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cm 3 melting point 29 c 20 f 244 k boiling point 176 5 c 349 7 f 449 6 k log p 1 16 acidity p k a 4 8 h 2 o magnetic susceptibility χ 67 7 10 6 cm 3 mol related compounds related carboxylic acids butyric acid β hydroxybutyric acid β hydroxy β methylbutyric acid related compounds valeric acid hazards ghs labelling 1 pictograms the template below ghs corrosion is being considered for merging with ghs pictogram see templates for discussion to help reach a consensus signal word danger hazard statements h314 precautionary statements p280 p301 p330 p331 p303 p361 p353 p304 p340 p310 p305 p351 p338 p363 flash point 80 c 176 f 353 k except where otherwise noted data are given for materials in their standard state at 25 c 77 f 100 kpa infobox references chemical compound isovaleric acid also known as 3 methylbutanoic acid or β methylbutyric acid is a branched chain alkyl carboxylic acid with the chemical formula ch 3 2 chch 2 co 2 h it is classified as a short chain fatty acid like other low molecular weight carboxylic acids it has an unpleasant odor the compound occurs naturally and can be found in many foods such as cheese soy milk and apple juice history edit 3 methylbutanoic acid is a minor constituent of the perennial flowering plant valerian valeriana officinalis from which it got its trivial name isovaleric acid an isomer of valeric acid which shares its unpleasant odor 2 the dried root of this plant has been used medicinally since antiquity 3 4 their chemical identity was first investigated in the 19th century by oxidation of the components of fusel alcohol which includes the five carbon amyl alcohols 5 manufacture edit in industry 3 methylbutanoic acid is produced by the hydroformylation 6 of isobutylene with syngas forming isovaleraldehyde 7 which is oxidised to the final product 8 ch 3 2 c ch 2 h 2 co ch 3 2 chch 2 cho 3 methylbutanoic acid reactions edit 3 methylbutanoic acid reacts as a typical carboxylic acid it can form amide ester anhydride and chloride derivatives 9 the acid chloride is commonly used as the intermediate to obtain the others the acid has been used to synthesize β hydroxyisovaleric acid otherwise known as β hydroxy β methylbutyric acid via microbial oxidation by the fungus galactomyces reessii 10 acetone diacetone alcohol β hydroxy β methylbutyric acid 3 methylbutanoic acid alternative syntheses of β hydroxy β methylbutyric acid uses edit isovaleric acid has a strong pungent cheesy or sweaty smell 11 but its volatile esters such as ethyl isovalerate 12 have pleasant odors and are widely used in perfumery it is also the primary flavor added to wine when made using brettanomyces yeasts 13 other compounds produced by brettanomyces yeasts include 4 ethylphenol 4 vinylphenol and 4 ethylguaiacol 14 an excess of isovaleric acid in wine is generally seen as a defect 14 as it can smell sweaty leathery or like a barnyard but in small amounts it can smell smokey spicy or medicinal 13 these phenomena may be prevented by killing any brettanomyces yeasts such as by sterile filtration by the addition of relatively large quantities of sulfur dioxide and sometimes sorbic acid by mixing in alcoholic spirit to give a fortified wine of sufficient strength to kill all yeast and bacteria or by pasteurization isovaleric acid can also be found in beer and excepting some english style ales is usually considered a flaw 15 it can be produced by the oxidation of hop resins or by brettanomyces yeasts present 15 the compound s safety as a food additive was reviewed by an fao and who panel who concluded that there were no concerns at the likely levels of intake 16 biology edit since isovaleric acid and its esters