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Sigma-Aldrich

Amygdalin

BioXtra, ≥97.0% (HPLC)

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:
57646792
NACRES:
NA.25

biological source

synthetic

Quality Level

200

product line

BioXtra

assay

≥97.0% (HPLC)

form

powder

optical activity

[α]20/D −39±2°, c = 2% in H2O

technique(s)

HPLC: suitable

loss

≤7.5% loss on drying, 110 °C

color

white to off-white

solubility

H2O: 0.1 g/mL, clear to very faintly turbid, colorless (hot)

anion traces

chloride (Cl-): ≤50 mg/kg
sulfate (SO42-): ≤300 mg/kg

cation traces

Ca: ≤30 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤5 mg/kg
K: ≤300 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
Na: ≤50 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Zn: ≤5 mg/kg

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.
Review: Cyanogenic glycosides

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

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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Int. Rev. Biochem. (Biochemistry of Nutrition 1A, A. Neuberger, T.H. Jukes, eds., 27, 21-21 (1979)
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Journal of the American Veterinary Medical Association, 171(3), 284-286 (1977-08-01)
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