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

• ChemBase ID: 177083
• Molecular Formular: C14H17NO6
• Molecular Mass: 295.28788
• Monoisotopic Mass: 295.10558727
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)OC(c1ccccc1)C#N)O)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](OC(c2ccccc2)C#N)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C14H17NO6/c15-6-9(8-4-2-1-3-5-8)20-14-13(19)12(18)11(17)10(7-16)21-14/h1-5,9-14,16-19H,7H2/t9?,10-,11-,12+,13-,14-/m1/s1
• InChIKey: ZKSZEJFBGODIJW-MXNNCRBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile
• IUPAC Traditional name: prunasin
• Synonyms: (αR)-α-(β-D-Glucopyranosyloxy)benzeneacetonitrile; (2R)-Prunasin; D-Prunasin; (R)-Prunasin

Database IDs

• CAS Number: 99-18-3
• PubChem SID: 164232993
• PubChem CID: 120639

CALCULATED PROPERTIES

• Acid pKa: 12.207629
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.81705123
• LogD (pH = 7.4): -0.8170579
• Log P: -0.8170511
• Molar Refractivity: 70.0964 cm^3
• Polarizability: 28.165382 Å^3
• Polar Surface Area: 123.17 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 129-131°C

Safety Information

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

DETAILS

Toronto Research Chemicals - P839000

Used in the synthesis of cyanogen glycoside. A component of antiperspirants, deodorants, body soaps, shampoos, hair rinses, and hair; it inhibits volatile steroid formation by resident bacteria.

REFERENCES

• Marouf, A., et al.: Pharm. Biol., 39, 263 (2001)
• Fukuda, T., et al.: Biol. Pharm. Bull., 26, 271 (2001)
• Butler, M., et al.: J. Nat. Prod., 67, 2141 (2001)
• He, J., et al.: J. Nat. Prod., 69, 121 (2001)