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Key Documents

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:
Molecular Weight:
457.43
Beilstein:
66856
EC Number:
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, 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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Amygdalin (Laetrile) and veterinary medicine.
D W Macy
Journal of the American Veterinary Medical Association, 171(3), 284-286 (1977-08-01)
Juan J Perez
Future medicinal chemistry, 5(7), 799-808 (2013-05-09)
Psoriasis is one of the most prevalent immune-mediated illness worldwide. The disease can still only be managed rather than cured, so treatments are aimed at clearing skin lesions and preventing their recurrence. Several treatments are available depending on the extent
Li Liu et al.
Journal of ethnopharmacology, 139(2), 381-387 (2011-11-30)
Persicae Semen (Taoren) and Carthami Flos (Honghua) used in pair which is named as Taoren-Honghua (TH) herb pair has been used in traditional Chinese medicine (TCM) for promoting blood circulation to dissipate blood stasis for many years in China. This
Claudia Cervellati et al.
Journal of biotechnology, 159(4), 312-319 (2011-09-24)
In apricot the bitter flavor of seeds is determined by the amount of amygdalin, a cyanogenic glucoside whose cleavage by endogenous enzymes, upon seed crushing, releases toxic hydrogen cyanide. The presence of such a poisonous compound is an obstacle to
Stefania Milazzo et al.
The Cochrane database of systematic reviews, (11)(11), CD005476-CD005476 (2011-11-11)
Laetrile is the name for a semi-synthetic compound which is chemically related to amygdalin, a cyanogenic glycoside from the kernels of apricots and various other species of the genus Prunus. Laetrile and amygdalin are promoted under various names for the

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