Amygdalin

Amygdalin
Names


IUPAC name [(6-O-β-D-Glucopyranosyl-β-D-glucopyranosyl)oxy](phenyl)acetonitrile
Identifiers
CAS Number	29883-15-6^N
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:17019^Y
ChEMBL	ChEMBL461727^Y
ChemSpider	570897^Y
ECHA InfoCard	100.045.372
MeSH	Amygdalin
PubChem	34751
UNII	214UUQ9N0H^Y
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^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
SMILES 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
Chemical formula	C₂₀H₂₇NO₁₁
Molar mass	457.429
Melting point	223-226 °C(lit.)
Solubility in water	H2O: 0.1 g/mL hot, clear to very faintly turbid, colorless
Hazards
Safety data sheet	A6005
GHS pictograms
GHS signal word	Warning
GHS hazard statements	H302
GHS precautionary statements	P264, P270, P301+312, P330, P501
NFPA 704	0 1 0
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 ^YN ?)
Infobox references

Laetrile
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
CAS Number	1332-94-1
3D model (Jmol)	Interactive image
ChemSpider	4588479
ECHA InfoCard	100.045.372
PubChem	5484354
InChI InChI=1S/C14H15NO7/c15-6-8(7-4-2-1-3-5-7)21-14-11(18)9(16)10(17)12(22-14)13(19)20/h1-5,8-12,14,16-18H,(H,19,20)/t8-,9-,10-,11+,12-,14+/m0/s1 Key: XLSLFPQAPYONPW-WHUHBCJBSA-N
SMILES c1ccc(cc1)[C@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C(=O)O)O)O)O
Properties
Chemical formula	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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