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Amygdalin

Cyanogenic glycoside present in kernels of fruit / From Wikipedia, the free encyclopedia

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Amygdalin
Names
IUPAC name
(2R)-[(6-O-β-D-Glucopyranosyl-β-D-glucopyranosyl)oxy]phenylacetonitrile
Preferred IUPAC name
(2R)-Phenyl{[(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
Identifiers
3D model (JSmol)
66856
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.045.372
EC Number
  • 249-925-3
MeSH Amygdalin
UNII
  • 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 Y
    Key: XUCIJNAGGSZNQT-JHSLDZJXSA-N Y
  • InChI=1/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
    Key: XUCIJNAGGSZNQT-JHSLDZJXBT
  • O[C@@H]3[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]3OC[C@H]2O[C@@H](OC(C#N)c1ccccc1)[C@H](O)[C@@H](O)[C@@H]2O
  • N#C[C@H](O[C@@H]2O[C@H](CO[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)[C@@H](O)[C@H](O)[C@H]2O)c3ccccc3
Properties
C20H27NO11
Molar mass 457.429
Melting point 223-226 °C(lit.)
H2O: 0.1 g/mL hot, clear to very faintly turbid, colorless
Hazards
GHS labelling:
Warning
H302
P264, P270, P301+P312, P330, P501
NFPA 704 (fire diamond)
1
0
0
Safety data sheet (SDS) A6005
Related compounds
Related compounds
Vicianin, laetrile, prunasin, sambunigrin
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Amygdalin (from Ancient Greek: ἀμυγδαλή amygdalē "almond") is a naturally occurring chemical compound found in many plants, most notably in the seeds (kernels) of apricots, bitter almonds, apples, peaches, cherries, and plums.

Amygdalin is classified as a cyanogenic glycoside because each amygdalin molecule includes a nitrile group, which can be released as the toxic cyanide anion by the action of a beta-glucosidase. Eating amygdalin will cause it to release cyanide in the human body, and may lead to cyanide poisoning.[1]

Since the early 1950s, both amygdalin and a chemical derivative named laetrile have been promoted as alternative cancer treatments, often under the misnomer vitamin B17 (neither amygdalin nor laetrile is a vitamin).[2] Scientific study has found them to not only be clinically ineffective in treating cancer, but also potentially toxic or lethal when taken by mouth due to cyanide poisoning.[3] The promotion of laetrile to treat cancer has been described in the medical literature as a canonical example of quackery,[4][5] and as "the slickest, most sophisticated, and certainly the most remunerative cancer quack promotion in medical history".[2]