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146455 Aldrich

Isovaleraldehyde

97%

Synonym: 3-Methylbutyraldehyde, 3-Methylbutanal, NSC 404119

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Properties

Related Categories Acacia, Aldehydes, Building Blocks, C1 to C6, Carbonyl Compounds,
vapor density   2.96 (vs air)
vapor pressure   30 mmHg ( 20 °C)
assay   97%
autoignition temp.   464 °F
refractive index   n20/D 1.388(lit.)
bp   90 °C(lit.)
solubility   alcohol: miscible
  diethyl ether: miscible
  water: slightly soluble
density   0.803 g/mL at 25 °C(lit.)
storage temp.   2-8°C

Description

Packaging

25, 100, 500 mL in glass bottle

Application

Isovaleraldehyde was used as standard to evaluate the quality of olive oils by headspace solid-phase microextraction-gas chromatography using flame ionization detection and multivariate analysis1. It was used as internal standard in determination of wine aroma carbonyl compounds with 5-8 carbon atoms2.

General description

Isovaleraldehyde is an attractant and its interaction with zoospores of the fungus Phytophthora palmivora has been studied by binding techniques3.

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Isobutyraldehyde

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Isovaleraldehyde

analytical standard

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 1989BE 3 / PGII
WGK Germany 
2
RTECS 
ES3450000
Flash Point(F) 
24.8 °F
Flash Point(C) 
-4 °C

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

1. Comparison of the amounts of volatile compounds in French protected designation of origin virgin olive oils. Berlioz B, Cordella C, Cavalli JF, et al. J. Agric. Food Chem. 54(26), 10092-101, (2006)

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2. Analysis for wine C5-C8 aldehydes through the determination of their O-(2, 3, 4, 5, 6-pentafluorobenzyl) oximes formed directly in the solid phase extraction cartridge. Culleré L, et al. Anal. Chim. Acta 524(1), 201-206, (2004)

3. Binding of isovaleraldehyde, an attractant, to zoospores of the fungus Phytophthora palmivora in relation to zoospore chemotaxis. Cameron JN and Carlile MJ J. Cell Sci. 49, 273-81, (1981)

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anti-selective direct asymmetric Mannich reactions catalyzed by axially chiral amino sulfonamide as an organocatalyst. Kano T, Yamaguchi Y, Tokuda O, et al. J. Am. Chem. Soc. 127(47), 16408-9, (2005)

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Diversity of L-leucine catabolism in various microorganisms involved in dairy fermentations, and identification of the rate-controlling step in the formation of the potent flavour component 3-methylbutanal. Smit BA, Engels WJ, Wouters JT, et al. Appl. Microbiol. Biotechnol. 64(3), 396-402, (2004)

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A gas chromatographic--mass spectrometric study of profiles of volatile metabolites in hepatic encephalopathy. Goldberg EM, Blendis LM, and Sandler S J. Chromatogr. A 226(2), 291-9, (1981)

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Chemical profile of rums as a function of their origin. The use of chemometric techniques for their identification. Sampaio OM, Reche RV, and Franco DW J. Agric. Food Chem. 56(5), 1661-8, (2008)

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Glu 103 Gln site-directed mutation causes an alteration in physical properties of spinach betaine aldehyde dehydrogenase. Incharoensakdi A, Hibino T, and Takabe T J. Biochem. Mol. Biol. Biophys. 6(4), 243-8, (2002)

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Identification of chemical markers for the sensory shelf-life of saveloy. Holm ES, Schäfer A, Skov T, et al. Meat Science 90(2), 314-22, (2012)

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Quality changes during storage of cooked and sliced meat products measured with PTR-MS and HS-GC-MS. Holm ES, Adamsen AP, Feilberg A, et al. Meat Science 95(2), 302-10, (2013)

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Quantitative model studies on the formation of aroma-active aldehydes and acids by strecker-type reactions. Hofmann T, Münch P, and Schieberle P J. Agric. Food Chem. 48(2), 434-40, (2000)

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Identification and quantification of aroma-active components that contribute to the distinct malty flavor of buckwheat honey. Zhou Q, Wintersteen CL, and Cadwallader KR J. Agric. Food Chem. 50(7), 2016-21, (2002)

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Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. Garner CE, Smith S, de Lacy Costello B, et al. FASEB J. 21(8), 1675-88, (2007)

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Evidence of Strecker aldehyde excretion by yeast in cold contact fermentations. Perpète P and Collin S J. Agric. Food Chem. 48(6), 2384-6, (2000)

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Development of a high throughput screening method to test flavour-forming capabilities of anaerobic micro-organisms. Smit BA, Engels WJ, Bruinsma J, et al. J. Appl. Microbiol. 97(2), 306-13, (2004)

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Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Silva CL, Passos M, and Câmara JS Talanta 89, 360-8, (2012)

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Experimental demonstration of masking phenomena between competing odorants via an air dilution sensory test. Kim KH Sensors (Basel.) 10(8), 7287-302, (2010)

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Structural characterization of new malvidin 3-glucoside-catechin aryl/alkyl-linked pigments. Pissarra J, Lourenço S, González-Paramás AM, et al. J. Agric. Food Chem. 52(17), 5519-26, (2004)

