Amygdalin
Cyanogenic glycoside present in kernels of fruit / From Wikipedia, the free encyclopedia
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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, and in the roots of manioc.
Names | |
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IUPAC name
(2R)-[β-D-Glucopyranosyl-(1→6)-β-D-glucopyranosyloxy]phenylacetonitrile | |
Systematic 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) |
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66856 | |
ChEBI | |
ChEMBL | |
ChemSpider |
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ECHA InfoCard | 100.045.372 |
EC Number |
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MeSH | Amygdalin |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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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) | |
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 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]