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(1E)-4-Isothiocyanato-1-(methylsulfinyl)-1-butene

Names

[ CAS No. ]:
592-95-0

[ Name ]:
(1E)-4-Isothiocyanato-1-(methylsulfinyl)-1-butene

[Synonym ]:
4-isothiocyanato-1-(methylsulfinyl)-1-buten
S-SULFORAPHENE
(1E)-4-Isothiocyanato-1-(methylsulfinyl)-1-butene
SULFORAPHENE,L
4-methylsulfinyl-3-butenyl isothiocyanate
1-Butene, 4-isothiocyanato-1-(methylsulfinyl)-, (1E)-
RAPHANIN
L-SULFORAPHENE
L-SULPHORAPHENE
4-Methylsulfinyl-3-butenyl-isothiocyanat (Sulphoraphen)
SULFORAPHANE,DL-(SH)
sativin

Biological Activity

[Description]:

Sulforaphene, isolated from radish seeds, exhibits an ED50 against velvetleaf seedlings approximately 2 x 10-4 M. Sulforaphene promotes cancer cells apoptosis and inhibits migration via inhibiting EGFR, p-ERK1/2, NF‐κB and other signals[1][2][3][4].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer
Signaling Pathways >> JAK/STAT Signaling >> EGFR
Signaling Pathways >> Protein Tyrosine Kinase/RTK >> EGFR
Signaling Pathways >> MAPK/ERK Pathway >> ERK
Signaling Pathways >> Stem Cell/Wnt >> ERK

[References]

[1]. Kuang P, et al. Separation and purification of sulforaphene from radish seeds using macroporous resin and preparative high-performance liquid chromatography. Food Chem. 2013 Jan 15;136(2):342-7.

[2]. Anita M. Brinker, et al. Herbicidal activity of sulforaphene from stock (Matthiola incana). Journal of Chemical Ecology. Vol. 19. No. 10, 1993.

[3]. Mondal A, et al. Sulforaphene promotes Bax/Bcl2, MAPK-dependent human gastric cancer AGS cells apoptosis and inhibits migration via EGFR, p-ERK1/2 down-regulation. General Physiology and Biophysics, 27 Nov 2015, 35(1):25-34.

[4]. Ren K, et al. Sulforaphene enhances radiosensitivity of hepatocellular carcinoma through suppression of the NF-κB pathway. J Biochem Mol Toxicol. 2017 Aug;31(8).

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
362.2±42.0 °C at 760 mmHg

[ Molecular Formula ]:
C6H9NOS2

[ Molecular Weight ]:
175.272

[ Flash Point ]:
172.8±27.9 °C

[ Exact Mass ]:
175.012558

[ PSA ]:
80.73000

[ LogP ]:
0.47

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

[ Index of Refraction ]:
1.567

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
NX8944000
CHEMICAL NAME :
Isothiocyanic acid, 4-(methylsulfinyl)-3-butenyl ester
CAS REGISTRY NUMBER :
592-95-0
LAST UPDATED :
199206
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C6-H9-N-O-S2
MOLECULAR WEIGHT :
175.28

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
10 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 8(2),357,1982

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds