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Amygdalin

Amygdalin
Amygdalin structure.svg
Amygdalin-from-xtal-3D-balls.png
Names
IUPAC name
[(6-O-β-D-Glucopyranosyl-β-D-glucopyranosyl)oxy](phenyl)acetonitrile
Identifiers
29883-15-6 N
3D model (Jmol) Interactive image
Interactive image
ChEBI CHEBI:17019 YesY
ChEMBL ChEMBL461727 YesY
ChemSpider 570897 YesY
ECHA InfoCard 100.045.372
MeSH Amygdalin
PubChem 34751
UNII 214UUQ9N0H YesY
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
Safety data sheet A6005
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word Warning
H302
P264, P270, P301+312, P330, P501
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
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).
N  (what is YesYN ?)
Infobox references
Laetrile
Laetrile.svg
Names
IUPAC name
(2S,3S,4S,5R,6R)-6-[(R)-cyano(phenyl)methoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Other names
L-mandelonitrile-β-D-glucuronide, Vitamin B₁₇
Identifiers
1332-94-1
3D model (Jmol) Interactive image
ChemSpider 4588479
ECHA InfoCard 100.045.372
PubChem 5484354
Properties
C14H15NO7
Molar mass 309.2714
Melting point 214 to 216 °C (417 to 421 °F; 487 to 489 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Amygdalin (from Ancient Greek: ἀμυγδαλή amygdálē "almond") is a poisonous cyanogenic glycoside found in many plants, but most notably in the seeds (kernels) of apricot, bitter almonds, apple, peach, and plum.

Since the early 1950s, both amygdalin and a modified form named laetrile have been promoted as alternative cancer treatments, often using the misnomer Vitamin B17. But studies have found them to be clinically ineffective in the treatment of cancer, as well as potentially toxic or lethal when taken by mouth, due to cyanide poisoning. Neither amygdalin nor laetrile is a vitamin.

The promotion of laetrile to treat cancer has been described in the medical literature as a canonical example of quackery, and as "the slickest, most sophisticated, and certainly the most remunerative cancer quack promotion in medical history."

Amygdalin is a cyanogenic glycoside derived from the aromatic amino acid phenylalanine. Amygdalin and prunasin are very common among plants of the Rosaceae family, particularly the genus Prunus, Poaceae (grasses), Fabaceae (legumes), and in other food plants, including linseed and manioc. Sambunigrin, obtained from leaves of the elder tree (Sambucus nigra), is isomeric to prunasin. Within these plants, amygdalin and the enzymes necessary to hydrolyze them are stored in separate locations so that they will mix in response to tissue damage. This provides a natural defense system


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