3 methylbutanoic acid

Manufactured by Merck Group

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Sourced in Germany, United States, United Kingdom

About the product

3-methylbutanoic acid is a chemical compound with the molecular formula C5H10O2. It is a clear, colorless liquid with a characteristic odor. 3-methylbutanoic acid is commonly used as a reference standard or analytical reagent in laboratory settings.

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Lab products found in correlation

Hexanoic acid, by Merck Group (17 mentions) Acetic acid, by Merck Group (16 mentions) Octanoic acid, by Merck Group (13 mentions) Ethyl hexanoate, by Merck Group (12 mentions) Butanoic acid, by Merck Group (11 mentions) 2 methylbutanoic acid, by Merck Group (11 mentions) 2 phenylethanol, by Merck Group (9 mentions) Linalool, by Merck Group (9 mentions) Ethyl 3 methylbutanoate, by Merck Group (8 mentions) Ethyl butanoate, by Merck Group (8 mentions) 3 methylbutanal, by Merck Group (7 mentions) 2 methylbutanal, by Merck Group (7 mentions) Ethyl acetate, by Merck Group (7 mentions) Ethyl octanoate, by Merck Group (7 mentions) Decanoic acid, by Merck Group (7 mentions) Phenylacetaldehyde, by Merck Group (6 mentions) Ethyl 2 methylbutanoate, by Merck Group (6 mentions) 4 hydroxy 2 5 dimethyl 3 2h furanone, by Merck Group (6 mentions) Ethyl decanoate, by Merck Group (6 mentions) Pentanoic acid, by Merck Group (6 mentions)

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Acids (2 citations) 3-methylbutanoic (1 citations) Acides (1 citations)

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37 protocols using 3 methylbutanoic acid

Extraction and Identification of Aroma Compounds

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The following chemicals were used: sodium sulfate, dichloromethane (DCM) (VWR International GmbH, Darmstadt, Germany) - prior to use, DCM was freshly distilled; alkanes C₆-C₃₄, nonanal (purity: 95%) (Fluka, Steinheim, Germany); octanal (n.a.), oct-1-en-3-one (50%), (E)-non-2-enal (97%), undecanal (97%), dodecanoic acid (99,5%), do decanal (n.a.), (2E,4E)-deca-2,4-dienal (85%), 3-methylbutanoic acid (99%), 4-ethyl octanoic acid (98%), 4-methylphenol (in the following: p-cresol; > 98%), octanoic acid (98%), 4-(4-hydroxyphenyl)butan-2-one (in the following: raspberry ketone; 99%), 5-heptyloxolan-2-one (in the following: γ-undecalactone; 98%), (2E,4E)-nona-2,4-dienal (85%), 4-hydroxy-2,3-dimethyl-2H-furan-5-one (in the following: sotolone; 97%) (Aldrich, Steinheim, Germany); 6-methylhept-5-en-2-one (>98%), (E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one (in the following: α-isomethylionone; ≥95%), 6,10-dimethylundeca-5,9-dien-2-one (in the following: geranyl acetone; > 97%), 3,7-dimethylocta-1,6-dien-3-ol (in the following: linalool; 97%) (Sigma Aldrich, Steinheim, Germany); decanal (>98%), (3R,5S,8R,9S,10S,13R,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol (in the following: 5α-androst-16-en-3α-ol; n.a.), (5S,8R,9S,10S,13R,14S)-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15-dodecahydrocyclopenta[a]phenanthren-3-one (in the following: 5α-androst-16-en-3-one; n.a.), (Z)-tetradec-9-enoic acid (in the following: myristoleic acid; > 99%) (Sigma, Steinheim, Germany); (E)-2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-en-1-ol (in the following: sandranol; n.a.), (E)-3,3-dimethyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol (in the following: polysantol; n.a.) (kindly provided by Symrise AG, Holzminden, Germany); (E)-3-[(2S,3S)-3-pentyloxiran-2-yl]prop-2-enal (in the following: (E)-4,5-epoxy-(E)-2-decenal; 97%) (AromaLab GmbH, Martinsried, Germany); 4-hydroxy-3-methoxybenzaldehyde (in the following: vanillin; 99%), 2-methylheptanoic acid (98%) (ABCR, Karlsruhe, Deutschland); 5-octyloxolan-2-one (in the following: γ-dodecalacton; 97%) (SAFC, Steinheim, Germany); (1R,3R,6S,7S,8S)-2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undecan-3-ol (in the following: patchouli alcohol; > 98%) (Biozol, Eching, Germany); n-triacontane (>98%) (Alfa Aesar by Thermo Fisher Scientific, Kandel, Germany).
The following isotopically labeled standards were ordered: 6-methylhept-5-en-2-one d6, (2E)-3,7-dimethylocta-2,6-dien-1-ol d2 (in the following: geraniol d2; AromaLAB GmbH, Martinsried, Germany).

