2-Methylbutyl (E)-(+)-2-methylisocrotonate

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  • Identifiers

    CAS number
    61692-80-6

    Molecular formula
    C10H18O2

    SMILES
    CCC(C)COC(=O)/C(=C/C)/C

  • Odor profile

    Fruity 84.82%
    Floral 72.85%
    Herbal 63.24%
    Chamomile 52.28%
    Apple 51.54%
    Sweet 48.29%
    Rose 45.72%
    Green 44.46%
    Woody 41.35%
    Winey 41.22%

    Scent© AI

  • Properties

    XLogP3-AA
    3.0

    Molecular weight
    170.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    203°C

    Flash point est.
    70.1 ˚C

  • Synonyms

    • EINECS 262-903-8
    • 61692-80-6
    • 2-Methylbutyl 2-methyl-2-butenoate (E)-
    • AI3-33802
    • 2-Butenoic acid, 2-methyl-, 2-methylbutyl ester, (E)-
    • 2-Methylbutyl (E)-(+)-2-methylisocrotonate
    • 97752-29-9
    • EINECS 307-791-4
    • 2-methylbutyl tiglate
    • 2-Methylbutyl (E)-(-)-2-methylisocrotonate
    • Butyl tiglate 2-methyl-1-
    • 97752-27-7
    • SCHEMBL10605323
    • EINECS 307-789-3
    • NS00065676

