S-Prenyl thioisobutyrate

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  • Identifiers

    CAS number
    53626-94-1

    Molecular formula
    C9H16OS

    SMILES
    CC(C)C(=O)SCC=C(C)C

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fruity 93.97%
    Sulfurous 83.52%
    Tropical 82.82%
    Green 47.5%
    Cheesy 42.12%
    Black currant 40.75%
    Vegetable 34.76%
    Onion 33.17%
    Grapefruit 31.6%
    Grape 31.11%

    Scent© AI

  • Properties

    XLogP3-AA
    3.2

    Molecular weight
    172.29 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    224°C

    Flash point est.
    74.74 ˚C

  • Synonyms

    • S-Prenyl thioisobutyrate
    • 53626-94-1
    • 7HQZ604M8H
    • UNII-7HQZ604M8H
    • Propanethioic acid, 2-methyl-, S-(3-methyl-2-butenyl) ester
    • Propanethioic acid, 2-methyl-, S-(3-methyl-2-buten-1-yl) ester
    • FEMA NO. 4760
    • DTXSID101020169
    • S-(3-Methyl-2-butenyl) 2-methylpropanethioate
    • S-3-METHYLBUT-2-ENYL 2-METHYLPROPANETHIOATE
    • SCHEMBL17941531
    • CHEBI:173792
    • GZNOAIURTRJISH-UHFFFAOYSA-N
    • DTXCID401478018
    • NS00121808
    • S-(3-methylbut-2-enyl) 2-methylpropanethioate
    • Q27268316

