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Sulforaphene

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Related articles

Sulforaphene Basic information
Pharmacological action Cancer Treatment
Product Name:Sulforaphene
Synonyms:(E)-4-Isothiocyanato-1-(methylsulfinyl)-1-butene;sativin;sulforaphene;S-Sulforaphenefromradishseeds;SULFORAPHANE, DL-(SH);1-Butene,4-isothiocyanato-1-(Methylsulfinyl)-;L-SULFORAPHENE;L-SULPHORAPHENE
CAS:592-95-0
MF:C6H9NOS2
MW:175.27
EINECS:
Product Categories:Miscellaneous Natural Products
Mol File:592-95-0.mol
Sulforaphene Structure
Sulforaphene Chemical Properties
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
InChIInChI=1S/C6H9NOS2/c1-10(8)5-3-2-4-7-6-9/h3,5H,2,4H2,1H3
InChIKeyQKGJFQMGPDVOQE-UHFFFAOYSA-N
SMILESC(S(C)=O)=CCCN=C=S
CAS DataBase Reference592-95-0
Safety Information
MSDS Information
Sulforaphene Usage And Synthesis
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.

Chemical PropertiesBrown liquid, soluble in methanol, ethanol, DMSO and other organic solvents, from broccoli Brassica oleracea L. var. italic Planch. seeds; cabbage Brassica oleracea var. capitata; carrot.
UsesSulforaphene is an extract from the seeds of Raphanus sativus and displays anti-inflammatory and anti-cancer 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.
Sulforaphene Preparation Products And Raw materials
Raw materials4-(METHYLTHIO)-3-BUTENYLISOTHIOCYANATE-->Glucoraphenin
Tag:Sulforaphene(592-95-0) Related Product Information
Fluorescein isothiocyanate Tiglic aldehyde 1,4-PHENYLENE DIISOTHIOCYANATE Phenyl isothiocyanate GLUCOTROPAEOLIN Z-LIGUSTILIDE ALPHA-CARYOPHYLLENE Hydroxycitric acid Xanthiside Muscone ISOQUERCITRIN ERUCIN Allyl isothiocyanate ISOTHIOCYANIC ACID 3-BUTEN-1-YL ESTER SULFORAPHENE, L-(RG) Sulforaphene ISOTHIOCYANATE, POLYMER-BOUND, 200-400

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