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mandelonitrile
acetonitrile, hydroxyphenyl-

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CAS Number: 532-28-5Picture of molecule3D/inchi
Other(deleted CASRN):613-88-7
ECHA EINECS - REACH Pre-Reg:208-532-7
FDA UNII: 584322E08A
Nikkaji Web:J6.985J
Beilstein Number:2207122
MDL:MFCD00004487
XlogP3:1.00 (est)
Molecular Weight:133.14999000
Formula:C8 H7 N O
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:information only not used for fragrances or flavors
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:reddish-brown to dark red-brown liquid (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity:1.11500 to 1.12600 @ 20.00 °C.
Pounds per Gallon - (est).: 9.289 to 9.380
Refractive Index:1.53000 to 1.53700 @ 20.00 °C.
Boiling Point: 282.70 °C. @ 760.00 mm Hg (est)
Flash Point: 207.00 °F. TCC ( 97.22 °C. )
logP (o/w): 0.830 (est)
Soluble in:
 water, 4.629e+004 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Santa Cruz Biotechnology
For experimental / research use only.
Mandelonitrile
Sigma-Aldrich: Aldrich
For experimental / research use only.
Mandelonitrile technical grade
TCI AMERICA
For experimental / research use only.
Mandelonitrile >97.0%(GC)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intravenous-mouse LD50 5600 ug/kg
U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#07767

Dermal Toxicity:
subcutaneous-frog LDLo 600 ug/kg
PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 5, Pg. 161, 1899.

subcutaneous-mouse LDLo 23 mg/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 12, Pg. 447, 1904.

subcutaneous-rabbit LDLo 6 mg/kg
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 5, Pg. 161, 1899.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
information only not used for fragrances or flavors
Recommendation for mandelonitrile usage levels up to:
 not for fragrance use.
 
Recommendation for mandelonitrile flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):532-28-5
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10758
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-hydroxy-2-phenylacetonitrile
Chemidplus:0000532285
EPA/NOAA CAMEO:hazardous materials
RTECS:OO8400000 for cas# 532-28-5
 
References:
 2-hydroxy-2-phenylacetonitrile
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):10758
Pubchem (sid):134976676
Pherobase:View
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C00561
HMDB (The Human Metabolome Database):HMDB34666
FooDB:FDB013525
YMDB (Yeast Metabolome Database):YMDB01642
Export Tariff Code:2926.90.4800
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
 acetonitrile, hydroxyphenyl-
 amygdalonitrile
 benzaldehyde cyanohydrin
 benzaldehydkyanhydrin
 benzeneacetonitrile, alpha-hydroxy-
 glycolonitrile, phenyl-
2-hydroxy-2-phenylacetonitrile
(+-)-alpha-hydroxybenzeneacetonitrile
alpha-hydroxybenzeneacetonitrile
 mandelic acid nitrile
 mandelonitrile, (+-)-
 phenylglycolonitrile
 

Articles:

PubMed:Characterization of amygdalin-degrading Lactobacillus species.
PubMed:Uncovering divergent evolution of α/β-hydrolases: a surprising residue substitution needed to convert Hevea brasiliensis hydroxynitrile lyase into an esterase.
PubMed:Improvement of the amides forming capacity of the arylacetonitrilase from Pseudomonas fluorescens EBC191 by site-directed mutagenesis.
PubMed:Metabolomic insights into the bioconversion of isonitrosoacetophenone in Arabidopsis thaliana and its effects on defense-related pathways.
PubMed:Structural and functional analysis of hydroxynitrile lyase from Baliospermum montanum with crystal structure, molecular dynamics and enzyme kinetics.
PubMed:Chemical Composition and Antimicrobial Activity of the Essential Oil of Apricot Seed.
PubMed:Discovery of a novel (R)-selective bacterial hydroxynitrile lyase from Acidobacterium capsulatum.
PubMed:Chemical composition of essential oils and hydrosols from fresh flowers of Cerasus subhirtella and Cerasus serrulata from East China.
PubMed:Increasing the reaction rate of hydroxynitrile lyase from Hevea brasiliensis toward mandelonitrile by copying active site residues from an esterase that accepts aromatic esters.
