2-Butenoic acid, 3-methyl-, phenylmethyl ester

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  • Identifiers

    CAS number
    37526-89-9

    Molecular formula
    C12H14O2

    SMILES
    CC(=CC(=O)OCC1=CC=CC=C1)C

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Herbal 74.03%
    Sweet 73.52%
    Balsamic 56.14%
    Spicy 55.39%
    Fruity 54.45%
    Green 54.44%
    Floral 47.91%
    Woody 39.0%
    Warm 38.88%
    Mint 32.71%

    Scent© AI

  • Properties

    XLogP3-AA
    3.4

    Molecular weight
    190.24 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    270°C

    Flash point est.
    118.62 ˚C

  • Synonyms

    • benzyl 3-methylbut-2-enoate
    • 37526-89-9
    • 2-Butenoic acid, 3-methyl-, phenylmethyl ester
    • Benzyl 3-methylcrotonate
    • Benzyl 3-methyl-2-butenoate
    • EINECS 253-545-3
    • AI3-28735
    • DTXSID9068035
    • Phenylmethyl 3-methyl-2-butenoate
    • Benzyl 3,3-dimethylacrylate
    • 3-methyl-but-2-enoic acid benzyl ester
    • benzyl3-methylbut-2-enoate
    • 3H7Y5V4CY3
    • SCHEMBL2030640
    • Benzyl 3-methyl-2-butenoate #
    • DTXCID0039352
    • 3-Methyl-2-butenoic acid, benzyl ester
    • DA-35088
    • NS00030210
    • EN300-4290222
    • 253-545-3

