CAS Number29883-15-6
SynonymsMandelonitrile b-Glucuronide; Vitamin B17; rile; (2R)-{[6-O-(β-D-Glucopyranosyl)-β-D-glucopyranosyl]oxy}(phenyl)acetonitrile; Mygdalin; D-amygdalin; EINECS 249-925-3; Mandelonitrile-b-gentiobioside; amygdaloside; D-Mandelonitrile 6-O-β-D-glucosido-β-D-glucoside; (2R)-{[6-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl]oxy}(phenyl)ethanenitrile; D-AMYGLADIN; D-Mandelonitrile-β-gentiobioside; Laetrile; Nitrilosides; mandelonitrile-β-gentiobioside; (R)-amygdalin; D-Mandelonitrile-b-D-glucosido-6-b-D-glucoside; [(6-O-b-D-Glucopyranosyl-b-D-glucopyranosyl)oxy]benzeneacetonitrile; Amygdalin; MFCD00006598
Molecular FormulaC20H27NO11
Molecular Weight457.43
Purity≥99 (HPLC)%
Density1.6±0.1 g/cm3
Boiling Point743.3±60.0 °C at 760 mmHg
Melting Point223-226 °C
Appearancepowder
EINECS249-925-3
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 29883-15-6 |
| Catalog No. | 2A-9009187 |
| Chinese Name | 扁桃苷; 苦杏仁甙 |
| Synonyms | Mandelonitrile b-Glucuronide; Vitamin B17; rile; (2R)-{[6-O-(β-D-Glucopyranosyl)-β-D-glucopyranosyl]oxy}(phenyl)acetonitrile; Mygdalin; D-amygdalin; EINECS 249-925-3; Mandelonitrile-b-gentiobioside; amygdaloside; D-Mandelonitrile 6-O-β-D-glucosido-β-D-glucoside; (2R)-{[6-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl]oxy}(phenyl)ethanenitrile; D-AMYGLADIN; D-Mandelonitrile-β-gentiobioside; Laetrile; Nitrilosides; mandelonitrile-β-gentiobioside; (R)-amygdalin; D-Mandelonitrile-b-D-glucosido-6-b-D-glucoside; [(6-O-b-D-Glucopyranosyl-b-D-glucopyranosyl)oxy]benzeneacetonitrile; Amygdalin; MFCD00006598 |
| Molecular Formula | C20H27NO11 |
| Molecular Weight | 457.43 |
| Purity | ≥99 (HPLC) |
| Density | 1.6±0.1 g/cm3 |
| Boiling Point | 743.3±60.0 °C at 760 mmHg |
| Melting Point | 223-226 °C |
| Appearance | powder |
| Water Solubility | 83 g/L (25 ºC) |
| Storage Condition | Keep the receptacle sealed, stored in a cool, dry |
| Packaging | III |
| Application | Mandelic acid is a plant glucoside isolated from the pits of rose fruits, such as apricots, peaches, almonds, cherries and plums. |
| EINECS | 249-925-3 |
| PubChem ID | 24891046 |
| MDL Number | MFCD00006598 |
| SMILES | 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 |
| InChI Key | XUCIJNAGGSZNQT-SWRVSKMJSA-N |
| Beilstein/REAXYS | 66856 |
| NACRES Code | NA.25 |
| UNSPSC | 12352201 |
| Hazard Symbols | 6.1(b) |
| MSDS | msds/9187_1_29883_15_6.pdf |
| Bioactivity | Amygdalin is a plant glucoside isolated from the stones of rosaceous fruits, such as apricots, peaches, almond, cherries, and plums. Related Catalog Signaling Pathways >> Others >> Others Research Areas >> Cancer Natural Products >> Saccharides and Glycosides In Vitro Amygdalin has antitumor activity. Some advances had been made on the antitumor mechanism of amygdalin[1]. Amygdalin downregulates especially genes belonging to cell cycle category: exonuclease 1, ATP-binding cassette, sub-family F, member 2, MRE11 meiotic recombination 11 homolog A, topoisomerase (DNA) I, and FK506 binding protein 12-rapamycin-associated protein 1. RT-PCR analysis reveals that mRNA levels of these genes are also decreased by amygdalin treatment in SNU-C4 human colon cancer cells[2]. In Vivo Amygdalin is effective at alleviating inflammatory pain and that it can be used as an analgesic with anti-nociceptive and anti-inflammatory