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A83202

Sigma-Aldrich

D-Amygdalin

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C20H27NO11
CAS Number:
29883-15-6
Molecular Weight:
457.43
Beilstein:
66856
EC Number:
249-925-3
MDL number:
MFCD00006598
UNSPSC Code:
12352103

optical activity

[α]22/D −38°, c = 1.2 in H2O

mp

223-226 °C (lit.)

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

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.

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Certificates of Analysis (COA)

Lot/Batch Number
08601KR
06818TR
02423JM
12129DA
02519PA

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Ping Deng et al.
Foods (Basel, Switzerland), 10(2) (2021-03-07)
To reveal the accumulation pattern of cyanogenic glycosides (amygdalin and prunasin) in bitter apricot kernels to further understand the metabolic mechanisms underlying differential accumulation during kernel development and ripening and explore the association between cyanogenic glycoside accumulation and the physical
James P Tauber et al.
Insects, 11(11) (2020-11-15)
Amygdalin, a cyanogenic glycoside, is found in the nectar and pollen of almond trees, as well as in a variety of other crops, such as cherries, nectarines, apples and others. It is inevitable that western honeybees (Apis mellifera) consistently consume

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