  • Applications

    2-Butenoic acid, 3-methyl-, phenylmethyl ester (CAS 37526-89-9), also known as benzyl tiglate or benzyl 3-methyl-2-butenoate, is used primarily as a fragrance ingredient for its green–fruity, slightly spicy tiglate character combined with the sweet floral nuance of the benzyl moiety, providing lift, diffusion and roundness to white-floral (jasmine, ylang, tuberose), fruity (apple, pear, apricot) and fresh-green accords in fine fragrances, personal-care and household scents; in flavor work, some exploratory formulations employ it at very low levels to support green–fruity notes, but actual use depends strictly on local regulations and safety assessment; in organic synthesis it serves as an intermediate/building block to introduce the tiglate motif or as a removable benzyl ester handle in protection–deprotection sequences, and it can be used as a reference standard for GC/LC method development and structure–odor relationship studies; practical deployment requires verification of purity, geometric isomer ratio (E/Z), stability in the intended matrix, and compliance with applicable safety and regulatory guidance.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 569.15
    methanol 530.87
    isopropanol 444.99
    water 0.65
    ethyl acetate 542.56
    n-propanol 429.66
    acetone 997.23
    n-butanol 405.8
    acetonitrile 617.18
    DMF 1179.07
    toluene 134.16
    isobutanol 351.79
    1,4-dioxane 834.47
    methyl acetate 576.23
    THF 1083.43
    2-butanone 743.87
    n-pentanol 297.15
    sec-butanol 431.86
    n-hexane 71.14
    ethylene glycol 102.5
    NMP 682.44
    cyclohexane 59.81
    DMSO 806.67
    n-butyl acetate 416.98
    n-octanol 167.57
    chloroform 1425.78
    n-propyl acetate 356.33
    acetic acid 797.15
    dichloromethane 1027.59
    cyclohexanone 767.07
    propylene glycol 207.24
    isopropyl acetate 330.72
    DMAc 850.96
    2-ethoxyethanol 382.1
    isopentanol 370.85
    n-heptane 28.04
    ethyl formate 319.99
    1,2-dichloroethane 880.6
    n-hexanol 353.39
    2-methoxyethanol 663.76
    isobutyl acetate 237.85
    tetrachloromethane 79.46
    n-pentyl acetate 187.16
    transcutol 1364.53
    n-heptanol 155.03
    ethylbenzene 142.21
    MIBK 325.8
    2-propoxyethanol 511.26
    tert-butanol 583.3
    MTBE 452.09
    2-butoxyethanol 276.2
    propionic acid 447.9
    o-xylene 110.13
    formic acid 198.8
    diethyl ether 458.43
    m-xylene 122.66
    p-xylene 191.56
    chlorobenzene 327.85
    dimethyl carbonate 228.24
    n-octane 14.92
    formamide 323.96
    cyclopentanone 900.73
    2-pentanone 549.34
    anisole 369.83
    cyclopentyl methyl ether 405.49
    gamma-butyrolactone 855.41
    1-methoxy-2-propanol 545.32
    pyridine 556.25
    3-pentanone 410.96
    furfural 641.85
    n-dodecane 14.78
    diethylene glycol 364.34
    diisopropyl ether 133.95
    tert-amyl alcohol 469.87
    acetylacetone 549.97
    n-hexadecane 16.61
    acetophenone 314.65
    methyl propionate 424.32
    isopentyl acetate 370.67
    trichloroethylene 1525.46
    n-nonanol 146.55
    cyclohexanol 319.56
    benzyl alcohol 245.53
    2-ethylhexanol 210.73
    isooctanol 134.23
    dipropyl ether 222.99
    1,2-dichlorobenzene 328.84
    ethyl lactate 187.22
    propylene carbonate 518.15
    n-methylformamide 448.25
    2-pentanol 321.12
    n-pentane 40.5
    1-propoxy-2-propanol 394.82
    1-methoxy-2-propyl acetate 383.14
    2-(2-methoxypropoxy) propanol 335.51
    mesitylene 88.99
    ε-caprolactone 581.61
    p-cymene 81.83
    epichlorohydrin 1011.59
    1,1,1-trichloroethane 642.27
    2-aminoethanol 253.9
    morpholine-4-carbaldehyde 699.19
    sulfolane 853.25
    2,2,4-trimethylpentane 28.15
    2-methyltetrahydrofuran 692.86
    n-hexyl acetate 320.99
    isooctane 24.35
    2-(2-butoxyethoxy)ethanol 476.12
    sec-butyl acetate 256.47
    tert-butyl acetate 379.0
    decalin 44.3
    glycerin 240.03
    diglyme 736.58
    acrylic acid 406.73
    isopropyl myristate 134.03
    n-butyric acid 574.54
    acetyl acetate 339.52
    di(2-ethylhexyl) phthalate 123.03
    ethyl propionate 319.5
    nitromethane 1172.32
    1,2-diethoxyethane 378.89
    benzonitrile 308.8
    trioctyl phosphate 89.57
    1-bromopropane 458.8
    gamma-valerolactone 905.75
    n-decanol 111.11
    triethyl phosphate 135.43
    4-methyl-2-pentanol 198.56
    propionitrile 445.23
    vinylene carbonate 473.9
    1,1,2-trichlorotrifluoroethane 667.26
    DMS 290.46
    cumene 106.38
    2-octanol 116.59
    2-hexanone 413.42
    octyl acetate 168.89
    limonene 125.09
    1,2-dimethoxyethane 684.33
    ethyl orthosilicate 128.83
    tributyl phosphate 125.71
    diacetone alcohol 460.71
    N,N-dimethylaniline 227.55
    acrylonitrile 557.05
    aniline 242.25
    1,3-propanediol 362.4
    bromobenzene 315.05
    dibromomethane 714.67
    1,1,2,2-tetrachloroethane 1428.5
    2-methyl-cyclohexyl acetate 221.28
    tetrabutyl urea 154.37
    diisobutyl methanol 115.41
    2-phenylethanol 257.16
    styrene 182.71
    dioctyl adipate 195.94
    dimethyl sulfate 315.62
    ethyl butyrate 272.38
    methyl lactate 249.04
    butyl lactate 189.56
    diethyl carbonate 198.85
    propanediol butyl ether 293.24
    triethyl orthoformate 184.08
    p-tert-butyltoluene 83.2
    methyl 4-tert-butylbenzoate 252.53
    morpholine 953.67
    tert-butylamine 349.71
    n-dodecanol 85.48
    dimethoxymethane 510.59
    ethylene carbonate 397.35
    cyrene 260.81
    2-ethoxyethyl acetate 268.68
    2-ethylhexyl acetate 269.58
    1,2,4-trichlorobenzene 377.77
    4-methylpyridine 481.12
    dibutyl ether 203.75
    2,6-dimethyl-4-heptanol 115.41
    DEF 528.02
    dimethyl isosorbide 456.34
    tetrachloroethylene 671.15
    eugenol 261.17
    triacetin 297.81
    span 80 272.9
    1,4-butanediol 139.86
    1,1-dichloroethane 842.84
    2-methyl-1-pentanol 299.13
    methyl formate 349.53
    2-methyl-1-butanol 332.44
    n-decane 22.87
    butyronitrile 423.13
    3,7-dimethyl-1-octanol 178.54
    1-chlorooctane 115.42
    1-chlorotetradecane 48.24
    n-nonane 22.5
    undecane 17.75
    tert-butylcyclohexane 45.43
    cyclooctane 18.96
    cyclopentanol 341.46
    tetrahydropyran 755.85
    tert-amyl methyl ether 322.89
    2,5,8-trioxanonane 507.97
    1-hexene 258.56
    2-isopropoxyethanol 294.93
    2,2,2-trifluoroethanol 217.51
    methyl butyrate 429.89

    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
Jonquil (Japan) 8023-75-4 Narcissus jonquilla L., fam. Amaryllidaceae 0.03%