are natural components of many foods it is present in mammals including humans 17 also isovaleryl coenzyme a is an intermediate in the metabolism of branched chain amino acids 18 isovaleric acid is a major component of the cause of intense foot odor as it is produced by skin bacteria metabolizing leucine and in rare cases a condition called isovaleric acidemia can lead to heightened levels of this metabolite 19 salts and esters edit an isovalerate or 3 methylbutanoate ion is ch 3 2 chch 2 coo the conjugate base of the acid it is the form found in biological systems at physiological ph an isovalerate or 3 methylbutanoate compound is a salt or ester of the acid examples edit ethyl isovalerate menthyl isovalerate isovaleryl coa testosterone isovalerate see also edit 2 methylbutanoic acid an isomer valeric acid an isomer references edit sigma aldrich isovaleric acid retrieved 2020 09 29 chisholm hugh ed 1911 valeric acid encyclopædia britannica vol 27 11th ed cambridge university press p 859 patočka jiří jakl jiří 2010 biomedically relevant chemical constituents of valeriana officinalis journal of applied biomedicine 8 11 18 doi 10 2478 v10136 009 0002 z eadie mervyn j november 2004 could valerian have been the first anticonvulsant epilepsia 45 11 1338 1343 doi 10 1111 j 0013 9580 2004 27904 x pmid 15509234 s2cid 7314227 pedler alexander 1868 on the isomeric forms of valeric acid journal of the chemical society 21 74 76 doi 10 1039 js8682100074 franke robert selent detlef börner armin 2012 applied hydroformylation chemical reviews 112 11 5675 5732 doi 10 1021 cr3001803 pmid 22937803 kohlpaintner christian schulte markus falbe jürgen lappe peter weber jürgen frey guido d 2013 aldehydes aliphatic ullmann s encyclopedia of industrial chemistry doi 10 1002 14356007 a01_321 pub3 isbn 978 3 527 30673 2 riemenschneider wilhelm 2000 carboxylic acids aliphatic ullmann s encyclopedia of industrial chemistry doi 10 1002 14356007 a05_235 isbn 3 527 30673 0 jenkins p r 1985 carboxylic acids and derivatives general and synthetic methods vol 7 pp 96 160 doi 10 1039 9781847556196 00096 isbn 978 0 85186 884 4 lee iy nissen sl rosazza jp 1997 conversion of beta methylbutyric acid to beta hydroxy beta methylbutyric acid by galactomyces reessii applied and environmental microbiology 63 11 4191 5 bibcode 1997apenm 63 4191l doi 10 1128 aem 63 11 4191 4195 1997 pmc 168736 pmid 9361403 isovaleric acid the good scents company retrieved 2020 09 30 ethyl 3 methylbutanoate the good scents company retrieved 2020 09 30 1 2 jackson ron s 2008 wine science principles and applications 3rd ed academic press p 495 isbn 978 0 12 373646 8 1 2 kirk othmer 2007 wine food and feed technology volume 2 john wiley sons p 702 isbn 978 0 470 17448 7 1 2 oliver garrett ed 2012 the oxford companion to beer oxford university press p 498 isbn 978 0 19 536713 3 fao who expert committee on food additives 1998 safety evaluation of certain food additives and contaminants retrieved 2020 09 30 metabocard for isovaleric acid human metabolome database 2020 02 26 retrieved 2020 09 30 wilson jacob m fitschen peter j campbell bill wilson gabriel j zanchi nelo taylor lem wilborn colin kalman douglas s stout jeffrey r hoffman jay r ziegenfuss tim n lopez hector l kreider richard b smith ryan abbie e antonio jose 2013 international society of sports nutrition position stand beta hydroxy beta methylbutyrate hmb journal of the international society of sports nutrition 10 1 6 doi 10 1186 1550 2783 10 6 pmc 3568064 pmid 23374455 ara katsutoshi hama masakatsu akiba syunichi koike kenzo okisaka koichi hagura toyoki kamiya tetsuro tomita fusao april 2006 foot odor due to microbial metabolism and its control canadian journal