activities. The intramuscular injection of amygdalin significantly reduced the formalin-induced tonic pain in both early (the initial 10 min after formalin injection) and late phases (10-30 min following the initial formalin injection). During the late phase, amygdalin reduces the formalin-induced pain in a dose-dependentmanner in a dose range less than 1 mg/kg[3]. Cell Assay Cell viability is determined by MTT assay. Cells are seeded in triplicate at a concentration of 1×105 cells/well on a 96-well plate. SNU-C4 cells are treated with amygdalin at concentrations of 0.25, 0.5, 2.5, and 5 mg/mL for 24 h. After MTT is added to each group, the cells are incubated for 4 h. Then, they are further incubated for 1 h, including the solution in which MTT is dissolved[2]. Animal Admin Rats: The amygdalin powder is dissolved in saline and diluted with appropriate medium. Male Sprague-Dawley rats weighing 230-250 g are used for this experiment. 50mL of 5% formalin are injected to produce fomalin-induced pain in the rats. Thirty minutes before the formalin injection to induce pain, the rats are given an intramuscular injection of amygdalin solution (0.1, 0.5, 1.0, 10 mg/kg), or saline as a vehicle control[3]. References [1]. Song Z, et al. Advanced research on anti-tumor effects of amygdalin. J Cancer Res Ther. 2014 Aug;10 Suppl 1:3-7. [2]. Park HJ,et al. Amygdalin inhibits genes related to cell cycle in SNU-C4 human colon cancer cells. World J Gastroenterol. 2005 Sep 7;11(33):5156-61. [3]. Hwang HJ,et al. Antinociceptive effect of amygdalin isolated from Prunus armeniaca on formalin-induced pain in rats. Biol Pharm Bull. 2008 Aug;31(8):1559-64. Chemical & Physical Properties Density 1.6±0.1 g/cm3 Boiling Point 743.3±60.0 °C at 760 mmHg Melting Point 223-226 °C(lit.) Molecular Formula C20H27NO11 Molecular Weight 457.428 Flash Point 403.3±32.9 °C Exact Mass 457.158417 PSA 202.32000 LogP -0.36 Vapour Pressure 0.0±2.6 mmHg at 25°C Index of Refraction 1.650 InChIKey XUCIJNAGGSZNQT-ZPVJLWCPSA-N SMILES N#CC(OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O)c1ccccc1 Water Solubility 83 g/L (25 ºC) |
| Use of | Amygdalin is a plant glucoside isolated from the stones of rosaceous fruits, such as apricots, peaches, almond, cherries, and plums. Properties Articles40 Name Amygdalin Synonym More Synonyms Amygdalin Biological Activity Description Amygdalin is a plant glucoside isolated from the stones of rosaceous fruits, such as apricots, peaches, almond, cherries, and plums. Related Catalog Signaling Pathways >> Others >> Others Research Areas >> Cancer Natural Products >> Saccharides and Glycosides References [1]. Song Z, et al. Advanced research on anti-tumor effects of amygdalin. J Cancer Res Ther. 2014 Aug;10 Suppl 1:3-7. [2]. Park HJ,et al. Amygdalin inhibits genes related to cell cycle in SNU-C4 human colon cancer cells. World J Gastroenterol. 2005 Sep 7;11(33):5156-61. [3]. Hwang HJ,et al. Antinociceptive effect of amygdalin isolated from Prunus armeniaca on formalin-induced pain in rats. Biol Pharm Bull. 2008 Aug;31(8):1559-64. Chemical & Physical Properties Molecular Formula C20H27NO11 Exact Mass 457.158417 PSA 202.32000 LogP -0.36 Index of Refraction 1.650 InChIKey XUCIJNAGGSZNQT-ZPVJLWCPSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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