ChemicalBook--->CAS DataBase List--->592-95-0

592-95-0

592-95-0 Structure

592-95-0 Structure
IdentificationBack Directory
[Name]

Sulforaphene
[CAS]

592-95-0
[Synonyms]

sativin
RAPHANIN
Sul aphene
sulforaphene
Sulphoraphen
L-SULFORAPHENE
S-SULFORAPHENE
L-SULPHORAPHENE
SULFORAPHENE, L-
Sulforaphen (6CI)
SULFORAPHANE, DL-(SH)
Sulforaphene USP/EP/BP
S-Sulforaphenefromradishseeds
4-Methylsulfinylbut-3-enyl isothiocyanate
4-isothiocyanato-1-(methylsulfinyl)-1-buten
4-isothiocyanato-1-(methylsulfinyl)-1-butene
4-ISOTHIOCYANATO-4R(METHYLSULFINYL)-1-BUTENE
1-Butene,4-isothiocyanato-1-(Methylsulfinyl)-
(-)4 ISOTHIOCYANATO-4R-METHYLSULFINYL)-1-BUTENE
(E)-4-Isothiocyanato-1-(methylsulfinyl)-1-butene
(-)4-ISOTHIOCYANATO-4S-(METHYLSULFINYL)-1-BUTENE
(-)-4-ISOTHIOCYANATO-(1S)-(METHYLSUFINYL)-1-BUTENE
(-)-4-ISOTHIOCYANATO-(1R)-(METHYLSULFINYL)-1-BUTENE
isothiocyanicacid,4-(methylsulfinyl)-3-butenylester
Isothiocyanicacid, 4-(methylsulfinyl)-3-butenyl ester (7CI,8CI)
[Molecular Formula]

C6H9NOS2
[MDL Number]

MFCD00189462
[MOL File]

592-95-0.mol
[Molecular Weight]

175.27
Chemical PropertiesBack Directory
[alpha ]

D19 -107° (c = 1.37 in chloroform); D14 -136° (c = 1.38 in alcohol)
[Boiling point ]

bp0.015 125-130°
[density ]

1.16±0.1 g/cm3(Predicted)
[storage temp. ]

Refrigerator, Under inert atmosphere
[solubility ]

Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Slightly), Ethylacetate (Slightly)
[form ]

Slightly yellowish liquid.
[color ]

Colourless to Yellow
[InChI]

InChI=1S/C6H9NOS2/c1-10(8)5-3-2-4-7-6-9/h3,5H,2,4H2,1H3
[InChIKey]

QKGJFQMGPDVOQE-UHFFFAOYSA-N
[SMILES]

C(S(C)=O)=CCCN=C=S
[CAS DataBase Reference]

592-95-0
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302
[Precautionary statements ]

P264-P270-P301+P312-P330-P501
Questions And AnswerBack Directory
[Pharmacological action]

Sulforaphene, or raphanin, is the main sulfur component found in radish seeds of Raphanus sativus and is also found in broccoli and red cabbage. It was first described by G. Ivanovics and S. Horvath in 1947. Sulforaphene inhibits activity of viruses, some fungi and various bacteria including Staphylococcus, Streptococcus, Pneumococcus and Escherichia coli. The effect is stronger against Gram-positive than Gram-negative bacteria and against DNA than RNA viruses; it is suppressed by serum and by sulfur compounds such as hydrogen sulfide, mercaptoacetic acid, cystine and glutathione. The antibacterial, antifungal and antiviral effects from consuming radishes were recognized in traditional Chinese medicine. However, in the abstract to his 1947 paper, Ivanovics noted that because sulforaphene is highly toxic, it did not "hold the promise of a useful therapeutic agent".

[Cancer Treatment]

Sulforaphene may be a potential anti-triple negative breast cancer natural compound and its antiproliferation effects may be mediated by tumor suppressor Egr1; it has chemotherapeutic potential, it promotes Bax/Bcl2, MAPK-dependent human gastric cancer AGS cells apoptosis and inhibits migration via EGFR, p-ERK1/2 down-regulation; it enhances radiosensitivity of hepatocellular carcinoma through suppression of the NF-κB pathway. Sulforaphene has anti-proliferative and antibacterial properties. Sulforaphene also has herbicidal activity, the ED50 of it against velvetleaf seedlings was approximately 2×10-4 M.

Hazard InformationBack Directory
[Chemical Properties]

A brown liquid, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from the seeds of broccoli (Brassica oleracea L.var.italic Planch.); cabbage (Brassica oleracea var. capitata); and carrots.
[Uses]

Shows antitumor activity.
[Synthesis Reference(s)]

Tetrahedron, 22, p. 2139, 1966 DOI: 10.1016/S0040-4020(01)82133-5
[in vivo]

Sulforaphene (1 and 5 mg/kg, i.p., everyday) inhibits tumor growth in a mouse HCT116 xenograft model[6].

Animal Model:Mouse HCT116 xenograft model[6]
Dosage:1 and 5 mg/kg
Administration:i.p., everyday
Result:Inhibited tumor growth, and increased CDK1, MK2, and p38 phosphorylation.
[storage]

4°C, protect from light
Spectrum DetailBack Directory
[Spectrum Detail]

Sulforaphene(592-95-0)1HNMR
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