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116025 Aldrich

Mandelonitrile

technical grade

Synonym: α-Hydroxyphenylacetonitrile, Benzaldehyde cyanohydrin, Mandelic acid nitrile

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Properties

Related Categories Building Blocks, C8 to C9, Chemical Synthesis, Cyanides/Nitriles, Nitrogen Compounds,
grade   technical grade
refractive index   n20/D 1.530(lit.)
bp   170 °C(lit.)
solubility   alcohol: freely soluble
  chloroform: freely soluble
  diethyl ether: freely soluble
density   1.117 g/mL at 25 °C(lit.)

Description

Packaging

50 g in glass bottle

Application

Mandelonitrile has been used to extract mandeloamide by the nitrilase variants1.

Price and Availability

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Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Hazard Codes (Europe) 
T
Risk Statements (Europe) 
Safety Statements (Europe) 
22-26-36/37/39-45
RIDADR 
UN 3276 6.1 / PGIII
WGK Germany 
3
RTECS 
OO8400000
Flash Point(F) 
206.6 °F
Flash Point(C) 
97 °C

Protocols & Articles

Peer-Reviewed Papers

References

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1. Random mutagenesis of the arylacetonitrilase from Pseudomonas fluorescens EBC191 and identification of variants, which form increased amounts of mandeloamide from mandelonitrile. Sosedov O and Stolz A Appl. Microbiol. Biotechnol., (2013)

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Investigative mining of sequence data for novel enzymes: a case study with nitrilases. Seffernick JL, Samanta SK, Louie TM, et al. J. Biotechnol. 143(1), 17-26, (2009)

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Utilization of arylaliphatic nitriles by haloalkaliphilic Halomonas nitrilicus sp. nov. isolated from soda soils. Chmura A, Shapovalova AA, van Pelt S, et al. Appl. Microbiol. Biotechnol. 81(2), 371-8, (2008)

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Evaluation of the hydroxynitrile lyase activity in cell cultures of capulin (Prunus serotina). Hernández L, Luna H, Navarro-Ocaña A, et al. Sheng Wu Gong Cheng Xue Bao 24(7), 1199-201, (2008)

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A biocatalytic Henry reaction--the hydroxynitrile lyase from Hevea brasiliensis also catalyzes nitroaldol reactions. Purkarthofer T, Gruber K, Gruber-Khadjawi M, et al. Angew. Chem. Int. Ed. Engl. 45(21), 3454-6, (2006)

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Cleaving of S-mandelonitrile catalyzed by S-hydroxynitrile lyase from Hevea brasiliensis--a kinetic investigation based on the rate curve method. Yeow YL, Leong YK, Cheah MY, et al. J. Biotechnol. 111(1), 31-9, (2004)

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Comprehensive Step-by-Step Engineering of an (R)-Hydroxynitrile Lyase for Large-Scale Asymmetric Synthesis. Glieder, A., et al Angew. Chem. Int. Ed. Engl. 42(39), 4815-4818, (2003)

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Metabolites of amygdalin under simulated human digestive fluids. Shim SM and Kwon H Int. J. Food Sci. Nutr. 61(8), 770-9, (2010)

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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. Dreveny I, Andryushkova AS, Glieder A, et al. Biochemistry 48(15), 3370-7, (2009)

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Identification of amino acid residues responsible for the enantioselectivity and amide formation capacity of the Arylacetonitrilase from Pseudomonas fluorescens EBC191. Kiziak C and Stolz A Appl. Environ. Microbiol. 75(17), 5592-9, (2009)

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A high-throughput amenable colorimetric assay for enantioselective screening of nitrilase-producing microorganisms using pH sensitive indicators. Banerjee A, Kaul P, Sharma R, et al. J. Biomol. Screen. 8(5), 559-65, (2003)

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Cloning and biochemical properties of a highly thermostable and enantioselective nitrilase from Alcaligenes sp. ECU0401 and its potential for (R)-(-)-mandelic acid production. Zhang ZJ, Xu JH, He YC, et al. Bioprocess Biosyst. Eng. 34(3), 315-22, (2011)

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Discovery and characterization of a highly efficient enantioselective mandelonitrile hydrolase from Burkholderia cenocepacia J2315 by phylogeny-based enzymatic substrate specificity prediction. Wang H, Sun H, and Wei D BMC Biotechnol. 13, 14, (2013)