PubMed:Identification and characterization of CYP79D16 and CYP71AN24 catalyzing the first and second steps in L-phenylalanine-derived cyanogenic glycoside biosynthesis in the Japanese apricot, Prunus mume Sieb. et Zucc.
PubMed:Crosslinked enzyme aggregates of hydroxynitrile lyase partially purified from Prunus dulcis seeds and its application for the synthesis of enantiopure cyanohydrins.
PubMed:Improvement of Alcaligenes faecalis nitrilase by gene site saturation mutagenesis and its application in stereospecific biosynthesis of (R)-(-)-mandelic acid.
PubMed:Purification and characterization of arylacetonitrile-specific nitrilase of Alcaligenes sp. MTCC 10675.
PubMed:Biosynthesis of benzoylformic acid from benzoyl cyanide with a new bacterial isolate of Brevibacterium sp. CCZU12-1.
PubMed:Efficient production of (R)-(-)-mandelic acid using glutaraldehyde cross-linked Escherichia coli cells expressing Alcaligenes sp. nitrilase.
PubMed:Mini-review: recent developments in hydroxynitrile lyases for industrial biotechnology.
PubMed:Optimization of arylacetonitrilase production from Alcaligenes sp. MTCC 10675 and its application in mandelic acid synthesis.
PubMed:HCN production and hydroxynitrile lyase: a natural activity in plants and a renewed biotechnological interest.
PubMed:Biochemical and structural characterization of a novel bacterial manganese-dependent hydroxynitrile lyase.
PubMed:Chemistry of the sternal gland secretion of the Mediterranean centipede Himantarium gabrielis (Linnaeus, 1767) (Chilopoda: Geophilomorpha: Himantariidae).
PubMed:Efficient production of (R)-(-)-mandelic acid in biphasic system by immobilized recombinant E. coli.
PubMed:Fusion of a flavin-based fluorescent protein to hydroxynitrile lyase from Arabidopsis thaliana improves enzyme stability.
PubMed:Random mutagenesis of the arylacetonitrilase from Pseudomonas fluorescens EBC191 and identification of variants, which form increased amounts of mandeloamide from mandelonitrile.
PubMed:Reports on the distribution of aromatic cyanogenic glycosides in Australian tropical rainforest tree species of the Lauraceae and Sapindaceae.
PubMed:A comparative study of nitrilases identified by genome mining.
PubMed:Discovery and characterization of a highly efficient enantioselective mandelonitrile hydrolase from Burkholderia cenocepacia J2315 by phylogeny-based enzymatic substrate specificity prediction.
PubMed:Immobilisation of hydroxynitrile lyases.
PubMed:Structural characterization and identification of major constituents in Jitai tablets by high-performance liquid chromatography/diode-array detection coupled with electrospray ionization tandem mass spectrometry.
PubMed:Hydroxynitrile lyases with α/β-hydrolase fold: two enzymes with almost identical 3D structures but opposite enantioselectivities and different reaction mechanisms.
PubMed:Synthesis of chiral cyanohydrins by recombinant Escherichia coli cells in a micro-aqueous reaction system.
PubMed:The cyanogenic syndrome in rubber tree Hevea brasiliensis: tissue-damage-dependent activation of linamarase and hydroxynitrile lyase accelerates hydrogen cyanide release.
PubMed:Characterization of two bacterial hydroxynitrile lyases with high similarity to cupin superfamily proteins.
PubMed:Conversion of sterically demanding α,α-disubstituted phenylacetonitriles by the arylacetonitrilase from Pseudomonas fluorescens EBC191.
PubMed:Cloning and expression of hydroxynitrile lyase gene from Eriobotrya japonica in Pichia pastoris.
PubMed:Gene cloning, expression, and characterization of a nitrilase from Alcaligenes faecalis ZJUTB10.
PubMed:Isolation, identification and quantitation of hydroxycinnamic acid conjugates, potential platform chemicals, in the leaves and stems of Miscanthus × giganteus using LC-ESI-MSn.
PubMed:Purification and characterization of heterologously expressed nitrilases from filamentous fungi.
