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Amygdalin

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-A3019

  • Specification : 98%

  • CAS number : 29883-15-6

  • Formula : C20H27NO11

  • Molecular Weight : 457.43

  • PUBCHEM ID : 656516

  • Volume : 25mg

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Catalogue Number

BF-A3019

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

457.43

Appearance

White crystalline powder

Botanical Source

Eriobotrya japonica,Eleutherococcus senticosus,Amygdalus persica,Armeniaca vulgaris,Cerasus japonica

Structure Type

Others

Category

Standards;Natural Pytochemical;API

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

Synonyms

Mandelonitrile b-Glucuronide/Vitamin B17/rile/(2R)-{[6-O-(β-D-Glucopyranosyl)-β-D-glucopyranosyl]oxy}(phenyl)acetonitrile/Mygdalin/D-amygdalin/(2R)-Phenyl{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}methyl)tetrahydro-2H-pyran-2-yl]oxy}acetonitrile/Mandelonitrile-b-gentiobioside/amygdaloside/D-Mandelonitrile 6-O-β-D-glucosido-β-D-glucoside/(2R)-{[6-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl]oxy}(phenyl)ethanenitrile/D-AMYGLADIN/D-Mandelonitrile-β-gentiobioside/Laetrile/Nitrilosides/mandelonitrile-β-gentiobioside/(R)-amygdalin/D-Mandelonitrile-b-D-glucosido-6-b-D-glucoside/Benzeneacetonitrile, α-[(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-, (αR)-/[(6-O-b-D-Glucopyranosyl-b-D-glucopyranosyl)oxy]benzeneacetonitrile/Amygdalin

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

Density

1.6±0.1 g/cm3

Solubility

Methanol; Water; Acetontrile

Flash Point

403.3±32.9 °C

Boiling Point

743.3±60.0 °C at 760 mmHg

Melting Point

223-226 °C(lit.)

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:29883-15-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29308747

Abstract

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.

KEYWORDS

Amygdalin; Bax; Bcl-2; apoptosis; cancer; caspase-3..

Title

Amygdalin From Apricot Kernels Induces Apoptosis and Causes Cell Cycle Arrest in Cancer Cells: An Updated Review

Author

Mohammad Saleem 1 , Jawaria Asif 2 , Muhammad Asif 2 , Uzma Saleem 2

Publish date

2018

PMID

29486614

Abstract

Amygdalin, named as ‘laetrile’ and ‘vitamin B-17’ was initially supposed to be a safe drug for cancer treatment and was recognized by followers of natural medicine since it has been considered to be hydrolyzed only in cancer cells releasing toxic hydrogen cyanide (HCN), and thus destroying them. Unfortunately, current studies have shown that HCN is also released in normal cells, therefore it may not be safe for human organism. However, there have still been research works conducted on anti-cancer properties of this compound. In vitro experiments have shown induction of apoptosis by amygdalin as a result of increased expression of Bax protein and caspase-3 and reduced expression of antiapoptotic BcL-2protein. Amygdalin has also been shown to inhibit the adhesion of breast cancer cells, lung cancer cells and bladder cancer cells by decreased expression of integrin’s, reduction of catenin levels and inhibition of the Akt-mTOR pathway, which may consequently lead to inhibition of metastases of cancer cells. It has also been revealed that amygdalin in renal cancer cells increased expression of p19 protein resulting in inhibition of cell transfer from G1-phase to S-phase, and thus inhibited cell proliferation. Other studies have indicated that amygdalin inhibits NF-kβ and NLRP3 signaling pathways, and consequently has anti-inflammatory effect due to reducing the expression of proinflammatory cytokines such as pro-IL-1β. Moreover, the effect of amygdalin on TGFβ/CTGF pathway, anti-fibrous activity and expression of follistatin resulting in activation of muscle cells growth has been reported. This compound might be applicable in the treatment of various cancer cell types.

KEYWORDS

Amygdalin; Bax; Bcl-2; apoptosis; cancer; caspase-3..

Title

Molecular Mechanism of Amygdalin Action in Vitro: Review of the Latest Research

Author

Przemysław Liczbiński 1 , Bożena Bukowska 1

Publish date

2018 Jun

PMID

31610669

Abstract

Background: Amygdalin is a natural compound primarily found in seeds of fruit trees. In the human body, it is hydrolyzed to benzaldehyde, glucose, and cyanide, which is considered the active component of amygdalin. The semi-synthetic form of amygdalin is known under the commercial name Laetrile® or as vitamin B17.
Purpose: This review aims to provide a comprehensive overview of studies that evaluated the potential therapeutic effects of amygdalin in oncology. Preclinical studies provided information about the mechanisms of action of amygdalin in vitro and in vivo and its toxicity. Recent in vitro studies demonstrated the effects of amygdalin on the cell cycle, apoptosis, and synthesis of cyclooxygenase-2, inducible nitric oxide synthase, E-cadherin, and integrins β1 and β4. However, amygdalin exhibited no or low treatment efficiency in preclinical in vivo studies. Conversely, many case studies describe the anti-tumor effects of amygdalin, but these have not been confirmed in clinical trials. Only two clinical studies published almost 40 years ago focused on the safety of amygdalin administered orally and intravenously. Although these studies reported that amygdalin had no benefit in 178 cancer patients, this compound has recently come to the attention of both scientists and patients. The results of recent in vitro studies are promising and indicate that amygdalin has a oncopreventive effect, although this must be confirmed by in vivo studies and clinical trials. Considering its proven toxicity and unconvincing clinical effects, amygdalin cannot currently be recommended to oncology patients as a supportive treatment.

KEYWORDS

adverse effects; amygdalin; cancer; toxicity.

Title

Can Amygdalin Provide Any Benefit in Integrative Anticancer Treatment?

Author

Alžběta Třiskova, Jana Ruda-Kucerova

Publish date

2019


Description :

Amygdalin is a plant glucoside isolated from the stones of rosaceous fruits, such as apricots, peaches, almond, cherries, and plums.