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M54058 Aldrich

Methylmalonic acid

99%

Synonym: 2-Methylpropanedioic acid

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Properties

Related Categories Building Blocks, C1 to C5, Carbonyl Compounds, Carboxylic Acids, Chemical Synthesis,
assay   99%
mp   128-130 °C(lit.)

Description

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5, 25 g in glass bottle

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Protocols & Articles

Articles

Characteristic Metabolites for Inborn Errors of Amino Acid Metabolism

Inborn errors of metabolism are caused by changes in specific enzymatic reactions and hundreds of different such alterations, which affect about 1 of every 5000 newborns, have been characterized. The...
Keywords: Indicators, Metabolism, Metabolites

Peer-Reviewed Papers

References

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The effect of increased concentrations of homocysteine on the concentration of (E)-4-hydroxy-2-nonenal in the plasma and cerebrospinal fluid of patients with Alzheimer's disease. Selley ML, Close DR, and Stern SE Neurobiol. Aging 23(3), 383-8, (2002)

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The human serum metabolome. Psychogios N, Hau DD, Peng J, et al. PLoS ONE 6(2), e16957, (2011)

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Diagnostic use of cerebral and extracerebral oxysterols. Leoni V, Masterman T, Mousavi FS, et al. Clin. Chem. Lab Med. 42(2), 186-91, (2004)

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Cobalamin and folate status predicts mental development scores in North Indian children 12-18 mo of age. Strand TA, Taneja S, Ueland PM, et al. Am. J. Clin. Nutr. 97(2), 310-7, (2013)

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Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Guneral F and Bachmann C Clin. Chem. 40(6), 862-6, (1994)

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Systematic review with dose-response meta-analyses between vitamin B-12 intake and European Micronutrient Recommendations Aligned's prioritized biomarkers of vitamin B-12 including randomized controlled trials and observational studies in adults and elderly persons. Dullemeijer C, Souverein OW, Doets EL, et al. Am. J. Clin. Nutr. 97(2), 390-402, (2013)

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Cobalamin related parameters and disease patterns in patients with increased serum cobalamin levels. Arendt JF and Nexo E PLoS ONE 7(9), e45979, (2012)

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Vitamin B₁₂ status, cognitive decline and dementia: a systematic review of prospective cohort studies. O'Leary F, Allman-Farinelli M, and Samman S Br. J. Nutr. 108(11), 1948-61, (2012)

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Serum cobalamin, urine methylmalonic acid, and plasma total homocysteine concentrations in Border Collies and dogs of other breeds. Lutz S, Sewell AC, Bigler B, et al. Am. J. Vet. Res. 73(8), 1194-9, (2012)

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Homocysteine and methylmalonic acid in diagnosis and risk assessment from infancy to adolescence. Bjørke Monsen AL and Ueland PM Am. J. Clin. Nutr. 78(1), 7-21, (2003)

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Cobalamin supplementation improves motor development and regurgitations in infants: results from a randomized intervention study. Torsvik I, Ueland PM, Markestad T, et al. Am. J. Clin. Nutr. 98(5), 1233-40, (2013)

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High resolution melting analysis of the MMAA gene in patients with cblA and in those with undiagnosed methylmalonic aciduria. Dempsey-Nunez L, Illson ML, Kent J, et al. Mol. Genet. Metab. 107(3), 363-7, (2012)

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Automated assay of methylmalonic acid in serum and urine by derivatization with 1-pyrenyldiazomethane, liquid chromatography, and fluorescence detection. Schneede J and Ueland PM Clin. Chem. 39(3), 392-9, (1993)

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[Blood and urinary level of methylmalonic acid: an important index in evaluating cobalamin deficiency]. Sela BA, Mouallem M, Zlotnik J, et al. Harefuah 132(12), 866-71, (1997)

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[Methylmalonic acid]. Tanaka A and Isshiki G Nihon Rinsho. 53 Su Pt 1, 600-2, (1995)

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Laboratory evaluation for vitamin B12 deficiency: the case for cascade testing. Berg RL and Shaw GR Clin. Med. Res. 11(1), 7-15, (2013)

