Isobutyrylshikonin

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  • Identifiers

    CAS number
    52438-12-7

    Molecular formula
    C20H22O6

    SMILES
    CC(C)C(=O)O[C@H](CC=C(C)C)C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sweet 38.88%
    Fruity 37.89%
    Odorless 34.88%
    Green 28.16%
    Herbal 28.16%
    Spicy 26.82%
    Mint 26.02%
    Woody 24.55%
    Floral 24.32%
    Dry 23.63%

     

    Flavor
    Bitter 89.69%
    Odorless 26.98%
    Bland 23.1%
    Cedarleaf 19.87%
    Parsley 19.09%
    Broom 18.96%
    Lovage 18.93%
    Heather 18.87%
    Sweet-like 18.84%
    Genet 18.53%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    4.6

    pKa est.
    7.63 (neutral)

    Molecular weight
    358.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    478°C

    Flash point

    • 219.88 ˚C est.

  • Synonyms

    • Isobutyrylshikonin
    • Isobutylshikonin
    • 52438-12-7
    • RefChem:149129
    • 932-567-3
    • [(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 2-methylpropanoate
    • (1r)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-methylpropanoate
    • (R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl isobutyrate
    • orb1297533
    • SCHEMBL3298557
    • SCHEMBL29377598
    • CHEBI:81070
    • DTXSID901316067
    • MFCD00144512
    • EBC-617616
    • AC-35024
    • DA-54402
    • MS-25632
    • C17414
    • Q27155026
    • [(1R)-1-(5,8-dihydroxy-1,4-dioxo-2-naphthyl)-4-methyl-pent-3-enyl] 2-methylpropanoate
    • 52438-12-7

