Mandelonitrile benzoate
Basic information
- CAS
4242-46-0- Standard SMILES
N#CC(OC(=O)c1ccccc1)c1ccccc1- InChIKey
AXAACNNFMJZAGJ-UHFFFAOYSA-N- Molecular formula
- C15H11NO2
- Average molar mass
- 237.25 g/mol
- Monoisotopic mass
- 237.07897859
Names & identifiers
- Preferred name
- Mandelonitrile benzoate
- IUPAC
- [cyano(phenyl)methyl] benzoate
- English name
- 2-(Benzoyloxy)-2-phenylacetonitrile
- Molecular formula
- C15H11NO2
- Molecular weight
- 237.25
Names & synonyms
Mandelonitrile benzoate4242-46-0Mandelonitrile, benzoate (ester)alpha-Cyanobenzyl benzoate.alpha.-Cyanobenzyl benzoateBenzeneacetonitrile, .alpha.-(benzoyloxy)-NSC 121785Benzoic acid, alpha-cyanobenzyl esterBenzeneacetonitrile, alpha-(benzoyloxy)-RefChem:155565Mandelonitrile, benzoate (ester) (8CI)Benzeneacetonitrile, alpha-(benzoyloxy)-(9CI)
Show more names
NSC121785NSC-121785α-Cyanobenzyl benzoateCyano-(phenyl)-methyl benzoateBenzoic acid α-cyanobenzyl esterBenzeneacetonitrile, α-(benzoyloxy)-
AXAACNNFMJZAGJ-UHFFFAOYSA-N[cyano(phenyl)methyl] benzoate2-(Benzoyloxy)-2-phenylacetonitrileMLS002707138Benzeneacetonitrile, alpha-(benzoyloxy)- (9CI)(cyano-phenylmethyl) benzoateCyano(phenyl)methyl benzoate #orb1696187
Database identifiers
- CAS
4242-46-0- PubChem CID
- 92983
- ChEMBL
CHEMBL1714899- Nikkaji
- J99.778A
Properties
Computed structural properties
- XLogP
- 3.3
- Topological polar surface area
- 50.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 319
Chemistry & industry
Applications
UsesMandelonitrile benzoate is a defensive secretion of millipedes that releases other chemicals during the cyanidation process in addition to hydrocyanic acid (HCN) and benzaldehyde. Several families of millipedes, including Polydesmidae, Paradoxosomatidae, and Euryuridae, have been shown to secrete phenols and guaiaeol, with one Paradoxosomatid also producing ethylbenzoic acid and benzoic acid. In addition, members of the Xystodesmidae family commonly produce three compounds: benzoic acid, mandelonitrile benzoate, and benzoyl cyanide. Benzoyl cyanide has not been previously discovered as a natural product. These additional natural products are discussed as defensive antipredator and antibiotic agents. Benzoyl cyanide appears to have anesthetic properties for some predators. The study provides a preliminary chemotaxonomic basis for distinguishing various taxonomic groups of millipedes.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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