Owsienko D., Goppelt L., Hierl K., Schäfer L., Croy I, & Loos H.M. (2024). Body odor samples from infants and post-pubertal children differ in their volatile profiles. Communications Chemistry, 7, 53.

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Analytical Method for Volatile Fatty Acids

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Analytical-grade hydrochloric acid (HCl) fuming 37%, diethyl ether (DE), and anhydrous acetic acid were purchased from Merck (Darmstadt, Germany). Analytical-grade anhydrous sodium sulfate, butyric acid, propionic acid, 2-methylpropionic acid, pentanoic acid, 2-methylbutanoic acid, 3-methylbutanoic acid, 3-methylpentanoic acid, 4-methylpentanoic acid, hexanoic acid, 2-methylhexanoic acid, 4-methylhexanoic acid, and heptanoic acid were purchased from Sigma-Aldrich (MO, USA). Propionic-d₅ acid (Pro-D₅), which was used as the internal standard (IS), was purchased from CDN Isotope Inc. (Quebec, Canada). Milli-Q water was provided by Milli-Q Advantage A10 Water Purification System from Merck (Darmstadt, Germany) with resistivity value of 18.2 MΩ·cm at 25 °C; ≤ 5 ppb.

Manokasemsan W., Jariyasopit N., Poungsombat P., Kaewnarin K., Wanichthanarak K., Kurilung A., Duangkumpha K., Limjiasahapong S., Pomyen Y., Chaiteerakij R., Tansawat R., Srisawat C., Sirivatanauksorn Y., Sirivatanauksorn V, & Khoomrung S. (2024). Quantifying fecal and plasma short-chain fatty acids in healthy Thai individuals. Computational and Structural Biotechnology Journal, 23, 2163-2172.

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Flavor Compound Identification Protocol

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Reference odorants were obtained from the
commercial sources given in parentheses: acetic acid (Merck, Darmstadt,
Germany); butanoic acid, δ-decalactone, δ-dodecalactone,
ethyl butanoate, ethyl hexanoate, hexanoic acid, 3-methylbutanal,
3-methylbutanoic acid, 3-methyl-1-butanol, pentanoic acid, 2-phenylacetic
acid, and 2-phenylethanol (Sigma-Aldrich Chemie, Taufkirchen, Germany).
Diethyl ether, sodium carbonate, sodium chloride, and anhydrous
sodium sulfate were purchased from Merck (Germany). Liquid nitrogen
was obtained from Linde (Munich, Germany). Dess-Martin periodinane
and 4-methylumbelliferyl butanoate were obtained from Sigma-Aldrich
Chemie. Diethyl ether was freshly distilled prior to use.

Duensing P.W., Hinrichs J, & Schieberle P. (2024). Formation of Key Aroma Compounds During 30 Weeks of Ripening in Gouda-Type Cheese Produced from Pasteurized and Raw Milk. Journal of Agricultural and Food Chemistry, 72(19), 11072-11079.

