rel-(2R,5S)-2-(1-Mercapto-1-methylethyl)-5-methylcyclohexanone

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  • Identifiers

    CAS number
    33284-96-7

    Molecular formula
    C10H18OS

    SMILES
    C[C@H]1CC[C@H](C(=O)C1)C(C)(C)S

    Retention indicies (RI)

    • Carbowax: 1888.0

  • Odor profile

    Fruity 76.17%
    Tropical 72.06%
    Sulfurous 69.77%
    Herbal 66.42%
    Green 64.88%
    Mint 57.88%
    Grapefruit 57.88%
    Black currant 57.61%
    Citrus 41.46%
    Woody 37.9%

    Scent© AI

  • Properties

    XLogP3-AA
    2.3

    Molecular weight
    186.32 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    256°C

    Flash point est.
    92.75 ˚C

  • Synonyms

    • 33284-96-7
    • rel-(2R,5S)-2-(1-Mercapto-1-methylethyl)-5-methylcyclohexanone
    • 8-Mercaptomenthon
    • RVOKNSFEAOYULQ-JGVFFNPUSA-N
    • DTXSID701176752
    • NS00087119
    • rel-(2R,5S)-2-(2-Mercaptopropan-2-yl)-5-methylcyclohexan-1-one

  • Applications

    rel-(2R,5S)-2-(1-Mercapto-1-methylethyl)-5-methylcyclohexanone (CAS 33284-96-7) is a multifunctional thiol–ketone used as a stereochemically defined intermediate in advanced organic synthesis and medicinal chemistry, enabling the construction of sulfur-containing motifs with stereocontrol (formation of thioethers, thioesters, disulfides, and oxidized sulfoxide/sulfone derivatives), serving as a building block for SAR libraries, as a thiol ligand/anchoring handle for metal-surface functionalization and self-assembled monolayers in sensing and nanotechnology, participating in thiol–ene/thiol–yne reactions for UV-cured coatings and adaptive polymer networks, acting as a reference/benchmark in chiral GC/LC method development and stereochemical stability studies, providing a precursor to trace sulfur odor notes or for calibrating sulfur detectors, and being exploited for heavy-metal capture chemistry as well as a redox-tunable attachment point when designing more soluble or fluorescently labeled derivatives.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 482.97
    methanol 663.35
    isopropanol 387.75
    water 3.79
    ethyl acetate 226.83
    n-propanol 329.12
    acetone 345.55
    n-butanol 305.58
    acetonitrile 366.0
    DMF 395.61
    toluene 201.88
    isobutanol 235.98
    1,4-dioxane 658.41
    methyl acetate 243.44
    THF 882.57
    2-butanone 267.85
    n-pentanol 199.35
    sec-butanol 264.68
    n-hexane 37.16
    ethylene glycol 97.8
    NMP 377.09
    cyclohexane 88.66
    DMSO 238.86
    n-butyl acetate 232.6
    n-octanol 174.2
    chloroform 983.37
    n-propyl acetate 155.47
    acetic acid 415.73
    dichloromethane 579.92
    cyclohexanone 466.5
    propylene glycol 166.95
    isopropyl acetate 157.96
    DMAc 251.85
    2-ethoxyethanol 206.32
    isopentanol 224.52
    n-heptane 42.31
    ethyl formate 213.68
    1,2-dichloroethane 261.97
    n-hexanol 358.76
    2-methoxyethanol 417.07
    isobutyl acetate 124.82
    tetrachloromethane 147.09
    n-pentyl acetate 150.01
    transcutol 656.26
    n-heptanol 162.57
    ethylbenzene 105.9
    MIBK 153.47
    2-propoxyethanol 404.78
    tert-butanol 363.71
    MTBE 217.11
    2-butoxyethanol 219.71
    propionic acid 240.58
    o-xylene 124.49
    formic acid 162.15
    diethyl ether 228.73
    m-xylene 144.94
    p-xylene 149.39
    chlorobenzene 275.93
    dimethyl carbonate 79.62
    n-octane 17.33
    formamide 159.44
    cyclopentanone 461.86
    2-pentanone 219.45
    anisole 183.39
    cyclopentyl methyl ether 283.66
    gamma-butyrolactone 493.21
    1-methoxy-2-propanol 314.93
    pyridine 425.82
    3-pentanone 148.24
    furfural 472.41
    n-dodecane 16.72
    diethylene glycol 306.53
    diisopropyl ether 78.15
    tert-amyl alcohol 236.32
    acetylacetone 243.4
    n-hexadecane 19.3
    acetophenone 171.92
    methyl propionate 162.99
