(2R)-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: 72917
• Molecular Formular: C20H27NO11
• Molecular Mass: 457.42848
• Monoisotopic Mass: 457.15841069
• SMILES: [C@H]1([C@H]([C@@H](O[C@@H]([C@H]1O)CO)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@H](c1ccccc1)C#N)O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@H](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+/m0/s1
• InChIKey: XUCIJNAGGSZNQT-JHSLDZJXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-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: vitamin B17; laetrile
• Synonyms: Amygdaloside; Glucoprunasin; Amygdalin; Amygdalin

Database IDs

• CAS Number: 29883-15-6
• EC Number: 249-925-3
• PubChem SID: 162037837
• PubChem CID: 656516; 34751
• CHEBI ID: 17019
• CHEMBL: 461727
• Chemspider ID: 570897
• MeSH Name: Amygdalin
• Unique Ingredient Identifier: 214UUQ9N0H
• Wikipedia Title: Amygdalin

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

• Apperance: Powder

Safety Information

• Storage Condition: -20°C
• RTECS: OO8450000
• European Hazard Symbols: Harmful (Xn)
• Risk Statements: R:22
• Safety Statements: S:36/37/39
• NFPA704:
  

  0

  1

  0

Product Information

• Salt Data: Free Base
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 05202055

MP Biomedicals Rare Chemical collection

Selleck Chemicals - S2260

Research Area: Cancer
Biological Activity:
Amygdalin is a glycoside initially isolated from the seeds of the tree Prunus dulcis, also known as bitter almonds. The metabolism of amygdalin produces hydrogen cyanide, a potent toxin. Beta-glucosidase, one of the enzymes that catalyzes the release of cyanide from amygdalin, is present in human small intestine and in a variety of common foods. This leads to an unpredictable and potentially lethal toxicity when amygdalin or laetrile is taken orally. Ingestion of purified amygdalin or apricot seeds can cause severe toxicity and death due to cyanide poisoning. Numerous case reports in the medical literature describe serious cyanide poisoning in patients who ingested laetrile as a cancer treatment. [1] 

REFERENCES

• http://en.wikipedia.org/wiki/Amygdalin