  • Applications

    2-Methylbutyl (E)-(+)-2-methylisocrotonate (2-methylbutyl tiglate, CAS 61692-80-6) is a pleasant fruity–floral ester used as a fragrance ingredient in fine fragrances, deodorants, personal-care products, and as a scent note in household cleaners; in foods and beverages it can serve as a flavoring material to impart apple, pear, pineapple, or tropical nuances (subject to regional regulations), and as a synthetic intermediate/precursor for preparing other tiglate esters via transesterification or for obtaining tiglic acid or 2-methylbutanol by hydrolysis; owing to its chirality, the (+) enantiomer is studied in olfactory stereodiscrimination, employed as a chiral building block in asymmetric synthesis, explored in pheromone/semiochemical research, and used as a reference or internal standard for GC–MS, flavor stability testing, and esterification kinetics studies.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3287.3
    methanol 2922.5
    isopropanol 2918.0
    water 1.39
    ethyl acetate 3137.48
    n-propanol 2605.17
    acetone 2890.58
    n-butanol 2927.03
    acetonitrile 3158.65
    DMF 2073.28
    toluene 1607.75
    isobutanol 2443.86
    1,4-dioxane 4032.49
    methyl acetate 2514.8
    THF 3144.06
    2-butanone 3218.76
    n-pentanol 2105.46
    sec-butanol 3497.08
    n-hexane 715.01
    ethylene glycol 185.39
    NMP 1678.0
    cyclohexane 1089.3
    DMSO 1172.07
    n-butyl acetate 3078.68
    n-octanol 1253.12
    chloroform 6792.31
    n-propyl acetate 2079.37
    acetic acid 2567.12
    dichloromethane 5134.56
    cyclohexanone 3763.71
    propylene glycol 405.96
    isopropyl acetate 1881.67
    DMAc 2021.18
    2-ethoxyethanol 1668.19
    isopentanol 3068.24
    n-heptane 275.95
    ethyl formate 1734.7
    1,2-dichloroethane 3292.15
    n-hexanol 2539.75
    2-methoxyethanol 2053.05
    isobutyl acetate 1286.27
    tetrachloromethane 1242.49
    n-pentyl acetate 1575.68
    transcutol 5201.73
    n-heptanol 1181.33
    ethylbenzene 1158.88
    MIBK 1390.93
    2-propoxyethanol 2091.44
    tert-butanol 4108.75
    MTBE 4442.63
    2-butoxyethanol 1439.9
    propionic acid 1607.61
    o-xylene 1019.92
    formic acid 514.1
    diethyl ether 3510.2
    m-xylene 953.74
    p-xylene 1682.03
    chlorobenzene 2190.36
    dimethyl carbonate 398.49
    n-octane 158.04
    formamide 821.23
    cyclopentanone 2554.12
    2-pentanone 2323.37
    anisole 1692.57
    cyclopentyl methyl ether 1858.57
    gamma-butyrolactone 2307.84
    1-methoxy-2-propanol 1496.54
    pyridine 4115.55
    3-pentanone 1567.66
    furfural 2320.9
    n-dodecane 114.99
    diethylene glycol 892.27
    diisopropyl ether 1024.21
    tert-amyl alcohol 4543.37
    acetylacetone 1755.06
    n-hexadecane 133.55
    acetophenone 1487.16
    methyl propionate 1448.16
    isopentyl acetate 2821.15
    trichloroethylene 6576.39
    n-nonanol 1057.26
    cyclohexanol 2668.71
    benzyl alcohol 1336.45
    2-ethylhexanol 1609.76
    isooctanol 1069.16
    dipropyl ether 1206.85
    1,2-dichlorobenzene 1720.92
    ethyl lactate 524.58
    propylene carbonate 1594.11
    n-methylformamide 1190.74
    2-pentanol 2451.89
    n-pentane 505.83
    1-propoxy-2-propanol 1633.27
    1-methoxy-2-propyl acetate 1464.27
    2-(2-methoxypropoxy) propanol 1114.02
    mesitylene 610.93
    ε-caprolactone 3135.87
    p-cymene 613.19
    epichlorohydrin 3368.37
    1,1,1-trichloroethane 4254.38
    2-aminoethanol 654.39
    morpholine-4-carbaldehyde 2024.07
    sulfolane 1826.33
    2,2,4-trimethylpentane 334.94
    2-methyltetrahydrofuran 3541.66
    n-hexyl acetate 2157.7
    isooctane 239.62
    2-(2-butoxyethoxy)ethanol 1641.18
    sec-butyl acetate 1555.4
    tert-butyl acetate 1705.82
    decalin 448.7
    glycerin 401.69
    diglyme 2916.59
    acrylic acid 1125.56
    isopropyl myristate 675.99
    n-butyric acid 3040.2
    acetyl acetate 1470.93
    di(2-ethylhexyl) phthalate 561.68
    ethyl propionate 1469.78
    nitromethane 3058.66
    1,2-diethoxyethane 2457.65
    benzonitrile 2318.56
    trioctyl phosphate 393.75
    1-bromopropane 2574.37
    gamma-valerolactone 3156.28
    n-decanol 715.39
    triethyl phosphate 512.28
    4-methyl-2-pentanol 1289.46
    propionitrile 2542.05
    vinylene carbonate 1596.09
    1,1,2-trichlorotrifluoroethane 1826.25
    DMS 931.68
    cumene 773.82
    2-octanol 1001.47
    2-hexanone 2219.17
    octyl acetate 867.73
    limonene 957.83
    1,2-dimethoxyethane 3296.16
    ethyl orthosilicate 570.95
    tributyl phosphate 537.74
    diacetone alcohol 1462.3
    N,N-dimethylaniline 1031.21
    acrylonitrile 2387.7
    aniline 1627.81
    1,3-propanediol 1338.01
    bromobenzene 2419.85
    dibromomethane 3768.65
    1,1,2,2-tetrachloroethane 5265.96
    2-methyl-cyclohexyl acetate 1145.94
    tetrabutyl urea 609.25
    diisobutyl methanol 772.94
    2-phenylethanol 1493.36
    styrene 1429.31
    dioctyl adipate 805.03
    dimethyl sulfate 466.75
    ethyl butyrate 1648.63
    methyl lactate 436.1
    butyl lactate 913.84
    diethyl carbonate 990.19
    propanediol butyl ether 1186.18
    triethyl orthoformate 986.67
    p-tert-butyltoluene 575.17
    methyl 4-tert-butylbenzoate 996.82
    morpholine 4609.24
    tert-butylamine 3050.49
    n-dodecanol 508.09
    dimethoxymethane 1157.73
    ethylene carbonate 1402.39
    cyrene 764.38
    2-ethoxyethyl acetate 1607.95
    2-ethylhexyl acetate 2107.11
    1,2,4-trichlorobenzene 1851.42
    4-methylpyridine 4291.97
    dibutyl ether 1480.53
    2,6-dimethyl-4-heptanol 772.94
    DEF 2284.15
    dimethyl isosorbide 1468.8
    tetrachloroethylene 3384.56
    eugenol 1065.88
    triacetin 1131.69
    span 80 1149.78
    1,4-butanediol 556.05
    1,1-dichloroethane 4460.67
    2-methyl-1-pentanol 2415.09
    methyl formate 830.88
    2-methyl-1-butanol 3009.78
    n-decane 214.07
    butyronitrile 3363.86
    3,7-dimethyl-1-octanol 1302.94
    1-chlorooctane 861.84
    1-chlorotetradecane 301.23
    n-nonane 216.4
    undecane 149.52
    tert-butylcyclohexane 430.84
    cyclooctane 266.52
    cyclopentanol 1756.85
    tetrahydropyran 4837.16
    tert-amyl methyl ether 2861.36
    2,5,8-trioxanonane 1609.63
    1-hexene 2090.89
    2-isopropoxyethanol 1373.81
    2,2,2-trifluoroethanol 544.21
    methyl butyrate 2367.63

    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
Roman chamomile (India) 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 0.07%
Roman chamomile (Japan) 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 0.18%
Roman chamomile (Germany) 1a hydrodistillate 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 0.17%