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A6005

Sigma-Aldrich

Amygdalin

≥99% (HPLC), from apricot kernels

Synonym(s):

D-Mandelonitrile 6-O-β-D-glucosido-β-D-glucoside, D-Mandelonitrile-β-gentiobioside, Amygdaloside, Laetrile

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About This Item

Empirical Formula (Hill Notation):
C20H27NO11
CAS Number:
29883-15-6
Molecular Weight:
457.43
Beilstein/REAXYS Number:
66856
EC Number:
249-925-3
MDL number:
MFCD00006598
UNSPSC Code:
12352201
PubChem Substance ID:
24891046
NACRES:
NA.25

biological source

apricot kernels

assay

≥99% (HPLC)

form

powder

technique(s)

HPLC: suitable

impurities

<11% water (Karl Fischer)

color

white

mp

223-226  °C

solubility

water: 50 mg/mL, clear to slightly hazy, colorless

storage temp.

room temp

SMILES string

OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC(C#N)c3ccccc3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

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-/m1/s1

InChI key

XUCIJNAGGSZNQT-SWRVSKMJSA-N

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Application

Amygdalin, a cyanide containing glycoside, may be used as a substrate to identify, differentiate and characterize enzymes such as maltase(s), emulsin(s) and β-glucosidase(s).

Biochem/physiol Actions

Cyanogenic glycoside that is a component of bitter almonds and apricot pits. There is no scientific evidence that amygdalin itself is an effective anti-cancer agent. Recent studies using β−glucoside linked to a tumor-associated monoclonal antibody to release cyanide at the tumor cell has shown significant cytotoxicity.

Other Notes

To gain a comprehensive understanding of our extensive range of Disaccharides for your research, we encourage you to visit our Carbohydrates Category page.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Geraldine A Wright et al.
Current biology : CB, 20(24), 2234-2240 (2010-12-07)
Avoiding toxins in food is as important as obtaining nutrition. Conditioned food aversions have been studied in animals as diverse as nematodes and humans [1, 2], but the neural signaling mechanisms underlying this form of learning have been difficult to
Lishuang Yu et al.
Electrophoresis, 32(2), 218-222 (2011-01-22)
A new method for separation and determination of amygdalin and its epimer (neoamygdalin) in the epimerization of amygdalin by MEEKC is proposed. For the chiral separation of amygdalin and neoamygdalin, a running buffer composed of 80 mM sodium cholate, 5.0% v/v
Ebenezer O Farombi et al.
International journal of environmental research and public health, 8(6), 2533-2555 (2011-07-22)
Recently, considerable attention has been focused on dietary and medicinal phytochemicals that inhibit, reverse or retard diseases caused by oxidative and inflammatory processes. Vernonia amygdalina is a perennial herb belonging to the Asteraceae family. Extracts of the plant have been
Alexander M Abdelnoor
Expert opinion on therapeutic patents, 19(8), 1057-1071 (2009-07-02)
It is hypothesized that psoriasis is an autoimmune disease. The most recent therapeutic approach that proved to be more effective than earlier methods of treatment is the use of mAb/fusion proteins. Efforts nowadays are focused on investigating the antipsoriatic affect
Fang Hu et al.
AMB Express, 9(1), 37-37 (2019-03-20)
The aim of the present study was to evaluate the protective effects of combined atorvastatin and amygdalin in a rat model of endometriosis. Tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), matrix metalloproteinase-2 (MMP-2) and MMP-9 levels in the peritoneal fluid were
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