Dhurrin

Base Information

• Chemical Name: Dhurrin
• CAS No.: 499-20-7
• Molecular Formula: C14H17NO7
• Molecular Weight: 311.291
• European Community (EC) Number: 207-878-6
• UNII: P5999IY65C
• DSSTox Substance ID: DTXSID90198142
• Nikkaji Number: J10.589I
• Wikipedia: Dhurrin
• Wikidata: Q908811
• Metabolomics Workbench ID: 51471
• Mol file: 499-20-7.mol

Synonyms:dhurrin

Chemical Property of Dhurrin

Chemical Property:

• Melting Point: 200oC (dec.)
• Boiling Point: 586.7±50.0 °C(Predicted)
• PKA: 9.19±0.26(Predicted)
• Flash Point: 308.6oC
• PSA: 143.40000
• Density: 1.56±0.1 g/cm3(Predicted)
• LogP: -1.22662
• Storage Temp.: room temp
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 311.10050188
• Heavy Atom Count: 22
• Complexity: 403

Purity/Quality:

98% ^*data from raw suppliers

Dhurrin ≥95% (HPLC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-45

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(C#N)OC2C(C(C(C(O2)CO)O)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1[C@@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O
• Uses: Dhurrin is a cyanogenic glucoside produced by sorghum and is considered a natural defense compound producing hydrogen cyanide to deter animal herbivores.

Technology Process of Dhurrin

There total 9 articles about Dhurrin 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:

methanol (67-56-1) + taxiphyllin 6'-O-gallate → methyl galloate (99-24-1) + (2R)-2-(β-D-glucopyranosyloxy)-4-hydroxyphenylacetonitrile (499-20-7,13115-69-0,21401-21-8)

Guidance literature:

With sodium methylate; at 20 ℃; for 4h;

DOI:10.1248/cpb.c14-00352

Reference yield:

amygdalin (29883-15-6,672-72-0) → (2R)-2-(β-D-glucopyranosyloxy)-4-hydroxyphenylacetonitrile (499-20-7,13115-69-0,21401-21-8)

Guidance literature:

With extracellular enzymes from Aspergillus niger; at 37 ℃; for 4h;

DOI:10.1016/j.procbio.2011.10.030

Reference yield:

4-formylphenyl acetate (878-00-2) → (2R)-2-(β-D-glucopyranosyloxy)-4-hydroxyphenylacetonitrile (499-20-7,13115-69-0,21401-21-8)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium perchlorate / neat (no solvent) / 0.5 h / 20 °C / Inert atmosphere

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

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

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

DOI:10.1021/acs.jnatprod.5b01121

upstream raw materials:

4-formylphenyl acetate

C₁₃H₁₇NO₃Si

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

amygdalin

Downstream raw materials:

dhurrinamide