1-isothiocyanato-4-methanesulfinylbutane

• ChemBase ID: 177994
• Molecular Formular: C6H11NOS2
• Molecular Mass: 177.28764
• Monoisotopic Mass: 177.02820598
• SMILES: CS(=O)CCCCN=C=S
• Canonical SMILES: S=C=NCCCCS(=O)C
• InChI: InChI=1S/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3
• InChIKey: SUVMJBTUFCVSAD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-isothiocyanato-4-methanesulfinylbutane
• IUPAC Traditional name: sulforaphane
• Synonyms: 1-Isothiocyanato-4-(methylsulfinyl)-butane; 4-Methylsulfinylbutyl Isothiocyanate; Sulforaphan; D,L-Sulforaphane

Database IDs

• CAS Number: 4478-93-7
• PubChem SID: 164233904
• PubChem CID: 5350

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.21977109
• LogD (pH = 7.4): 0.21977109
• Log P: 0.21977109
• Molar Refractivity: 49.5677 cm^3
• Polarizability: 19.27231 Å^3
• Polar Surface Area: 29.43 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Diethyl Ether
• Apperance: Light Yellow Liquid
• Boiling Point: 125-135°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - S699115

Potent, selective inducer of phase II detoxification enzymes with anticarcinogenic properties. Occurs naturally in broccoli. It was found to inhibit chemically induced mammary tumor formation in rats. Antitumor agent.

REFERENCES

• Zhang, Y., et al.: Proc. Natl. Acad. Sci. USA, 89, 2399 (1992)
• Shikita, M., et al.: Biochem. J., 341, 725 (1992)
• Wittich, S., et al.: J. Med. Chem., 45, 3296 (1992)
• Lee, J., et al.: Cancer Lett., 224, 171 (1992)