PubMed:Functional expression of a plant hydroxynitrile lyase in Escherichia coli by directed evolution: creation and characterization of highly in vivo soluble mutants.
PubMed:A simple analytical method for dhurrin content evaluation in cyanogenic plants for their utilization in fodder and biofumigation.
PubMed:Release of hydrogen cyanide via a post-secretion Schotten-Baumann reaction in defensive fluids of polydesmoid millipedes.
PubMed:Significant enhancement of (R)-mandelic acid production by relieving substrate inhibition of recombinant nitrilase in toluene-water biphasic system.
PubMed:Cloning and biochemical properties of a highly thermostable and enantioselective nitrilase from Alcaligenes sp. ECU0401 and its potential for (R)-(-)-mandelic acid production.
PubMed:Defensive secretions in three species of polydesmids (Diplopoda, Polydesmida, Polydesmidae).
PubMed:Switching from an esterase to a hydroxynitrile lyase mechanism requires only two amino acid substitutions.
PubMed:Chiral solvating agents for cyanohydrins and carboxylic acids.
PubMed:Enantioselective biocatalytic hydrolysis of (R,S)-mandelonitrile for production of (R)-(-)-mandelic acid by a newly isolated mutant strain.
PubMed:Catalytic mechanism of hydroxynitrile lyase from Hevea brasiliensis: a theoretical investigation.
PubMed:Metabolites of amygdalin under simulated human digestive fluids.
PubMed:Biocatalytic synthesis of (R)-(-)-mandelic acid from racemic mandelonitrile by cetyltrimethylammonium bromide-permeabilized cells of Alcaligenes faecalis ECU0401.
PubMed:Construction and application of variants of the Pseudomonas fluorescens EBC191 arylacetonitrilase for increased production of acids or amides.
PubMed:Discovery and utilization of biocatalysts for chiral synthesis: an overview of Chinese scientists' research and development.
PubMed:Identification of amino acid residues responsible for the enantioselectivity and amide formation capacity of the Arylacetonitrilase from Pseudomonas fluorescens EBC191.
PubMed:Investigative mining of sequence data for novel enzymes: a case study with nitrilases.
PubMed:Uneven twins: comparison of two enantiocomplementary hydroxynitrile lyases with alpha/beta-hydrolase fold.
PubMed:Bioproduction of glycolic acid from glycolonitrile with a new bacterial isolate of Alcaligenes sp. ECU0401.
PubMed:Substrate binding in the FAD-dependent hydroxynitrile lyase from almond provides insight into the mechanism of cyanohydrin formation and explains the absence of dehydrogenation activity.
PubMed:Evaluation of the hydroxynitrile lyase activity in cell cultures of capulin (Prunus serotina).
PubMed:Utilization of arylaliphatic nitriles by haloalkaliphilic Halomonas nitrilicus sp. nov. isolated from soda soils.
PubMed:Enantioselective nitrilase from Pseudomonas putida: cloning, heterologous expression, and bioreactor studies.
PubMed:Expression of hydroxynitrile lyase from Manihot esculenta in yeast and its application in (S)-mandelonitrile production using an immobilized enzyme reactor.
PubMed:Purification and characterization of a novel (R)-hydroxynitrile lyase from Eriobotrya japonica (Loquat).
PubMed:Simultaneous expression of an arylacetonitrilase from Pseudomonas fluorescens and a (S)-oxynitrilase from Manihot esculenta in Pichia pastoris for the synthesis of (S)-mandelic acid.
PubMed:Laboratory evolved biocatalysts for stereoselective syntheses of substituted benzaldehyde cyanohydrins.
PubMed:Influence of different carboxy-terminal mutations on the substrate-, reaction- and enantiospecificity of the arylacetonitrilase from Pseudomonas fluorescens EBC191.
PubMed:Vicianin hydrolase is a novel cyanogenic beta-glycosidase specific to beta-vicianoside (6-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside) in seeds of Vicia angustifolia.
PubMed:Amygdalin suppresses lipopolysaccharide-induced expressions of cyclooxygenase-2 and inducible nitric oxide synthase in mouse BV2 microglial cells.
PubMed:Discovery of a mandelonitrile hydrolase from Bradyrhizobium japonicum USDA110 by rational genome mining.
