(+-)-Shikonin

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  • Identifiers

    CAS number
    54952-43-1

    Molecular formula
    C16H16O5

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

    Safety labels

    Irritant
    Irritant

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Sweet 42.33%
    Odorless 39.16%
    Spicy 35.31%
    Phenolic 25.47%
    Mint 24.28%
    Herbal 24.0%
    Woody 23.18%
    Balsamic 22.32%
    Vanilla 22.18%
    Bitter 21.76%

     

    Flavor
    Bitter 89.98%
    Odorless 25.91%
    Bland 20.25%
    Cedarleaf 19.85%
    Lovage 19.74%
    Sweet-like 19.1%
    Nitrile 19.02%
    Parsley 18.81%
    Basil 18.79%
    Leaves 18.51%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.0

    pKa est.
    8.38 (weak base)

    Molecular weight
    288.29 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    560°C

    Melting point expt.

    • 116 - 117 °C

    Flash point

    • 231.32 ˚C est.

  • Synonyms

    • 54952-43-1
    • (+-)-Shikonin
    • RefChem:905516
    • SHIKALKIN
    • C.I. Natural Red 20
    • (Rac)-Shikonin
    • 5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione
    • (+/-)-Shikonin
    • ARNEBIN-4
    • (+/-)-Alkannin
    • 5,8-DIHYDROXY-2-(1-HYDROXY-4-METHYLPENT-3-EN-1-YL)NAPHTHALENE-1,4-DIONE
    • MFCD00016668
    • 23444-65-7
    • C.I. 75530
    • NSC94524
    • NSC252844
    • NSC407295
    • 5,8-dihydroxy-2-(1-hydroxy-4-methyl-pent-3-enyl)naphthalene-1,4-dione
    • 5,8-Dihydroxy-6-(1-hydroxy-4-methylpent-3-en-1-yl)naphthalene-1,4-dione
    • 1,4-Naphthalenedione, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)- (9CI)
    • 11019-15-1
    • (+-)-Alkannin
    • C.I. 75535;Isoarnebin 4
    • C.I. Natural Red 20 (VAN)
    • 1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (S)-
    • 1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (-)-
    • 1, 5,8-dihydroxy-6-(1-hydroxy-4-methyl-3-pentenyl)-, (-)-
    • natural red 20
    • Shikonin (7b)
    • (+-)-Shikalkin
    • NSC 291845
    • ALKANNIN, 1-
    • KBioGR_000610
    • KBioSS_000610
    • CHEMBL29285
    • SCHEMBL3182028
    • Shikonin, >=98% (HPLC)
    • SCHEMBL29410804
    • KBio2_000610
    • KBio2_003178
    • KBio2_005746
    • KBio3_001079
    • KBio3_001080
    • NEZONWMXZKDMKF-UHFFFAOYSA-
    • CHEBI:174748
    • BDBM178090
    • Bio2_000475
    • Bio2_000955
    • HMS1362P11
    • ECA95243
    • HY-N6004
    • 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone
    • NSC291845
    • 1,4-Naphthalenedione, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-
    • AKOS016034343
    • ( inverted exclamation markA)-Shikonin
    • EBC-617774
    • NSC-291845
    • NSC-407295
    • 5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)-1,4-dihydronaphthalene-1,4-dione
    • IDI1_002230
    • QTL1_000075
    • SMP2_000188
    • 85251-58-7
    • DA-67567
    • LS-14485
    • NCI60_002031
    • SY232843
    • DB-082640
    • CS-0032051
    • H1780
    • NS00018361
    • NS00123717
    • 952S431
    • 1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-
    • 1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (R)-
    • 1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (+)-
    • InChI=1/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3
    • 54952-43-1