    isopentyl acetate 228.85
    trichloroethylene 596.18
    n-nonanol 148.97
    cyclohexanol 303.08
    benzyl alcohol 190.67
    2-ethylhexanol 171.05
    isooctanol 122.1
    dipropyl ether 142.34
    1,2-dichlorobenzene 227.79
    ethyl lactate 101.38
    propylene carbonate 340.34
    n-methylformamide 225.1
    2-pentanol 184.88
    n-pentane 45.79
    1-propoxy-2-propanol 281.39
    1-methoxy-2-propyl acetate 233.31
    2-(2-methoxypropoxy) propanol 212.98
    mesitylene 94.53
    ε-caprolactone 390.73
    p-cymene 97.41
    epichlorohydrin 458.93
    1,1,1-trichloroethane 354.41
    2-aminoethanol 205.5
    morpholine-4-carbaldehyde 417.88
    sulfolane 382.27
    2,2,4-trimethylpentane 22.91
    2-methyltetrahydrofuran 487.18
    n-hexyl acetate 245.35
    isooctane 22.21
    2-(2-butoxyethoxy)ethanol 291.67
    sec-butyl acetate 116.05
    tert-butyl acetate 181.53
    decalin 36.07
    glycerin 210.4
    diglyme 425.48
    acrylic acid 215.08
    isopropyl myristate 100.72
    n-butyric acid 337.46
    acetyl acetate 178.12
    di(2-ethylhexyl) phthalate 111.57
    ethyl propionate 124.23
    nitromethane 410.2
    1,2-diethoxyethane 209.72
    benzonitrile 305.24
    trioctyl phosphate 85.62
    1-bromopropane 209.82
    gamma-valerolactone 621.03
    n-decanol 110.34
    triethyl phosphate 88.21
    4-methyl-2-pentanol 112.13
    propionitrile 267.29
    vinylene carbonate 321.55
    1,1,2-trichlorotrifluoroethane 342.04
    DMS 161.25
    cumene 79.59
    2-octanol 119.04
    2-hexanone 183.21
    octyl acetate 126.51
    limonene 128.62
    1,2-dimethoxyethane 340.99
    ethyl orthosilicate 90.79
    tributyl phosphate 97.39
    diacetone alcohol 217.86
    N,N-dimethylaniline 123.85
    acrylonitrile 276.43
    aniline 233.42
    1,3-propanediol 281.44
    bromobenzene 259.01
    dibromomethane 404.85
    1,1,2,2-tetrachloroethane 462.69
    2-methyl-cyclohexyl acetate 167.01
    tetrabutyl urea 113.88
    diisobutyl methanol 99.28
    2-phenylethanol 250.75
    styrene 121.35
    dioctyl adipate 134.24
    dimethyl sulfate 106.82
    ethyl butyrate 158.24
    methyl lactate 117.71
    butyl lactate 150.57
    diethyl carbonate 115.75
    propanediol butyl ether 245.03
    triethyl orthoformate 131.66
    p-tert-butyltoluene 96.9
    methyl 4-tert-butylbenzoate 179.25
    morpholine 645.96
    tert-butylamine 239.08
    n-dodecanol 84.37
    dimethoxymethane 248.19
    ethylene carbonate 255.28
    cyrene 197.79
    2-ethoxyethyl acetate 192.87
    2-ethylhexyl acetate 178.44
    1,2,4-trichlorobenzene 272.38
    4-methylpyridine 421.45
    dibutyl ether 124.12
    2,6-dimethyl-4-heptanol 99.28
    DEF 188.9
    dimethyl isosorbide 316.88
    tetrachloroethylene 303.1
    eugenol 184.0
    triacetin 208.19
    span 80 225.81
    1,4-butanediol 113.38
    1,1-dichloroethane 377.43
    2-methyl-1-pentanol 161.62
    methyl formate 193.53
    2-methyl-1-butanol 202.64
    n-decane 28.13
    butyronitrile 318.05
    3,7-dimethyl-1-octanol 151.2
    1-chlorooctane 96.21
    1-chlorotetradecane 42.25
    n-nonane 26.41
    undecane 21.0
    tert-butylcyclohexane 33.4
    cyclooctane 27.96
    cyclopentanol 320.4
    tetrahydropyran 571.48
    tert-amyl methyl ether 143.53
    2,5,8-trioxanonane 293.91
    1-hexene 114.9
    2-isopropoxyethanol 158.5
    2,2,2-trifluoroethanol 150.85
    methyl butyrate 167.79

    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
Buchu leaf 84649-93-4 Agathosma betulina (Berg.) Pillans (Barosma betulina Bertl.), fam. Rutacea 0.5%
Buchu leaf (South Africa) 1a 84649-93-4 Agathosma betulina (Berg.) Pillans (Barosma betulina Bertl.), fam. Rutacea 2.33%
Buchu leaf (South Africa) 1c (hybrid) 84649-93-4 Agathosma betulina x crenulata, fam. Rutaceae 2.81%
Buchu leaf (South Africa) 2 84649-93-4 Agathosma betulina (Berg.) Pillans (Barosma betulina Bertl.), fam. Rutacea 2.5%