Amygdalin

• CAS: 29883-15-6
• Catalog Number: ACM29883156-1
• Category: Material of Cosmetics
• Molecular Weight: 457.43
• Molecular Formula: C20H27NO11
• Description: relieving cough, relieving asthma, anti-inflammatory, relieve pain
• Synonyms: Mandelonitrile-beta-gentiobioside
• IUPAC Name: (2R)-2-Phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile
• SMILES: C1=CC=C(C=C1)C(C#N)OC2C(C(C(C(O2)COC3C(C(C(C(O3)CO)O)O)O)O)O)O
• InChI: 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+/m0/s1
• InChI Key: XUCIJNAGGSZNQT-JHSLDZJXSA-N
• Boiling Point: 563.27 °C
• Melting Point: 223-226 °C
• Flash Point: 403.3 °C
• Density: 1.4474 g/cm³
• Appearance: White to off-white powder
• Storage: Sealed in dry, room temperature
• Complexity: 638
• Effective Constituent: amygdalin
• Exact Mass: 457.15841068
• Isomeric SMILES: C1=CC=C(C=C1)[C@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O
• Monoisotopic Mass: 457.15841068
• pKa: 12.69±0.70(Predicted)
• Plant Origin: nut of semen armeniacae amarae
• Refractive Index: -40 ° (C=2, H₂O)
• Solubility In Water: 83 g/L
• Topological Polar Surface Area: 202 Ų

Case Study

Amygdalin for the Inhibition of 17β-Estradiol-Induced Epithelial-Mesenchymal Transition via TGF-β/Smad Signaling

Hu F, et al. Reproductive Biology, 2026, 26(2), 101184.

Amygdalin was experimentally evaluated for its ability to suppress 17β-estradiol-induced epithelial-mesenchymal transition (EMT) in endometrial epithelial cells. In vitro assays were conducted using both normal epithelial cells (NECs) and eutopic epithelial cells (EECs) derived from endometriosis patients. Cells were treated with 17β-estradiol to induce EMT and subsequently exposed to amygdalin at defined concentrations. Cellular proliferation was assessed using viability assays, while migration and invasion were evaluated through transwell and wound-healing assays. EMT progression was examined by analyzing the expression of epithelial and mesenchymal markers using Western blotting and quantitative PCR. In the experimental application, amygdalin treatment was used to pharmacologically modulate signaling pathways, where inhibition of the TGF-β/Smad pathway was validated through TGF-β knockdown experiments and pathway-specific inhibitors, enabling mechanistic confirmation of its role in suppressing EMT. These findings demonstrate that amygdalin effectively attenuates estradiol-induced EMT and invasive phenotypes, highlighting its potential utility in experimental models of endometriosis.

Custom Q&A

What is the PubChem CID for amygdalin?

PubChem CID for amygdalin is 656516.

What is the molecular formula of amygdalin?

The molecular formula of amygdalin is C20H27NO11.

What is the molecular weight of amygdalin?

The molecular weight of amygdalin is 457.4 g/mol.

What is the IUPAC name of amygdalin?

The IUPAC name of amygdalin is (2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile.

What is the InChI of amygdalin?

The InChI of amygdalin is 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+/m0/s1.

What is the canonical SMILES of amygdalin?

The canonical SMILES of amygdalin is C1=CC=C(C=C1)C(C#N)OC2C(C(C(C(O2)COC3C(C(C(C(O3)CO)O)O)O)O)O)O.

What is the CAS number of amygdalin?

The CAS number of amygdalin is 29883-15-6.

What is the ChEBI ID of amygdalin?

The ChEBI ID of amygdalin is CHEBI4619.

What is the XLogP3-AA value of amygdalin?

The XLogP3-AA value of amygdalin is -2.7.

How many hydrogen bond acceptors does amygdalin have?

Amygdalin has 12 hydrogen bond acceptors.

Synthetic Use

Downstream Synthesis Route 1

• 29883-15-6

• 87-74-1

Reference: [1]Bulletin de la Societe Chimique de France,1885,vol. <2> 43,p. 530

Downstream Synthesis Route 2

• 29883-15-6

• 74-90-8

Reference: [1]Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften,1856,p. 679
[2]Justus Liebigs Annalen der Chemie,1837,vol. 22,p. 17

* For details of the synthesis route, please refer to the original source to ensure accuracy.