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Odorant Reference Compounds for Research

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Reference compounds of the odorants identified
were obtained from the commercial sources given in parentheses: acetic
acid (Merck, Darmstadt, Germany); butane-2,3-dione, butanoic acid,
γ-decalactone, δ-decalactone, γ-dodecalactone, δ-dodecalactone,
ethyl butanoate, ethyl hexanoate, 5-ethyl-3-hydroxy-4-methyl-2(5H)-furanone, hexanoic acid, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, 4-hydroxy-3-methoxybenzaldehyde (vanillin),
2-isopropyl-3-methoxypyrazine, 3-methylbutanal, 2-methylbutanoic acid,
3-methylbutanoic acid, 3-methylbutanol, 2-methylpropanoic acid, γ-nonalactone,
(E)-2-nonenal, pentanoic acid, 2-phenylacetic acid
and 2-phenylethanol (Sigma-Aldrich Chemie, Taufkirchen, Germany);
and 4-ethyloctanoic acid (ABCR GmbH & Co. KG, Karlsruhe, Germany).
The following reference compounds were synthesized as previously
described: (Z)-2-nonenal^{27 (link)} and trans-4,5-epoxy-(E)-2-decenal.^{28 (link)}

Duensing P.W., Hinrichs J, & Schieberle P. (2024). Influence of Milk Pasteurization on the Key Aroma Compounds in a 30 Weeks Ripened Pilot-Scale Gouda Cheese Elucidated by the Sensomics Approach. Journal of Agricultural and Food Chemistry, 72(19), 11062-11071.

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Characterization of Flavor Compounds

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Commercially available compounds
were purchased at the highest purity available. Acetaldehyde (≥99%),
acetic acid (≥99%), butane-2,3-dione (97%), decanoic acid (≥98%),
1,1-diethoxyethane (99%), dimethyl sulfide (≥99%), ethyl acetate
(≥99%), ethyl butanoate (≥99%), ethyl decanoate (≥99%),
ethyl hexanoate (≥99%), ethyl 2-methylbutanoate (99%), ethyl
3-methylbutanoate (98%), ethyl 2-methylpropanoate (≥98%), ethyl
octanoate (≥98%), 3-hydroxybutan-2-one (97%), 2-methylbutanal
(95%), 3-methylbutanal (≥97%), 3-methylbutanoic acid (99%),
2-methylbutan-1-ol (≥99%), 3-methylbutan-1-ol (≥98%),
3-methylbutyl acetate (≥99%), 2-methylpropanal (≥99%),
2-methylpropyl acetate (99%), 3-(methylsulfanyl)propanal (96%), 3-(methylsulfanyl)propan-1-ol
(≥98%), octanoic acid (≥98%), phenylacetic acid (99%),
2-phenylethan-1-ol (≥99%) were from Merck (Darmstadt, Germany);
ethyl propanoate (≥99%), hexan-1-ol (99%), phenylAcetaldehyde
(95%), 2-phenylethyl acetate (98%) were from Thermo Fisher Scientific
(Dreieich, Germany); 2-methylpropan-1-ol (≥99%) was from TCI
(Eschborn, Germany). 3-Methylbut-2-ene-1-thiol was synthesized according
to a previously published procedure.^{26 (link)} The
absence of odor-active impurities in the reference odorants was confirmed
by GC–O.^{27 (link)}

Wang X., Frank S, & Steinhaus M. (2024). Molecular Insights into the Aroma Difference between Beer and Wine: A Meta-Analysis-Based Sensory Study Using Concentration Leveling Tests. Journal of Agricultural and Food Chemistry, 72(40), 22250-22257.

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Analytical Protocol for Flavor Compounds

