(3S,5S)-3-Ethyl-5-methyl-1,2,4-trithiolane

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  • Identifiers

    CAS number
    69098-44-8

    Molecular formula
    C5H10S3

    SMILES
    CC[C@H]1S[C@@H](SS1)C

  • Odor profile

    Sulfurous 78.5%
    Meaty 61.22%
    Onion 56.98%
    Roasted 53.59%
    Garlic 43.65%
    Alliaceous 43.22%
    Cooked 41.05%
    Savory 40.62%
    Beefy 34.85%
    Nutty 22.23%

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  • Properties

    XLogP3-AA
    2.9

    pKa est.
    3.53 (weak acid)

    Molecular weight
    166.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    230°C

    Flash point est.
    98.4 ˚C

  • Synonyms

    • DTXSID90797270
    • (3S,5S)-3-Ethyl-5-methyl-1,2,4-trithiolane
    • 69098-44-8
    • DTXCID20748013
    • SHLIDHGBMLQTDS-WHFBIAKZSA-N
    • trans-3-ethyl-5-methyl-1,2,4-trithiolane
    • trans-3-methyl-5-ethyl-1 ,2,4-trithiolane

  • Applications

    (3S,5S)-3-Ethyl-5-methyl-1,2,4-trithiolane is a sulfur heterocycle of the 1,2,4-trithiolane family prized for its powerful onion/garlic, roasted-meaty and smoky–toasty nuances; it is applied primarily as a flavor ingredient at trace levels to reinforce umami, fatty and caramelized notes in snacks, soups, sauces, dry seasonings, instant noodles, meat alternatives and pet palatants; it is also used in fragrance compositions to add subtle sulfur depth to roasted, smoky, meaty, onion or coffee themes; in research and quality control the (3S,5S) isomer serves as a reference/internal standard for GC–MS of volatile sulfur compounds, for heat-stability assessments, Maillard model systems and studies of Allium aroma biogenesis; it is useful in sensory training as a very low-threshold odor standard to calibrate panels; odor character depends strongly on stereochemical configuration, so maintaining stereochemical purity supports reproducible sensory profiles; commercially, use is subject to local flavor/fragrance regulations, and storage in tight, oxygen- and heat-limiting conditions away from reactive metals helps mitigate degradation and off-odor formation.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 301.29
    methanol 272.36
    isopropanol 289.29
    water 1.31
    ethyl acetate 846.33
    n-propanol 272.02
    acetone 1415.4
    n-butanol 290.57
    acetonitrile 632.7
    DMF 1749.3
    toluene 723.51
    isobutanol 235.22
    1,4-dioxane 1794.71
    methyl acetate 794.9
    THF 2384.15
    2-butanone 920.21
    n-pentanol 210.31
    sec-butanol 239.31
    n-hexane 46.42
    ethylene glycol 117.53
    NMP 1605.99
    cyclohexane 147.32
    DMSO 1582.83
    n-butyl acetate 833.35
    n-octanol 265.09
    chloroform 1817.9
    n-propyl acetate 521.13
    acetic acid 464.1
    dichloromethane 1558.82
    cyclohexanone 1701.3
    propylene glycol 144.63
    isopropyl acetate 694.8
    DMAc 1020.28
    2-ethoxyethanol 490.36
    isopentanol 271.72
    n-heptane 92.09
    ethyl formate 531.84
    1,2-dichloroethane 1008.92
    n-hexanol 352.55
    2-methoxyethanol 790.44
    isobutyl acetate 426.42
    tetrachloromethane 462.68
    n-pentyl acetate 569.45
    transcutol 1266.9
    n-heptanol 241.63
    ethylbenzene 283.61
    MIBK 632.52
    2-propoxyethanol 803.47
    tert-butanol 423.49
    MTBE 559.37
    2-butoxyethanol 503.25
    propionic acid 355.55
    o-xylene 418.96
    formic acid 111.13
    diethyl ether 587.8
    m-xylene 533.62
    p-xylene 365.56
    chlorobenzene 1015.0
    dimethyl carbonate 511.16
    n-octane 50.06
    formamide 234.17
    cyclopentanone 2166.29
    2-pentanone 861.55
    anisole 780.88
    cyclopentyl methyl ether 1039.36
    gamma-butyrolactone 2035.79
    1-methoxy-2-propanol 710.38
    pyridine 1273.05
    3-pentanone 684.83
    furfural 1935.84
    n-dodecane 47.75
    diethylene glycol 607.74
