2-Methoxy-3-(1-methylpropyl)pyrazine

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  • Identifiers

    CAS number
    24168-70-5

    Molecular formula
    C9H14N2O

    SMILES
    CCC(C)C1=NC=CN=C1OC

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • Carbowax: 1514.0

  • Odor profile

    Green 85.37%
    Earthy 70.14%
    Nutty 59.35%
    Vegetable 58.73%
    Roasted 43.17%
    Potato 41.04%
    Musty 38.46%
    Leafy 37.07%
    Cocoa 31.33%
    Woody 31.23%

    Scent© AI

  • Properties

    XLogP3-AA
    1.6

    Molecular weight
    166.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point

    • 50.00 °C. @ 1.00 mm Hg

    Flash point est.
    99.78 ˚C

    Solubility expt.

    • soluble in water, organic solvents, oils
    • miscible at room temperature (in ethanol)

  • Synonyms

    • 24168-70-5
    • 2-sec-Butyl-3-methoxypyrazine
    • 2-(sec-Butyl)-3-methoxypyrazine
    • 2-Methoxy-3-sec-butylpyrazine
    • 2-Methoxy-3-(1-methylpropyl)pyrazine
    • 3-sec-Butyl-2-methoxypyrazine
    • 2-butan-2-yl-3-methoxypyrazine
    • Pyrazine, 2-methoxy-3-(1-methylpropyl)-
    • FEMA No. 3433
    • Pyrazine, 2-sec-butyl-3-methoxy-
    • 2-s-butyl-3-methoxypyrazine
    • 62UR370ONE
    • DTXSID0047082
    • EINECS 246-050-9
    • MFCD00006136
    • DTXCID8027082
    • Pyrazine, 2-methoxy, 3-sec-butyl
    • 2-(butan-2-yl)-3-methoxypyrazine
    • 2-Methoxy-3-(1-methyl-propyl) pyrazine
    • Pyrazine, 3-methoxy-2-(1-methylpropyl)
    • (+/-)-2-METHOXY-3-(1-METHYLPROPYL)PYRAZINE
    • 2-METHOXY-3-(1-METHYLPROPYL)PYRAZINE [FHFI]
    • UNII-62UR370ONE
    • SBMP
    • 2-Secbutyl-3-methoxypyrazine
    • CHEMBL94514
    • SCHEMBL424900
    • 2-Ethoxy-3-isopropyl pyrazine
    • 2-sec-Butyl-3-methoxy-pyrazine
    • FEMA 3433
    • QMQDJVIJVPEQHE-UHFFFAOYSA-
    • CHEBI:190129
    • Tox21_301823
    • AC1469
    • 2-Sec-Butyl-3-methoxypyrazine, 8CI
    • 2-sec-Butyl-3-methoxypyrazine, 99%
    • AKOS003381940
    • AKOS016843169
    • 3-TERT-BUTYL-2-METHOXYPYRAZINE
    • CS-W017856
    • HY-W017140
    • 2-methoxy-3-(1-methylpropyl) pyrazine
    • 2-methoxy-3-(1-methylpropyl)-pyrazine
    • NCGC00256160-01
    • AC-11164
    • DS-16595
    • SY015398
    • CAS-24168-70-5
    • DB-003286
    • DB-251648
    • B2959
    • NS00012050
    • 2-Methoxy-3-(1-methylpropyl)pyrazine, >=98%, FG
    • Q15635537
    • InChI=1/C9H14N2O/c1-4-7(2)8-9(12-3)11-6-5-10-8/h5-7H,4H2,1-3H3
    • 246-050-9

