Sambunigrin

Base Information

• Chemical Name: Sambunigrin
• CAS No.: 99-19-4
• Molecular Formula: C14H17NO6
• Molecular Weight: 295.292
• UNII: 9UZJ2ZO1HS
• DSSTox Substance ID: DTXSID00912912
• Nikkaji Number: J617.645C
• Wikidata: Q2217000
• Metabolomics Workbench ID: 46787
• Mol file: 99-19-4.mol

Synonyms:sambunigrin

Chemical Property of Sambunigrin

Chemical Property:

• Vapor Pressure: 6.2E-12mmHg at 25°C
• Boiling Point: 527°C at 760 mmHg
• Flash Point: 272.5°C
• PSA: 123.17000
• Density: 1.45g/cm³
• LogP: -0.93222
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 295.10558726
• Heavy Atom Count: 21
• Complexity: 377

Purity/Quality:

99% ^*data from raw suppliers

(S)-Prunasin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C#N)OC2C(C(C(C(O2)CO)O)O)O
• 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)O)O)O
• Uses: (S)-Prunasin can be used in the synthesis of cyanogen glycoside. A component contains in antiperspirants, deodorants, body soaps, shampoos, hair rinses, and hair ria.

Technology Process of Sambunigrin

There total 5 articles about Sambunigrin 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:

6'-O-malonylprunasin → malonic acid (141-82-2) + (2S)-2-(β-D-glucopyranosyloxy)phenylacetonitrile (99-19-4) + prunasin (99-18-3)

Guidance literature:

With sodium carbonate; at 40 ℃; for 0.666667h;

DOI:10.1016/0031-9422(89)80064-0

Reference yield:

(2S)-2-β-D-glucopyranosyl-oxymandelamide → (2S)-2-(β-D-glucopyranosyloxy)phenylacetonitrile (99-19-4)

Guidance literature:

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

DOI:10.1080/07328303.2015.1105249

Reference yield:

phenyl(trimethylsiloxy)acetonitrile (25438-37-3) → (2S)-2-(β-D-glucopyranosyloxy)phenylacetonitrile (99-19-4)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 20 °C / Inert atmosphere

2: trifluorormethanesulfonic acid; methanol / 3 h / 20 °C / Inert atmosphere

With methanol; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1021/acs.jnatprod.5b01121

upstream raw materials:

prunasin

phenyl(trimethylsiloxy)acetonitrile

(2S)-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenylacetonitrile