Isovalerylshikonin

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  • Identifiers

    CAS number
    52387-14-1

    Molecular formula
    C21H24O6

    SMILES
    CC(C)CC(=O)OC(CC=C(C)C)C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Herbal 37.52%
    Odorless 35.78%
    Fruity 35.33%
    Sweet 32.32%
    Mint 30.83%
    Spicy 29.06%
    Green 25.91%
    Woody 23.98%
    Dry 21.43%
    Balsamic 21.27%

     

    Flavor
    Bitter 89.14%
    Odorless 27.19%
    Bland 23.63%
    Cedarleaf 19.85%
    Parsley 19.01%
    Lovage 18.95%
    Heather 18.93%
    Broom 18.84%
    Genet 18.57%
    Sweet-like 18.46%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    4.8

    pKa est.
    7.91 (neutral)

    Molecular weight
    372.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    499°C

    Flash point

    • 222.24 ˚C est.

  • Synonyms

    • Isovalerylshikonin
    • 52387-14-1
    • [1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-methylbutanoate
    • DTXSID60319387
    • (1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl) 3-methylbutanoate
    • RefChem:923825
    • DTXCID10270510
    • 76549-35-4
    • NSC344556
    • 1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbutanoate
    • Butanoic acid, 3-methyl-, 1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester
    • [1-(5,8-dihydroxy-1,4-dioxo-2-naphthyl)-4-methyl-pent-3-enyl] 3-methylbutanoate
    • MFCD00144522
    • Alkannin isovalerate
    • SCHEMBL13389448
    • UTOUNDHZJFIVPK-UHFFFAOYSA-
    • Butanoic acid, 3-methyl-, (1R)-1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester (9CI); Butanoic acid, 3-methyl-, 1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester, (R)-
    • ALKANNIN, ISOVALIRIC ACID ISVL
    • AKOS040760835
    • NSC-344556
    • PD119281
    • TS-10133
    • InChI=1/C21H24O6/c1-11(2)5-8-17(27-18(25)9-12(3)4)13-10-16(24)19-14(22)6-7-15(23)20(19)21(13)26/h5-7,10,12,17,22-23H,8-9H2,1-4H3
    • 52387-14-1