  • Applications

    Isobutyrylshikonin, CAS 52438-12-7, is a shikonin derivative often used as a colorant and synthetic intermediate in pigment-related applications. Real-world uses span cosmetic and personal care colorants; coatings and inks as a pigment; in polymers and plastics as a color additive for colored plastics; and as an intermediate in organic synthesis for pharmaceutical and agrochemical research; it is also studied as a platform for developing other shikonin derivatives in chemical industries.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 58.09
    methanol 49.52
    isopropanol 47.26
    water 0.04
    ethyl acetate 56.42
    n-propanol 64.21
    acetone 126.27
    n-butanol 48.96
    acetonitrile 53.32
    DMF 339.48
    toluene 13.69
    isobutanol 40.65
    1,4-dioxane 84.97
    methyl acetate 93.48
    THF 336.99
    2-butanone 138.59
    n-pentanol 40.81
    sec-butanol 61.42
    n-hexane 0.66
    ethylene glycol 7.69
    NMP 273.67
    cyclohexane 0.63
    DMSO 362.13
    n-butyl acetate 37.26
    n-octanol 9.21
    chloroform 120.5
    n-propyl acetate 41.66
    acetic acid 110.65
    dichloromethane 99.69
    cyclohexanone 115.0
    propylene glycol 17.33
    isopropyl acetate 34.76
    DMAc 473.2
    2-ethoxyethanol 96.7
    isopentanol 38.5
    n-heptane 0.22
    ethyl formate 39.89
    1,2-dichloroethane 79.84
    n-hexanol 25.19
    2-methoxyethanol 147.09
    isobutyl acetate 21.51
    tetrachloromethane 7.46
    n-pentyl acetate 21.23
    transcutol 97.29
    n-heptanol 12.6
    ethylbenzene 10.94
    MIBK 37.21
    2-propoxyethanol 88.1
    tert-butanol 48.99
    MTBE 33.07
    2-butoxyethanol 46.49
    propionic acid 53.0
    o-xylene 10.66
    formic acid 34.69
    diethyl ether 35.63
    m-xylene 7.91
    p-xylene 14.92
    chlorobenzene 24.24
    dimethyl carbonate 49.53
    n-octane 0.19
    formamide 70.99
    cyclopentanone 197.31
    2-pentanone 78.17
    anisole 43.96
    cyclopentyl methyl ether 56.25
    gamma-butyrolactone 187.62
    1-methoxy-2-propanol 101.47
    pyridine 95.36
    3-pentanone 54.25
    furfural 111.31
    n-dodecane 0.29
    diethylene glycol 52.95
    diisopropyl ether 5.37
    tert-amyl alcohol 56.09
    acetylacetone 73.19
    n-hexadecane 0.34
    acetophenone 49.38
    methyl propionate 72.53
    isopentyl acetate 33.49
    trichloroethylene 168.13
    n-nonanol 10.01
    cyclohexanol 37.53
    benzyl alcohol 47.57
    2-ethylhexanol 14.25
    isooctanol 10.55
    dipropyl ether 12.7
    1,2-dichlorobenzene 25.21
    ethyl lactate 29.92
    propylene carbonate 70.28
    n-methylformamide 106.61
    2-pentanol 27.41
    n-pentane 0.46
    1-propoxy-2-propanol 49.02
    1-methoxy-2-propyl acetate 49.47
    2-(2-methoxypropoxy) propanol 46.59
    mesitylene 3.96
    ε-caprolactone 99.55
    p-cymene 5.19
    epichlorohydrin 241.32
    1,1,1-trichloroethane 51.66
    2-aminoethanol 26.13
    morpholine-4-carbaldehyde 188.58
    sulfolane 227.35
    2,2,4-trimethylpentane 0.66
    2-methyltetrahydrofuran 129.58
    n-hexyl acetate 27.23
    isooctane 0.34
    2-(2-butoxyethoxy)ethanol 53.7
    sec-butyl acetate 26.16
    tert-butyl acetate 36.81
    decalin 1.07
    glycerin 30.65
    diglyme 98.43
    acrylic acid 48.33
    isopropyl myristate 10.4
    n-butyric acid 63.85
    acetyl acetate 33.39
    di(2-ethylhexyl) phthalate 16.34
    ethyl propionate 38.55
    nitromethane 179.64
    1,2-diethoxyethane 32.85
    benzonitrile 36.64
    trioctyl phosphate 11.4
    1-bromopropane 35.96
    gamma-valerolactone 205.33
    n-decanol 7.2
    triethyl phosphate 19.95
    4-methyl-2-pentanol 14.16
    propionitrile 46.68
    vinylene carbonate 56.33
    1,1,2-trichlorotrifluoroethane 132.15
    DMS 35.38
    cumene 7.33
    2-octanol 7.83
    2-hexanone 55.12
    octyl acetate 15.57
    limonene 6.85
    1,2-dimethoxyethane 135.93
    ethyl orthosilicate 18.39
    tributyl phosphate 14.59
    diacetone alcohol 66.53
    N,N-dimethylaniline 29.34
    acrylonitrile 60.81
    aniline 41.53
    1,3-propanediol 51.76
    bromobenzene 19.76
    dibromomethane 59.73
    1,1,2,2-tetrachloroethane 131.81
    2-methyl-cyclohexyl acetate 24.37
    tetrabutyl urea 22.04
    diisobutyl methanol 6.94
    2-phenylethanol 38.19
    styrene 13.89
    dioctyl adipate 20.28
    dimethyl sulfate 94.46
    ethyl butyrate 25.15
    methyl lactate 48.31
    butyl lactate 25.36
    diethyl carbonate 19.95
    propanediol butyl ether 31.42
    triethyl orthoformate 21.09
    p-tert-butyltoluene 4.69
    methyl 4-tert-butylbenzoate 36.08
    morpholine 161.83
    tert-butylamine 16.95
    n-dodecanol 5.14
    dimethoxymethane 139.59
    ethylene carbonate 47.07
    cyrene 62.95
    2-ethoxyethyl acetate 37.34
    2-ethylhexyl acetate 23.83
    1,2,4-trichlorobenzene 39.13
    4-methylpyridine 95.86
    dibutyl ether 10.13
    2,6-dimethyl-4-heptanol 6.94
    DEF 100.0
    dimethyl isosorbide 80.69
    tetrachloroethylene 60.12
    eugenol 39.76
    triacetin 34.13
    span 80 30.93
    1,4-butanediol 20.04
    1,1-dichloroethane 66.65
    2-methyl-1-pentanol 38.0
    methyl formate 71.78
    2-methyl-1-butanol 47.53
    n-decane 0.46
    butyronitrile 42.34
    3,7-dimethyl-1-octanol 10.95
    1-chlorooctane 4.34
    1-chlorotetradecane 1.8
    n-nonane 0.33
    undecane 0.35
    tert-butylcyclohexane 0.9
    cyclooctane 0.19
    cyclopentanol 57.44
    tetrahydropyran 80.48
    tert-amyl methyl ether 33.22
    2,5,8-trioxanonane 68.72
    1-hexene 6.35
    2-isopropoxyethanol 60.28
    2,2,2-trifluoroethanol 35.25
    methyl butyrate 54.48

    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