PubMed:Structural determinants of the enantioselectivity of the hydroxynitrile lyase from Hevea brasiliensis.
PubMed:Stereoselective biocatalytic synthesis of (S)-2-hydroxy-2-methylbutyric acid via substrate engineering by using "thio-disguised" precursors and oxynitrilase catalysis.
PubMed:Serine scanning: a tool to prove the consequences of N-glycosylation of proteins.
PubMed:Quantitative evaluation of the mechanism of electroreduction of benzoyl cyanides.
PubMed:The apoplastic antioxidant system in Prunus: response to long-term plum pox virus infection.
PubMed:Enzymatic synthesis of (R)-cyanohydrins by a novel (R)-oxynitrilase from Vicia sativa L.
PubMed:Unexpected stereorecognition in nitrilase-catalyzed hydrolysis of beta-hydroxy nitriles.
PubMed:Amygdalin induces apoptosis through regulation of Bax and Bcl-2 expressions in human DU145 and LNCaP prostate cancer cells.
PubMed:Synthesis and configurational assignment of the amino alcohol in the eastern fragment of the GE2270 antibiotics by regio- and stereoselective addition of 2-metalated 4-bromothiazoles to alpha-chiral electrophiles.
PubMed:A biocatalytic Henry reaction--the hydroxynitrile lyase from Hevea brasiliensis also catalyzes nitroaldol reactions.
PubMed:Male-fertility genes expressed in male flower buds of Silene latifolia include homologs of anther-specific genes.
PubMed:Absorption of toxic beta-glucosides produced by plants and their effect on tissue trehalases from insects.
PubMed:Enhancing the catalytic potential of nitrilase from Pseudomonas putida for stereoselective nitrile hydrolysis.
PubMed:Screening for new hydroxynitrilases from plants.
PubMed:Purification and characterization of an enantioselective arylacetonitrilase from Pseudomonas putida.
PubMed:Cyanogenic glycosides from the rare Australian endemic rainforest tree Clerodendrum grayi (Lamiaceae).
PubMed:Nitrilase from Pseudomonas fluorescens EBC191: cloning and heterologous expression of the gene and biochemical characterization of the recombinant enzyme.
PubMed:Hydroxynitrile lyase catalysis in ionic liquid-containing systems.
PubMed:Synthesis of (R)-2-trimethylsilyl-2-hydroxyl-ethylcyanide catalyzed with (R)-oxynitrilase from loquat seed meal.
PubMed:Cross-linked aggregates of (R)-oxynitrilase: a stable, recyclable biocatalyst for enantioselective hydrocyanation.
PubMed:Hydrolysis of nitriles using an immobilized nitrilase: applications to the synthesis of methionine hydroxy analogue derivatives.
PubMed:The role of carboxyl, guanidine and imidazole groups in catalysis by a midgut trehalase purified from an insect larvae.
PubMed:Cleaving of S-mandelonitrile catalyzed by S-hydroxynitrile lyase from Hevea brasiliensis--a kinetic investigation based on the rate curve method.
PubMed:Structural determinants of substrate specificity in family 1 beta-glucosidases: novel insights from the crystal structure of sorghum dhurrinase-1, a plant beta-glucosidase with strict specificity, in complex with its natural substrate.
PubMed:A high-throughput amenable colorimetric assay for enantioselective screening of nitrilase-producing microorganisms using pH sensitive indicators.
PubMed:Comprehensive step-by-step engineering of an (R)-hydroxynitrile lyase for large-scale asymmetric synthesis.
PubMed:Kinetic analysis of hexose transport to determine the mechanism of amygdalin and prunasin absorption in the intestine.
PubMed:The in vitro substrate regiospecificity of recombinant UGT85B1, the cyanohydrin glucosyltransferase from Sorghum bicolor.
PubMed:A single residual replacement improves the folding and stability of recombinant cassava hydroxynitrile lyase in E. coil.
PubMed:(R)-oxynitrilase-catalysed synthesis of chiral silicon-containing aliphatic (R)-ketone-cyanohydrins.
PubMed:Cyanogenic Eucalyptus nobilis is polymorphic for both prunasin and specific beta-glucosidases.
