Image Cyanohydrin general 2D skeletal.png thumb right size The structure of a general cyanohydrin. A cyanohydrin is a functional group found in organic compound s. Cyanohydrins have the formula R sub 2 sub C OH CN, where R is H, alkyl , or aryl . Cyanohydrins are industrially important precursors to carboxylic acid s and some amino acid s. Cyanohydrins can be formed by the cyanohydrin reaction , which involves treating a ketone or an aldehyde with hydrogen cyanide HCN in the presence of excess amounts of sodium cyanide NaCN as a catalyst RR C O HCN RR C OH CN In this reaction, the nucleophilic CN sup sup ion attacks the electrophilic carbonyl carbon in the ketone, followed by protonation by HCN, thereby regenerating the cyanide anion . Cyanohydrins are also prepared by displacement of sulfite by cyanide salts ref name Corson OrgSynth author Corson, B. B. Dodge, R. A. Harris, S. A. Yeaw, J. S. title Mandelic Acid collvol 1 collvolpages 336 year 1941 prep cv1p0336 ref Image Cyanation of aldehyde with bisulfate.svg 300px Cyanohydrins are intermediates in the Strecker amino acid synthesis . Acetone cyanohydrins Acetone cyanohydrin , CH sub 3 sub sub 2 sub C OH CN is the cyanohydrin of acetone ... Haroutounian, S. A. Acetone Cyanohydrin Encyclopedia of Reagents for Organic Synthesis 2001, John Wiley & Sons. doi 10.1002 047084289X.ra014 ref Thus, acetone cyanohydrin can be used for the preparation ... Koch reaction formylation of arene s. Treatment of this cyanohydrin with lithium hydride affords anhydrous lithium cyanide Image LiCN from acetone cyanohydrin 2D skeletal.png 400px ..., such as amygdalin . Glycolonitrile , also called hydroxyacetonitrile or formaldehyde cyanohydrin, is the organic compound with the formula HOCH sub 2 sub CN. It is the simplest cyanohydrin, being ... 2D skeletal.png 100px center center glycolonitrile center center acetone cyanohydrin center ... da Cyanohydrin de Cyanhydrine es Cianohidrina fr Cyanohydrine it Cianidrine nl Cyanohydrine ja ... more details
A Cyanohydrin reaction is an organic reaction organic chemical reaction by an aldehyde or ketone with a cyanide anion or a nitrile to form a cyanohydrin . This nucleophilic addition is a reversible reaction but with aliphatic carbonyl compounds equilibrium is in favor of the reaction products. The cyanide ... Cyanohydrin acetone reaction.svg thumb 400px center Reaction of acetone with sodium cyanide to hydroxyacetonitrile Image Benzoquinone cyanohydrin reaction.svg thumb 600px center Reaction of benzoquinone ... 6 Image Xylose cyanohydrin reaction.svg thumb 800px center chain extension of D xylose in equilibrium with its hemiacetal with KCN to the cyclic ester Reaction mechanism center Image Cyanohydrin mechanism 2D.png 400px Mechanism of the cyanohydrin reaction center Asymmetric synthesis The asymmetric synthesis asymmetric cyanohydrin reaction of benzaldehyde with trimethylsilylcyanide is made possible ... Catalyst for Cyanohydrin Synthesis Manabu Hatano, Takumi Ikeno, Takashi Miyamoto, and Kazuaki ... Complex. Image Asymetric cyanohydrin reaction.gif center Asymmetric reaction of benzaldehyde with R Binol lithium i propyloxy gives S cyanohydrin with 98 Enantiomer ee center small Asymmetric reaction of benzaldehyde with R Binol lithium i propyloxy gives S cyanohydrin with 98 Enantiomer ee small ... of Urech cyanohydrin method . With HCN in acidic conditions i.e. the cyanohydrin is the functional group CN C OH External links Cyanohydrin reaction of formaldehyde to hydroxyacetonitrile or glycolonitrile ... 56 http www.orgsyn.org orgsyn prep.asp?prep cv2p0387 Article Cyanohydrin reaction of formaldehyde with potassium ... orgsyn prep.asp?prep cv3p0436 Article Cyanohydrin reaction of acetophenone with potassium cyanide ...?prep cv4p0058 Article Cyanohydrin reaction of D xylose with potassium cyanide Organic Syntheses Coll ... Cyanohydrin reaction of acetone with potassium cyanide Organic Syntheses Coll. Vol. 2, p. 7 Vol. 15, p. 1 http www.orgsyn.org orgsyn prep.asp?prep cv2p0007 Article Cyanohydrin reaction of benzoquinone ... more details
