Isovaleric acid

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  • Identifiers

    CAS number
    503-74-2

    Molecular formula
    C5H10O2

    SMILES
    CC(C)CC(=O)O

    Safety labels

    Corrosive
    Corrosive

    Retention indicies (RI)

    • DB5: 863.67
    • Carbowax: 1658.29

  • Odor profile

    Fruity 95.47%
    Cheesy 88.22%
    Sour 69.47%
    Sweaty 56.58%
    Dairy 54.39%
    Pungent 49.69%
    Sharp 45.91%
    Fatty 44.53%
    Buttery 41.14%
    Ripe 39.68%

    Scent© AI

    Odor threshold

    • Odor Threshold Low: 0.0015 [mmHg]. Odor Threshold High: 0.72 [mmHg]. Odor threshold from CHEMINFO

  • Properties

    XLogP3-AA
    1.2

    pKa est.
    8.43 (weak base)

    Molecular weight
    102.13 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Melting point expt.

    • -29.3 °C

    Boiling point

    • 176.5 °C
    • 176.5 °C @ 760 MM HG
    • 175.00 to 177.00 °C. @ 760.00 mm Hg

    Flash point est.
    71.49 ˚C

    Flash point expt.

    • 70 °C

    Solubility expt.

    • 40700 mg/L (at 20 °C)
    • SOL IN 24 PARTS WATER; SOL IN ALCOHOL, ETHER, CHLOROFORM
    • In water, 4.07X10+4 mg/l at 20 °C
    • 40.7 mg/mL
    • soluble in alcohol, ether and water

  • Synonyms

    • ISOVALERIC ACID
    • 3-Methylbutanoic acid
    • 503-74-2
    • Isopentanoic acid
    • 3-Methylbutyric acid
    • Delphinic acid
    • Isopropylacetic acid
    • Isovalerianic acid
    • Butanoic acid, 3-methyl-
    • Isobutylformic acid
    • Isovalerianic
    • beta-Methylbutyric acid
    • Acetic acid, isopropyl-
    • 3-Methylbutyrate
    • Butyric acid, 3-methyl-
    • 3-methyl-butanoic acid
    • Kyselina isovalerova
    • Isobutyl formic acid
    • Isovaleriansaeure
    • FEMA No. 3102
    • 3-methyl-n-butyric acid
    • Isovaleric acid (natural)
    • FEMA Number: 3102
    • 3-Methylbuttersaeure
    • 3-methyl butyric acid
    • 3-methyl-butyric acid
    • MFCD00002726
    • NSC 62783
    • HSDB 629
    • .beta.-Methylbutyric acid
    • EINECS 207-975-3
    • UNII-1BR7X184L5
    • BRN 1098522
    • DELPHINIC-ACID
    • DTXSID5029182
    • CHEBI:28484
    • AI3-24132
    • 1BR7X184L5
    • NSC-62783
    • 3,4-Diisovaleryl adrenaline
    • DTXCID309182
    • EC 207-975-3
    • 4-02-00-00895 (Beilstein Handbook Reference)
    • Butanoic acid, 3-methyl-, (R)-
    • IVA
    • ISOVALERIC ACID (MART.)
    • ISOVALERIC ACID [MART.]
    • Kyselina isovalerova [Czech]
    • 92634-50-9
    • METHYLBUTANOIC ACID
    • b-Methylbutyrate
    • iso-valeric acid
    • 3-Methylbutanoicacid
    • b-Methylbutyric acid
    • iso-C4H9COOH
    • Isovaleric acid, 99%
    • bmse000373
    • Isovaleric acid (Standard)
    • SCHEMBL43436
    • ISOVALERIC ACID [MI]
    • ISOVALERIC ACID [FCC]
    • ISOVALERIC ACID [FHFI]
    • ISOVALERIC ACID [HSDB]
    • CHEMBL568737
    • WLN: QV1Y1&1
    • ISOVALERIC ACID [WHO-DD]
    • BCP32116
    • HY-W012980R
    • NSC62783
    • STR08356
    • Isovaleric acid, analytical standard
    • Tox21_201604
    • BBL027399
    • Isovaleric acid (mixture of isomers)
    • LMFA01020181
    • s6287
    • STL146358
    • AKOS000119861
    • Isovaleric acid, >=99%, FCC, FG
    • CS-W013696
    • DB03750
    • FM15957
    • HY-W012980
    • 3-Methylbutyric acid: isopropyl-Acetate
    • Isovaleric acid sodium salt (Salt/Mix)
    • Isovaleric acid, natural, >=98%, FG
    • NCGC00249082-01
    • NCGC00259153-01
    • 35915-22-1
    • CAS-503-74-2
    • 3-Methylbutyric acid: isopropyl-Acetic acid
    • M0182
    • NS00001831
    • EN300-19718
    • C08262
    • D78213
    • Q415536
    • F2191-0067
    • Z104474910
    • 3-Methylbutanoic acid;3-Methylbutyric acid;Isopentanoic acid
    • InChI=1/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7
    • 207-975-3

