Arnebin I

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  • Identifiers

    CAS number
    5162-01-6

    Molecular formula
    C21H22O6

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

    Safety labels

  • Odor profile

    Fragrance
    Herbal 44.09%
    Sweet 43.59%
    Mint 37.0%
    Spicy 35.48%
    Green 34.74%
    Fruity 31.28%
    Woody 31.0%
    Floral 28.92%
    Odorless 28.11%
    Warm 25.69%

     

    Flavor
    Bitter 84.1%
    Odorless 25.9%
    Bland 20.09%
    Cedarleaf 19.86%
    Lovage 19.77%
    Heather 19.61%
    Broom 19.55%
    Parsley 19.25%
    Genet 19.2%
    Basil 19.1%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    5.0

    pKa est.
    7.83 (neutral)

    Molecular weight
    370.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    546°C

    Flash point

    • 227.68 ˚C est.

  • Synonyms

    • Arnebin I
    • 5162-01-6
    • RefChem:119136
    • Beta, beta-dimethylacrylshikonin
    • Dmask
    • Arnebin 1
    • (Rac)-Arnebin 1
    • (beta,beta-Dimethylacryl)shikonin
    • [1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-methylbut-2-enoate
    • Isoarnebin I
    • NSC140377
    • 34539-65-6
    • 1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbut-2-enoate
    • 23444-70-4
    • 2-Butenoic acid, 3-methyl-, 1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester, (+)-
    • Alkanin,.beta.-dimethylacrylate
    • orb1302734
    • SCHEMBL4279672
    • CHEMBL2002642
    • SCHEMBL29391875
    • DTXSID10947396
    • beta,beta'-Dimethyl-acry-lalkannin
    • HY-N5112
    • .beta.,.beta.-Dimethylacrylshikonin
    • AKOS037515608
    • EBC-615561
    • NSC-140377
    • 5,8-Dihydroxy-2-[1-(beta,beta-dimethylacryloyloxy)-4-methyl-3-pentenyl]-1,4-naphthalenedione
    • Shikonin .beta.,.beta.-dimethylacrylate
    • NCI60_000890
    • DS-013077
    • CS-0032426
    • D2118
    • [1-(5,8-dihydroxy-1,4-dioxo-2-naphthyl)-4-methyl-pent-3-enyl] 3-methylbut-2-enoate
    • 1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-4-methyl-3-pentenyl 3-methyl-2-butenoate #
    • 2-Butenoic acid, 1-(5,8-dihydro- 1,4-dihydroxy-5,8-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester
    • 2-Butenoic acid, 3-methyl-, 1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester
    • 2-Butenoic acid,3-methyl-,1-(5,8-dihydro-1,4-dihydroxy-5,8-dioxo-2-naphthalenyl)-4-methyl-3-pentenylester, (s)-(9ci)
    • Crotonic acid, 3-methyl-, ester with 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone
    • 5162-01-6