  • Applications

    S-Prenyl thioisobutyrate (CAS 53626-94-1) is an organic thioester combining an activated isobutyryl fragment with a sulfur-linked prenyl chain; in organic synthesis it can serve as a mild acyl-transfer reagent to introduce the isobutyryl group into amines, alcohols, or thiols via thioester exchange or base/DMAP catalysis, as a building block toward prenyl–sulfide derivatives, and as a precursor that can release isobutyric acid or prenyl mercaptan upon hydrolysis/S-acyl cleavage; in biochemistry and mechanistic studies it is used as a model substrate to probe thioester reactivity (hydrolysis, acyl transfer, thioesterase activity) and to optimize thioester-based chemoselective ligations; in medicinal, agrochemical, and materials discovery it functions as a synthetic intermediate for installing isobutyryl or prenyl motifs and as a reference standard during development/validation of GC-MS/LC-MS methods for volatile sulfur compounds; additionally, owing to the odor characteristics of thioesters and the prenyl moiety, it is explored at trace levels in flavor and fragrance research as a controlled source/precursor of sulfur notes, subject to applicable safety and regulatory requirements.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1652.98
    methanol 1280.68
    isopropanol 1552.68
    water 1.77
    ethyl acetate 1980.45
    n-propanol 1381.48
    acetone 2728.91
    n-butanol 1595.65
    acetonitrile 1988.71
    DMF 2414.5
    toluene 1484.32
    isobutanol 1297.31
    1,4-dioxane 2825.3
    methyl acetate 1730.25
    THF 3422.39
    2-butanone 2203.36
    n-pentanol 1061.77
    sec-butanol 1618.93
    n-hexane 552.87
    ethylene glycol 197.02
    NMP 2973.12
    cyclohexane 883.85
    DMSO 1366.63
    n-butyl acetate 1964.64
    n-octanol 732.34
    chloroform 5349.39
    n-propyl acetate 1231.23
    acetic acid 1910.38
    dichloromethane 3559.39
    cyclohexanone 3522.92
    propylene glycol 379.44
    isopropyl acetate 1314.61
    DMAc 2040.87
    2-ethoxyethanol 1186.47
    isopentanol 1570.89
    n-heptane 288.32
    ethyl formate 1097.74
    1,2-dichloroethane 2379.82
    n-hexanol 1464.69
    2-methoxyethanol 1624.54
    isobutyl acetate 811.65
    tetrachloromethane 1251.3
    n-pentyl acetate 1208.46
    transcutol 3878.15
    n-heptanol 723.52
    ethylbenzene 811.41
    MIBK 1189.28
    2-propoxyethanol 1629.67
    tert-butanol 2223.3
    MTBE 2402.32
    2-butoxyethanol 1055.23
    propionic acid 1209.32
    o-xylene 923.63
    formic acid 451.4
    diethyl ether 2151.31
    m-xylene 991.25
    p-xylene 1142.05
    chlorobenzene 1770.48
    dimethyl carbonate 459.22
    n-octane 118.19
    formamide 693.21
    cyclopentanone 3107.55
    2-pentanone 1975.77
    anisole 1190.93
    cyclopentyl methyl ether 1985.04
    gamma-butyrolactone 2851.4
    1-methoxy-2-propanol 1277.13
    pyridine 2643.07
    3-pentanone 1416.49
    furfural 2564.64
    n-dodecane 73.63
    diethylene glycol 904.82
    diisopropyl ether 730.96
    tert-amyl alcohol 2026.36
    acetylacetone 1688.25
    n-hexadecane 88.18
    acetophenone 1182.49
    methyl propionate 1216.85
    isopentyl acetate 1701.59
    trichloroethylene 5181.64
    n-nonanol 632.27
    cyclohexanol 1995.27
    benzyl alcohol 944.98
    2-ethylhexanol 992.56
    isooctanol 588.37
    dipropyl ether 1019.22
    1,2-dichlorobenzene 1528.54
    ethyl lactate 443.24
    propylene carbonate 1874.73
    n-methylformamide 1107.22
    2-pentanol 1370.77
    n-pentane 444.45
    1-propoxy-2-propanol 1385.77
    1-methoxy-2-propyl acetate 1411.97
    2-(2-methoxypropoxy) propanol 886.65
    mesitylene 623.58
    ε-caprolactone 2830.27
    p-cymene 508.87
    epichlorohydrin 3147.12
    1,1,1-trichloroethane 3570.48
    2-aminoethanol 550.81
    morpholine-4-carbaldehyde 2640.74
    sulfolane 2593.18
    2,2,4-trimethylpentane 217.3
    2-methyltetrahydrofuran 3309.16
    n-hexyl acetate 1655.44
    isooctane 184.19
    2-(2-butoxyethoxy)ethanol 1266.1
    sec-butyl acetate 1013.78
    tert-butyl acetate 1497.77
    decalin 346.34
    glycerin 464.02
    diglyme 2141.48
    acrylic acid 984.55
    isopropyl myristate 503.62
    n-butyric acid 2055.25
    acetyl acetate 1221.07
    di(2-ethylhexyl) phthalate 440.15
    ethyl propionate 955.46
    nitromethane 2665.96
    1,2-diethoxyethane 1756.64
    benzonitrile 1636.49
    trioctyl phosphate 317.53
    1-bromopropane 1760.49
    gamma-valerolactone 3617.34
    n-decanol 422.24
    triethyl phosphate 431.28
    4-methyl-2-pentanol 722.32
    propionitrile 1403.36
    vinylene carbonate 1575.55
    1,1,2-trichlorotrifluoroethane 1971.51
    DMS 933.27
    cumene 526.7
    2-octanol 602.46
    2-hexanone 1400.52
    octyl acetate 640.0
    limonene 860.15
    1,2-dimethoxyethane 2071.56
    ethyl orthosilicate 491.65
    tributyl phosphate 443.54
    diacetone alcohol 1395.47
    N,N-dimethylaniline 784.19
    acrylonitrile 1487.55
    aniline 1331.9
    1,3-propanediol 954.11
    bromobenzene 1908.27
    dibromomethane 2685.86
    1,1,2,2-tetrachloroethane 4403.69
    2-methyl-cyclohexyl acetate 909.84
    tetrabutyl urea 515.6
    diisobutyl methanol 568.92
    2-phenylethanol 1026.92
    styrene 979.43
    dioctyl adipate 612.83
    dimethyl sulfate 707.18
    ethyl butyrate 1052.91
    methyl lactate 538.35
    butyl lactate 771.25
    diethyl carbonate 668.54
    propanediol butyl ether 989.06
    triethyl orthoformate 762.31
    p-tert-butyltoluene 501.11
    methyl 4-tert-butylbenzoate 856.38
    morpholine 3152.38
    tert-butylamine 1616.58
    n-dodecanol 301.82
    dimethoxymethane 1148.91
    ethylene carbonate 1384.88
    cyrene 821.19
    2-ethoxyethyl acetate 1350.73
    2-ethylhexyl acetate 1396.22
    1,2,4-trichlorobenzene 1804.09
    4-methylpyridine 3252.49
    dibutyl ether 1026.42
    2,6-dimethyl-4-heptanol 568.92
    DEF 2126.19
    dimethyl isosorbide 1465.8
    tetrachloroethylene 2941.97
    eugenol 822.12
    triacetin 1084.3
    span 80 913.91
    1,4-butanediol 401.8
    1,1-dichloroethane 3157.52
    2-methyl-1-pentanol 1123.01
    methyl formate 839.68
    2-methyl-1-butanol 1459.46
    n-decane 147.33
    butyronitrile 1867.23
    3,7-dimethyl-1-octanol 771.34
    1-chlorooctane 616.66
    1-chlorotetradecane 208.16
    n-nonane 151.52
    undecane 99.03
    tert-butylcyclohexane 313.14
    cyclooctane 273.79
    cyclopentanol 1621.11
    tetrahydropyran 3234.05
    tert-amyl methyl ether 1657.55
    2,5,8-trioxanonane 1228.33
    1-hexene 1329.98
    2-isopropoxyethanol 965.55
    2,2,2-trifluoroethanol 623.67
    methyl butyrate 1373.8

    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 apiculata Agathosma apiculata G.F.W. Mey, fam. Diosmeae (Rutaceae) 34.9%
Agathosma clavisepala Agathosma clavisepala R.A. Dyer, fam. Diosmeae (Rutaceae) 7.1%
Agathosma puberula Agathosma puberula Fourcade, fam. Diosmeae (Rutaceae) 5.0%
Agathosma rosmarinifolia Agathosma rosmarinifolia (Bartl.) Williams, fam. Diosmea (Rutaceae) 26.2%
Phyllosma capensis Phyllosma capensis Bolus, fam. Diosmeae 17.3%