chembox verifiedrevid 443658192 ImageFile Acetone cyanohydrin.svg ImageFile2 Acetone cyanohydrin 3D.png IUPACName 2 hydroxy 2 methylpropanenitrile OtherNames Section1 Chembox Identifiers KEGG Ref keggcite correct kegg KEGG C02659 InChI 1 C4H7NO c1 4 2,6 3 5 h6H,1 2H3 InChIKey MWFMGBPGAXYFAR UHFFFAOYAL StdInChI Ref stdinchicite correct chemspider StdInChI 1S C4H7NO c1 4 2,6 3 5 h6H,1 2H3 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey MWFMGBPGAXYFAR UHFFFAOYSA N CASNo 75 86 5 CASNo Ref cascite correct CAS EC number 200 909 4 ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 6166 PubChem 6406 ChEBI Ref ebicite correct EBI ChEBI 15348 DrugBank Ref drugbankcite correct drugbank DrugBank DB02203 SMILES N CC O C C Section2 Chembox Properties Formula C sub 4 sub H sub 7 sub NO MolarMass 85.105 g mol Appearance Density 0.932 g cm sup 3 sup MeltingPt 19 C BoilingPt 95 C Solubility Section7 Chembox Hazards ExternalMSDS https fscimage.fishersci.com msds 11030.htm Fisher MSDS EUIndex 608 004 00 X NFPA H 4 NFPA F 1 NFPA R 2 FlashPt Autoignition Acetone cyanohydrin ACH is an organic compound used in the production of methyl methacrylate , the monomer of the transparent plastic polymethyl methacrylate PMMA , also known as acrylic. Preparation The compound is generated as part of the acetone cyanohydrin route to methyl methacrylate. It is treated with sulfuric acid to give the sulfate ester of the methacrylamide, methanolysis of which gives ammonium bisulfate and MMA ... ref OrgSynth first1 R. F. B. last1 Cox first2 R. T. last2 Stormont title Acetone Cyanohydrin ... these compounds and produces acetone cyanohydrin, which is potentially lethally toxic. Safety Acetone cyanohydrin is classified as an List of extremely hazardous substances extremely hazardous substance ... cyanohydrin arise from its ready decomposition on contact with water, which releases highly toxic hydrogen cyanide . References reflist External links SIDS name Acetone cyanohydrin id 75865 Category ... more details
enzyme Name cyanohydrin beta glucosyltransferase EC number 2.4.1.85 CAS number 55354 52 4 IUBMB EC number 2 4 1 85 GO code 0047792 image width caption In enzymology , a cyanohydrin beta glucosyltransferase EC number 2.4.1.85 is an enzyme that catalysis catalyzes the chemical reaction UDP D glucose S 4 hydroxymandelonitrile math rightleftharpoons math UDP S 4 hydroxymandelonitrile beta D glucoside Thus, the two substrate biochemistry substrates of this enzyme are UDP D glucose and S 4 hydroxymandelonitrile , whereas its two product chemistry products are uridine diphosphate UDP and S 4 hydroxymandelonitrile beta D glucoside . This enzyme belongs to the family of glycosyltransferase s, specifically the hexosyltransferases. The systematic name of this enzyme class is UDP D glucose S 4 hydroxymandelonitrile beta D glucosyltransferase . Other names in common use include uridine diphosphoglucose p hydroxymandelonitrile , glucosyltransferase , UDP glucose p hydroxymandelonitrile glucosyltransferase , uridine diphosphoglucose cyanohydrin glucosyltransferase , uridine diphosphoglucose aldehyde cyanohydrin , beta glucosyltransferase , UDP glucose S 4 hydroxymandelonitrile beta D glucosyltransferase , UGT85B1 , and UDP glucose p hydroxymandelonitrile O glucosyltransferase . This enzyme participates in tyrosine metabolism and cyanoamino acid metabolism . References reflist 1 cite journal author Reay PF, Conn EE date 1974 title The purification and properties of a uridine diphosphate glucose aldehyde cyanohydrin beta glucosyltransferase from sorghum seedlings journal J. Biol. Chem. volume 249 pages 5826&ndash 30 pmid 4416442 issue 18 cite journal author Jones PR, Moller BL, Hoj PB date 1999 title 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 ... substrate regiospecificity of recombinant UGT85B1, the cyanohydrin glucosyltransferase from ... more details