  • Applications

    Arnebin I (CAS 5162-01-6) is seen as an intermediate in organic synthesis and may be used as a solvent or processing aid in a range of industrial formulations; it can also act as a stabilizer and/or metal-chelating agent in plastic and polymer systems; it is used as a component in coatings, inks, and adhesives and is considered for applications in the polymer and plastics sector as well as plastic processing; other potential uses include cleaning formulations and surface-finishing aids, depending on formulation requirements and local regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 35.48
    methanol 29.73
    isopropanol 29.65
    water 0.01
    ethyl acetate 28.73
    n-propanol 41.75
    acetone 93.42
    n-butanol 32.94
    acetonitrile 28.62
    DMF 228.69
    toluene 11.09
    isobutanol 25.45
    1,4-dioxane 56.55
    methyl acetate 48.53
    THF 340.15
    2-butanone 87.74
    n-pentanol 26.24
    sec-butanol 36.75
    n-hexane 0.64
    ethylene glycol 4.18
    NMP 217.46
    cyclohexane 0.61
    DMSO 325.36
    n-butyl acetate 24.62
    n-octanol 7.09
    chloroform 97.35
    n-propyl acetate 26.18
    acetic acid 58.84
    dichloromethane 73.03
    cyclohexanone 88.71
    propylene glycol 12.92
    isopropyl acetate 18.83
    DMAc 330.29
    2-ethoxyethanol 56.97
    isopentanol 25.51
    n-heptane 0.25
    ethyl formate 23.45
    1,2-dichloroethane 53.94
    n-hexanol 17.49
    2-methoxyethanol 94.02
    isobutyl acetate 15.33
    tetrachloromethane 5.07
    n-pentyl acetate 14.56
    transcutol 63.74
    n-heptanol 9.27
    ethylbenzene 7.98
    MIBK 26.71
    2-propoxyethanol 64.71
    tert-butanol 31.31
    MTBE 17.02
    2-butoxyethanol 31.8
    propionic acid 32.4
    o-xylene 7.39
    formic acid 17.2
    diethyl ether 19.67
    m-xylene 6.24
    p-xylene 10.51
    chlorobenzene 16.25
    dimethyl carbonate 28.54
    n-octane 0.18
    formamide 34.01
    cyclopentanone 162.14
    2-pentanone 53.32
    anisole 26.06
    cyclopentyl methyl ether 42.45
    gamma-butyrolactone 139.06
    1-methoxy-2-propanol 72.24
    pyridine 65.79
    3-pentanone 37.64
    furfural 64.8
    n-dodecane 0.28
    diethylene glycol 33.78
    diisopropyl ether 3.05
    tert-amyl alcohol 33.06
    acetylacetone 47.45
    n-hexadecane 0.32
    acetophenone 32.83
    methyl propionate 44.75
    isopentyl acetate 23.15
    trichloroethylene 112.01
    n-nonanol 7.67
    cyclohexanol 26.61
    benzyl alcohol 28.56
    2-ethylhexanol 10.24
    isooctanol 7.95
    dipropyl ether 10.15
    1,2-dichlorobenzene 16.22
    ethyl lactate 20.66
    propylene carbonate 46.12
    n-methylformamide 65.88
    2-pentanol 17.82
    n-pentane 0.46
    1-propoxy-2-propanol 37.95
    1-methoxy-2-propyl acetate 33.69
    2-(2-methoxypropoxy) propanol 34.96
    mesitylene 3.06
    ε-caprolactone 68.91
    p-cymene 3.95
    epichlorohydrin 170.24
    1,1,1-trichloroethane 34.44
    2-aminoethanol 16.84
    morpholine-4-carbaldehyde 124.78
    sulfolane 205.47
    2,2,4-trimethylpentane 0.51
    2-methyltetrahydrofuran 94.3
    n-hexyl acetate 18.51
    isooctane 0.24
    2-(2-butoxyethoxy)ethanol 38.1
    sec-butyl acetate 16.48
    tert-butyl acetate 21.53
    decalin 0.79
    glycerin 20.49
    diglyme 66.19
    acrylic acid 29.44
    isopropyl myristate 7.91
    n-butyric acid 39.68
    acetyl acetate 16.27
    di(2-ethylhexyl) phthalate 12.54
    ethyl propionate 24.23
    nitromethane 106.88
    1,2-diethoxyethane 20.68
    benzonitrile 23.28
    trioctyl phosphate 9.02
    1-bromopropane 28.39
    gamma-valerolactone 151.92
    n-decanol 5.71
    triethyl phosphate 14.24
    4-methyl-2-pentanol 10.01
    propionitrile 33.02
    vinylene carbonate 35.04
    1,1,2-trichlorotrifluoroethane 89.64
    DMS 22.78
    cumene 5.48
    2-octanol 5.97
    2-hexanone 39.24
    octyl acetate 11.28
    limonene 5.39
    1,2-dimethoxyethane 92.08
    ethyl orthosilicate 12.81
    tributyl phosphate 11.55
    diacetone alcohol 46.76
    N,N-dimethylaniline 20.29
    acrylonitrile 39.91
    aniline 25.76
    1,3-propanediol 31.67
    bromobenzene 13.64
    dibromomethane 45.96
    1,1,2,2-tetrachloroethane 94.2
    2-methyl-cyclohexyl acetate 19.02
    tetrabutyl urea 18.86
    diisobutyl methanol 5.37
    2-phenylethanol 24.94
    styrene 9.41
    dioctyl adipate 15.6
    dimethyl sulfate 58.01
    ethyl butyrate 17.5
    methyl lactate 32.12
    butyl lactate 18.05
    diethyl carbonate 13.27
    propanediol butyl ether 21.73
    triethyl orthoformate 14.97
    p-tert-butyltoluene 3.54
    methyl 4-tert-butylbenzoate 26.28
    morpholine 113.91
    tert-butylamine 11.0
    n-dodecanol 4.14
    dimethoxymethane 97.66
    ethylene carbonate 29.55
    cyrene 46.43
    2-ethoxyethyl acetate 23.17
    2-ethylhexyl acetate 16.86
    1,2,4-trichlorobenzene 25.63
    4-methylpyridine 60.18
    dibutyl ether 7.68
    2,6-dimethyl-4-heptanol 5.37
    DEF 65.37
    dimethyl isosorbide 63.75
    tetrachloroethylene 42.2
    eugenol 28.88
    triacetin 21.8
    span 80 22.65
    1,4-butanediol 12.26
    1,1-dichloroethane 45.65
    2-methyl-1-pentanol 25.07
    methyl formate 40.72
    2-methyl-1-butanol 29.24
    n-decane 0.44
    butyronitrile 30.04
    3,7-dimethyl-1-octanol 8.32
    1-chlorooctane 3.55
    1-chlorotetradecane 1.54
    n-nonane 0.32
    undecane 0.34
    tert-butylcyclohexane 0.68
    cyclooctane 0.18
    cyclopentanol 44.22
    tetrahydropyran 59.63
    tert-amyl methyl ether 18.65
    2,5,8-trioxanonane 49.46
    1-hexene 5.44
    2-isopropoxyethanol 35.14
    2,2,2-trifluoroethanol 16.6
    methyl butyrate 35.53

    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