Amygdalin
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Category | Others |
Catalog number | BBF-03756 |
CAS | 29883-15-6 |
Molecular Weight | 457.43 |
Molecular Formula | C20H27NO11 |
Purity | >98% |
Ordering Information
Catalog Number | Size | Price | Stock | Quantity |
---|---|---|---|---|
BBF-03756 | 500 g | $398 | In stock |
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Amygdalin is a glycoside initially isolated from the seeds of the tree Prunus dulcis, also known as bitter almonds. The active ingredient of amygdalin is a naturally occurring cyanide, which is a human metabolite and can only play a role in cancer cells.
Specification
Related CAS | 672-72-0 (Deleted CAS) |
Synonyms | Benzeneacetonitrile, α-[(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-, (αR)-; (αR)-α-[(6-O-β-D-Glucopyranosyl-β-D-glucopyranosyl)oxy]benzeneacetonitrile; Benzeneacetonitrile, α-[(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-, (R)-; (-)-Amygdalin; (R)-Amygdalin; D-Amygdalin; Amygdaloside; Amygdaloside (disaccharide); Mandelonitrile-β-gentiobioside; NSC 15780 |
Storage | Store at 2-8°C |
IUPAC Name | (2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile |
Canonical SMILES | C1=CC=C(C=C1)C(C#N)OC2C(C(C(C(O2)COC3C(C(C(C(O3)CO)O)O)O)O)O)O |
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 |
InChI Key | XUCIJNAGGSZNQT-JHSLDZJXSA-N |
Source | Fruit seeds and pits. |
Properties
Appearance | White to Off-white Solid |
Application | Antitumor/antifibrotic |
Antibiotic Activity Spectrum | neoplastics (Tumor) |
Boiling Point | 743.3±60.0°C at 760 mmHg |
Melting Point | 223-226°C |
Density | 1.59±0.1 g/cm3 |
Solubility | Soluble in DMSO (Sparingly), Methanol (Slightly), Water |
Toxicity
Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
Mechanism Of Toxicity | Amygdalin can be metabolized into hydrogen cyanide in the stomach causing discomfort or illness. (L402) Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. |
Reference Reading
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C20H27NO11
Molecular Weight (Monoisotopic Mass): 457.1584 Da
Molecular Weight (Avergae Mass): 457.4285 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2