PubMed:Interfacial versus homogeneous enzymatic cleavage of mandelonitrile by hydroxynitrile lyase in a biphasic system.
PubMed:Synthesis of degraded cyanogenic glycosides from Sambucus nigra.
PubMed:Mutational and structural analysis of aglycone specificity in maize and sorghum beta-glucosidases.
PubMed:Cyclooxygenase inhibitory and antioxidant compounds from crabapple fruits.
PubMed:Apoptosis induction of Persicae Semen extract in human promyelocytic leukemia (HL-60) cells.
PubMed:A simple and highly sensitive spectrophotometric method for the determination of cyanide in equine blood.
PubMed:The toxicokinetics of cyanide and mandelonitrile in the horse and their relevance to the mare reproductive loss syndrome.
PubMed:Purification and characterization of three beta-glycosidases from midgut of the sugar cane borer, Diatraea saccharalis.
PubMed:Chromatographic determination of cyanoglycosides prunasin and amygdalin in plant extracts using a porous graphitic carbon column.
PubMed:A practical high through-put continuous process for the synthesis of chiral cyanohydrins.
PubMed:Lipases and (R)-oxynitrilases: useful tools in organic synthesis.
PubMed:Investigation of the microheterogeneity and aglycone specificity-conferring residues of black cherry prunasin hydrolases.
PubMed:Potential active-site residues in polyneuridine aldehyde esterase, a central enzyme of indole alkaloid biosynthesis, by modelling and site-directed mutagenesis.
PubMed:A kinetic model for enzyme interfacial activity and stability: pa-hydroxynitrile lyase at the diisopropyl ether/water interface.
PubMed:Tertiary pentyl groups enhance salen titanium catalyst for highly enantioselective trimethylsilylcyanation of aldehydes.
PubMed:Biocatalytic synthesis of hydroxylated natural products using aldolases and related enzymes.
PubMed:The active site of hydroxynitrile lyase from Prunus amygdalus: modeling studies provide new insights into the mechanism of cyanogenesis.
PubMed:Development of a process model to describe the synthesis of (R)-mandelonitrile by Prunus amygdalus hydroxynitrile lyase in an aqueous-organic biphasic reactor.
PubMed:Structure determinants of substrate specificity of hydroxynitrile lyase from Manihot esculenta.
PubMed:Purification and characterization of a beta-glucosidase from Citrus sinensis var. Valencia fruit tissue.
PubMed:Production of a cyanogenic secretion by a thyridid caterpillar (Calindoea trifascialis, Thyrididae, Lepidoptera).
PubMed:Purification, molecular cloning, and properties of a beta-glycosidase isolated from midgut lumen of Tenebrio molitor (Coleoptera) larvae.
PubMed:Asymmetric synthesis of an (R)-cyanohydrin using enzymes entrapped in lens-shaped gels.
PubMed:Role of organic solvents on Pa-hydroxynitrile lyase interfacial activity and stability.
PubMed:[Cloning, expression and preliminary application of a alpha-hydroxynitrile lyase from cassave].
PubMed:The mechanism of substrate (aglycone) specificity in beta -glucosidases is revealed by crystal structures of mutant maize beta -glucosidase-DIMBOA, -DIMBOAGlc, and -dhurrin complexes.
PubMed:Estimation of kinetic parameters by progress curve analysis for the synthesis of (R)-mandelonitrile by Prunus amygdalus hydroxynitrile lyase.
PubMed:The synthesis of chiral cyanohydrins by oxynitrilases.
PubMed:The aglycone specificity-determining sites are different in 2, 4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA)-glucosidase (Maize beta -glucosidase) and dhurrinase (Sorghum beta -glucosidase).
PubMed:Oxynitrilases for asymmetric C-C bond formation.
PubMed:The UDP-glucose:p-hydroxymandelonitrile-O-glucosyltransferase that catalyzes the last step in synthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor. Isolation, cloning, heterologous expression, and substrate specificity.
PubMed:Visualization of enzyme-catalyzed reactions using pH indicators: rapid screening of hydrolase libraries and estimation of the enantioselectivity.
