Linustatin - Moligand™,≥98% , CAS No.72229-40-4

CAS: 72229-40-4 Cat. No.: L768357 Molecular Weight: 409.39 EC Number: 889-208-8

GRADE & PURITY Moligand™, ≥98%

Synonyms

2-Methyl-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)propanenitrile

Storage

Protected from light,Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Linustatin is a cyanogenic glycoside that can be isolated from linseed meal.

Specifications

Synonyms

2-Methyl-2-(((2S, 3R, 4S, 5S, 6R)-3, 4, 5-trihydroxy-6-((((2R, 3R, 4S, 5S, 6R)-3, 4, 5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)propanenitrile

Specifications & Purity

Moligand™, ≥98%

Storage

Protected from light, Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC(C)(C#N)OC1C(C(C(C(O1)COC2C(C(C(C(O2)CO)O)O)O)O)O)O
• IUPAC Name: 2-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxypropanenitrile
• InChIKey: FERSMFQBWVBKQK-CXTTVELOSA-N
• INCHI: 1S/C16H27NO11/c1-16(2,5-17)28-15-13(24)11(22)9(20)7(27-15)4-25-14-12(23)10(21)8(19)6(3-18)26-14/h6-15,18-24H,3-4H2,1-2H3/t6-,7-,8-,9-,10+,11+,12-,13-,14-,15+/m1/s1
• Isomeric SMILES: CC(C)(C#N)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)O
• Alternate CAS: 72229-40-4
• MeSH Entry Terms: linustatin
• Molecular Weight: 409.39

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Glycosyl compounds
          • Level6 Cyanogenic glycosides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Glycosyl compounds
• Direct Parent: Cyanogenic glycosides
• Alternative Parents: O-glycosyl compounds Disaccharides Oxanes Secondary alcohols Polyols Oxacyclic compounds Nitriles Acetals Primary alcohols Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Cyanogenic glycoside - Disaccharide - O-glycosyl compound - Oxane - Secondary alcohol - Organoheterocyclic compound - Polyol - Acetal - Nitrile - Carbonitrile - Oxacycle - Primary alcohol - Organonitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Organic nitrogen compound - Alcohol - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group.
• External Descriptors: Cyanogenic glucosides derived from valine or isoleucine

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: light & Moisture sensitive
• Molecular Weight: 409.390 g/mol
• XLogP3: -3.800
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 6
• Exact Mass: 409.158 Da
• Monoisotopic Mass: 409.158 Da
• Topological Polar Surface Area: 202.000 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 566.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yang Wenjuan, Tang Sidi, Xu Rubing, Zhang Lu, Zhou Zihao, Yang Yong, Li Yanyan, Xiang Haibo.  (2024)  LC-MS based metabolomics identification of natural metabolites against Fusarium oxysporum.  Frontiers in Plant Science,      [PMID:39290733] [10.3389/fpls.2024.1435963]