DISPLAYTITLE C sub 4 sub H sub 7 sub NO The molecular formula C sub 4 sub H sub 7 sub NO may refer to Acetone cyanohydrin 2 Pyrrolidone MolFormDisambig ... more details
enzyme Name linamarin synthase EC number 2.4.1.63 CAS number 37277 68 2 IUBMB EC number 2 4 1 63 GO code 0050057 image width caption In enzymology , a linamarin synthase EC number 2.4.1.63 is an enzyme that catalysis catalyzes the chemical reaction UDP glucose 2 hydroxy 2 methylpropanenitrile math rightleftharpoons math UDP linamarin Thus, the two substrate biochemistry substrates of this enzyme are UDP glucose and 2 hydroxy 2 methylpropanenitrile , whereas its two product chemistry products are uridine diphosphate UDP and linamarin . This enzyme belongs to the family of glycosyltransferase s, specifically the hexosyltransferases. The systematic name of this enzyme class is UDP glucose 2 hydroxy 2 methylpropanenitrile beta D glucosyltransferase . Other names in common use include uridine diphosphoglucose ketone glucosyltransferase , uridine diphosphate glucose ketone cyanohydrin , beta glucosyltransferase , UDP glucose ketone cyanohydrin glucosyltransferase , UDP glucose ketone cyanohydrin beta glucosyltransferase , and uridine diphosphoglucose ketone cyanohydrin glucosyltransferase . References reflist 1 cite journal author Hahlbrock K, Conn EE date 1970 title The biosynthesis of cyanogenic glycosides in higher plants. I Purification and properties of a uridine diphosphate glucose ketone cyanohydrin beta glucosyltransferase from Linum usitatissimum L journal J. Biol. Chem. volume 245 pages 917&ndash 22 pmid 5417265 issue 5 enzyme stub Category EC 2.4.1 Category Enzymes of unknown structure it Linamarina sintasi ... more details
enzyme Name acetone cyanhydrin lyase EC number 4.1.2.37 CAS number 112567 89 2 IUBMB EC number 4 1 2 37 GO code 0047606 image width caption In enzymology , a hydroxynitrilase EC number 4.1.2.37 is an enzyme that catalysis catalyzes the chemical reaction acetone cyanohydrin math rightleftharpoons math cyanide acetone Hence, this enzyme has one substrate biochemistry substrate , acetone cyanohydrin , and two product chemistry products , cyanide and acetone . This enzyme belongs to the family of lyase s, specifically the aldehyde lyases, which cleave carbon carbon bonds. The systematic name of this enzyme class is acetone cyanohydrin acetone lyase cyanide forming . Other names in common use include alpha hydroxynitrile lyase , hydroxynitrile lyase , acetone cyanhydrin lyase mis spelt , acetone cyanohydrin acetone lyase , oxynitrilase , 2 hydroxyisobutyronitrile acetone lyase , 2 hydroxyisobutyronitrile acetone lyase cyanide forming , and acetone cyanohydrin lyase . References reflist 1 cite journal author Xu LL, Singh BK, Conn EE date 1988 title Purification and characterization of acetone cyanohydrin lyase from Linum usitatissimum journal Arch. Biochem. Biophys. volume 263 pages 256&ndash 63 pmid 3377504 doi 10.1016 0003 9861 88 90634 0 issue 2 cite journal author Selmar D, Lieberei R, Biehl B, Conn EE date 1989 title alpha Hydroxynitrile lyase in Hevea brasiliensis and its significance for rapid cyanogenesis journal Physiol. Plant volume 75 pages 97&ndash 101 doi 10.1111 j.1399 3054.1989.tb02069.x 4.1 enzyme stub Category EC 4.1.2 Category Enzymes of unknown structure ... more details
