A glycoside with diverse biological activities
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Amygdalin

Item No. 26668

Technical Information
Formal Name
αR-[(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-benzeneacetonitrile
CAS Number
29883-15-6
Synonyms
  • (–)-Amygdalin
  • (D)-Amygdalin
  • (R)-Amygdalin
  • Amygdaloside
  • NSC 15780
Molecular Formula
C20H27NO11
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 14 mg/mlDMSO: 10 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
263 nm
SMILES
OC[C@H]1O[C@@H](OC[C@@H]2[C@@H](O)[C@H](O)[C@@H](O)[C@H](O[C@@H](C#N)C3=CC=CC=C3)O2)[C@H](O)[C@@H](O)[C@@H]1O
InChi Code
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
Origin
Plant/Amygdalus communis vas
Shipping & Storage Information
Storage
4°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Amygdalin is a cyanogenic glycoside that has been found in seeds from plants of the Rosaceae family and has diverse biological activities.1,2,3,4,5 It induces cell cycle arrest at the G0/G1 phase, decreases cyclin A and Cdk2 levels, and inhibits cell growth in UMUC-3, RT112, and TCCSUP bladder cancer cells when used at concentrations ranging from 1.25 to 10 mg/ml.2 Amygdalin (3 mg/kg) reduces the number of primary microtubules and microvessels in aortic rings isolated from rats with diabetes induced by streptozotocin (Item No. 13104).3 In vivo, amygdalin reduces triglyceride, total cholesterol, and LDL levels and aortic sinus plaque area in an LDLR-/- mouse model of atherosclerosis.4 It also reduces production of TNF-α, IL-1β, and IL-6, as well as neutrophil and macrophage infiltration, in bronchoalveolar lavage fluid (BALF) in a mouse model of LPS-induced acute lung injury.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wahab, M.F., Breitbach, Z.S., Armstrong, D.W., et alProblems and pitfalls in the analysis of amygdalin and its epimer. J. Agric. Food Chem. 63(40), 8966-8973 (2015).

    2. Makarević, J., Rutz, J., Juengel, E., et alAmygdalin blocks bladder cancer cell growth in vitro by diminishing cyclin A and cdk2. PLoS One 9(8), e105590 (2014).

    3. Mirmiranpour, H., Khaghani, S., Zandieh, A., et alAmygdalin inhibits angiogenesis in the cultured endothelial cells of diabetic rats. Indian J. Pathol. Microbiol. 55(2), 211-214 (2012).

    4. Lv, J., Xiong, W., Lei, T., et alAmygdalin ameliorates the progression of atherosclerosis in LDL receptor‑deficient mice. Mol. Med. Rep. 16(6), 8171-8179 (2017).

    5. Zhang, A., Pan, W., Lv, J., et alProtective effect of amygdalin on LPS-induced acute lung injury by inhibiting NF-κB and NLRP3 signaling pathways. Inflammation 40(3), 745-751 (2017).