PubMed:Hydroxynitrile lyase at the diisopropyl ether/water interface: evidence for interfacial enzyme activity.
PubMed:The cyanogenic glucoside, prunasin (D-mandelonitrile-beta-D-glucoside), is a novel inhibitor of DNA polymerase beta.
PubMed:Molecular analysis of (R)-(+)-mandelonitrile lyase microheterogeneity in black cherry.
PubMed:Kinetic studies on the enzyme (S)-hydroxynitrile lyase from hevea brasiliensis using initial rate methods and progress curve analysis
PubMed:An unusual reversible sol-Gel transition phenomenon in organogels and its application for enzyme immobilization in gelatin membranes
PubMed:Molecular cloning of the cDNA coding for the (R)-(+)-mandelonitrile lyase of Prunus amygdalus: temporal and spatial expression patterns in flowers and mature seeds.
PubMed:Ortho hydroxy-substituted molecules might be of importance for the prevention of bloodsucking by mosquitoes.
PubMed:Analysis of mandelonitrile lyase and beta-glucosidase from sweet almonds by combined electrophoretic techniques.
PubMed:Sequencing, genomic organization, and preliminary promoter analysis of a black cherry (R)-(+)-mandelonitrile lyase gene.
PubMed:Crystallographic studies and preliminary X-ray investigation of (S)-p-hydroxy-mandelonitrile lyase from Sorghum bicolor (L.).
PubMed:Two-step hydrolysis of amygdalin in molds.
PubMed:Purification and Characterization of a Novel (R)-Mandelonitrile Lyase from the Fern Phlebodium aureum.
PubMed:Temporal and spatial expression of amygdalin hydrolase and (R)-(+)-mandelonitrile lyase in black cherry seeds.
PubMed:Immunocytochemical Localization of Prunasin Hydrolase and Mandelonitrile Lyase in Stems and Leaves of Prunus serotina.
PubMed:Utilization of Amygdalin during Seedling Development of Prunus serotina.
PubMed:Crystallization and preliminary X-ray diffraction studies of mandelonitrile lyase from almonds.
PubMed:Transient inactivation of almond mandelonitrile lyase by 3-methyleneoxindole: a photooxidation product of the natural plant hormone indole-3-acetic acid.
PubMed:Improved purification of an (R)-oxynitrilase from Linum usitatissimum (flax) and investigation of the substrate range.
PubMed:Improved activity retention of enzymes deposited on solid supports.
PubMed:Tissue and Subcellular Localization of Enzymes Catabolizing (R)-Amygdalin in Mature Prunus serotina Seeds.
PubMed:Prunus serotina Amygdalin Hydrolase and Prunasin Hydrolase : Purification, N-Terminal Sequencing, and Antibody Production.
PubMed:Exolytic hydrolysis of toxic plant glucosides by guinea pig liver cytosolic beta-glucosidase.
PubMed:Development of the Potential for Cyanogenesis in Maturing Black Cherry (Prunus serotina Ehrh.) Fruits.
PubMed:Continuous spectrophotometric assays for beta-glucosidases acting on the plant glucosides L-picein and prunasin.
PubMed:A new catalytic function of halohydrin hydrogen-halide-lyase, synthesis of beta-hydroxynitriles from epoxides and cyanide.
PubMed:Production of R-(-)-mandelic acid from mandelonitrile by Alcaligenes faecalis ATCC 8750.
PubMed:Immunocytochemical Localization of Mandelonitrile Lyase in Mature Black Cherry (Prunus serotina Ehrh.) Seeds.
PubMed:Formation of C-C bonds by mandelonitrile lyase in organic solvents.
PubMed:Mandelonitrile in larval secretion of mountain ash sawfly,Pristiphora geniculata (Hymenoptera: Tenthredinidae).
PubMed:Mandelonitrile lyase from Ximenia americana L.: stereospecificity and lack of flavin prosthetic group.
PubMed:Purification and characterization of acetone cyanohydrin lyase from Linum usitatissimum.
PubMed:Catabolism of Cyanogenic Glycosides by Purified Vicianin Hydrolase from Squirrel's Foot Fern (Davallia Trichomanoides Blume).