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[Biological markers for the status of vitamins B12 and D: the importance of some analytical aspects in relation to clinical interpretation of results]. Boulat O, Rey F, and Mooser V Rev. Med. Suisse 8(360), 2052-4, 2056-8, (2012)

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[Abnormal findings during newborn period of 160 patients with early-onset methylmalonic aciduria]. Liu YP, Ma YY, Wu TF, et al. Zhonghua Er Ke Za Zhi. 50(6), 410-4, (2012)

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[Determination of homocysteine and methylmalonic acid in cobalamin deficiency. Diagnostic problem with a solution?]. Schneede J, Refsum H, Slørdal L, et al. Tidsskr. Nor. Laegeforen. 111(4), 450-5, (1991)

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[Measurement of methylmalonic acid, homocysteine and methionine in cobalamin and folate deficiencies and homocysteinuria]. Ueland PM and Schneede J Tidsskr. Nor. Laegeforen. 128(6), 690-3, (2008)

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Monitoring of chemical elements and oxidative damage in patients affected by Alzheimer's disease. Bocca B, Forte G, Petrucci F, et al. Ann. Ist. Super. Sanita 41(2), 197-203, (2005)

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[Connection between changing the vitamin and immune status and the character of the throat microflora in patients with chronic tonsillitis]. Aleszczyk J Otolaryngol. Pol. 57(2), 221-4, (2003)

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[Homocysteine and methylmalonic acid as markers of cobalamin/folate status. The association to neuropsychiatric symptoms in the elderly is explored]. Hultberg B, Isaksson A, Nilsson K, et al. Lakartidningen. 97(38), 4131-4, 4136, (2000)

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[Methylmalonic acid]. Tanaka A Nihon Rinsho. 57 Suppl, 660-2, (1999)

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Serum cobalamin and methylmalonic acid in Alzheimer dementia. Kristensen MO, Gulmann NC, Christensen JE, et al. Acta Neurol. Scand 87(6), 475-81, (1993)

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Brain damage in methylmalonic aciduria: 2-methylcitrate induces cerebral ammonium accumulation and apoptosis in 3D organotypic brain cell cultures. Jafari P, Braissant O, Zavadakova P, et al. Orphanet J. Rare Dis. 8, 4, (2013)

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Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. Shoemaker JD and Elliott WH J. Chromatogr. A 562(1-2), 125-38, (1991)

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Cobalamin and haptocorrin in human milk and cobalamin-related variables in mother and child: a 9-mo longitudinal study. Greibe E, Lildballe DL, Streym S, et al. Am. J. Clin. Nutr. 98(2), 389-95, (2013)

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Biomarkers of cobalamin (vitamin B-12) status in the epidemiologic setting: a critical overview of context, applications, and performance characteristics of cobalamin, methylmalonic acid, and holotranscobalamin II. Carmel R Am. J. Clin. Nutr. 94(1), 348S-358S, (2011)

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Cognitive function in an elderly population: interaction between vitamin B12 status, depression, and apolipoprotein E ε4: the Hordaland Homocysteine Study. Vogiatzoglou A, Smith AD, Nurk E, et al. Psychosom. Med. 75(1), 20-9, (2013)

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Cobalamin and folate evaluation: measurement of methylmalonic acid and homocysteine vs vitamin B(12) and folate. Klee GG Clin. Chem. 46(8 Pt 2), 1277-83, (2000)

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Clinical practice. Vitamin B12 deficiency. Stabler SP N. Engl. J. Med. 368(2), 149-60, (2013)

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Elevation of serum cystathionine levels in patients with cobalamin and folate deficiency. Stabler SP, Lindenbaum J, Savage DG, et al. Blood 81(12), 3404-13, (1993)

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Assay of methylmalonic acid in the serum of patients with cobalamin deficiency using capillary gas chromatography-mass spectrometry. Stabler SP, Marcell PD, Podell ER, et al. J. Clin. Invest. 77(5), 1606-12, (1986)

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Ratio of 8-hydroxyguanine in intact DNA to free 8-hydroxyguanine is increased in Alzheimer disease ventricular cerebrospinal fluid. Lovell MA and Markesbery WR Arch. Neurol. 58(3), 392-6, (2001)