  • Applications

    Isovalerylshikonin (CAS 52387-14-1) is a naphthoquinone ester primarily used as a natural pigment/colorant and as an important intermediate in the synthesis of related naphthoquinone derivatives; in practical applications, it serves as a colorant in cosmetics and personal care, a dye for textiles and leather, a pigment additive in coatings and printing inks, and as an intermediate for the production of related shikonin compounds in chemical manufacturing.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 80.33
    methanol 72.27
    isopropanol 64.81
    water 0.03
    ethyl acetate 39.58
    n-propanol 83.7
    acetone 143.0
    n-butanol 66.94
    acetonitrile 45.03
    DMF 340.84
    toluene 12.21
    isobutanol 50.78
    1,4-dioxane 66.84
    methyl acetate 68.96
    THF 330.59
    2-butanone 120.32
    n-pentanol 49.89
    sec-butanol 70.37
    n-hexane 0.76
    ethylene glycol 9.73
    NMP 302.69
    cyclohexane 0.7
    DMSO 411.33
    n-butyl acetate 33.56
    n-octanol 9.78
    chloroform 140.08
    n-propyl acetate 35.35
    acetic acid 130.98
    dichloromethane 107.83
    cyclohexanone 115.53
    propylene glycol 28.13
    isopropyl acetate 26.35
    DMAc 441.29
    2-ethoxyethanol 91.42
    isopentanol 49.72
    n-heptane 0.25
    ethyl formate 36.64
    1,2-dichloroethane 83.58
    n-hexanol 29.31
    2-methoxyethanol 157.08
    isobutyl acetate 20.95
    tetrachloromethane 8.08
    n-pentyl acetate 20.73
    transcutol 104.36
    n-heptanol 13.41
    ethylbenzene 9.28
    MIBK 37.25
    2-propoxyethanol 95.96
    tert-butanol 55.64
    MTBE 23.23
    2-butoxyethanol 48.71
    propionic acid 60.04
    o-xylene 8.93
    formic acid 41.26
    diethyl ether 25.87
    m-xylene 7.64
    p-xylene 12.37
    chlorobenzene 22.78
    dimethyl carbonate 39.35
    n-octane 0.19
    formamide 69.19
    cyclopentanone 197.38
    2-pentanone 73.41
    anisole 31.52
    cyclopentyl methyl ether 48.0
    gamma-butyrolactone 173.81
    1-methoxy-2-propanol 118.99
    pyridine 82.04
    3-pentanone 48.21
    furfural 97.83
    n-dodecane 0.26
    diethylene glycol 58.01
    diisopropyl ether 3.89
    tert-amyl alcohol 56.12
    acetylacetone 66.41
    n-hexadecane 0.31
    acetophenone 43.02
    methyl propionate 59.06
    isopentyl acetate 32.01
    trichloroethylene 164.79
    n-nonanol 10.14
    cyclohexanol 42.5
    benzyl alcohol 44.6
    2-ethylhexanol 14.21
    isooctanol 11.47
    dipropyl ether 10.8
    1,2-dichlorobenzene 23.1
    ethyl lactate 30.81
    propylene carbonate 68.85
    n-methylformamide 115.65
    2-pentanol 34.02
    n-pentane 0.61
    1-propoxy-2-propanol 53.77
    1-methoxy-2-propyl acetate 45.61
    2-(2-methoxypropoxy) propanol 49.52
    mesitylene 3.77
    ε-caprolactone 94.94
    p-cymene 4.63
    epichlorohydrin 230.56
    1,1,1-trichloroethane 53.03
    2-aminoethanol 36.62
    morpholine-4-carbaldehyde 183.5
    sulfolane 255.86
    2,2,4-trimethylpentane 0.64
    2-methyltetrahydrofuran 109.95
    n-hexyl acetate 25.43
    isooctane 0.34
    2-(2-butoxyethoxy)ethanol 57.5
    sec-butyl acetate 21.69
    tert-butyl acetate 29.37
    decalin 0.93
    glycerin 41.45
    diglyme 93.56
    acrylic acid 54.14
    isopropyl myristate 9.42
    n-butyric acid 72.95
    acetyl acetate 23.76
    di(2-ethylhexyl) phthalate 17.39
    ethyl propionate 30.05
    nitromethane 168.56
    1,2-diethoxyethane 27.66
    benzonitrile 33.68
    trioctyl phosphate 12.19
    1-bromopropane 37.61
    gamma-valerolactone 212.37
    n-decanol 7.36
    triethyl phosphate 17.57
    4-methyl-2-pentanol 17.18
    propionitrile 47.73
    vinylene carbonate 53.14
    1,1,2-trichlorotrifluoroethane 134.21
    DMS 31.2
    cumene 6.7
    2-octanol 8.24
    2-hexanone 51.36
    octyl acetate 14.45
    limonene 6.16
    1,2-dimethoxyethane 115.79
    ethyl orthosilicate 15.65
    tributyl phosphate 15.6
    diacetone alcohol 68.86
    N,N-dimethylaniline 23.98
    acrylonitrile 59.49
    aniline 36.84
    1,3-propanediol 66.85
    bromobenzene 18.03
    dibromomethane 66.32
    1,1,2,2-tetrachloroethane 138.3
    2-methyl-cyclohexyl acetate 24.61
    tetrabutyl urea 24.04
    diisobutyl methanol 6.95
    2-phenylethanol 36.28
    styrene 11.21
    dioctyl adipate 20.04
    dimethyl sulfate 77.94
    ethyl butyrate 21.55
    methyl lactate 49.52
    butyl lactate 28.09
    diethyl carbonate 16.9
    propanediol butyl ether 37.37
    triethyl orthoformate 18.18
    p-tert-butyltoluene 4.13
    methyl 4-tert-butylbenzoate 34.92
    morpholine 144.37
    tert-butylamine 18.69
    n-dodecanol 5.16
    dimethoxymethane 126.16
    ethylene carbonate 45.31
    cyrene 64.75
    2-ethoxyethyl acetate 34.62
    2-ethylhexyl acetate 22.29
    1,2,4-trichlorobenzene 36.17
    4-methylpyridine 80.6
    dibutyl ether 8.57
    2,6-dimethyl-4-heptanol 6.95
    DEF 87.65
    dimethyl isosorbide 82.67
    tetrachloroethylene 63.85
    eugenol 40.46
    triacetin 30.21
    span 80 33.69
    1,4-butanediol 27.49
    1,1-dichloroethane 70.8
    2-methyl-1-pentanol 44.61
    methyl formate 69.89
    2-methyl-1-butanol 55.64
    n-decane 0.42
    butyronitrile 45.28
    3,7-dimethyl-1-octanol 11.5
    1-chlorooctane 3.84
    1-chlorotetradecane 1.59
    n-nonane 0.32
    undecane 0.33
    tert-butylcyclohexane 0.78
    cyclooctane 0.2
    cyclopentanol 67.67
    tetrahydropyran 68.97
    tert-amyl methyl ether 23.18
    2,5,8-trioxanonane 66.22
    1-hexene 6.99
    2-isopropoxyethanol 54.93
    2,2,2-trifluoroethanol 35.98
    methyl butyrate 46.24

    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