  • Applications

    (+-)-Shikonin (CAS 54952-43-1) is a natural naphthoquinone pigment primarily used as a colorant in cosmetics and in coatings and printing inks; it is also employed as a colorant additive in plastics and other polymer formulations to impart coloration. It is considered a starting material or core structure for organic synthesis and pharmaceutical research, with shikonin derivatives examined in medicinal chemistry. The compound's biological properties and potential agricultural applications are being studied to explore non-pharmaceutical uses.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 15.78
    methanol 17.28
    isopropanol 9.54
    water 0.03
    ethyl acetate 7.73
    n-propanol 15.8
    acetone 19.81
    n-butanol 11.7
    acetonitrile 11.32
    DMF 115.89
    toluene 1.93
    isobutanol 8.23
    1,4-dioxane 17.21
    methyl acetate 16.96
    THF 161.2
    2-butanone 27.27
    n-pentanol 8.41
    sec-butanol 9.68
    n-hexane 0.08
    ethylene glycol 6.14
    NMP 81.91
    cyclohexane 0.11
    DMSO 226.5
    n-butyl acetate 9.59
    n-octanol 3.88
    chloroform 7.59
    n-propyl acetate 8.85
    acetic acid 17.22
    dichloromethane 6.15
    cyclohexanone 28.67
    propylene glycol 8.19
    isopropyl acetate 5.57
    DMAc 170.71
    2-ethoxyethanol 32.19
    isopentanol 10.68
    n-heptane 0.06
    ethyl formate 8.87
    1,2-dichloroethane 7.47
    n-hexanol 8.03
    2-methoxyethanol 66.5
    isobutyl acetate 4.47
    tetrachloromethane 1.11
    n-pentyl acetate 5.0
    transcutol 23.43
    n-heptanol 4.87
    ethylbenzene 2.03
    MIBK 8.35
    2-propoxyethanol 35.49
    tert-butanol 15.9
    MTBE 4.67
    2-butoxyethanol 16.36
    propionic acid 10.8
    o-xylene 2.04
    formic acid 13.21
    diethyl ether 3.26
    m-xylene 1.66
    p-xylene 2.67
    chlorobenzene 2.41
    dimethyl carbonate 11.85
    n-octane 0.06
    formamide 28.67
    cyclopentanone 67.76
    2-pentanone 13.32
    anisole 9.71
    cyclopentyl methyl ether 14.45
    gamma-butyrolactone 53.76
    1-methoxy-2-propanol 39.37
    pyridine 19.99
    3-pentanone 8.56
    furfural 28.39
    n-dodecane 0.1
    diethylene glycol 29.0
    diisopropyl ether 0.79
    tert-amyl alcohol 13.48
    acetylacetone 15.69
    n-hexadecane 0.12
    acetophenone 12.61
    methyl propionate 14.34
    isopentyl acetate 9.67
    trichloroethylene 17.42
    n-nonanol 4.05
    cyclohexanol 7.73
    benzyl alcohol 11.97
    2-ethylhexanol 4.68
    isooctanol 4.09
    dipropyl ether 3.44
    1,2-dichlorobenzene 3.28
    ethyl lactate 9.91
    propylene carbonate 14.84
    n-methylformamide 37.19
    2-pentanol 4.41
    n-pentane 0.04
    1-propoxy-2-propanol 18.55
    1-methoxy-2-propyl acetate 14.3
    2-(2-methoxypropoxy) propanol 16.54
    mesitylene 1.04
    ε-caprolactone 23.0
    p-cymene 1.69
    epichlorohydrin 65.78
    1,1,1-trichloroethane 5.23
    2-aminoethanol 14.42
    morpholine-4-carbaldehyde 48.38
    sulfolane 88.95
    2,2,4-trimethylpentane 0.1
    2-methyltetrahydrofuran 33.7
    n-hexyl acetate 7.35
    isooctane 0.07
    2-(2-butoxyethoxy)ethanol 18.64
    sec-butyl acetate 5.5
    tert-butyl acetate 8.47
    decalin 0.19
    glycerin 19.55
    diglyme 33.91
    acrylic acid 10.21
    isopropyl myristate 2.98
    n-butyric acid 12.18
    acetyl acetate 4.88
    di(2-ethylhexyl) phthalate 5.15
    ethyl propionate 9.22
    nitromethane 38.37
    1,2-diethoxyethane 6.52
    benzonitrile 8.39
    trioctyl phosphate 4.05
    1-bromopropane 2.99
    gamma-valerolactone 57.06
    n-decanol 2.92
    triethyl phosphate 6.89
    4-methyl-2-pentanol 3.73
    propionitrile 12.12
    vinylene carbonate 12.08
    1,1,2-trichlorotrifluoroethane 39.56
    DMS 8.64
    cumene 1.58
    2-octanol 2.69
    2-hexanone 12.84
    octyl acetate 4.47
    limonene 1.96
    1,2-dimethoxyethane 47.33
    ethyl orthosilicate 6.1
    tributyl phosphate 4.52
    diacetone alcohol 24.19
    N,N-dimethylaniline 7.88
    acrylonitrile 17.96
    aniline 7.95
    1,3-propanediol 22.8
    bromobenzene 1.83
    dibromomethane 3.45
    1,1,2,2-tetrachloroethane 15.01
    2-methyl-cyclohexyl acetate 7.81
    tetrabutyl urea 8.19
    diisobutyl methanol 2.56
    2-phenylethanol 12.14
    styrene 2.06
    dioctyl adipate 5.84
    dimethyl sulfate 27.55
    ethyl butyrate 7.09
    methyl lactate 16.84
    butyl lactate 7.57
    diethyl carbonate 6.0
    propanediol butyl ether 11.93
    triethyl orthoformate 6.33
    p-tert-butyltoluene 1.52
    methyl 4-tert-butylbenzoate 11.71
    morpholine 41.13
    tert-butylamine 4.04
    n-dodecanol 2.01
    dimethoxymethane 44.08
    ethylene carbonate 10.09
    cyrene 23.33
    2-ethoxyethyl acetate 8.39
    2-ethylhexyl acetate 6.89
    1,2,4-trichlorobenzene 5.59
    4-methylpyridine 17.15
    dibutyl ether 2.61
    2,6-dimethyl-4-heptanol 2.56
    DEF 22.22
    dimethyl isosorbide 30.07
    tetrachloroethylene 8.05
    eugenol 14.21
    triacetin 8.39
    span 80 10.41
    1,4-butanediol 7.62
    1,1-dichloroethane 4.34
    2-methyl-1-pentanol 8.64
    methyl formate 21.01
    2-methyl-1-butanol 10.45
    n-decane 0.15
    butyronitrile 10.14
    3,7-dimethyl-1-octanol 3.86
    1-chlorooctane 1.23
    1-chlorotetradecane 0.54
    n-nonane 0.1
    undecane 0.12
    tert-butylcyclohexane 0.18
    cyclooctane 0.05
    cyclopentanol 15.29
    tetrahydropyran 14.22
    tert-amyl methyl ether 5.88
    2,5,8-trioxanonane 26.1
    1-hexene 0.74
    2-isopropoxyethanol 17.55
    2,2,2-trifluoroethanol 7.63
    methyl butyrate 14.27

    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