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Hydroxy acid metabolites of branched-chain amino acids in amniotic fluid. Jakobs C, Sweetman L, and Nyhan WL Clin. Chim. Acta 140(2), 157-66, (1984)

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In vitro and in vivo comparison of 18F and 123I-labeled ML10 with 68Ga-Cys2-AnxA5 for molecular imaging of apoptosis. Bauwens M, De Saint-Hubert M, Cleynhens J, et al. Q. J. Nucl. Med. Mol. Imaging 57(2), 187-200, (2013)

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Development of transgenic mice containing an introduced stop codon on the human methylmalonyl-CoA mutase locus. Buck NE, Dashnow H, Pitt JJ, et al. PLoS ONE 7(9), e44974, (2012)

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Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Gronwald W, Klein MS, Zeltner R, et al. Kidney Int. 79(11), 1244-53, (2011)

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Methylmalonic acid measured in plasma and urine by stable-isotope dilution and electrospray tandem mass spectrometry. Magera MJ, Helgeson JK, Matern D, et al. Clin. Chem. 46(11), 1804-10, (2000)

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Increased plasma homocysteine levels without signs of vitamin B12 deficiency in patients with multiple sclerosis assessed by blood and cerebrospinal fluid homocysteine and methylmalonic acid. Vrethem M, Mattsson E, Hebelka H, et al. Mult. Scler. 9(3), 239-45, (2003)

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Patterns of cerebrospinal fluid catechols support increased central noradrenergic responsiveness in aging and Alzheimer's disease. Raskind MA, Peskind ER, Holmes C, et al. Biol. Psychiatry 46(6), 756-65, (1999)

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Physiology and pathophysiology of organic acids in cerebrospinal fluid. Hoffmann GF, Meier-Augenstein W, Stöckler S, et al. J. Inherit. Metab. Dis. 16(4), 648-69, (1993)

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Glycerophosphocholine is elevated in cerebrospinal fluid of Alzheimer patients. Walter A, Korth U, Hilgert M, et al. Neurobiol. Aging 25(10), 1299-303, (2004)

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Homocysteine and methylmalonic acid concentrations in cerebrospinal fluid: relation with age and Alzheimer's disease. Serot JM, Barbé F, Arning E, et al. J. Neurol. Neurosurg. Psychiatr. 76(11), 1585-7, (2005)

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Advanced age as a risk factor for folate-associated functional cobalamin deficiency. Solomon LR J. Am. Geriatr. Soc. 61(4), 577-82, (2013)

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Elevation of 2-methylcitric acid I and II levels in serum, urine, and cerebrospinal fluid of patients with cobalamin deficiency. Allen RH, Stabler SP, Savage DG, et al. Metabolism 42(8), 978-88, (1993)

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Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Tavazzi B, Lazzarino G, Leone P, et al. Clin. Biochem. 38(11), 997-1008, (2005)

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Cerebrospinal fluid and plasma distribution of myo-inositol and other polyols in Alzheimer disease. Shetty HU, Holloway HW, and Schapiro MB Clin. Chem. 42(2), 298-302, (1996)

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Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Fonteh AN, Harrington RJ, Tsai A, et al. Amino Acids 32(2), 213-24, (2007)

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Microdetermination of methylmalonic acid and other short chain dicarboxylic acids by gas chromatography: use in prenatal diagnosis of methylmalonic acidemia and in studies of isovaleric acidemia. Nakamura E, Rosenberg LE, and Tanaka K Clin. Chim. Acta 68(2), 127-40, (1976)

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Pentosidine and N(epsilon)-(carboxymethyl)-lysine in Alzheimer's disease and vascular dementia. Bär KJ, Franke S, Wenda B, et al. Neurobiol. Aging 24(2), 333-8, (2003)

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Management of methylmalonic acidaemia by combined liver-kidney transplantation. Nagarajan S, Enns GM, Millan MT, et al. J. Inherit. Metab. Dis. 28(4), 517-24, (2005)