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Dichloromethane, freshly distilled prior to use, and anhydrous sodium sulfate were purchased from Th. Geyer GmbH & Co. KG (Renningen, Germany). To determine the retention indices, a diluted solution of a homologous series of n-alkanes in pentane (> 99%, Sigma-Aldrich, Steinheim, Germany) was prepared, comprising the alkanes from n-hexane to n-triacontane (Fluka, Aldrich and Sigma-Aldrich; Steinheim, Germany).
The reference compounds with IUPAC names (trivial/alternative names) and purity given in brackets wherever applicable, and their suppliers are provided in the following: 2-phenylethanol (99%), hexanal (98%), (Z)-4-heptenal (98%), oct-1-en-3-one (1-octen-3-one) (50%), (E)-oct-2-enal [(E)-2-octenal] (94%), (2E,6Z)-nona-2,6-dienal [(E, Z)-2,6-nonadienal] (95%), 2-methylbutanoic acid (98%), 3-methylbutanoic acid (99%), (2E,4E)-nona-2,4-dienal [(E, E)-2,4-nonadienal] (85%), 5-pentyloxolan-2-one (γ-nonalactone) (98%), dodecanoic acid (98%), 2-phenyl acetic acid (phenylacetic acid) (99%), 4-(4-hydroxyphenyl)butan-2-one (raspberry ketone) (99%), acetic acid (99%), decanal (98%), 4-hydroxy-2,3-dimethyl-2H-furan-5-one (sotolone) (97%), 3,7-dimethylocta-1,6-dien-3-ol (linalool) (97%) were obtained from Sigma-Aldrich (Steinheim, Germany); 5-octyloxolan-2-one (γ-dodecalactone) (97%) was obtained from SAFC (Steinheim, Germany); 4-hydroxy-3-methoxybenzaldehyde (vanillin) (99%) was obtained from ABCR (Karlsruhe, Germany); 5-butyloxolan-2-one (γ-octalactone) was obtained from EGA Chemie (Steinheim, Germany); and (E)-3-(3-pentyloxiran-2-yl)prop-2-enal [tr-4,5-epoxy-(E)-2-decenal] (97%) was obtained from AromaLab (Planegg, Germany).

Wang Q., Baum A., Schreiner L., Slavik B., Buettner A., & Loos H.M. (2024). Sensory characterization and identification of odorants in birch wood (Betula pendula Roth). Wood Science and Technology.

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Aroma Profiling of Model Wine Compounds

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The following chemical standards were used in the aroma base and were obtained from Sigma-Aldrich Co. (St. Louis, MO, USA): ethanol (≥99%), 2,3-butanedione (97%), hexan-1-ol (98%), methionol (≥98%), butanoic acid (≥99%), decanoic acid (≥98%), 2-methylpropanoic acid (99%), 2-methylbutanoic acid (98%), 3-methylbutanoic acid (99%), 2-methylpropyl ethanoate (≥97%), ethyl phenylacetate (≥99%), ethyl 3-methylbutanoate (98%), ethyl 2-methylpropanoate ((≥98%), ethyl 2-methylbutyrate (99%), ethyl butanoate (≥98%), ethyl decanoate (≥99%), ethyl hexanoate (≥99%), ethyl octanoate (≥98%), hexanoic acid (99%), octanoic acid (≥99%), 2-methylpropan-1-ol (≥99%), ethyl acetate (≥99%) and isoamyl acetate (≥99%). Acetic acid (≥99%) was obtained from VWR International (Radnor, PA, USA). The terpenes compound added to the model wine for the treatments were: (S)-(−)-limonene (96%), (R)-(+)-limonene (97%), linalool (≥97%) and α-terpineol, which were purchased from Sigma-Aldrich Co. (St. Louis, MO, USA).

Chigo-Hernandez M.M, & Tomasino E. (2023). Aroma Perception of Limonene, Linalool and α-Terpineol Combinations in Pinot Gris Wine. Foods, 12(12), 2389.

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Analytical Standards for Volatile Compounds