chembox verifiedrevid 434561909 ImageFile1 Glycolonitrile 2D skeletal.png ImageSize1 150px ImageFileL2 Glycolonitrile 3D balls A.png ImageSizeL2 120px ImageFileR2 Glycolonitrile 3D vdW A.png ImageSizeR2 120px IUPACName 2 Hydroxyacetonitrile OtherNames Formaldehyde cyanohydrin Hydroxyacetonitrile Glycolic nitrile Cyanomethanol Hydroxymethylnitrile Section1 Chembox Identifiers CASNo Ref cascite correct ?? CASNo 107 16 4 PubChem 7857 SMILES C C N O Section2 Chembox Properties C 2 H 3 N 1 O 1 Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Glycolonitrile , also called hydroxyacetonitrile or formaldehyde cyanohydrin , is the organic compound with the formula HOCH sub 2 sub CN. It is the simplest cyanohydrin and it is derived from formaldehyde . ref OrgSynth author Gaudry, R. title Glycolonitrile collvol 3 collvolpages 436 year 1955 prep cv3p0436 ref Because glycolonitrile decomposes readily into formaldehye and hydrogen cyanide , it is listed as an List of extremely hazardous substances extremely hazardous substance . Synthesis Glycolonitrile can be synthesized by reacting formaldehyde with hydrogen cyanide under acidic conditions. This reaction takes place spontaneously even under aqueous conditions. ref name Arrhenius http www.oci.uzh.ch efiles CHE728 SmallMoleculePapers 97JOC5522 OriginOfLife.pdf Arrhenius et al. , J. Org. Chem. 1997, 62, 5522 5525 ref Properties Chemical properties Gylcolonitrile polymerizes under alkaline conditions above pH 7.0. Arrhenius et al. have proposed the following mechanism for polymerization ref name Arrhenius ref file Glycolonitrile polymerisation.gif 700px center As the product of polymerization is an amine with a basic character, the reaction is self catalysed, gaining in speed with ongoing conversion. References reflist Category Cyanohydrins organic compound stub fa nl Glycolnitril zh ... more details
enzyme Name hydroxymandelonitrile glucosyltransferase EC number 2.4.1.178 CAS number 89287 39 8 IUBMB EC number 2 4 1 178 GO code 0047239 image width caption In enzymology , a hydroxymandelonitrile glucosyltransferase EC number 2.4.1.178 is an enzyme that catalysis catalyzes the chemical reaction UDP glucose 4 hydroxymandelonitrile math rightleftharpoons math UDP taxiphyllin Thus, the two substrate biochemistry substrates of this enzyme are UDP glucose and 4 hydroxymandelonitrile , whereas its two product chemistry products are uridine diphosphate UDP and taxiphyllin . This enzyme belongs to the family of glycosyltransferase s, specifically the hexosyltransferases. The systematic name of this enzyme class is UDP glucose 4 hydroxymandelonitrile glucosyltransferase . Other names in common use include cyanohydrin glucosyltransferase , and uridine diphosphoglucose cyanohydrin glucosyltransferase . This enzyme participates in tyrosine metabolism . References reflist 1 cite journal author Hosel W, Schiel O date 1984 title Biosynthesis of cyanogenic glucosides in vitro analysis of the glucosylation step journal Arch. Biochem. Biophys. volume 229 pages 177&ndash 86 pmid 6230992 doi 10.1016 0003 9861 84 90142 5 issue 1 cite journal author Poulton JE and Shin S I date 1983 title Prunasin biosynthesis by cell free extracts from black cherry Prunus serotina Ehrh fruits and leaves journal Z. Naturforsch. C Biosci. volume 38 pages 369&ndash 374 enzyme stub Category EC 2.4.1 Category Enzymes of unknown structure ... more details
The Fischer oxazole synthesis is a chemical synthesis of the aromatic heterocycle oxazole from cyanohydrin s and aldehyde s in the presence of anhydrous hydrochloric acid . This method was discovered by Hermann Emil Fischer in 1896. Image Fischer Oxazole Synthesis.png center 500px Fischer Oxazole Synthesis References Emil Fischer Fischer, E. Chemische Berichte Ber. 1896 , 29 , 205. Wiley, R. H. Chem. Rev. 1945 , 37 , 401. reaction stub Category Heterocycle forming reactions Category Name reactions es S ntesis de oxazoles de Fischer id Sintesis oksazola Fischer nl Fischer oxazoolsynthese ja zh Fischer ... more details
that produces somewhat higher yields of the larger sugars. Instead of conversion of the cyanohydrin to a lactone, the cyanohydrin is organic reduction reduced with hydrogen , using palladium ... more details