  • Applications

    Isovaleric acid (3-methylbutanoic acid, CAS 503-74-2) is a short-chain fatty acid with the characteristic pungent “cheesy/foot” odour, and it finds wide-ranging applications from food and fragrance to fine chemistry: its esters are prepared to deliver green-fruit, berry and honey notes for candies, beverages and tobacco products; trace amounts of the free acid are blended directly as a flavour enhancer in cheese, butter and yogurt; it serves as an intermediate for fragrant esters, palatability stimulants in aquaculture feeds, sedative and anticonvulsant pharmaceuticals, pyrethroid insecticides, alkyd resins, lubricants and plasticisers; in laboratories it is employed as a GC/MS reference standard, an antimicrobial agent for simulating organic-acidic environments, and its isovalerate esters act as odour markers in insect chemical-ecology studies.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 318.27
    methanol 616.45
    isopropanol 172.09
    water 70.72
    ethyl acetate 74.15
    n-propanol 201.89
    acetone 120.85
    n-butanol 147.73
    acetonitrile 84.03
    DMF 149.53
    toluene 6.76
    isobutanol 111.85
    1,4-dioxane 129.5
    methyl acetate 71.68
    THF 319.52
    2-butanone 69.69
    n-pentanol 81.82
    sec-butanol 119.46
    n-hexane 10.74
    ethylene glycol 237.79
    NMP 316.82
    cyclohexane 6.18
    DMSO 211.06
    n-butyl acetate 77.33
    n-octanol 80.47
    chloroform 49.13
    n-propyl acetate 45.85
    acetic acid 701.68
    dichloromethane 37.78
    cyclohexanone 126.99
    propylene glycol 257.96
    isopropyl acetate 45.66
    DMAc 115.94
    2-ethoxyethanol 147.94
    isopentanol 94.54
    n-heptane 10.53
    ethyl formate 79.62
    1,2-dichloroethane 30.11
    n-hexanol 185.5
    2-methoxyethanol 333.75
    isobutyl acetate 31.69
    tetrachloromethane 10.32
    n-pentyl acetate 48.95
    transcutol 352.01
    n-heptanol 78.88
    ethylbenzene 7.68
    MIBK 51.11
    2-propoxyethanol 282.14
    tert-butanol 197.42
    MTBE 46.56
    2-butoxyethanol 121.51
    propionic acid 292.08
    o-xylene 9.62
    formic acid 405.96
    diethyl ether 38.29
    m-xylene 11.55
    p-xylene 10.3
    chlorobenzene 17.52
    dimethyl carbonate 31.02
    n-octane 4.02
    formamide 215.34
    cyclopentanone 199.38
    2-pentanone 70.13
    anisole 28.62
    cyclopentyl methyl ether 97.74
    gamma-butyrolactone 335.76
    1-methoxy-2-propanol 237.36
    pyridine 43.65
    3-pentanone 39.8
    furfural 188.28
    n-dodecane 3.98
    diethylene glycol 276.75
    diisopropyl ether 15.74
    tert-amyl alcohol 141.35
    acetylacetone 90.52
    n-hexadecane 4.12
    acetophenone 39.53
    methyl propionate 70.64
    isopentyl acetate 66.97
    trichloroethylene 59.43
    n-nonanol 68.37
    cyclohexanol 105.3
    benzyl alcohol 40.99
    2-ethylhexanol 80.91
    isooctanol 55.34
    dipropyl ether 45.65
    1,2-dichlorobenzene 24.17
    ethyl lactate 60.88
    propylene carbonate 166.39
    n-methylformamide 163.96
    2-pentanol 84.87
    n-pentane 7.8
    1-propoxy-2-propanol 189.88
    1-methoxy-2-propyl acetate 103.03
    2-(2-methoxypropoxy) propanol 139.1
    mesitylene 10.82
    ε-caprolactone 151.55
    p-cymene 15.87
    epichlorohydrin 157.62
    1,1,1-trichloroethane 26.93
    2-aminoethanol 313.01
    morpholine-4-carbaldehyde 235.11
    sulfolane 380.74
    2,2,4-trimethylpentane 6.51
    2-methyltetrahydrofuran 171.43
    n-hexyl acetate 99.05
    isooctane 6.42
    2-(2-butoxyethoxy)ethanol 204.92
    sec-butyl acetate 29.71
    tert-butyl acetate 73.41
    decalin 5.45
    glycerin 329.54
    diglyme 188.89
    acrylic acid 279.13
    isopropyl myristate 42.75
    n-butyric acid 241.74
    acetyl acetate 59.14
    di(2-ethylhexyl) phthalate 58.02
    ethyl propionate 47.48
    nitromethane 392.48
    1,2-diethoxyethane 52.05
    benzonitrile 38.17
    trioctyl phosphate 49.46
    1-bromopropane 17.03
    gamma-valerolactone 271.72
    n-decanol 52.67
    triethyl phosphate 32.72
    4-methyl-2-pentanol 57.3
    propionitrile 57.28
    vinylene carbonate 118.63
    1,1,2-trichlorotrifluoroethane 175.72
    DMS 62.3
    cumene 10.0
    2-octanol 49.34
    2-hexanone 45.77
    octyl acetate 64.16
    limonene 26.48
    1,2-dimethoxyethane 123.81
    ethyl orthosilicate 31.11
    tributyl phosphate 54.6
    diacetone alcohol 160.42
    N,N-dimethylaniline 25.33
    acrylonitrile 76.18
    aniline 29.66
    1,3-propanediol 276.24
    bromobenzene 11.43
    dibromomethane 25.68
    1,1,2,2-tetrachloroethane 57.32
    2-methyl-cyclohexyl acetate 60.8
    tetrabutyl urea 69.08
    diisobutyl methanol 43.84
    2-phenylethanol 70.32
    styrene 7.09
    dioctyl adipate 64.75
    dimethyl sulfate 64.55
    ethyl butyrate 51.2
    methyl lactate 96.16
    butyl lactate 73.7
    diethyl carbonate 34.32
    propanediol butyl ether 161.74
    triethyl orthoformate 38.77
    p-tert-butyltoluene 17.97
    methyl 4-tert-butylbenzoate 86.46
    morpholine 173.97
    tert-butylamine 94.17
    n-dodecanol 40.48
    dimethoxymethane 89.33
    ethylene carbonate 94.37
    cyrene 120.9
    2-ethoxyethyl acetate 64.13
    2-ethylhexyl acetate 47.26
    1,2,4-trichlorobenzene 34.25
    4-methylpyridine 39.19
    dibutyl ether 33.92
    2,6-dimethyl-4-heptanol 43.84
    DEF 68.35
    dimethyl isosorbide 203.34
    tetrachloroethylene 42.43
    eugenol 92.55
    triacetin 97.9
    span 80 162.79
    1,4-butanediol 103.27
    1,1-dichloroethane 22.62
    2-methyl-1-pentanol 61.87
    methyl formate 121.42
    2-methyl-1-butanol 88.98
    n-decane 5.96
    butyronitrile 54.76
    3,7-dimethyl-1-octanol 69.45
    1-chlorooctane 23.65
    1-chlorotetradecane 11.14
    n-nonane 5.7
    undecane 4.75
    tert-butylcyclohexane 8.25
    cyclooctane 3.02
    cyclopentanol 185.63
    tetrahydropyran 86.33
    tert-amyl methyl ether 46.44
    2,5,8-trioxanonane 187.28
    1-hexene 21.63
    2-isopropoxyethanol 89.13
    2,2,2-trifluoroethanol 205.04
    methyl butyrate 58.19