PubMed:Localization and catabolism of cyanogenic glycosides.
PubMed:Cyanogenesis and the role of cyanogenic compounds in insects.
PubMed:A colorimetric assay for alpha-hydroxynitrile lyase.
PubMed:Isolation and characterization of multiple forms of prunasin hydrolase from black cherry (Prunus serotina Ehrh.) seeds.
PubMed:Toxicity of D, L-mandelonitrile-beta-D-glucoside, "prulaurasin" in rat.
PubMed:Characterization of beta-glucosidases with high specificity for the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) moench seedlings.
PubMed:Purification and characterization of mandelonitrile lyase from Prunus lyonii.
PubMed:Intestinal first pass metabolism of amygdalin in the rat in vitro.
PubMed:Isolation and characterization of multiple forms of mandelonitrile lyase from mature black cherry (Prunus serotina Ehrh.) seeds.
PubMed:Solvent accessibility to flavin in oxynitrilase.
PubMed:Metabolism of mandelonitrile in the rat.
PubMed:Comments on: 'Chemical modification of hydroxynitrile lyase by selective reaction of an essential cysteine-SH group with alpha, beta-unsaturated propriophenones as pseudo-substrates' by L. Jaenicke and J. Preun.
PubMed:Leakage of Dhurrin and p-Hydroxybenzaldehyde from Young Sorghum Shoots Immersed in Various Solvents.
PubMed:Preparative and analytical separation of amygdalin and related compounds in injectables and tablets by reversed-phase HPLC and the effect of temperature on the separation.
PubMed:Alternate substrates of dopamine beta-hydroxylase. II. Inhibition by benzyl cyanides and reactivation of inhibited enzyme.
PubMed:Chemical modification of hydroxynitrile lyase by selective reaction of an essential cysteine-SH group with alpha, beta-unsaturated propiophenones as pseudo-substrates.
PubMed:New Acylated Cyanogenic Diglycosides from Fruits of Anthemis cairica.
PubMed:The pharmacokinetics of amygdalin.
PubMed:A rapid and sensitive spectrophotometric assay for prunasin hydrolase activity employing purified mandelonitrile lyase.
PubMed:Amygdalin (Laetrile) and prunasin beta-glucosidases: distribution in germ-free rat and in human tumor tissue.
PubMed:Formation of epoxide intermediates in the reaction of enzyme-bound 5-deazaflavin with peroxides.
PubMed:Subcellular Localization of Dhurrin beta-Glucosidase and Hydroxynitrile Lyase in the Mesophyll Cells of Sorghum Leaf Blades.
PubMed:Studies on the kinetics of cyanohydrin synthesis and cleavage by the the flavoenzyme oxynitrilase.
PubMed:Two components of laetrile (mandelonitrile and cyanide) stimulate guanylate cyclase activity.
PubMed:Tissue Distributions of Dhurrin and of Enzymes Involved in Its Metabolism in Leaves of Sorghum bicolor.
PubMed:Relationship of molecular structure to in vivo scintigraphic distribution of carbon-11-labeled compounds. 4. Carbon-11-labeled mandelonitriles, Mandelic acids, and their esters.
PubMed:Mandelonitrile beta-glucuronide: synthesis and characterization.
PubMed:Localization of Cinnamic Acid 4-Monooxygenase and the Membrane-bound Enzyme System for Dhurrin Biosynthesis in Sorghum Seedlings.
PubMed:Benzoyl cyanide in the defensive secretion of polydesmoid millipeds.
PubMed:[A new mandelonitrile lyase from the cherrylaurel (Prunus laurocerasus) (author's transl)].
PubMed:[Mandelonitrile-glycosides in cancer research and cancer therapy. The amygdalin problem].
PubMed:The enzymic hydrolysis of amygdalin.
PubMed:Cyanogenic Glandular Apparatus of a Millipede.
 
Notes:
metabolite of amygdalin. Glycosides widespread in (mostly higher) plants as cyanogenic glycosides. Glycosides of both enantiomers and of the racemate occur Mandelonitrile is a chemical compound of the cyanohydrin class. Small amounts of mandelonitrile occur in the pits of some fruits. (Wikipedia)
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