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Acetaldehyde (75-07-0) (98%), 2,3-butanedione (431-03-8) (97%), hexan-1-ol (111-27-3) (98%), 3-(methylthio)-1-propyl alcohol (505-10-2) (98%), 2-methylpropan-1-ol (78-83-1) (99%), butyric acid (107-92-6) (99%), decanoic acid (334-48-5) (98%), 2-methylpropanoic acid (79-31-2) (99%), 2-methylbutanoic acid (116-53-0) (98%), 3-methylbutanoic acid (503-74-2) (99%), hexanoic acid (142-62-1) (99%), octanoic acid (124-07-2) (99%), 2-methylpropyl acetate (110-19-0) (99%), 2-phenylethyl acetate (103-45-7) (98%), ethyl 3-methylbutanoate (108-64-5) (98%), ethyl 2-methylpropanoate (7452-79-1) (99%), ethyl butanoate (105-54-4) (99%), ethyl decanoate (110-38-3) (99%), ethyl hexanoate (123-66-0) (99%), ethyl octanoate (106-32-1) (99%), 3-methylbutyl acetate (123-92-2) (99%), hexyl acetate (142-92-7) (99%), 3-mercaptohexan-1-ol (51755-83-0) (≤100%), 3-mercaptohexyl acetate (136954-20-6) (≥98%), 4-methyl-4-sulfanylpentan-2-one (19872-52-7) (≤100%) were obtained from Millipore Sigma (St. Louis, MO, USA). Ethyl 2-hexenoate (1552-67-6) (>97%) was purchased from Tokyo Chemical Industry Co., Ltd. (Portland, OR, USA). Acetic acid (64-19-7) (99.7%) was obtained from VWR International, LLC (Radnor, PA, USA). Ethyl acetate (141-78-6) (99.9%) was purchased from Fisher International Scientific, Inc. (Hampton, NH, USA). Milli-Q water was obtained from a Millipore Continental water system (EMD-Millipore, Billerica, MA, USA). HPLC-grade ethanol (64-17-5) (100%) was obtained from Pharmco-AAPER (Vancouver, WA, USA). LiChrolut® EN was obtained from Millipore Sigma (St. Louis, MO, USA).

Iobbi A., Di Y, & Tomasino E. (2023). Revealing the sensory impact of different levels and combinations of esters and volatile thiols in Chardonnay wines. Heliyon, 9(1), e12862.

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Volatile Organic Compound Analysis

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The chemicals used during the study were the following: (i) 2-methyl-1-butanol; 1pentanol; 1-hexanol; benzyl alcohol; 2-methylbutanal; 3-methylbutanal; 2-methyl-2-butenal; methyl-hexanoate; 2-methylbutanoic acid; and 3-methylbutanoic acid; all were obtained from Sigma-Aldrich, distributed by Merck KGaA, Darmstadt, Germany. (ii) decanal; nhexane; nonane; dodecane; tetradecane; and hexadecane were obtained from Carlo Erba Reagents, Milano (Italy).

D’Eusanio V., Maletti L., Marchetti A., Roncaglia F., & Tassi L. (2023). Volatile Aroma Compounds of Gavina® Watermelon (Citrullus Lanatus L.) Dietary Fibers to Increase Food Sustainability. AppliedChem, 3(1), 66-88.

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Quantifying Valeric and Isovaleric Acids in Animal Feeds

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Valeric acid and isovaleric acid were extracted from the homogenized samples with Milli‐Q water according to our developed method for the analysis of animal feeds. The water extracts were acidified with sulfuric acid (pH <2) to obtain free acids (R‐COOH), which were extracted with diethyl ether (Merck) and analyzed with a gas chromatograph using a flame ionization detector. The acids were separated on a 10 m × 0.53 mm × 1.00 μm FFAP column using a temperature gradient in splitless mode. The injector was maintained at 220°C and the detector at 300°C, and the nitrogen flow (carrier gas) was 8 ml min⁻¹. The injected volume into the column was 1 μl, which was maintained at 80°C for 5 min. Then, the temperature was increased by 5°C min⁻¹ up to 130°C, and by 30°C min⁻¹ up to 200°C. The final temperature was maintained for 8 min. The retention times of valeric acid and isovaleric acid were 9.4 min and 11.0 min, respectively. The analytical standards for valeric acid (n‐valeric acid and pentanoic acid, CAS 109‐52‐4) and isovaleric acid (3‐methylbutanoic acid and 3‐methylbutyric acid, CAS 503‐74‐2) were from Sigma‐Aldrich (USA). All valeric acid was in the form of isovaleric acid. Isovaleric acid content results were expressed in g kg⁻¹ on a dry weight basis.

Sinkovič L., Sinkovič D.K, & Ugrinović K. (2023). Yield and nutritional quality of soil‐cultivated crisphead lettuce (Lactuca sativa L. var. capitata) and corn salad (Valerianella spp.) harvested at different growing periods. Food Science & Nutrition, 11(4), 1755-1769.

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