Linamarase , or beta D glucosidase EC number 3.2.1.21 , is an enzyme found in many plants including cassava and the butter bean . In cassava it is found in the cell wall s. When the plant is chewed or ground, it exposes the enzyme to compounds like linamarin and lotaustralin which release cyanide compounds that can be lethal to the eater. In human s, chronic toxicity is more likely than death. This action of the enzyme is used by many cultures to process cassava into an edible substance. The enzyme converts the cyanide containing compounds into acetone cyanohydrin , which spontaneously decomposes to hydrogen cyanide HCN . The HCN then either dissolves readily in water or is released into the air. Not all cyanide can be removed during processing. Linamarase can be inhibited by low pH via a dilute acid . References http jb.oxfordjournals.org cgi content abstract 101 4 847 T. Itoh Nashida, M. Hiraiwa and Y. Uda 1987. Purification and properties of beta D glucosidase linamarase from the butter bean, Phaseolus lunatus . Last accessed 13 November 2005. http www.ilw.agrl.ethz.ch ctc people heubergc index Heuberger, Christoph. 10 May 2005. Physicochemical properties of cassava tubers with focus on cyanide content in fermented products . Last accessed 13 November 2005. Category EC 3.2.1 Category Enzymes hydrolase stub ... more details
System ref among other plants. Lotaustralin is the glucoside of methyl ethyl ketone cyanohydrin and is structurally related to linamarin , the acetone cyanohydrin glucoside also found in these plants ... more details
ACH may refer to In American banking Automated Clearing House , an electronic banking network often used for direct deposit and electronic bill payment A business or organization Aluminum Corporation of China Limited ACH Food Companies, Inc. , American subsidiary of Associated British Foods Automotive Components Holdings , LLC, a Ford managed temporary company mandated to dispose of unprofitable operations of Visteon, its former parts division Alberta Children s Hospital , Calgary, Alberta Arkansas Children s Hospital , Little Rock, Arkansas AC Horsens , a Danish football club American College of Heraldry , an American heraldic organization Accion contra el Hambre, an NGO, part of the Action Against Hunger International Network In biology , chemistry , and medicine Acetylcholine ACh , a neurotransmitter Adrenocortical hormone Achondroplasia , a genetic disorder that is a common cause of dwarfism Aluminium chlorohydrate , an aluminium inorganic polymer used as a flocculant for water purification Acetone cyanohydrin , a highly toxic organic compound In transportation Achnashellach railway station the National Railway code in the United Kingdom St. Gallen Altenrhein Airport , Switzerland, IATA airport code Adelaide Crafers Highway Angeles Crest Highway Anti Condensation Heater In linguistics Acholi language ach , ISO 639 code In investigation Analysis of Competing Hypotheses , an investigation methodology In the United States military Advanced Combat Helmet , or MICH TC 2000 Combat Helmet , worn by army soldiers In heating, ventilation, and air conditioning Air changes per hour , a unit in ventilation Ach may refer to Ach, Iran , a village in Qazvin Province Bregenzer Ach , a tributary of Lake Constance Dornbirner Ach , a tributary of Lake Constance Friedberger Ach , a tributary of the Lech disambig geo de Ach eo ACH fa ACH fr ACH it ACH nl Ach pl Ach ... more details