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Biochemical and structural characterization of a novel bacterial manganese-dependent hydroxynitrile lyase. Hajnal I, Lyskowski A, Hanefeld U, et al. FEBS J. 280(22), 5815-28, (2013)

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Characterization of two bacterial hydroxynitrile lyases with high similarity to cupin superfamily proteins. Hussain Z, Wiedner R, Steiner K, et al. Appl. Environ. Microbiol. 78(6), 2053-5, (2012)

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Enantioselective biocatalytic hydrolysis of (R,S)-mandelonitrile for production of (R)-(-)-mandelic acid by a newly isolated mutant strain. Xue YP, Xu SZ, Liu ZQ, et al. J. Ind. Microbiol. Biotechnol. 38(2), 337-45, (2011)

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Uneven twins: comparison of two enantiocomplementary hydroxynitrile lyases with alpha/beta-hydrolase fold. Guterl JK, Andexer JN, Sehl T, et al. J. Biotechnol. 141(3-4), 166-73, (2009)

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Enhancing the catalytic potential of nitrilase from Pseudomonas putida for stereoselective nitrile hydrolysis. Banerjee A, Kaul P, and Banerjee UC Appl. Microbiol. Biotechnol. 72(1), 77-87, (2006)

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Screening for new hydroxynitrilases from plants Asano, Y., et al. Biosci. Biotechnol. Biochem. 69, 2349-57, (2005)

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Laboratory evolved biocatalysts for stereoselective syntheses of substituted benzaldehyde cyanohydrins. Liu Z, Pscheidt B, Avi M, et al. ChemBioChem. 9(1), 58-61, (2008)

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Enantioselective nitrilase from Pseudomonas putida: cloning, heterologous expression, and bioreactor studies. Banerjee A, Dubey S, Kaul P, et al. Mol. Biotechnol. 41(1), 35-41, (2009)

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Biocatalytic synthesis of (R)-(-)-mandelic acid from racemic mandelonitrile by cetyltrimethylammonium bromide-permeabilized cells of Alcaligenes faecalis ECU0401. He YC, Zhang ZJ, Xu JH, et al. J. Ind. Microbiol. Biotechnol. 37(7), 741-50, (2010)

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Serine scanning: a tool to prove the consequences of N-glycosylation of proteins. Weis R, Gaisberger R, Gruber K, et al. J. Biotechnol. 129(1), 50-61, (2007)

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Purification and characterization of an enantioselective arylacetonitrilase from Pseudomonas putida. Banerjee A, Kaul P, and Banerjee UC Arch. Microbiol. 184(6), 407-18, (2006)

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Expression of hydroxynitrile lyase from Manihot esculenta in yeast and its application in (S)-mandelonitrile production using an immobilized enzyme reactor. Semba H, Dobashi Y, and Matsui T Biosci. Biotechnol. Biochem. 72(6), 1457-63, (2008)

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Release of hydrogen cyanide via a post-secretion Schotten-Baumann reaction in defensive fluids of polydesmoid millipedes. Kuwahara Y, Shimizu N, and Tanabe T J. Chem. Ecol. 37(3), 232-8, (2011)

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Hydroxynitrile lyase catalysis in ionic liquid-containing systems. Lou WY, Xu R, and Zong MH Biotechnol. Lett. 27(18), 1387-90, (2005)

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Optimization of arylacetonitrilase production from Alcaligenes sp. MTCC 10675 and its application in mandelic acid synthesis. Bhatia SK, Mehta PK, Bhatia RK, et al. Appl. Microbiol. Biotechnol., (2013)

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Merck 14,5719

Beil. 10,IV,578

Aldrich MSDS 1, 1157:A / Corp MSDS 1 (2), 2192:D / FT-IR 1 (2), 426:B / FT-IR 2 (2), 3112:B / FT-NMR 1 (2), 1483:B / IR-Spectra (3), 1117:C / IR-Spectra (2), 973:B / NMR-Reference 2 (2), 401:C / RegBook 1 (2), 2107:C / Sax 6, 1728 / Sigma FT-IR 1 (2), 698:D / Structure Index 1, 333:D:3

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