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The importance of methylmalonic acid dosage on the assessment of patients with neurological manifestations following bariatric surgery. Vieira C, Cosmo C, and Lucena R Obes. Surg. 21(12), 1971-4, (2011)

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Methylmalonic acid--an endogenous toxin? Kölker S and Okun JG Cell. Mol. Life Sci. 62(6), 621-4, (2005)

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Serum cobalamin and methylmalonic acid concentrations in dogs with chronic gastrointestinal disease. Berghoff N, Parnell NK, Hill SL, et al. Am. J. Vet. Res. 74(1), 84-9, (2013)

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Methylmalonic acid: a test whose time has come? Elin RJ and Winter WE Arch. Pathol. Lab. Med. 125(6), 824-7, (2001)

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Applicability of an enzymatic quantitation of methylmalonic, propionic, and acetic acids in normal and megaloblastic states. Frenkel EP and Kitchens RL Blood 49(1), 125-37, (1977)

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Megaloblastic anemia as a result of an abnormal transcobalamin II (Cardeza). Haurani FI, Hall CA, and Rubin R J. Clin. Invest. 64(5), 1253-9, (1979)

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Utility and limitations of biochemical markers of vitamin B12 deficiency. Herrmann W and Obeid R Eur. J. Clin. Invest. 43(3), 231-7, (2013)

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Remarkable increase in the concentration of 8-hydroxyguanosine in cerebrospinal fluid from patients with Alzheimer's disease. Abe T, Tohgi H, Isobe C, et al. J. Neurosci. Res. 70(3), 447-50, (2002)

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Sani-cloth wipe mimics rare enzyme deficiency malonic aciduria on newborn screen. Reindl BA, Lynch DW, Ramirez M, et al. Pediatrics 130(5), e1363-8, (2012)

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A vitamin B-12 supplement of 500 μg/d for eight weeks does not normalize urinary methylmalonic acid or other biomarkers of vitamin B-12 status in elderly people with moderately poor vitamin B-12 status. Hill MH, Flatley JE, Barker ME, et al. J. Nutr. 143(2), 142-7, (2013)

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Modeling a methylmalonic acid-derived change point for serum vitamin B-12 for adults in NHANES. Bailey RL, Durazo-Arvizu RA, Carmel R, et al. Am. J. Clin. Nutr. 98(2), 460-7, (2013)

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Comparison of post-mortem urinary and vitreous humour organic acids. Bennett MJ, Ragni MC, Hood I, et al. Ann. Clin. Biochem. 29 ( Pt 5), 541-5, (1992)

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Vitamin B-12 supplementation of rural Mexican women changes biochemical vitamin B-12 status indicators but does not affect hematology or a bone turnover marker. Shahab-Ferdows S, Anaya-Loyola MA, Vergara-Castañeda H, et al. J. Nutr. 142(10), 1881-7, (2012)

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[Methylmalonic aciduria. Classification, diagnosis and therapy (author's transl)]. Leupold D Klin. Wochenschr. 55(2), 57-63, (1977)

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Acute renal failure potentiates methylmalonate-induced oxidative stress in brain and kidney of rats. Schuck PF, Alves L, Pettenuzzo LF, et al. Free Radic. Res. 47(3), 233-40, (2013)

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Genetic polymorphisms modulate the folate metabolism of Brazilian individuals with Down syndrome. Biselli JM, Zampieri BL, Goloni-Bertollo EM, et al. Mol. Biol. Rep. 39(10), 9277-84, (2012)

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Elevated serum methylmalonic acid. How much comes from cobalamin deficiency and how much comes from the kidneys? Lindgren A Scand. J. Clin. Lab. Invest. 62(1), 15-9, (2002)

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Failure to detect beta-leucine in human blood or leucine 2,3-aminomutase in rat liver using capillary gas chromatography-mass spectrometry. Stabler SP, Lindenbaum J, and Allen RH J. Biol. Chem. 263(12), 5581-8, (1988)

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Cardiomyopathy and hypotonia in a 5-month-old infant with malonyl-coa decarboxylase deficiency: potential for preclinical diagnosis with expanded newborn screening. Ficicioglu C, Chrisant MR, Payan I, et al. Pediatr. Cardiol. 26(6), 881-3, (2005)