Other uses AIB disambiguation chembox Verifiedfields changed verifiedrevid 477197928 Name 2 Aminoisobutyric acid ImageFile 2 aminoisobutyric acid.svg IUPACName 2 Amino 2 methylpropanoic acid OtherNames Aminoisobutyric acid br 2 Methylalanine Section1 Chembox Identifiers ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 5891 KEGG Ref keggcite correct kegg KEGG C03665 InChI 1 C4H9NO2 c1 4 2,5 3 6 7 h5H2,1 2H3, H,6,7 ChEBI Ref ebicite correct EBI ChEBI 27971 SMILES O C O C N C C InChIKey FUOOLUPWFVMBKG UHFFFAOYAD StdInChI Ref stdinchicite correct chemspider StdInChI 1S C4H9NO2 c1 4 2,5 3 6 7 h5H2,1 2H3, H,6,7 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey FUOOLUPWFVMBKG UHFFFAOYSA N CASNo 62 57 7 CASNo Ref cascite correct CAS EC number 200 544 0 PubChem 6119 DrugBank Ref drugbankcite changed drugbank DrugBank EXPT00471 Section2 Chembox Properties C 4 H 9 N 1 O 2 MolarMass 103.12 g mol pKa 2.36 carboxyl , 10.21 amino ref Dawson, R.M.C., et al., Data for Biochemical Research , Oxford, Clarendon Press, 1959. ref 2 Aminoisobutyric acid , or aminoisobutyric acid AIB or methylalanine or 2 methylalanine , is an amino acid with the structural formula is H sub 2 sub N C CH sub 3 sub sub 2 sub COOH. It is contained in some antibiotic s of fungus fungal origin, e.g. alamethicin and some lantibiotic s. It is not one of the Proteinogenic amino acid proteinogenic amino acids and rather rare in nature. Aminoisobutyric acid is a strong helix inducer in peptide s. Its oligomers form 3 10 helices. In the laboratory, 2 aminoisobutyric acid may be prepared from acetone cyanohydrin , by reaction with ammonia followed by hydrolysis. ref OrgSynth last1 Clarke first1 H. T. last2 Bean first2 H. J. title Aminoisobutyric acid prep cv2p0029 year 1931 volume 11 pages 4 collvol 2 collvolpages 29 . ref References references DEFAULTSORT Aminoisobutyric acid, 2 Category Branched chain amino acids Category Amino acids fa ... more details
distinguish methyl acrylate chembox Verifiedfields changed verifiedrevid 462250505 Name Methyl methacrylate ImageFile methyl methacrylate skeletal.png ImageSize 175px ImageName Methyl methacrylate ImageFile1 Methyl methacrylate 3d.png ImageSize1 175px IUPACName methyl 2 methylpropenoate OtherNames MMA, br 2 methoxycarbonyl 1 propene Section1 Chembox Identifiers ChEBI Ref ebicite correct EBI ChEBI 34840 SMILES O C OC C C C UNII Ref fdacite correct FDA UNII 196OC77688 ChEMBL Ref ebicite correct EBI ChEMBL 49996 StdInChI Ref stdinchicite correct chemspider StdInChI 1S C5H8O2 c1 4 2 5 6 7 3 h1H2,2 3H3 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey VVQNEPGJFQJSBK UHFFFAOYSA N CASNo Ref cascite correct CAS CASNo 80 62 6 ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 6406 RTECS OZ5075000 KEGG Ref keggcite changed kegg KEGG C14527 Section2 Chembox Properties C 5 H 8 O 2 Appearance Colorless liquid Density 0.94 g cm Solubility 1.5 g 100 ml MeltingPtC 48 BoilingPtC 101 pKb Viscosity 0.6 c Poise P at 20 C Section3 Chembox Structure Dipole 1.6 1.97 Debye D Section7 Chembox Hazards ExternalMSDS http www.jtbaker.com msds englishhtml m5616.htm Methyl methacrylate MSDS MainHazards Flammable FlashPt convert 2 C F Autoignition convert 435 C F RSPhrases Methyl methacrylate is an organic compound with the chemical formula formula CH sub 2 sub C CH sub 3 sub COOCH sub 3 sub . This colourless liquid, the methyl ester of methacrylic acid MAA is a monomer produced on a large scale for the production of poly methyl methacrylate PMMA . Production The compound is manufactured by several methods, the principal one being the acetone cyanohydrin ACH route, using acetone and hydrogen cyanide as raw materials. The intermediate cyanohydrin is converted with sulfuric acid to a sulfate ester of the methacrylamide, methanolysis of which gives ammonium bisulfate and MMA. Although widely used, the ACH route coproduces substantial amounts of ammonium sulfate . Some producers ... more details
