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

• ChemBase ID: 106097
• Molecular Formular: C20H27NO11
• Molecular Mass: 457.42848
• Monoisotopic Mass: 457.15841069
• SMILES: c1ccc(cc1)C(C#N)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC(c3ccccc3)C#N)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C20H27NO11/c21-6-10(9-4-2-1-3-5-9)30-20-18(28)16(26)14(24)12(32-20)8-29-19-17(27)15(25)13(23)11(7-22)31-19/h1-5,10-20,22-28H,7-8H2/t10?,11-,12-,13-,14-,15+,16+,17-,18-,19-,20-/m1/s1
• InChIKey: XUCIJNAGGSZNQT-SWRVSKMJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile
• IUPAC Traditional name: amygdalin
• Synonyms: D-Mandelonitrile β-gentiobioside; D-Mandelonitrile 6-O-β-D-glucosido-β-D-glucoside; D-Mandelonitrile-β-gentiobioside; Amygdalin; Laetrile; D-Amygdalin; Amygdalin; D-Mandelonitrile 6-O-β-D-glucosido-β-D-glucoside, D-Mandelonitrile β-gentiobioside; D-AMYGLADIN; D-扁桃腈-β-龙胆二糖苷; D-扁桃腈6-O-β-D-葡糖基-β-D-葡萄糖苷; D-杏仁腈β-龙胆二糖苷; 扁桃苷; 苦杏仁苷; D-苦杏苷; 扁桃苷

Database IDs

• CAS Number: 29883-15-6
• EC Number: 249-925-3
• MDL Number: MFCD00006598
• Beilstein Number: 66856
• PubChem SID: 24846528; 162087187; 24891046
• PubChem CID: 34751

CALCULATED PROPERTIES

• Acid pKa: 11.9090805
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -2.587887
• LogD (pH = 7.4): -2.5879002
• Log P: -2.5878868
• Molar Refractivity: 102.5097 cm^3
• Polarizability: 41.94759 Å^3
• Polar Surface Area: 202.32 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear to very faintly turbid, colorless (hot)
• Melting Point: 210-215 °C; 223-226 °C(lit.)
• Optical Rotation: [α]20/D -39±2°, c = 2% in H2O; [α]22/D -38°, c = 1.2 in H2O

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: OO8450000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; R:22
• Safety Statements: 26-36/37/39-45; S:20-46-36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: ≥97.0% (HPLC); ≥99%
• Cation Traces: Ca: ≤30 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤300 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤300 mg/kg
• Biological Source: from apricot kernels
• Loss on Drying: ≤5% loss on drying, 110 °C
• Quality Level: PREMIUM
• Product Line: BioXtra
• Empirical Formula (Hill Notation): C20H27NO11

DETAILS

Sigma Aldrich - 10050

Biochem/physiol Actions
Cyanogenic glycoside that is a component of bitter almonds and apricot pits. There is no scientific evidence that amygdalin itself is an effective anti-cancer agent. Recent studies using β-glucoside linked to a tumor-associated monoclonal antibody to release cyanide at the tumor cell has shown significant cytotoxicity.
Other Notes
Review: Cyanogenic glycosides1
Application
Amygdalin, a cyanide containing glycoside, may be used as a substrate to identify, differentiate and characterize enzymes such as maltase(s), emulsin(s) and β-glucosidase(s).

Sigma Aldrich - A6005

Biochem/physiol Actions
Cyanogenic glycoside that is a component of bitter almonds and apricot pits. There is no scientific evidence that amygdalin itself is an effective anti-cancer agent. Recent studies using β-glucoside linked to a tumor-associated monoclonal antibody to release cyanide at the tumor cell has shown significant cytotoxicity.
Application
Amygdalin, a cyanide containing glycoside, may be used as a substrate to identify, differentiate and characterize enzymes such as maltase(s), emulsin(s) and β-glucosidase(s).

Sigma Aldrich - A83202

Biochem/physiol Actions
Cyanogenic glycoside that is a component of bitter almonds and apricot pits. There is no scientific evidence that amygdalin itself is an effective anti-cancer agent. Recent studies using β-glucoside linked to a tumor-associated monoclonal antibody to release cyanide at the tumor cell has shown significant cytotoxicity.