    diisopropyl ether 300.87
    tert-amyl alcohol 313.94
    acetylacetone 1565.53
    n-hexadecane 57.89
    acetophenone 717.38
    methyl propionate 671.03
    isopentyl acetate 733.35
    trichloroethylene 2086.86
    n-nonanol 251.43
    cyclohexanol 468.56
    benzyl alcohol 453.91
    2-ethylhexanol 285.84
    isooctanol 209.95
    dipropyl ether 496.95
    1,2-dichlorobenzene 987.43
    ethyl lactate 282.16
    propylene carbonate 1093.81
    n-methylformamide 596.97
    2-pentanol 243.14
    n-pentane 56.3
    1-propoxy-2-propanol 626.33
    1-methoxy-2-propyl acetate 957.17
    2-(2-methoxypropoxy) propanol 510.32
    mesitylene 391.15
    ε-caprolactone 1251.94
    p-cymene 279.75
    epichlorohydrin 1786.5
    1,1,1-trichloroethane 1397.65
    2-aminoethanol 182.08
    morpholine-4-carbaldehyde 1888.93
    sulfolane 2415.9
    2,2,4-trimethylpentane 52.83
    2-methyltetrahydrofuran 1339.18
    n-hexyl acetate 683.72
    isooctane 58.18
    2-(2-butoxyethoxy)ethanol 645.21
    sec-butyl acetate 409.48
    tert-butyl acetate 883.54
    decalin 100.29
    glycerin 262.37
    diglyme 1284.56
    acrylic acid 366.3
    isopropyl myristate 365.47
    n-butyric acid 557.77
    acetyl acetate 826.96
    di(2-ethylhexyl) phthalate 295.62
    ethyl propionate 478.99
    nitromethane 1245.11
    1,2-diethoxyethane 749.45
    benzonitrile 843.78
    trioctyl phosphate 229.96
    1-bromopropane 534.17
    gamma-valerolactone 2513.07
    n-decanol 199.03
    triethyl phosphate 329.13
    4-methyl-2-pentanol 193.91
    propionitrile 468.57
    vinylene carbonate 1104.41
    1,1,2-trichlorotrifluoroethane 1045.06
    DMS 667.69
    cumene 211.14
    2-octanol 201.26
    2-hexanone 576.21
    octyl acetate 410.5
    limonene 409.36
    1,2-dimethoxyethane 1030.03
    ethyl orthosilicate 309.01
    tributyl phosphate 276.19
    diacetone alcohol 736.35
    N,N-dimethylaniline 474.67
    acrylonitrile 654.04
    aniline 618.25
    1,3-propanediol 326.1
    bromobenzene 1180.19
    dibromomethane 987.02
    1,1,2,2-tetrachloroethane 1466.07
    2-methyl-cyclohexyl acetate 531.96
    tetrabutyl urea 361.84
    diisobutyl methanol 242.55
    2-phenylethanol 587.6
    styrene 406.39
    dioctyl adipate 440.09
    dimethyl sulfate 897.49
    ethyl butyrate 589.4
    methyl lactate 404.81
    butyl lactate 357.06
    diethyl carbonate 403.92
    propanediol butyl ether 424.16
    triethyl orthoformate 450.06
    p-tert-butyltoluene 318.36
    methyl 4-tert-butylbenzoate 663.54
    morpholine 1385.62
    tert-butylamine 249.91
    n-dodecanol 164.63
    dimethoxymethane 1182.84
    ethylene carbonate 938.03
    cyrene 642.21
    2-ethoxyethyl acetate 802.3
    2-ethylhexyl acetate 637.09
    1,2,4-trichlorobenzene 1073.19
    4-methylpyridine 1320.01
    dibutyl ether 424.93
    2,6-dimethyl-4-heptanol 242.55
    DEF 852.88
    dimethyl isosorbide 1163.63
    tetrachloroethylene 930.86
    eugenol 575.72
    triacetin 700.33
    span 80 497.12
    1,4-butanediol 155.81
    1,1-dichloroethane 1096.41
    2-methyl-1-pentanol 198.36
    methyl formate 646.76
    2-methyl-1-butanol 238.49
    n-decane 72.73
    butyronitrile 510.38
    3,7-dimethyl-1-octanol 279.8
    1-chlorooctane 268.65
    1-chlorotetradecane 136.63
    n-nonane 69.71
    undecane 56.96
    tert-butylcyclohexane 90.6
    cyclooctane 80.61
    cyclopentanol 533.91
    tetrahydropyran 1185.8
    tert-amyl methyl ether 432.23
    2,5,8-trioxanonane 921.75
    1-hexene 155.08
    2-isopropoxyethanol 404.55
    2,2,2-trifluoroethanol 280.08
    methyl butyrate 590.61

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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
Onion, welsh 8002-72-0 Allium fistulosum L. var. Maichuon, fam. Liliaceae 0.28%
Scallion Allium fistulosum L. var. Caespitosum, fam. Liliaceae 1.37%