Benzeneacetonitrile, (R)-

Base Information

• Chemical Name: Benzeneacetonitrile, (R)-
• CAS No.: 29883-15-6
• Molecular Formula: C20H27NO11
• Molecular Weight: 457.434
• Hs Code.: 29389090
• European Community (EC) Number: 249-925-3
• NSC Number: 15780
• Wikipedia: Amygdalin
• Wikidata: Q105342111
• NCI Thesaurus Code: C28801
• Metabolomics Workbench ID: 126099
• ChEMBL ID: CHEMBL2007233
• Mol file: 29883-15-6.mol

Synonyms:Amygdalin;Amygdaloside;Laetrile;Mandelonitrile beta Gentiobioside;Mandelonitrile-beta-Gentiobioside;Neoamygdalin;Vitamin B17

Chemical Property of Benzeneacetonitrile, (R)-

Chemical Property:

• Appearance/Colour: white fine crystalline powder
• Vapor Pressure: 3.35E-23mmHg at 25°C
• Melting Point: 223-226 °C(lit.)
• Refractive Index: -40 ° (C=2, H2O)
• Boiling Point: 743.3 °C at 760 mmHg
• PKA: 12.69±0.70(Predicted)
• Flash Point: 403.3 °C
• PSA: 202.32000
• Density: 1.59 g/cm³
• LogP: -3.10802
• Storage Temp.: -20°C
• Solubility.: H2O: 0.1 g/mL hot, clear to very faintly turbid, colorless
• Water Solubility.: 83 g/L (25 ºC)
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 7
• Exact Mass: 457.15841068
• Heavy Atom Count: 32
• Complexity: 638

Purity/Quality:

50%, ^*data from raw suppliers

D-Mandelonitrile-b-gentiobioside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 26-36/37/39-45-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical 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
• Isomeric SMILES: C1=CC=C(C=C1)[C@H](C#N)OC2C(C(C(C(O2)COC3C(C(C(C(O3)CO)O)O)O)O)O)O
• Description: Amygdalin is a cyanogenic glycoside that has been found in seeds from plants of the Rosaceae family and has diverse biological activities. 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. Amygdalin (3 mg/kg) reduces the number of primary microtubules and microvessels in aortic rings isolated from rats with diabetes induced by streptozotocin . In vivo, amygdalin reduces triglyceride, total cholesterol, and LDL levels and aortic sinus plaque area in an LDLR-/- mouse model of atherosclerosis. 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.
• Uses: antiinflammatory, experimental antineoplastic 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). A cyanogenic glycoside occurring in seeds of Rosaceae, principally in bitter almonds and peach and apricot pits. Some time ago it was said to be effective in the treatment of cancer, but controlled clinical trials repeatedly failed to confirm such claims.

Technology Process of Benzeneacetonitrile, (R)-

There total 4 articles about Benzeneacetonitrile, (R)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(R)-(6-O-β-D-glucopyranosyl-β-D-glucopyranosyloxy)(phenyl)acetamide (66427-91-6) → amygdalin (29883-15-6,672-72-0)

Guidance literature:

With pyridine; trifluoroacetic anhydride; In 1,4-dioxane; at 20 ℃; for 2h;

DOI:10.1080/07328303.2015.1105249

Reference yield:

prupersin E → amygdalin (29883-15-6,672-72-0)

Guidance literature:

With sodium hydroxide; In methanol; water; at 20 ℃; for 4h;

DOI:10.1021/np4000922

Reference yield:

amygdalin (29883-15-6,29883-16-7,51371-34-7,672-72-0) → neoamygdalin (29883-15-6,29883-16-7,51371-34-7,672-72-0)

Guidance literature:

With acetate buffer; acetic acid; ascorbic acid; racemization, effect of temperature, pH, time and ascorbic acid;

upstream raw materials:

(R)-(6-O-β-D-glucopyranosyl-β-D-glucopyranosyloxy)(phenyl)acetamide

amygdalin

Downstream raw materials:

D-glucoheptonic acid

hydrogen cyanide

(RS)-mandelonitrile

(R)-Mandelonitrile

Refernces

• 1、 Chen, Xiao-Yan,Wang, Hong-Qing,Zhang, Ting,Liu, Chao,Kang, Jie,Chen, Ruo-Yun,Yu, De-Quan. "Aromatic glucosides from the seeds of Prunus davidiana". . p. 1528 - 1534. Retrieved 2013/10/22.