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Merck

10050

Sigma-Aldrich

Amygdalin

BioXtra, ≥97.0% (HPLC)

Synonym(e):

D-Mandelsäurenitril-β-gentiobiosid, D-Mandelsäurenitril-6-O-β-D-glucosido-β-D-glucosid, Amygdalosid, Laetril

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About This Item

Empirische Formel (Hill-System):
C20H27NO11
CAS-Nummer:
Molekulargewicht:
457.43
Beilstein:
66856
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352201
PubChem Substanz-ID:
NACRES:
NA.25

Biologische Quelle

synthetic

Produktlinie

BioXtra

Assay

≥97.0% (HPLC)

Form

powder

Optische Aktivität

[α]20/D −39±2°, c = 2% in H2O

Methode(n)

HPLC: suitable

Verlust

≤7.5% loss on drying, 110 °C

Farbe

white to off-white

Löslichkeit

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

Anionenspuren

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

Kationenspuren

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

InChIKey

XUCIJNAGGSZNQT-SWRVSKMJSA-N

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Anwendung

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. Wirkung

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.

Sonstige Hinweise

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

Piktogramme

Exclamation mark

Signalwort

Warning

H-Sätze

Gefahreneinstufungen

Acute Tox. 4 Oral

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Persönliche Schutzausrüstung

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


Analysenzertifikate (COA)

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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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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
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
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