AMYGDALINE
Amygdalin is a naturally occurring cyanogenic glycoside found in some seeds and plants. It has been promoted for unproven anticancer effects. Its breakdown may release cyanide, posing toxicity risks. Side effects include headache, dizziness, nausea, hypotension, and potentially severe cyanide poisoning, making clinical use unsafe without strict controls.
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Product Description
Mechanism of action
Amygdalin is a cyanogenic glycoside that releases hydrogen cyanide (HCN) when hydrolysed by β‑glucosidases. HCN inhibits cytochrome c oxidase (complex IV) in the mitochondrial electron transport chain, arresting oxidative phosphorylation and cellular respiration.
Benefits and advantages
Used exclusively in enzymology and toxicology research, particularly in studying cyanogenesis, mitochondrial inhibition and detoxification pathways.
Side effects and risks
Extremely toxic. Symptoms of cyanide poisoning include seizures, cardiac collapse, hypoxia and metabolic acidosis. Requires full hazardous‑materials protection.
Datasheet
| Molecular Formula | C20H27NO11 |
|---|---|
| Molecular Weight | 457.43 g/mol |
| CAS Number | 29883-15-6 |
| Storage Condition | Store in a cool, dry place. Keep container tightly closed. Protect from moisture and light. |
| Solubility | Solubility depends on solvent and conditions (e.g., pH). Please contact us for solvent-specific guidance. |
| Purity | Purity information is available upon request (COA). |
| Synonym | 2-phenyl-2-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile; 2-Phenyl-2-(3,4,5-Trihydroxy-6-((3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl)Oxymethyl)Oxan-2-Yl)Oxyacetonitrile; RefChem:1064132; Amygdaloside; DL-Amygdalin |
| IUPAC/Chemical Name | Phenyl cyanohydrin β-D-diglucoside |
| InChl Key | JAQXQHSKWZZGPL-UHFFFAOYSA-N |
| InChl Code | 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 |
| References |
3D Conformer.
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