135362-74-2

Basic information

• Product Name: (R)-methyl propyl ketone cyanohydrin
• CAS NO: 135362-74-2
• Molecular Weight: 113.159
• Mol File: 135362-74-2.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (R)-methyl propyl ketone cyanohydrin(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-methyl propyl ketone cyanohydrin(135362-74-2)
• EPA Substance Registry System: (R)-methyl propyl ketone cyanohydrin(135362-74-2)

Safety Data

• Hazardous Substances Data: 135362-74-2(Hazardous Substances Data)

Upstream product

• 91390-80-6 2-methyl-2-(trimethylsiloxy)pentanenitrile 
• 151-50-8 potassium cyanide 
• 107-87-9 2-Pentanone 
• 195434-02-7 (R)-2-((2S,4S,5S)-3,4-Dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yloxy)-2-methyl-pentanenitrile 
• 4111-09-5 2-Hydroxy-2-methyl-pentanenitrile 
• 74-90-8 hydrogen cyanide 

Relevant articles and documents

Screening for new hydroxynitrilases from plants

We established a simple HPLC method to determine the activity and stereochemistry of the chiral mandelonitrile synthesized from benzaldehyde and cyanide, and applied it to screen for hydroxynitrile lyase (HNL) activity of plant origin. A total of 163 species of plants among 74 families were examined for (R)- and (S)-HNL activities using the method. We discovered that homogenate of leaves of Baliospermum montanum shows (S)-HNL activity, while leaves and seeds from Passiflora edulis, and seeds from Eriobotrya japonica, Chaenomles sinensis, Sorbus aucuparia, Prunus mume, and Prunus persica show (R)-HNL activity. Partially purified (R)-HNLs from Passiflora edulis and Eriobotrya japonica acted not only on benzaldehyde but also on aliphatic ketone. The enantiomeric excess of (R)-methylpropylketone cyanohydrin synthesized from 2-pentanone using homogenate from leaves of Passiflora edulis was 87.0%, and that of (R)-mandelonitrile synthesized by homogenate from seeds of Eriobotrya japonica was 85.0%.

Synthesis of aliphatic and α-halogenated ketone cyanohydrins with the hydroxynitrile lyase from Manihot esculenta

The potential of the hydroxynitrile lyase from Manihot esculenta towards ketone substrates was investigated. It was observed that the length of the aliphatic chain is a key parameter for the conversion of aliphatic, non-branched ketones. Smaller substrates are readily converted with high enantioselectivites, but the elongation of the chain length causes a significant loss in enzyme activity. For a number of halogenated, herein especially fluorinated, acetophenone derivatives the corresponding cyanohydrins have been synthesized with good to moderate enantioselectivities. Overcoming limitations: Ketone cyanohydrins are extremely useful intermediates for the synthesis of unusual tertiary alcohols. In this contribution, the limits of the hydroxynitrile lyase from Manihot esculenta towards such substrates are investigated and evaluated. High enantioselectivities are obtained in a simple two-phase system, even with very challenging fluorinated acetophenone derivatives.

A new (R)-hydroxynitrile lyase from Prunus mume: Asymmetric synthesis of cyanohydrins

A new hydroxynitrile lyase (HNL) was isolated from the seed of Japanese apricot (Prunus mume). The enzyme has similar properties with HNL isolated from other Prunus species and is FAD containing enzyme. It accepts a large number of unnatural substrates (benzaldehyde and its variant) for the addition of HCN to produce the corresponding cyanohydrins in excellent optical and chemical yields. A new HPLC based enantioselective assay technique was developed for the enzyme, which promotes the addition of KCN to benzaldehyde in a buffered solution (pH=4.5).