of microbiology 52 4 357 364 doi 10 1139 w05 130 pmid 16699586 v t e gaba a receptor positive modulators alcohols brometone butanol chloralodol chlorobutanol cloretone ethanol alcohol alcoholic drink ethchlorvynol isobutanol isopropanol menthol methanol methylpentynol pentanol petrichloral propanol tert butanol 2m2p tert pentanol 2m2b tribromoethanol trichloroethanol triclofos trifluoroethanol barbiturates dmbb allobarbital alphenal amobarbital aprobarbital barbexaclone barbital benzobarbital benzylbutylbarbiturate brallobarbital brophebarbital butabarbital secbutabarbital butalbital buthalital butobarbital butallylonal carbubarb crotylbarbital cyclobarbital cyclopentobarbital difebarbamate enallylpropymal ethallobarbital eterobarb febarbamate heptabarb heptobarbital hexethal hexobarbital methallatal metharbital methitural methohexital methylphenobarbital narcobarbital nealbarbital pentobarbital phenallymal phenobarbital phetharbital primidone probarbital propallylonal propylbarbital proxibarbital reposal secobarbital sigmodal spirobarbital talbutal tetrabamate tetrabarbital thialbarbital thiamylal thiobarbital thiobutabarbital thiopental thiotetrabarbital valofane vinbarbital vinylbital benzodiazepines 2 oxoquazepam 3 hydroxyphenazepam adinazolam alprazolam arfendazam avizafone bentazepam bretazenil bromazepam bromazolam brotizolam camazepam carburazepam chlordiazepoxide ciclotizolam cinazepam cinolazepam clazolam climazolam clobazam clonazepam clonazolam cloniprazepam clorazepate clotiazepam cloxazolam cp 1414s cyprazepam delorazepam demoxepam diazepam diclazepam dimdazenil doxefazepam elfazepam estazolam ethyl carfluzepate ethyl dirazepate ethyl loflazepate etizolam fg 8205 fletazepam flubromazepam flubromazolam fludiazepam flunitrazepam flunitrazolam flurazepam flutazolam flutemazepam flutoprazepam fosazepam gidazepam halazepam haloxazolam iclazepam imidazenil irazepine ketazolam lofendazam lopirazepam loprazolam lorazepam lormetazepam meclonazepam medazepam menitrazepam metaclazepam mexazolam midazolam motrazepam n desalkylflurazepam nifoxipam nimetazepam nitrazepam nitrazepate nitrazolam nordazepam nortetrazepam oxazepam oxazolam phenazepam pinazepam pivoxazepam prazepam premazepam proflazepam pyrazolam qh ii 66 quazepam reclazepam remimazolam rilmazafone ripazepam ro48 6791 ro48 8684 sh 053 r ch3 2 f sulazepam temazepam tetrazepam tolufazepam triazolam triflubazam triflunordazepam ro5 2904 tuclazepam uldazepam zapizolam zolazepam zomebazam carbamates carisbamate carisoprodol clocental cyclarbamate difebarbamate emylcamate ethinamate febarbamate felbamate hexapropymate hydroxyphenamate lorbamate mebutamate meprobamate nisobamate pentabamate phenprobamate procymate styramate tetrabamate tybamate flavonoids 6 methylapigenin ampelopsin dihydromyricetin apigenin baicalein baicalin catechin egc egcg hispidulin linarin luteolin rc ome skullcap constituents e g baicalin wogonin imidazoles etomidate metomidate methoxyetomidate propoxate isopropoxate butomidate iso butomidate sec butomidate cf2 etomidate cf3 etomidate cf3 propoxate flutomidate 2 6 dichloro 3 fluoroetomidate kava constituents 10 methoxyyangonin 11 methoxyyangonin 11 hydroxyyangonin desmethoxyyangonin 11 methoxy 12 hydroxydehydrokavain 7 8 dihydroyangonin kavain 5 hydroxykavain 5 6 dihydroyangonin 7 8 dihydrokavain 5 6 7 8 tetrahydroyangonin 5 6 dehydromethysticin methysticin 7 8 dihydromethysticin yangonin monoureides acecarbromal apronal apronalide bromisoval carbromal capuride ectylurea neurosteroids acebrochol allopregnanolone brexanolone alfadolone alfaxalone 3α androstanediol androstenol androsterone certain anabolic androgenic steroids cholesterol cortisol hydrocortisone dhdoc 3α dhp 5α