chembox verifiedrevid 415296922 ImageFile1 Linamarin.svg ImageSize1 200px ImageFile2 Linamarin3d.png ImageSize2 200px ImageFile3 Linamarin 3D sticks.png IUPACName 2 methyl 2 2 S ,3 R ,4 S ,5 S ,6 R 3,4,5 trihydroxy 6 br hydroxymethyl oxan 2 yl oxy propanenitrile OtherNames Phaseolunatin Section1 Chembox Identifiers CASNo 554 35 8 PubChem 11128 SMILES CC C C N O C H 1 C H C H C H C H br O1 CO O O O Section2 Chembox Properties MolarMass 247.248 g mol Appearance colorless needles ref name dofc Shmuel Yannai Dictionary of Food Compounds with CD ROM Additives, Flavors, and Ingredients. CRC Press, 2003, ISBN 9781584884163, P. 695 ref C 10 H 17 N 1 O 6 Density 1.41 g· cm sup 3 sup MeltingPt 143 144 C ref name dofc Solubility good ref name dofc BoilingPt Section3 Chembox Hazards MainHazards FlashPt Autoignition Linamarin is a cyanide cyanogenic glucoside found in the leaves and roots of plants such as cassava , lima bean s, and flax . It is a glucoside of acetone cyanohydrin . Upon exposure to enzyme s and gut flora in the human intestine , linamarin and its methyl ated relative lotaustralin can decompose to the toxic chemical hydrogen cyanide hence food uses of plants that contain significant quantities of linamarin require extensive preparation and detoxification. Ingested and absorbed linamarin is rapidly excreted in the urine and the glucoside itself does not appear to be acutely toxic. Consumption of cassava products with low levels of linamarin is widespread in the low land tropics. Ingestion of food prepared from insufficiently processed cassava roots with high linamarin levels has been associated with dietary toxicity, particularly with the upper motor neuron disease known as konzo to the African populations in which it was first described by Trolli and later through the research network initiated by Hans Rosling . However, the toxicity is believed to be induced by ingestion of acetone cyanohydrin , the breakdown product of linamarin. ref name Banea Banea ... more details
The Bucherer Bergs reaction is the chemical reaction of carbonyl compounds aldehydes or ketones or cyanohydrin s with ammonium carbonate and potassium cyanide to give hydantoin s. ref Bucherer, H. T. Fischbeck, H. T. J. Prakt. Chem. 1934 , 140 , 69. ref ref Bucherer, H. T. Steiner, W. J. Prakt. Chem. 1934 , 140 , 291. ref ref Bergs, H. Ger. pat. 566,094 1929 . ref ref Ware, E. Chem. Rev. 1950 , 46 , 403. Review DOI 10.1021 cr60145a001 ref The reaction is named after Hans Theodor Bucherer . Overall Reaction Image Overall Bucherer Bergs reaction.png center 450px The Bucherer Bergs reaction Reaction Mechanism File Bucherer BergsReactionMechanism.png thumb border center middle 900x300px Reaction Mechanism The addition of KCN to the carbonyl compound gives rise to the cyanohydrin . This is followed by an S sub N sub 2 reaction with NH sub 3 sub to form aminonitrile. Nucleophilic addition of aminonitrile to CO sub 2 sub leads to cyano carbamic acid, which undergoes an intramolecular ring closing to 5 imino oxazolidin 2 one. The 5 imino oxazolidin 2 one rearranges to form the hydantoin product via an isocyanate intermediate. Citation needed date July 2011 History Reactions similar to the Bucherer Bergs reaction were first seen in 1905 and 1914 by Ciamician and Silber, who obtained 5,5 dimethylhydantoin from a mixture of acetone and hydrocyanic acid after it had been exposed to sunlight for five to seven months. In 1929, Bergs issued a patent that described his own synthesis of a number of 5 substituted hydantoins. Bucherer improved on Bergs method, finding that lower temperatures and pressures for the reaction were permissible. Bucherer and Steiner also found that cyanohydrins would react just as well as carbonyl compounds to produce hydantoins . Later, Bucherer and Lieb found that 50 alcohol was an effective solvent for the reaction. With this solvent, aldehydes reacted well, and ketones gave excellent yields. In 1934 Bucherer and Steiner proposed a mechanism for the reaction ... more details
