(2S,4S,5S)-2-{[(1Z)-1-(hydroxyimino)-5-methanesulfinylpentyl]sulfanyl}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 166700
• Molecular Formular: C12H23NO7S2
• Molecular Mass: 357.44352
• Monoisotopic Mass: 357.09159408
• SMILES: [C@@H]1([C@@H](C([C@@H](OC1CO)S/C(=N\O)/CCCCS(=O)C)O)O)O
• Canonical SMILES: OCC1O[C@@H](S/C(=N\O)/CCCCS(=O)C)C([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C12H23NO7S2/c1-22(19)5-3-2-4-8(13-18)21-12-11(17)10(16)9(15)7(6-14)20-12/h7,9-12,14-18H,2-6H2,1H3/b13-8-/t7?,9-,10+,11?,12+,22?/m1/s1
• InChIKey: UYHMVWFYYZIVOP-RUAQSNJLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5S)-2-{[(1Z)-1-(hydroxyimino)-5-methanesulfinylpentyl]sulfanyl}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,4S,5S)-2-{[(1Z)-1-(hydroxyimino)-5-methanesulfinylpentyl]sulfanyl}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: 1-Thio-1-[N-hydroxy-5-(methylsulfinyl)pentanimidate] β-D-Glucopyranose; 4-Methylsulfinylbutyldesulfoglucosinolate; Desulfo Glucoraphanin

Database IDs

• CAS Number: 287966-62-5
• PubChem SID: 162260833
• PubChem CID: 71315835

CALCULATED PROPERTIES

• Acid pKa: 9.395626
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -2.6995087
• LogD (pH = 7.4): -2.703795
• Log P: -2.699448
• Molar Refractivity: 83.6272 cm^3
• Polarizability: 33.623367 Å^3
• Polar Surface Area: 139.81 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White to Pale Beige Solid
• Melting Point: 140-143°C

Safety Information

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

DETAILS

Toronto Research Chemicals - D297910

Glucosinolate analog of Glucoraphanin found in cruciferous vegetables such as broccoli and cauliflower.

REFERENCES

• Lee, J.G. et al.: Horticult. Env. Biotech., 50, 509 (2009)
• KIm, J.K. et al.: Food Chem., 119, 423 (2009)