2-Ethyl-3,5,6-trimethylpyrazine

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  • Identifiers

    CAS number
    17398-16-2

    Molecular formula
    C9H14N2

    SMILES
    CCC1=NC(=C(N=C1C)C)C

  • Odor profile

    Nutty 75.98%
    Roasted 70.91%
    Cocoa 62.19%
    Earthy 62.04%
    Burnt 61.83%
    Musty 59.14%
    Hazelnut 57.46%
    Coffee 54.12%
    Chocolate 52.16%
    Potato 46.11%

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  • Properties

    XLogP3-AA
    1.8

    pKa est.
    4.82 (weak acid)

    Molecular weight
    150.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    211°C

    Flash point est.
    71.78 ˚C

  • Synonyms

    • 2-ETHYL-3,5,6-TRIMETHYLPYRAZINE
    • 17398-16-2
    • Ethyltrimethylpyrazine
    • Pyrazine, ethyltrimethyl-
    • Pyrazine, 2-ethyl-3,5,6-trimethyl-
    • 2,3,5-Trimethyl-6-ethylpyrazine
    • Trimethylethylpyrazine
    • UNII-HGS2G1S1XY
    • 2,3,6-Trimethyl-5-ethylpyrazine
    • HGS2G1S1XY
    • Pyrazine, ethyltrimethyl
    • DTXSID10169738
    • 6-Ethyl-2,3,5-trimethylpyrazine
    • MFCD08457808
    • Pyrazine, ethyltrimethyl- (8CI,9CI)
    • SCHEMBL3457245
    • DTXCID2092229
    • CHEBI:213093
    • AKOS006290969
    • DS-6991
    • CS-0186633
    • NS00113830
    • C73333
    • Q27279925