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction

Botanical

Name CAS Botanical Proportion
Atractylis Atractylodes lancea (Thunb.) DC. (A. ovata Thunb.; A. chinensis (Bunge)DC) 0.05%
Blackcurrant bud 1 68606-81-5 Ribes nigrum L., fam. Grossulariaceae 0.13%
Viburnum orientale leaf Viburnum orientale Pallas, fam. Caprifoliaceae 5.4%
Zizyphus jujuba fruit (Malaysia) Zizyphus jujuba Mill. var. inermis, fam. Rhamnaceae 0.62%
Spearmint, scotch (Japan) Mentha gracilis Sole, fam. Lamiaceae (Labiatae) 3.8%
Genipap fruit (Brazil) Genipa americana L., fam. Rubiaceae 0.05%
Chicory root, roasted 2 68650-43-1 Cichorium intybus L., fam. Asteraceae (Compositae) 7.93%
Chicory root, roasted 1a 68650-43-1 Cichorium intybus L., fam. Asteraceae (Compositae) 0.11%
Cordia nitida fruit Cordia nitida Vahl., fam. Borraginaceae 1.8%
Geneps fruit (Cuba) Melicocca bijuga L., fam. Sapindaceae 0.01%
Baga fruit Annona glabra L., fam. Annonaceae 0.01%
Banana passa headspace extract (Brazil) 89957-82-4 Musa cavendishii cultivar nanica, fam. Musaceae 0.2%
Mango (Cameroon) headspace of ripe fruit 90063-86-0 Mangifera indica L., fam. Anacardiaceae 0.01%
Papaya (Cameroon) headspace of ripe fruit Carica papaya L., 0.01%