chembox verifiedrevid 443932431 Name Mandelonitrile ref name SA http www.sigmaaldrich.com catalog search ProductDetail ALDRICH 469653 Sigma Aldrich product page ref ImageFile Racemic mandelonitrile 2D skeletal.png ImageSize IUPACName 2 hydroxy 2 phenylacetonitrile OtherNames hydroxybenzeneacetonitrile Section1 Chembox Identifiers Abbreviations ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 10304 InChI 1 C8H7NO c9 6 8 10 7 4 2 1 3 5 7 h1 5,8,10H InChIKey NNICRUQPODTGRU UHFFFAOYAG StdInChI Ref stdinchicite correct chemspider StdInChI 1S C8H7NO c9 6 8 10 7 4 2 1 3 5 7 h1 5,8,10H StdInChIKey Ref stdinchicite correct chemspider StdInChIKey NNICRUQPODTGRU UHFFFAOYSA N CASNo 532 28 5 EINECS PubChem 10758 SMILES N CC O c1ccccc1 InC link rel stylesheet type text css href http en.wikipedia.org w index.php?title User Lupin navpop.css&action raw&ctype text css&dontcountme s hI R link rel stylesheet type text css href http en.wikipedia.org w index.php?title User Lupin navpop.css&action raw&ctype text css&dontcountme s TECS MeSHName ChEBI Ref ebicite correct EBI ChEBI 16910 KEGG Ref keggcite correct kegg KEGG C00561 AT link rel stylesheet type text css href http en.wikipedia.org w index.php?title User Lupin navpop.css&action raw&ctype text css&dontcountme s CCode prefix ATCCode suffix ATC Supplemental Section2 Chembox Properties Formula C sub 8 sub H sub 7 sub NO MolarMass 133.15 g mol sup 1 sup Appearance Density 1.117 g mL at 25 C MeltingPt 28 30 C Melting notes BoilingPt 170 C Boiling notes Solubility SolubleOther Solvent pKa pKb Section7 Chembox Hazards ExternalMSDS EUClass EUIndex MainHazards toxic NFPA H NFPA F NFPA R NFPA O RPhrases R23 24 25 R36 37 38 R41 SPhrases S22 S26 S36 37 39 S45 RSPhrases FlashPt 113 C Autoignition ExploLimits PEL Section8 Chembox Related OtherAnions OtherCations OtherFunctn Function OtherCpds mandelic acid , phenylacetonitrile Mandelonitrile is a chemical compound of the cyanohydrin class. Small amounts of mandelonitrile occur i ... more details
See also List of UN Numbers UN 1501 to UN 1600 class wikitable width 140px UN Number Class Proper Shipping Name UN 1502 5.1 Sodium perchlorate UN 1503 5.1 Sodium permanganate UN 1504 5.1 Sodium peroxide UN 1505 5.1 Sodium persulfate UN 1506 5.1 Strontium chlorate UN 1507 5.1 Strontium nitrate UN 1508 5.1 Strontium perchlorate UN 1509 5.1 Strontium peroxide UN 1510 5.1 Tetranitromethane UN 1511 5.1 Urea hydrogen peroxide UN 1512 5.1 Zinc ammonium nitrite UN 1513 5.1 Zinc chlorate UN 1514 5.1 Zinc nitrate UN 1515 5.1 Zinc permanganate UN 1516 5.1 Zinc peroxide UN 1517 4.1 Zirconium picramate , wetted with not less than 20 percent water, by mass UN 1541 6.1 Acetone cyanohydrin , stabilized UN 1544 6.1 Alkaloid s, solid, n.o.s. or Alkaloid salts, solid, n.o.s. poisonous UN 1545 6.1 Allyl isothiocyanate , stabilized UN 1546 6.1 Ammonium arsenate UN 1547 6.1 Aniline UN 1548 6.1 Aniline hydrochloride UN 1549 6.1 Antimony compounds, inorganic, solid, n.o.s. UN 1550 6.1 Antimony lactate UN 1551 6.1 Antimony potassium tartrate UN 1553 6.1 Arsenic acid , liquid UN 1554 6.1 Arsenic acid, solid UN 1555 6.1 Arsenic bromide UN 1556 6.1 Arsenic compounds, liquid, n.o.s. inorganic, including arsenates, n.o.s. arsenites, n.o.s. arsenic sulfides, n.o.s. and organic compounds of arsenic, n.o.s. UN 1557 6.1 Arsenic compounds, solid, n.o.s. inorganic, including arsenates, n.o.s. arsenites, n.o.s. arsenic sulfides, n.o.s. and organic compounds of arsenic, n.o.s. UN 1558 6.1 Arsenic UN 1559 6.1 Arsenic pentoxide UN 1560 6.1 Arsenic trichloride UN 1561 6.1 Arsenic trioxide UN 1562 6.1 Arsenical dust UN 1564 6.1 Barium compounds, n.o.s. UN 1565 6.1 Barium cyanide UN 1566 6.1 Beryllium compounds, n.o.s. UN 1567 6.1 Beryllium, powder UN 1569 6.1 Bromoacetone UN 1570 6.1 Brucine UN 1571 4.1 Barium azide , wetted with not less than 50 percent water, by mass UN 1572 6.1 Cacodylic acid UN 1573 6.1 Calcium arsenate UN 1574 6.1 Calcium arsenate and calcium arsenite , mixtures, solid UN 1575 6.1 Calc ... more details
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