  • Applications

    2-Ethyl-3,5,6-trimethylpyrazine (CAS 17398-16-2) is a highly potent pyrazine with roasted, nutty, cocoa and coffee notes, widely used as a flavor ingredient in foods and beverages (chocolate/cocoa, coffee and RTD coffee, baked goods, breakfast cereals, roasted/savory snacks, sauces and soups, processed meats and plant-based meat analogues) to build roasty–nutty character, as a flavor modulator/off-note masker in seasonings, in tobacco flavoring and pet-food palatants; it is also employed in R&D/quality control as a reference and calibration standard for GC-MS/GC-O, in Maillard reaction and reaction-flavor studies, in roast-profile assessment of coffee/cocoa, in microencapsulation and aroma-release work, and in packaging–aroma interaction studies; the compound has good thermal robustness and very high odor activity, so it is typically applied at trace levels and shows strong synergy with other pyrazines and sulfur-containing volatiles.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 636.34
    methanol 847.03
    isopropanol 462.01
    water 6.42
    ethyl acetate 661.53
    n-propanol 654.17
    acetone 597.51
    n-butanol 575.74
    acetonitrile 509.66
    DMF 923.56
    toluene 642.52
    isobutanol 498.56
    1,4-dioxane 1067.78
    methyl acetate 624.23
    THF 1294.31
    2-butanone 684.22
    n-pentanol 452.18
    sec-butanol 561.29
    n-hexane 348.91
    ethylene glycol 153.36
    NMP 1051.8
    cyclohexane 439.19
    DMSO 644.37
    n-butyl acetate 738.71
    n-octanol 419.7
    chloroform 2934.78
    n-propyl acetate 456.77
    acetic acid 375.49
    dichloromethane 2878.35
    cyclohexanone 1120.25
    propylene glycol 169.73
    isopropyl acetate 406.18
    DMAc 801.03
    2-ethoxyethanol 457.66
    isopentanol 430.88
    n-heptane 280.39
    ethyl formate 588.66
    1,2-dichloroethane 1445.18
    n-hexanol 587.31
    2-methoxyethanol 693.09
    isobutyl acetate 342.44
    tetrachloromethane 936.16
    n-pentyl acetate 541.49
    transcutol 687.56
    n-heptanol 363.08
    ethylbenzene 489.87
    MIBK 364.2
    2-propoxyethanol 612.64
    tert-butanol 438.17
    MTBE 581.36
    2-butoxyethanol 437.46
    propionic acid 446.1
    o-xylene 517.48
    formic acid 174.16
    diethyl ether 781.56
    m-xylene 470.99
    p-xylene 686.2
    chlorobenzene 916.75
    dimethyl carbonate 304.29
    n-octane 155.94
    formamide 218.46
    cyclopentanone 1135.75
    2-pentanone 573.95
    anisole 559.71
    cyclopentyl methyl ether 813.53
    gamma-butyrolactone 1200.01
    1-methoxy-2-propanol 471.04
    pyridine 1006.1
    3-pentanone 599.8
    furfural 1114.77
    n-dodecane 115.44
    diethylene glycol 332.55
    diisopropyl ether 282.24
    tert-amyl alcohol 496.11
    acetylacetone 536.79
    n-hexadecane 129.6
    acetophenone 529.9
    methyl propionate 548.09
    isopentyl acetate 626.49
    trichloroethylene 2252.49
    n-nonanol 336.38
    cyclohexanol 593.04
    benzyl alcohol 422.93
    2-ethylhexanol 448.55
    isooctanol 291.8
    dipropyl ether 568.21
    1,2-dichlorobenzene 932.91
    ethyl lactate 237.31
    propylene carbonate 754.5
    n-methylformamide 513.71
    2-pentanol 405.76
    n-pentane 295.09
    1-propoxy-2-propanol 453.64
    1-methoxy-2-propyl acetate 469.24
    2-(2-methoxypropoxy) propanol 302.07
    mesitylene 349.13
    ε-caprolactone 893.38
    p-cymene 405.55
    epichlorohydrin 1300.04
    1,1,1-trichloroethane 1434.6
    2-aminoethanol 272.15
    morpholine-4-carbaldehyde 896.6
    sulfolane 1194.85
    2,2,4-trimethylpentane 159.54
    2-methyltetrahydrofuran 1068.89
    n-hexyl acetate 678.08
    isooctane 98.82
    2-(2-butoxyethoxy)ethanol 373.82
    sec-butyl acetate 330.76
    tert-butyl acetate 387.72
    decalin 228.94
    glycerin 197.83
    diglyme 764.54
    acrylic acid 368.04
    isopropyl myristate 294.88
    n-butyric acid 576.74
    acetyl acetate 435.36
    di(2-ethylhexyl) phthalate 249.73
    ethyl propionate 484.72
    nitromethane 577.19
    1,2-diethoxyethane 551.03
    benzonitrile 703.04
    trioctyl phosphate 212.43
    1-bromopropane 1079.7
    gamma-valerolactone 1158.13
    n-decanol 258.38
    triethyl phosphate 306.05
    4-methyl-2-pentanol 230.53
    propionitrile 606.27
    vinylene carbonate 813.87
    1,1,2-trichlorotrifluoroethane 685.29
    DMS 474.65
    cumene 373.22
    2-octanol 328.37
    2-hexanone 503.76
    octyl acetate 367.34
    limonene 518.14
    1,2-dimethoxyethane 841.74
    ethyl orthosilicate 293.7
    tributyl phosphate 263.42
    diacetone alcohol 324.13
    N,N-dimethylaniline 485.16
    acrylonitrile 639.94
    aniline 518.84
    1,3-propanediol 380.42
    bromobenzene 1143.8
    dibromomethane 2031.12
    1,1,2,2-tetrachloroethane 1814.84
    2-methyl-cyclohexyl acetate 440.03
    tetrabutyl urea 320.71
    diisobutyl methanol 242.35
    2-phenylethanol 472.25
    styrene 531.57
    dioctyl adipate 352.55
    dimethyl sulfate 401.6
    ethyl butyrate 559.13
    methyl lactate 235.7
    butyl lactate 326.65
    diethyl carbonate 427.6
    propanediol butyl ether 315.27
    triethyl orthoformate 408.0
    p-tert-butyltoluene 363.39
    methyl 4-tert-butylbenzoate 449.1
    morpholine 945.13
    tert-butylamine 385.13
    n-dodecanol 210.63
    dimethoxymethane 755.07
    ethylene carbonate 682.03
    cyrene 331.87
    2-ethoxyethyl acetate 504.16
    2-ethylhexyl acetate 584.27
    1,2,4-trichlorobenzene 968.66
    4-methylpyridine 1021.32
    dibutyl ether 558.52
    2,6-dimethyl-4-heptanol 242.35
    DEF 723.42
    dimethyl isosorbide 603.85
    tetrachloroethylene 1454.72
    eugenol 379.87
    triacetin 438.71
    span 80 327.77
    1,4-butanediol 207.47
    1,1-dichloroethane 1357.66
    2-methyl-1-pentanol 395.86
    methyl formate 492.29
    2-methyl-1-butanol 497.63
    n-decane 184.48
    butyronitrile 717.4
    3,7-dimethyl-1-octanol 344.79
    1-chlorooctane 462.61
    1-chlorotetradecane 207.27
    n-nonane 204.58
    undecane 139.74
    tert-butylcyclohexane 211.66
    cyclooctane 200.14
    cyclopentanol 659.91
    tetrahydropyran 1122.22
    tert-amyl methyl ether 543.39
    2,5,8-trioxanonane 490.63
    1-hexene 627.04
    2-isopropoxyethanol 321.63
    2,2,2-trifluoroethanol 202.16
    methyl butyrate 600.78

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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
Freesia, Picked Flower Headspace Freesia refracta L. 0.2%