane is a far more potent inducer of the carcinogen-detoxifying enzyme systems in rat liver and lung than the S-isomer[1][2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

[References]

[1]. De Nicola GR, et al. Novel gram-scale production of enantiopure R-sulforaphane from Tuscan black kale seeds. Molecules. 2014 May 27;19(6):6975-86.

[2]. Abdull Razis AF, et al. The natural chemopreventive phytochemical R-sulforaphane is a far more potent inducer of the carcinogen-detoxifying enzyme systems in rat liver and lung than the S-isomer. Int J Cancer. 2011 Jun 15;128(12):2775-82.

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

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
S22-S23-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ 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

Sulforaphane prevents doxorubicin-induced oxidative stress and cell death in rat H9c2 cells.

Int. J. Mol. Med. 36 , 53-64, (2015)

Sulforaphane, a natural isothiocyanate compound found in cruciferous vegetables, has been shown to exert cardioprotective effects during ischemic heart injury. However, the effects of sulforaphane on ...

In vitro metabolic conversion of the organic breakdown products of glucosinolate to goitrogenic thiocyanate anion.

J. Sci. Food Agric. 95 , 2244-51, (2015)

Glucosinolates are abundant in Brassicaceae vegetables, and they are degraded into various organic breakdown products (BPs) (R-CN, -NCS and -SCN) by myrosinase when plant tissues are damaged. This stu...

Nrf2 Activation Promotes Keratinocyte Survival during Early Skin Carcinogenesis via Metabolic Alterations.

Cancer Res. 75 , 4817-29, (2015)

Pharmacologic activation of the transcription factor NRF2 has been suggested to offer a strategy for cancer prevention. In this study, we present evidence from murine tumorigenesis experiments suggest...