Ethyl 3-(methylthio)propionate

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  • Identifiers

    CAS number
    13327-56-5

    Molecular formula
    C6H12O2S

    SMILES
    CCOC(=O)CCSC

    Retention indicies (RI)

    • Carbowax: 1581.0

  • Odor profile

    Fruity 87.25%
    Sulfurous 82.82%
    Tropical 70.94%
    Cheesy 56.08%
    Pineapple 54.09%
    Sweet 53.05%
    Green 50.23%
    Onion 49.6%
    Vegetable 49.5%
    Cabbage 43.69%

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  • Properties

    XLogP3-AA
    1.1

    Molecular weight
    148.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point

    • 196.00 to 197.00 °C. @ 760.00 mm Hg

    Flash point est.
    68.68 ˚C

    Solubility expt.

    • 1 mL in 1 mL 95% alcohol (in ethanol)

  • Synonyms

    • 13327-56-5
    • Ethyl 3-(methylthio)propionate
    • Ethyl 3-(methylthio)propanoate
    • Ethyl 3-methylthiopropionate
    • Propanoic acid, 3-(methylthio)-, ethyl ester
    • ethyl 3-methylsulfanylpropanoate
    • Ethyl methyl mercaptopropionate
    • Ethyl 3-(methylsulfanyl)propanoate
    • 3-(Methylthio)propanoic acid ethyl ester
    • FEMA No. 3343
    • 3-(Methylthio)propionic acid ethylester
    • UNII-1AVT374NII
    • 1AVT374NII
    • Ethyl beta-methylthiopropionate
    • Ethyl 3-methylmercaptopropionate
    • Ethyl methylthiopropanoate
    • Propionic acid, 3-(methylthio)-, ethyl ester
    • EINECS 236-370-7
    • NSC 165650
    • NSC-165650
    • ethyl 3-methylthiopropanoate
    • 3-(Methylthio)propionic Acid Ethyl Ester
    • DTXSID2065414
    • CHEBI:87503
    • FEMA 3343
    • Ethyl .beta.-methylthiopropionate
    • Ethyl 3-(methylmercapto)propionate
    • ETHYL 3-METHYLTHIOPROPIONATE [FCC]
    • ETHYL 3-METHYLTHIOPROPIONATE [FHFI]
    • MFCD00039900
    • SCHEMBL1448036
    • Ethyl beta -methylthiopropionate
    • DTXCID0034142
    • Ethyl 3-methylthiopropionic acid
    • DTXCID70392782
    • Ethyl methyl mercaptopropionic acid
    • Ethyl 3-(methylthio)propanoic acid
    • Ethyl 3-(methylthio)propionic acid
    • Ethyl 3-methylmercaptopropionic acid
    • 3-(Methylthio)propanoate ethyl ester
    • NSC165650
    • AKOS008901304
    • CS-W010980
    • AS-66120
    • DB-042172
    • E0793
    • NS00021607
    • D90571
    • EN300-7055735
    • Ethyl 3-(methylthio)propionate, >=99%, FCC, FG
    • Q27159679

