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Merck

10050

Amygdalin

BioXtra, ≥97.0% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C20H27NO11
Número CAS:
Peso molecular:
457.43
UNSPSC Code:
12352201
NACRES:
NA.25
PubChem Substance ID:
EC Number:
249-925-3
Beilstein/REAXYS Number:
66856
MDL number:

Nombre del producto

Amygdalin, BioXtra, ≥97.0% (HPLC)

InChI key

XUCIJNAGGSZNQT-SWRVSKMJSA-N

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

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

biological source

synthetic

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

Quality Level

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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

Review: Cyanogenic glycosides
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

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

ppe

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


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Visite la Librería de documentos

E.E. Conn
Int. Rev. Biochem. (Biochemistry of Nutrition 1A, A. Neuberger, T.H. Jukes, eds., 27, 21-21 (1979)
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
Anne Vinther Morant et al.
Plant physiology, 147(3), 1072-1091 (2008-05-10)
Lotus japonicus accumulates the hydroxynitrile glucosides lotaustralin, linamarin, and rhodiocyanosides A and D. Upon tissue disruption, the hydroxynitrile glucosides are bioactivated by hydrolysis by specific beta-glucosidases. A mixture of two hydroxynitrile glucoside-cleaving beta-glucosidases was isolated from L. japonicus leaves and
Raquel Sánchez-Pérez et al.
Plant physiology, 158(4), 1916-1932 (2012-02-23)
Amygdalin is a cyanogenic diglucoside and constitutes the bitter component in bitter almond (Prunus dulcis). Amygdalin concentration increases in the course of fruit formation. The monoglucoside prunasin is the precursor of amygdalin. Prunasin may be degraded to hydrogen cyanide, glucose
Amygdalin (Laetrile) and veterinary medicine.
D W Macy
Journal of the American Veterinary Medical Association, 171(3), 284-286 (1977-08-01)

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