  • Applications

    2-Methoxy-3-(1-methylpropyl)pyrazine (also known as isobutyl methoxypyrazine, IBMP, CAS 24168-70-5) is an aroma molecule with an extremely low sensory threshold, widely applied as a “green bell-pepper/earthy” flavor modulator in food flavorings, wine, craft beer, roasted coffee and chocolate; employed as an analytical standard for GC-MS/GC-O calibration to quantify methoxypyrazines in grapes, coffee and fermentation substrates; utilized in plant-physiology research to monitor ripening and guide harvest timing, and in chemical ecology as a semiochemical that attracts pest insects for biotrap design; additionally exploited in perfumery for fresh woody accords, in packaging materials to impart desired scents, and in quality control laboratories to detect off-flavors in canned or processed foods.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 464.23
    methanol 505.75
    isopropanol 343.66
    water 2.35
    ethyl acetate 354.23
    n-propanol 406.18
    acetone 505.06
    n-butanol 330.86
    acetonitrile 463.49
    DMF 779.82
    toluene 205.84
    isobutanol 326.13
    1,4-dioxane 565.06
    methyl acetate 408.95
    THF 590.76
    2-butanone 418.5
    n-pentanol 258.42
    sec-butanol 345.23
    n-hexane 18.24
    ethylene glycol 181.4
    NMP 564.96
    cyclohexane 62.62
    DMSO 699.48
    n-butyl acetate 334.33
    n-octanol 146.2
    chloroform 2219.8
    n-propyl acetate 236.69
    acetic acid 784.02
    dichloromethane 2425.31
    cyclohexanone 710.86
    propylene glycol 196.21
    isopropyl acetate 168.5
    DMAc 434.54
    2-ethoxyethanol 358.08
    isopentanol 251.47
    n-heptane 24.98
    ethyl formate 557.31
    1,2-dichloroethane 1075.69
    n-hexanol 270.44
    2-methoxyethanol 603.38
    isobutyl acetate 137.61
    tetrachloromethane 386.38
    n-pentyl acetate 214.74
    transcutol 475.51
    n-heptanol 171.32
    ethylbenzene 116.88
    MIBK 138.31
    2-propoxyethanol 368.75
    tert-butanol 316.57
    MTBE 203.6
    2-butoxyethanol 266.17
    propionic acid 516.19
    o-xylene 160.4
    formic acid 296.28
    diethyl ether 181.08
    m-xylene 135.53
    p-xylene 185.84
    chlorobenzene 595.63
    dimethyl carbonate 151.83
    n-octane 16.31
    formamide 399.28
    cyclopentanone 662.67
    2-pentanone 259.66
    anisole 209.75
    cyclopentyl methyl ether 244.86
    gamma-butyrolactone 930.42
    1-methoxy-2-propanol 350.51
    pyridine 846.96
    3-pentanone 204.51
    furfural 1019.94
    n-dodecane 16.52
    diethylene glycol 300.46
    diisopropyl ether 53.51
    tert-amyl alcohol 300.86
    acetylacetone 293.27
    n-hexadecane 19.42
    acetophenone 245.1
    methyl propionate 293.64
    isopentyl acetate 249.6
    trichloroethylene 2339.21
    n-nonanol 124.53
    cyclohexanol 347.88
    benzyl alcohol 293.05
    2-ethylhexanol 170.42
    isooctanol 136.85
    dipropyl ether 110.85
    1,2-dichlorobenzene 528.81
    ethyl lactate 156.02
    propylene carbonate 630.71
    n-methylformamide 633.71
    2-pentanol 186.75
    n-pentane 22.54
    1-propoxy-2-propanol 249.44
    1-methoxy-2-propyl acetate 215.88
    2-(2-methoxypropoxy) propanol 158.9
    mesitylene 91.72
    ε-caprolactone 563.23
    p-cymene 119.13
    epichlorohydrin 1016.39
    1,1,1-trichloroethane 955.86
    2-aminoethanol 300.5
    morpholine-4-carbaldehyde 554.61
    sulfolane 993.7