  • Applications

    Ethyl 3-(methylthio)propionate (CAS 13327-56-5) is a sulfur-bearing ester with a ripe-fruity, slightly cheesy and roasted-meat aroma profile that is widely employed as a flavour additive in tropical juices, confectionery, alcoholic beverages, baked goods, instant soups, meat seasonings and fermented dairy products; its distinctive smoky-sulfidic nuance also allows perfumers to refine “cooked” notes in cosmetic fragrances, tobacco flavours and roasted-coffee accords, while the molecule serves as a versatile intermediate toward more complex thioesters in pharmaceuticals, agrochemicals and controlled-release aroma materials, and is further used as an analytical reference standard, an authenticity tracer for natural flavours, and a model compound for Maillard reaction and sensory studies in food science.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2003.09
    methanol 3043.27
    isopropanol 1441.2
    water 16.56
    ethyl acetate 678.8
    n-propanol 1349.69
    acetone 1438.59
    n-butanol 1112.53
    acetonitrile 1496.2
    DMF 2006.97
    toluene 626.43
    isobutanol 890.26
    1,4-dioxane 2202.32
    methyl acetate 791.82
    THF 1850.58
    2-butanone 905.97
    n-pentanol 854.32
    sec-butanol 1095.68
    n-hexane 196.69
    ethylene glycol 523.11
    NMP 1491.46
    cyclohexane 445.74
    DMSO 1920.54
    n-butyl acetate 500.06
    n-octanol 392.25
    chloroform 3432.79
    n-propyl acetate 484.28
    acetic acid 2400.47
    dichloromethane 2415.04
    cyclohexanone 1575.14
    propylene glycol 544.59
    isopropyl acetate 356.49
    DMAc 1360.87
    2-ethoxyethanol 1085.58
    isopentanol 748.07
    n-heptane 114.34
    ethyl formate 653.24
    1,2-dichloroethane 1251.74
    n-hexanol 682.2
    2-methoxyethanol 1825.63
    isobutyl acetate 290.06
    tetrachloromethane 533.24
    n-pentyl acetate 393.04
    transcutol 2038.72
    n-heptanol 318.0
    ethylbenzene 314.29
    MIBK 356.7
    2-propoxyethanol 923.31
    tert-butanol 1277.02
    MTBE 727.74
    2-butoxyethanol 561.11
    propionic acid 1050.25
    o-xylene 354.91
    formic acid 936.74
    diethyl ether 807.42
    m-xylene 343.43
    p-xylene 465.25
    chlorobenzene 876.26
    dimethyl carbonate 204.95
    n-octane 49.51
    formamide 1022.04
    cyclopentanone 1402.08
    2-pentanone 645.76
    anisole 595.45
    cyclopentyl methyl ether 740.72
    gamma-butyrolactone 1340.04
    1-methoxy-2-propanol 1065.16
    pyridine 2021.32
    3-pentanone 473.4
    furfural 1537.72
    n-dodecane 41.48
    diethylene glycol 736.13
    diisopropyl ether 173.05
    tert-amyl alcohol 938.51
    acetylacetone 646.28
    n-hexadecane 46.98
    acetophenone 564.96
    methyl propionate 489.42
    isopentyl acetate 400.32
    trichloroethylene 2494.86
    n-nonanol 319.73
    cyclohexanol 1156.94
    benzyl alcohol 681.14
    2-ethylhexanol 366.97
    isooctanol 245.37
    dipropyl ether 342.99
    1,2-dichlorobenzene 654.42
    ethyl lactate 238.94
    propylene carbonate 681.27
    n-methylformamide 1163.83
    2-pentanol 620.29
    n-pentane 171.86
    1-propoxy-2-propanol 599.48
    1-methoxy-2-propyl acetate 387.61
    2-(2-methoxypropoxy) propanol 454.44
    mesitylene 205.32
    ε-caprolactone 1165.86
    p-cymene 159.81
    epichlorohydrin 1352.72
    1,1,1-trichloroethane 1231.43
    2-aminoethanol 909.3
    morpholine-4-carbaldehyde 1544.61
    sulfolane 1391.61
    2,2,4-trimethylpentane 62.8
    2-methyltetrahydrofuran 1371.9
    n-hexyl acetate 553.72
    isooctane 42.03
    2-(2-butoxyethoxy)ethanol 669.54
    sec-butyl acetate 282.4
    tert-butyl acetate 350.19
    decalin 126.74
    glycerin 731.53
    diglyme 1264.45
    acrylic acid 986.38
    isopropyl myristate 200.5
    n-butyric acid 1228.74
    acetyl acetate 470.57
    di(2-ethylhexyl) phthalate 216.16
    ethyl propionate 353.76
    nitromethane 2108.52
    1,2-diethoxyethane 658.28
    benzonitrile 1078.96
    trioctyl phosphate 162.95
    1-bromopropane 816.4
    gamma-valerolactone 1821.15
    n-decanol 218.84
    triethyl phosphate 181.08
    4-methyl-2-pentanol 295.45
    propionitrile 1031.28
    vinylene carbonate 804.08
    1,1,2-trichlorotrifluoroethane 1210.09
    DMS 334.25
    cumene 188.85
    2-octanol 258.8
    2-hexanone 605.32
    octyl acetate 262.62
    limonene 259.72
    1,2-dimethoxyethane 1631.42
    ethyl orthosilicate 179.4
    tributyl phosphate 194.28
    diacetone alcohol 460.97
    N,N-dimethylaniline 407.83
    acrylonitrile 1223.16
    aniline 857.15
    1,3-propanediol 1099.38
    bromobenzene 891.36
    dibromomethane 1679.71
    1,1,2,2-tetrachloroethane 1909.28
    2-methyl-cyclohexyl acetate 303.88
    tetrabutyl urea 266.35
    diisobutyl methanol 190.62
    2-phenylethanol 496.0
    styrene 507.04
    dioctyl adipate 297.34
    dimethyl sulfate 327.63
    ethyl butyrate 350.29
    methyl lactate 316.99
    butyl lactate 323.96
    diethyl carbonate 251.88
    propanediol butyl ether 577.56
    triethyl orthoformate 258.53
    p-tert-butyltoluene 151.54
    methyl 4-tert-butylbenzoate 381.08
    morpholine 2442.04
    tert-butylamine 812.14
    n-dodecanol 165.2
    dimethoxymethane 790.97
    ethylene carbonate 633.17
    cyrene 425.81
    2-ethoxyethyl acetate 476.4
    2-ethylhexyl acetate 320.48
    1,2,4-trichlorobenzene 786.78
    4-methylpyridine 1673.72
    dibutyl ether 408.43
    2,6-dimethyl-4-heptanol 190.62
    DEF 863.27
    dimethyl isosorbide 594.56
    tetrachloroethylene 1498.05
    eugenol 449.71
    triacetin 481.26
    span 80 507.08
    1,4-butanediol 516.85
    1,1-dichloroethane 1374.07
    2-methyl-1-pentanol 612.6
    methyl formate 747.55
    2-methyl-1-butanol 739.6
    n-decane 72.37
    butyronitrile 1112.15
    3,7-dimethyl-1-octanol 327.33
    1-chlorooctane 244.86
    1-chlorotetradecane 95.56
    n-nonane 75.35
    undecane 51.59
    tert-butylcyclohexane 95.65
    cyclooctane 99.71
    cyclopentanol 1174.74
    tetrahydropyran 1910.0
    tert-amyl methyl ether 482.66
    2,5,8-trioxanonane 822.88
    1-hexene 573.39
    2-isopropoxyethanol 629.65
    2,2,2-trifluoroethanol 584.09
    methyl butyrate 571.1

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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
Mandrake fruit (Israel) Mandragora officinarum L., fam. Solanaceae 1.48%
Averrhoa bilimbi fruit (Malaysia) Averrhoa bilimbi L., fam. Oxalidaceae 0.1%
Ambarella fruit Spondias cytherea Sonnerat (Ambarella), fam. Anacardiaceae 0.18%
Pineapple pulp Ananas comosus (L.) Merr., fam. Bromeliaceae 1.12%