Prenyl thioacetate

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  • Identifiers

    CAS number
    33049-93-3

    Molecular formula
    C7H12OS

    SMILES
    CC(=CCSC(=O)C)C

    Safety labels

    Flammable
    Flammable

  • Odor profile

    Sulfurous 88.81%
    Fruity 88.53%
    Tropical 80.25%
    Green 75.59%
    Onion 48.87%
    Vegetable 47.7%
    Meaty 44.19%
    Black currant 41.6%
    Alliaceous 38.88%
    Garlic 35.74%

    Scent© AI

  • Properties

    XLogP3-AA
    2.2

    pKa est.
    8.72 (weak base)

    Molecular weight
    144.24 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point

    • 67.00 to 68.00 °C. @ 760.00 mm Hg

    Flash point est.
    71.83 ˚C

    Solubility expt.

    • insoluble in water; soluble in ethanol, triacetin and heptane

  • Synonyms

    • Prenyl thioacetate
    • 33049-93-3
    • S-prenyl thioacetate
    • 3-Methyl-2-butenyl acetothioate
    • S-(3-methylbut-2-enyl) ethanethioate
    • 3-METHYL-2-BUTEN-1-YL THIOLACETATE
    • 8UI6K2036L
    • UNII-8UI6K2036L
    • S-(3-Methyl-2-butenyl) ethanethioate
    • 3-Methyl-2-buten-1-yl Thiolacetate(3-Methyl-2-buten-1-thiol precursor)
    • S-(3-methylbut-2-en-1-yl) ethanethioate
    • FEMA NO. 3895
    • PRENYL THIOACETATE [FHFI]
    • DTXSID80186710
    • Ethanethioic acid, S-(3-methyl-2-butenyl) ester
    • ACETIC ACID, THIO-, S-(3-METHYL-2-BUTENYL) ESTER
    • ETHANETHIOIC ACID, S-(3-METHYL-2-BUTEN-1-YL) ESTER
    • 3-Methyl-2-buten-1-yl Thiolacetate (3-Methyl-2-buten-1-thiol precursor)
    • Ethanethioic Acid S-(3-Methyl-2-butenyl) Ester
    • SCHEMBL3506726
    • DTXCID20109201
    • CHEBI:173381
    • HYSBJYIGYSBFQN-UHFFFAOYSA-N
    • MFCD09840922
    • AKOS006326877
    • (3-Methyl-2-buten-1-thiol precursor)
    • NS00122130
    • 1-[(3-methylbut-2-en-1-yl)sulfanyl]ethan-1-one
    • Q27271036
    • 639-094-9