    2,2,4-trimethylpentane 22.03
    2-methyltetrahydrofuran 441.52
    n-hexyl acetate 262.22
    isooctane 14.08
    2-(2-butoxyethoxy)ethanol 238.96
    sec-butyl acetate 120.36
    tert-butyl acetate 153.49
    decalin 32.02
    glycerin 250.04
    diglyme 462.78
    acrylic acid 531.37
    isopropyl myristate 90.87
    n-butyric acid 578.78
    acetyl acetate 230.05
    di(2-ethylhexyl) phthalate 119.31
    ethyl propionate 174.87
    nitromethane 1013.74
    1,2-diethoxyethane 190.0
    benzonitrile 559.56
    trioctyl phosphate 95.31
    1-bromopropane 442.88
    gamma-valerolactone 865.29
    n-decanol 95.93
    triethyl phosphate 109.43
    4-methyl-2-pentanol 97.16
    propionitrile 405.56
    vinylene carbonate 723.2
    1,1,2-trichlorotrifluoroethane 831.43
    DMS 199.24
    cumene 92.47
    2-octanol 121.59
    2-hexanone 207.51
    octyl acetate 134.37
    limonene 145.42
    1,2-dimethoxyethane 451.32
    ethyl orthosilicate 100.27
    tributyl phosphate 107.46
    diacetone alcohol 206.3
    N,N-dimethylaniline 144.07
    acrylonitrile 666.2
    aniline 348.67
    1,3-propanediol 375.08
    bromobenzene 628.54
    dibromomethane 1401.75
    1,1,2,2-tetrachloroethane 1604.0
    2-methyl-cyclohexyl acetate 169.38
    tetrabutyl urea 130.32
    diisobutyl methanol 85.21
    2-phenylethanol 278.17
    styrene 162.68
    dioctyl adipate 142.05
    dimethyl sulfate 250.22
    ethyl butyrate 200.18
    methyl lactate 194.37
    butyl lactate 180.72
    diethyl carbonate 170.94
    propanediol butyl ether 238.04
    triethyl orthoformate 135.14
    p-tert-butyltoluene 105.36
    methyl 4-tert-butylbenzoate 215.97
    morpholine 604.37
    tert-butylamine 188.87
    n-dodecanol 75.72
    dimethoxymethane 319.36
    ethylene carbonate 536.96
    cyrene 211.55
    2-ethoxyethyl acetate 242.76
    2-ethylhexyl acetate 197.77
    1,2,4-trichlorobenzene 622.76
    4-methylpyridine 640.29
    dibutyl ether 111.44
    2,6-dimethyl-4-heptanol 85.21
    DEF 338.78
    dimethyl isosorbide 289.7
    tetrachloroethylene 1204.35
    eugenol 228.32
    triacetin 210.9
    span 80 180.91
    1,4-butanediol 203.93
    1,1-dichloroethane 1037.31
    2-methyl-1-pentanol 212.3
    methyl formate 569.84
    2-methyl-1-butanol 274.75
    n-decane 23.82
    butyronitrile 440.95
    3,7-dimethyl-1-octanol 125.51
    1-chlorooctane 114.73
    1-chlorotetradecane 49.9
    n-nonane 22.03
    undecane 19.64
    tert-butylcyclohexane 29.13
    cyclooctane 17.8
    cyclopentanol 400.01
    tetrahydropyran 473.62
    tert-amyl methyl ether 148.5
    2,5,8-trioxanonane 277.8
    1-hexene 79.49
    2-isopropoxyethanol 220.75
    2,2,2-trifluoroethanol 283.61
    methyl butyrate 297.0

    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
Orris butter 8002-73-1 Iris florentina L., fam. Iridaceae 0.01%
Galbanum 4 9000-24-2 Ferula galbaniflua Boiss. et Buhse, fam. Apiaceae (Umbelliferae) 0.01%
Hyacinth, picked flower headspace 1b Hyacinthus orientalis L., fam. Liliaceae 0.01%
Violet odorata flower headspace Viola odorata L., fam. Violaceae 0.01%
Ribes sanguineum flower headspace Ribes sanguineum L., fam. Grossulariaceae 0.01%
Parsley leaf (Germany) 2a 8000-68-8 Petroselinum crispun (Miller) A.W. Hill cv Hamburger Schnitt,fam. Apiaceae 0.01%
Parsley leaf (Germany) 2b 800-68-8 Petroselinum crispun (Miller) A.W. Hill cv Mooskrause, fam. Apiaceae 0.01%