Amygdalin

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Amygdalin
Category Others
Catalog number BBF-03756
CAS 29883-15-6
Molecular Weight 457.43
Molecular Formula C20H27NO11
Purity >98%

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BBF-03756 500 g $398 In stock

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Description

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

1.Amygdalin from Apricot Kernels Induces Apoptosis and Causes Cell Cycle Arrest in Cancer Cells: An Updated Review
Anticancer Agents Med Chem. 2018;18(12):1650-1655. doi: 10.2174/1871520618666180105161136.
Background: Amygdalin is a cyanogenic glycoside which is described as a naturally occurring anticancer agent. Current review highlights apoptosis-inducing attributes of amygdalin towards different cancers and its potential application as an anti-cancer agent in cancer therapy. Method: Data about amygdalin was retrieved from all major scientific databases i.e., PubMed, ScienceDirect, Google Scholar, Scopus and Medline by using combination of keywords like amygdalin, apoptosis, laetrile, vitamin B- 17, pro-apoptotic proteins, anti-apoptotic proteins, hydrogen cyanide, mechanism of action of amygdalin and amygdalin therapy on humans. However, no specific time frame was followed for collection of data. Results: Data collected from already published articles revealed that apoptosis is a central process activated by amygdalin in cancer cells. It is suggested to stimulate apoptotic process by upregulating expression of Bax (proapoptotic protein) and caspase-3 and downregulating expression of Bcl-2 (anti-apoptotic protein). It also promotes arrest of cell cycle in G0/G1 phase and decrease number of cells entering S and G2/M phases. Thus, it is proposed to enhance deceleration of cell cycle by blocking cell proliferation and growth. Conclusion: The current review epitomizes published information and provides complete interpretations about all known anti-cancer mechanisms of amygdalin, possible role of naturally occurring amygdalin in fight against cancer and mistaken belief about cyanide toxicity causing potential of amygdalin. However, well-planned clinical trials are still needed to be conducted to prove effectiveness of this substance in vivo and to get approval for human use.
2.Amygdalin: Toxicity, Anticancer Activity and Analytical Procedures for Its Determination in Plant Seeds
Molecules. 2021 Apr 13;26(8):2253. doi: 10.3390/molecules26082253.
Amygdalin (d-Mandelonitrile 6- O -β-d-glucosido-β-d-glucoside) is a natural cyanogenic glycoside occurring in the seeds of some edible plants, such as bitter almonds and peaches. It is a medically interesting but controversial compound as it has anticancer activity on one hand and can be toxic via enzymatic degradation and production of hydrogen cyanide on the other hand. Despite numerous contributions on cancer cell lines, the clinical evidence for the anticancer activity of amygdalin is not fully confirmed. Moreover, high dose exposures to amygdalin can produce cyanide toxicity. The aim of this review is to present the current state of knowledge on the sources, toxicity and anticancer properties of amygdalin, and analytical methods for its determination in plant seeds.
3.Amygdalin - A pharmacological and toxicological review
J Ethnopharmacol. 2020 May 23;254:112717. doi: 10.1016/j.jep.2020.112717.
Ethnopharmacological relevance: Amygdalin is commonly distributed in plants of the Rosaceae, such as peach, plum, loquat, apple and bayberry, but most notably in the seeds (kernels) of apricot almonds. As a naturally aromatic cyanogenic compound, it has long been used in Asia, Europe and other regions for the treatment of various diseases including cough, asthma, nausea, leprosy and leukoderma. Importantly, in recent years, an increasing attention has been paid to its antitumor effect. Aim of the study: The paper aims to review the pharmacological activities and toxicological effects of amygdalin and provide a reference and perspective for its further investigation. Methods: Electronic databases including the Web of Science, Cochrane Library, PubMed, EMBASE, the Chinese Biological Medicine Database, China National Knowledge Infrastructure, Wanfang database and VIP information database were searched up to November 2019 to identify eligible studies. A meticulous review was performed, an in-depth analysis on the pharmacological activity and toxicology of amygdalin was conducted, and perspectives for future research were also discussed. Results: A total of 110 papers about in vitro/in vivo studies on amygdalin have been reviewed. Analysis on the data suggested that this compound presented pharmacological activities of anti-tumor, anti-fibrotic, anti-inflammatory, analgesic, immunomodulatory, anti-atherosclerosis, ameliorating digestive system and reproductive system, improving neurodegeneration and myocardial hypertrophy, as well as reducing blood glucose. In addition, studies revealed that amygdalin's toxicity was caused by its poisonous decomposite product of benzaldehyde and hydrogen cyanide after oral ingestion, toxicity of intravenous administration route was far less than the oral route, and it can be avoidable with an oral dose ranging from 0.6 to 1 g per day. Conclusion: This paper has systematically reviewed the pharmacology and toxicology of amygdalin and provided comprehensive information on this compound. We hope this review highlights some perspectives for the future research and development of amygdalin.

Spectrum

Predicted LC-MS/MS Spectrum - 10V, Positive

Experimental Conditions

Ionization Mode: Positive
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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