  • Applications

    Prenyl thioacetate (CAS 33049-93-3) is an isoprenyl thioester used mainly as: (i) a flavor/fragrance ingredient imparting subtle sulfurous, tropical-fruity and grapefruit facets at trace levels to enhance authenticity in beverages, confectionery, baked goods and beer/spirits aromas; (ii) an organic intermediate/thiol surrogate (deprotection to 3-methyl-2-butenethiol) for thiol-ene and thiol-Michael chemistry, sulfide labeling, thioether synthesis, allylic nucleophilic substitution, and post-deprotection polymer surface modification; (iii) an analytical and sensory reference standard for studies of volatile sulfur compounds in foods, drinks and perfumery; it is also used in mechanistic studies of allylic rearrangements and radical processes and in odorant design featuring an isoprenyl motif; dosing, strong odor and oxidation-sensitive handling should be carefully controlled.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 386.19
    methanol 297.0
    isopropanol 323.09
    water 4.81
    ethyl acetate 304.34
    n-propanol 300.44
    acetone 431.96
    n-butanol 290.74
    acetonitrile 370.78
    DMF 417.5
    toluene 162.47
    isobutanol 227.17
    1,4-dioxane 652.06
    methyl acetate 310.26
    THF 892.14
    2-butanone 331.69
    n-pentanol 187.36
    sec-butanol 300.1
    n-hexane 58.53
    ethylene glycol 111.47
    NMP 574.8
    cyclohexane 111.77
    DMSO 353.0
    n-butyl acetate 251.25
    n-octanol 215.85
    chloroform 934.95
    n-propyl acetate 180.07
    acetic acid 427.49
    dichloromethane 596.22
    cyclohexanone 517.62
    propylene glycol 192.91
    isopropyl acetate 187.21
    DMAc 381.24
    2-ethoxyethanol 249.25
    isopentanol 221.27
    n-heptane 76.59
    ethyl formate 203.98
    1,2-dichloroethane 271.95
    n-hexanol 300.39
    2-methoxyethanol 414.81
    isobutyl acetate 130.58
    tetrachloromethane 151.71
    n-pentyl acetate 185.43
    transcutol 868.83
    n-heptanol 170.17
    ethylbenzene 114.45
    MIBK 166.33
    2-propoxyethanol 397.9
    tert-butanol 399.87
    MTBE 269.22
    2-butoxyethanol 264.78
    propionic acid 316.28
    o-xylene 130.27
    formic acid 119.31
    diethyl ether 241.8
    m-xylene 133.06
    p-xylene 146.85
    chlorobenzene 215.15
    dimethyl carbonate 108.24
    n-octane 29.55
    formamide 168.37
    cyclopentanone 582.63
    2-pentanone 271.5
    anisole 237.72
    cyclopentyl methyl ether 349.74
    gamma-butyrolactone 602.39
    1-methoxy-2-propanol 358.96
    pyridine 399.27
    3-pentanone 207.77
    furfural 533.03
    n-dodecane 26.37
    diethylene glycol 288.42
    diisopropyl ether 93.24
    tert-amyl alcohol 337.31
    acetylacetone 321.03
    n-hexadecane 29.45
    acetophenone 225.16
    methyl propionate 227.96
    isopentyl acetate 226.43
    trichloroethylene 589.22
    n-nonanol 185.03
    cyclohexanol 335.36
    benzyl alcohol 183.59
    2-ethylhexanol 207.73
    isooctanol 131.62
    dipropyl ether 218.96
    1,2-dichlorobenzene 211.92
    ethyl lactate 125.74
    propylene carbonate 397.96
    n-methylformamide 221.89
    2-pentanol 215.73
    n-pentane 62.6
    1-propoxy-2-propanol 333.45
    1-methoxy-2-propyl acetate 275.19
    2-(2-methoxypropoxy) propanol 289.61
    mesitylene 88.89
    ε-caprolactone 437.38
    p-cymene 109.14
    epichlorohydrin 513.98
    1,1,1-trichloroethane 378.17
    2-aminoethanol 220.81
    morpholine-4-carbaldehyde 611.29
    sulfolane 564.81
    2,2,4-trimethylpentane 35.12
    2-methyltetrahydrofuran 594.87
    n-hexyl acetate 304.28
    isooctane 24.93
    2-(2-butoxyethoxy)ethanol 381.61
    sec-butyl acetate 142.38
    tert-butyl acetate 211.37
    decalin 57.37
    glycerin 225.01
    diglyme 534.51
    acrylic acid 273.54
    isopropyl myristate 139.96
    n-butyric acid 360.26
    acetyl acetate 228.9
    di(2-ethylhexyl) phthalate 138.31
    ethyl propionate 170.09
    nitromethane 507.88
    1,2-diethoxyethane 297.96
    benzonitrile 256.17
    trioctyl phosphate 105.8
    1-bromopropane 206.99
    gamma-valerolactone 688.9
    n-decanol 138.69
    triethyl phosphate 124.31
    4-methyl-2-pentanol 120.75
    propionitrile 242.03
    vinylene carbonate 345.02
    1,1,2-trichlorotrifluoroethane 437.31
    DMS 205.09
    cumene 87.09
    2-octanol 135.21
    2-hexanone 206.63
    octyl acetate 181.07
    limonene 174.61
    1,2-dimethoxyethane 401.13
    ethyl orthosilicate 124.29
    tributyl phosphate 122.27
    diacetone alcohol 281.46
    N,N-dimethylaniline 165.62
    acrylonitrile 264.71
    aniline 211.11
    1,3-propanediol 271.79
    bromobenzene 207.39
    dibromomethane 416.83
    1,1,2,2-tetrachloroethane 516.18
    2-methyl-cyclohexyl acetate 215.33
    tetrabutyl urea 152.09
    diisobutyl methanol 123.89
    2-phenylethanol 213.74
    styrene 132.81
    dioctyl adipate 200.6
    dimethyl sulfate 147.44
    ethyl butyrate 208.59
    methyl lactate 166.97
    butyl lactate 177.35
    diethyl carbonate 154.09
    propanediol butyl ether 310.85
    triethyl orthoformate 166.62
    p-tert-butyltoluene 107.91
    methyl 4-tert-butylbenzoate 239.13
    morpholine 681.94
    tert-butylamine 275.98
    n-dodecanol 109.43
    dimethoxymethane 257.11
    ethylene carbonate 276.21
    cyrene 274.81
    2-ethoxyethyl acetate 237.31
    2-ethylhexyl acetate 193.52
    1,2,4-trichlorobenzene 283.09
    4-methylpyridine 376.99
    dibutyl ether 208.76
    2,6-dimethyl-4-heptanol 123.89
    DEF 279.07
    dimethyl isosorbide 453.85
    tetrachloroethylene 309.11
    eugenol 235.18
    triacetin 299.15
    span 80 320.42
    1,4-butanediol 114.0
    1,1-dichloroethane 360.81
    2-methyl-1-pentanol 161.93
    methyl formate 171.93
    2-methyl-1-butanol 224.58
    n-decane 43.33
    butyronitrile 287.16
    3,7-dimethyl-1-octanol 186.77
    1-chlorooctane 129.64
    1-chlorotetradecane 60.67
    n-nonane 43.69
    undecane 32.58
    tert-butylcyclohexane 51.09
    cyclooctane 41.78
    cyclopentanol 369.65
    tetrahydropyran 576.08
    tert-amyl methyl ether 217.47
    2,5,8-trioxanonane 420.31
    1-hexene 150.64
    2-isopropoxyethanol 201.99
    2,2,2-trifluoroethanol 173.17
    methyl butyrate 217.36

    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
Agathosma rosmarinifolia Agathosma rosmarinifolia (Bartl.) Williams, fam. Diosmea (Rutaceae) 4.8%
Phyllosma capensis Phyllosma capensis Bolus, fam. Diosmeae 25.6%