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Differential acetylcholine and choline concentrations in the cerebrospinal fluid of patients with Alzheimer's disease and vascular dementia. Jia JP, Jia JM, Zhou WD, et al. Chin. Med. J. 117(8), 1161-4, (2004)

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Cerebrospinal fluid levels of thiamine in patients with Alzheimer's disease. Molina JA, Jiménez-Jiménez FJ, Hernánz A, et al. J. Neural Transm. Gen. Sect. 109(7-8), 1035-44, (2002)

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Vitamin B(12) intake and status in early pregnancy among urban South Indian women. Samuel TM, Duggan C, Thomas T, et al. Ann. Nutr. Metab. 62(2), 113-22, (2013)

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Hyperammonaemia due to cobalamin malabsorption in a cat with exocrine pancreatic insufficiency. Watanabe T, Hoshi K, Zhang C, et al. J. Feline Med. Surg. 14(12), 942-5, (2012)

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Trichloroethylene and trichloroethanol-induced formic aciduria and renal injury in male F-344 rats following 12 weeks exposure. Yaqoob N, Evans A, Foster JR, et al. Toxicology 323, 70-7, (2014)

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Total blood mercury and rubella antibody concentrations in US children aged 6-11 years, NHANES 2003-2004. Gallagher CM, Smith DM, Golightly MG, et al. Sci. Total Environ. 442, 48-55, (2013)

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Organic acids in aqueous humour and plasma: post mortem study in infants and diagnosis of enzymopathies. Coude MM, Charpentier C, Bonnefont JP, et al. J. Inherit. Metab. Dis. 14(5), 668-73, (1991)

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Cobalamin status in sickle cell disease. Ajayi OI, Bwayo-Weaver S, Chirla S, et al. Int. J. Lab. Hematol. 35(1), 31-7, (2013)

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Chronic administration of methylmalonate on young rats alters neuroinflammatory markers and spatial memory. Ribeiro LR, Della-Pace ID, de Oliveira Ferreira AP, et al. Immunobiology 218(9), 1175-83, (2013)

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Semi-automated quantification of methylmalonic acid in human serum by LC-MS/MS. Nelson D, Xu N, and Carlson J Scand. J. Clin. Lab. Invest. 72(6), 441-6, (2012)

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Increased susceptibility of brain acetylcholinesterase activity to methylmalonate in young rats with renal failure. Affonso AC, Machado DG, Malgarin F, et al. Metab. Brain Dis. 28(3), 493-500, (2013)

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DHFR 19-bp deletion and SHMT C1420T polymorphisms and metabolite concentrations of the folate pathway in individuals with Down syndrome. Mendes CC, Raimundo AM, Oliveira LD, et al. Genet. Test. Mol. Biomarkers 17(4), 274-7, (2013)

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Role of serum holotranscobalamin (holoTC) in the diagnosis of patients with low serum cobalamin. Comparison with methylmalonic acid and homocysteine. Remacha AF, Sardà MP, Canals C, et al. Ann. Hematol. 93(4), 565-9, (2014)

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Combined use of gas chromatography, mass spectrometry, and computer in diagnosis and studies of metabolic disorders. Jellum E, Stokke O, and Eldjarn L Clin. Chem. 18(8), 800-9, (1972)

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Tandem mass spectrometric determination of malonylcarnitine: diagnosis and neonatal screening of malonyl-CoA decarboxylase deficiency. Santer R, Fingerhut R, Lässker U, et al. Clin. Chem. 49(4), 660-2, (2003)

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Beil. 2,IV,1932

Aldrich MSDS 1, 1267:D / Corp MSDS 1 (2), 2376:D / FT-IR 2 (1), 768:C / FT-IR 1 (1), 490:D / FT-NMR 1 (1), 765:A / IR-Spectra (3), 289:A / IR-Spectra (2), 260:D / NMR-Reference 2 (1), 427:B / RegBook 1 (1), 541:E / Sigma FT-IR 1 (2), 740:C / Structure Index 1, 76:A:6

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