dhp 5β dhp dht etiocholanolone etx 155 ganaxolone hydroxydione lpcn 1154 minaxolone nora 520 org 20599 org 21465 p1 185 posovolone prax 114 pregnanolone eltanolone progesterone renanolone sage 105 sage 324 sage 516 sage 689 sage 872 testosterone thdoc zuranolone nonbenzodiazepines cyclopyrrolones eszopiclone pagoclone pazinaclone suproclone suriclone zopiclone imidazopyridines alpidem ds 1 necopidem saripidem zolpidem pyrazolopyrimidines divaplon fasiplon indiplon lorediplon ocinaplon panadiplon taniplon zaleplon others adipiplon axs 17 baer 101 azd 7325 cgs 8216 cgs 9896 cgs 13767 cgs 20625 cl 218 872 cp 615 003 ctp 354 elb 139 enx 102 tpa 023b gbld 345 imepitoin jm 1232 l 838 417 lirequinil ro41 3696 miltirone rosmariquinone ns 2664 ns 2710 ns 11394 ns 11821 pipequaline rod 188 rwj 51204 sb 205 384 sx 3228 tgsc01aa tp 003 tpa 023 tp 13 u 89843a u 90042 viqualine y 23684 phenols cipepofol fospropofol propofol propofol hemisuccinate thymol piperidinediones glutethimide methyprylon piperidione pyrithyldione pyrazolopyridines cartazolate etazolate ici 190 622 tracazolate quinazolinones afloqualone cloroqualone diproqualone etaqualone mebroqualone mecloqualone methaqualone methylmethaqualone nitromethaqualone sl 164 volatiles gases acetone acetophenone acetylglycinamide chloral hydrate aliflurane benzene butane butylene centalun chloral chloral betaine chloral hydrate chloroform cryofluorane desflurane dichloralphenazone dichloromethane diethyl ether enflurane ethyl chloride ethylene fluroxene gasoline halopropane halothane isoflurane kerosine methoxyflurane methoxypropane nitric oxide nitrogen nitrous oxide norflurane paraldehyde propane propylene roflurane sevoflurane synthane teflurane toluene trichloroethane methyl chloroform trichloroethylene vinyl ether others unsorted 3 hydroxybutanal α emtbl aa 29504 alogabat avermectins e g ivermectin bromide compounds e g lithium bromide potassium bromide sodium bromide carbamazepine chloralose chlormezanone clomethiazole darigabat deabl deuterated etifoxine dihydroergolines e g dihydroergocryptine dihydroergosine dihydroergotamine ergoloid dihydroergotoxine ds2 efavirenz etazepine etifoxine fenamates e g flufenamic acid mefenamic acid niflumic acid tolfenamic acid fluoxetine flupirtine hopantenic acid krm ii 81 lanthanum lavender oil lignans e g 4 o methylhonokiol honokiol magnolol obovatol loreclezole menthyl isovalerate validolum monastrol nezavist dcuk oet nicotinic acid nicotinamide ntx 1955 ro 7308480 org 25 435 phenytoin propanidid retigabine ezogabine safranal seproxetine stiripentol sulfonylalkanes e g sulfonmethane sulfonal tetronal trional terpenoids e g borneol topiramate valerian constituents e g isovaleric acid isovaleramide valerenic acid valerenol unsorted benzodiazepine site positive modulators α pinene mrk 409 mk 0343 tcs 1105 tcs 1205 see also receptor signaling modulators gaba receptor modulators gaba metabolism transport modulators retrieved from https en wikipedia org w index php title isovaleric_acid oldid 1373913333 categories flavors alkanoic acids hemiterpenes acids in wine gaba analogues gabaa receptor positive allosteric modulators foul smelling chemicals fatty acids hidden categories articles with short description short description is different from wikidata echa infocard id from wikidata chembox having ghs data articles containing unverified chemical infoboxes chembox image size set short description matches wikidata wikipedia articles incorporating a citation from the 1911 encyclopaedia britannica with wikisource reference this page was last edited on 8 september 2026 at 18 15 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a 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