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Kinetic modeling of the generation of 2- and 3-methylbutanal in a heated extract of beef liver. Balagiannis DP, Parker JK, Pyle DL, et al. J. Agric. Food Chem. 57(21), 9916-22, (2009)

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Quantitation of odor-active compounds in rye flour and rye sourdough using stable isotope dilution assays. Kirchhoff E and Schieberle P J. Agric. Food Chem. 50(19), 5378-85, (2002)

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[Association of plasma ammonia and GABA levels and the degree of hepatic encephalopathy]. Campollo O, MacGillivray BB, and McIntyre N Rev. Invest. Clin. 44(4), 483-90, (1992)

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Enhanced nutty flavor formation in cheddar cheese made with a malty Lactococcus lactis adjunct culture. Whetstine ME, Drake MA, Broadbent JR, et al. J. Dairy Sci. 89(9), 3277-84, (2006)

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Volatiles, color, and lipid oxidation of broiler breast fillets irradiated before and after cooking. Du M, Hur SJ, Nam KC, et al. Poult. Sci. 80(12), 1748-53, (2001)

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A transcriptome analysis of isoamyl alcohol-induced filamentation in yeast reveals a novel role for Gre2p as isovaleraldehyde reductase. Hauser M, Horn P, Tournu H, et al. FEMS Yeast Res. 7(1), 84-92, (2007)

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Enhanced flavour formation by combination of selected lactococci from industrial and artisanal origin with focus on completion of a metabolic pathway. Ayad EH, Verheul A, Engels WJ, et al. J. Appl. Microbiol. 90(1), 59-67, (2001)

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Headspace analysis of Italian and New Zealand parmesan cheeses. Langford VS, Reed CJ, Milligan DB, et al. J. Food Sci. 77(6), C719-26, (2012)

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Identification of metabolic pathways involved in the biosynthesis of flavor compound 3-methylbutanal from leucine catabolism by Carnobacterium maltaromaticum LMA 28. Afzal MI, Delaunay S, Paris C, et al. Int. J. Food Microbiol. 157(3), 332-9, (2012)

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Preliminary characterization of wild lactic acid bacteria and their abilities to produce flavour compounds in ripened model cheese system. Randazzo CL, De Luca S, Todaro A, et al. J. Appl. Microbiol. 103(2), 427-35, (2007)

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Plasma 3-methylbutanal in man and its relationship to hepatic encephalopathy. Marshall AW, DeSouza M, and Morgan MY Clin. Physiol. 5(1), 53-62, (1985)

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Low-temperature catalytic oxidation of aldehyde mixtures using wood fly ash: kinetics, mechanism, and effect of ozone. Kolar P and Kastner JR Chemosphere 78(9), 1110-5, (2010)

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Plasma levels of pipecolic acid, both L- and D-enantiomers, in patients with chronic liver diseases, especially hepatic encephalopathy. Fujita T, Amuro Y, Hada T, et al. Clin. Chim. Acta 287(1-2), 99-109, (1999)

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Effect of oxygen on the biosynthesis of flavor compound 3-methylbutanal from leucine catabolism during batch culture in Carnobacterium maltaromaticum LMA 28. Afzal MI, Boulahya KA, Paris C, et al. J. Dairy Sci. 96(1), 352-9, (2013)

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Comparison of the flavor chemistry and flavor stability of mozzarella and cheddar wheys. Liaw IW, Evan Miracle R, Jervis SM, et al. J. Food Sci. 76(8), C1188-94, (2011)

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Individual variation in 3-methylbutanal: a putative link between human leukocyte antigen and skin microflora. Savelev SU, Antony-Babu S, Roberts SC, et al. J. Chem. Ecol. 34(9), 1253-7, (2008)

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Enzyme inactivation and quality preservation of sake by high-pressure carbonation at a moderate temperature. Tanimoto S, Matsumoto H, Fujii K, et al. Biosci. Biotechnol. Biochem. 72(1), 22-8, (2008)

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Headspace volatiles along with other instrumental and sensory analyses as indices of maturation of horse mackerel miso. Giri A, Okamoto A, Okazaki E, et al. J. Food Sci. 75(8), S406-17, (2010)

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An easy and efficient fluorescent method for detecting aldehydes and its application in biotransformation. Xing Y, Wang S, Mao X, et al. J. Fluoresc. 21(2), 587-94, (2011)

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Merck 14,5229

Beil. 1,IV,3291

Aldrich MSDS 1, 1127:B / Arctander, 3053 / Corp MSDS 1 (1), 2047:D / FT-IR 1 (1), 467:A / FT-IR 2 (1), 732:B / FT-NMR 1 (1), 729:A / Fenaroli / IR-Spectra (3), 276:H / IR-Spectra (2), 248:H / NMR-Reference 2 (1), 358:C / RegBook 53 (1), 509:J / RegBook 1 (1), 509:J / Sax 6, 1820 / Sigma FT-IR 1 (2), 673:D / Structure Index 1, 73:A:3 / Vapor Phase 3, 552:D

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