Linamarin

Base Information

• Chemical Name: Linamarin
• CAS No.: 554-35-8
• Molecular Formula: C10H17 N O6
• Molecular Weight: 247.248
• Hs Code.: 29400090
• European Community (EC) Number: 637-249-5
• UNII: H3V9RP3WLO
• DSSTox Substance ID: DTXSID8052857
• Nikkaji Number: J6.462I
• Wikipedia: Linamarin
• Wikidata: Q425157
• Metabolomics Workbench ID: 46161
• ChEMBL ID: CHEMBL3039425
• Mol file: 554-35-8.mol

Synonyms:1-cyano-1-methylethyl beta-D-glucoside;linamarin;phaseolunatin

Chemical Property of Linamarin

Chemical Property:

• Vapor Pressure: 6.02E-11mmHg at 25°C
• Melting Point: 142-143°C
• Refractive Index: 1.4610 (estimate)
• Boiling Point: 473.3°Cat760mmHg
• PKA: 12.73±0.70(Predicted)
• Flash Point: 240°C
• PSA: 123.17000
• Density: 1.41g/cm³
• LogP: -1.89492
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO, Methanol, and Ethanol
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 247.10558726
• Heavy Atom Count: 17
• Complexity: 311

Purity/Quality:

98%Min ^*data from raw suppliers

Linamarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CC(C)(C#N)OC1C(C(C(C(O1)CO)O)O)O
• Isomeric SMILES: CC(C)(C#N)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• Description: Linamarin is a glucoside of acetone cyanohydrin found in the leaves and roots of cassava, lima beans, and flax. It is thought to function in the transport of nitrogen from plant leaves to roots in young plants but also serves as a plant defense mechanism. Linamarin is converted to toxic hydrocyanic acid or prussic acid when it comes into contact with linamarase, an enzyme that is released when the cells of cassava roots are ruptured.
• Uses: Can be found in the seed skins and embryos of flax Can be found in the seed skins and embryos of flax.

Technology Process of Linamarin

There total 7 articles about Linamarin 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: 80.0%

2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)isobutyronitrile (66432-53-9) → linamarin (554-35-8)

Guidance literature:

With potassium carbonate; In methanol; for 0.25h;

DOI:10.1271/bbb.62.453

Reference yield: 6.8%

Isobutyronitrile (78-82-0) → linamarin (554-35-8)

Guidance literature:

With culture nutrient solution; Turnera angustifolia Miller shoots; In water; for 72h; illumination;

DOI:10.1016/0031-9422(96)00065-9

Reference yield:

linustatin (72229-40-4) → β-D-glucose (492-61-5) + linamarin (554-35-8)

Guidance literature:

With β-glucosidase (EC No. 3.2.1.21); In water; at 37 ℃; for 2h;

DOI:10.1021/jo01291a027

upstream raw materials:

linustatin

neolinustatin

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

Isobutyronitrile

Downstream raw materials:

β-D-glucose

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

Refernces

• 1、 Seigler,Bloomfield. "-". . p. 935. Retrieved 1969.
• 2、 Smith, Cecil R.,Weisleder, David,Miller, Roger W.,Palmer, Ivan S.,Olson, Oscar E.. "Linustatin and Neolinustatin: Cyanogenic Glycosides of Linseed Meal That Protect Animals against Selenium Toxicity". . p. 507 - 510. Retrieved 2007/10/02.