(2S)-2-(4-hydroxyphenyl)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile

• ChemBase ID: 126935
• Molecular Formular: C14H17NO7
• Molecular Mass: 311.28728
• Monoisotopic Mass: 311.10050189
• SMILES: c1cc(ccc1[C@@H](C#N)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@@H](c2ccc(cc2)O)C#N)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C14H17NO7/c15-5-9(7-1-3-8(17)4-2-7)21-14-13(20)12(19)11(18)10(6-16)22-14/h1-4,9-14,16-20H,6H2/t9-,10-,11-,12+,13-,14-/m1/s1
• InChIKey: NVLTYOJHPBMILU-YOVYLDAJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(4-hydroxyphenyl)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile
• IUPAC Traditional name: dhurrin
• Synonyms: (S)-4-Hydroxymandelnitrile-β-D-glucopyranoside; (S)-(β-D-Glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile; Dhurrin; (S)-(β-D-Glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile; (S)-4-Hydroxymandelonitrile β-D-glucoside; Dhurrin

Database IDs

• CAS Number: 499-20-7
• EC Number: 207-878-6
• MDL Number: MFCD18632527
• PubChem SID: 162221261
• PubChem CID: 161355
• Chemspider ID: 141737
• Wikipedia Title: Dhurrin

CALCULATED PROPERTIES

• Acid pKa: 9.456334
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -1.1206642
• LogD (pH = 7.4): -1.1243923
• Log P: -1.1206164
• Molar Refractivity: 72.0773 cm^3
• Polarizability: 28.835571 Å^3
• Polar Surface Area: 143.4 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C14H17NO7

DETAILS

Sigma Aldrich - 07743

General description
Dhurrin is a cyanogenic glucoside found expressed in the leaves of Sorghum plants. Studies have shown that as the plant ages, dhurrin expression depends are nitrogen availability. Dhurrin production shifts from the leaves to the stems during development. 1