Aristolone

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  • Identifiers

    CAS number
    6831-17-0

    Molecular formula
    C15H22O

    SMILES
    C[C@@H]1CCCC2=CC(=O)[C@@H]3[C@H]([C@@]12C)C3(C)C

    Retention indicies (RI)

    • DB5: 1756.0

  • Odor profile

    Woody 79.78%
    Cedar 49.1%
    Amber 44.71%
    Dry 41.02%
    Spicy 40.1%
    Fruity 37.87%
    Tobacco 32.53%
    Musk 30.17%
    Vetiver 30.04%
    Camphoreous 29.35%

    Scent© AI

  • Properties

    XLogP3-AA
    3.6

    pKa est.
    8.42 (weak base)

    Molecular weight
    218.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    321°C

    Flash point est.
    112.2 ˚C

  • Synonyms

    • Aristolone
    • 25274-27-5
    • 6831-17-0
    • Aristofone
    • (1aR,7R,7aR,7bS)-1,1,7,7a-tetramethyl-1a,4,5,6,7,7b-hexahydrocyclopropa[a]naphthalen-2-one
    • Aristol-9-en-8-one
    • (1aR)-1,1abeta,4,5,6,7,7a,7bbeta-Octahydro-1,1,7beta,7abeta-tetramethyl-2H-cyclopropa[a]naphthalen-2-one
    • (1aR,7R,7aR,7bS)-1,1,7,7a-Tetramethyl-1,1a,4,5,6,7,7a,7b-octahydro-2H-cyclopropa[a]naphthalen-2-one
    • 2H-Cyclopropa(a)naphthalen-2-one, 1,1a,4,5,6,7,7a,7b-octahydro-1,1,7,7a-tetramethyl-, (1aalpha,7alpha,7aalpha,7balpha)-
    • (1aR,7R,7aR,7bS)-1,1,7,7a-tetramethyl-1a,4,5,6,7,7b-hexahydrocyclopropa(a)naphthalen-2-one
    • Aristolone, (-)-isomer
    • CHEMBL512374
    • HY-N1464A
    • DTXSID10987838
    • 2H-Cyclopropa[a]naphthalen-2-one, 1,1a,4,5,6,7,7a,7b-octahydro-1,1,7,7a-tetramethyl-, (1a.alpha.,7.alpha.,7a.alpha.,7b.alpha.)-
    • 2H-Cyclopropa[a]naphthalen-2-one, 1,1a.beta.,4,5,6,7,7a,7b.beta.-octahydro-1,1,7.beta.,7a.beta.-tetramethyl-
    • MFCD22479204
    • s9283
    • CCG-266712
    • AC-34518
    • DA-50699
    • FA145208
    • MS-23208
    • CS-0019590
    • 2H-Cyclopropa(a)naphthalen-2-one, 1,1abeta,4,5,6,7,7a,7bbeta-octahydro-1,1,7beta,7abeta-tetramethyl-

  • Applications

    Aristolone (CAS 6831-17-0) is a sesquiterpene ketone with a dry woody, slightly camphoraceous odor, applied mainly in flavor–fragrance and natural products research: as an analytical reference/standard for GC–MS/GC–FID to identify and quantify trace levels in essential oils and plant extracts; as a tonal modifier contributing woody–herbal facets in the development of fine fragrances, candles, and household cleaners due to its odor tenacity and drying effect; as a chemical marker for botanical authentication and quality control of herbal materials, teas, and spices; as a model compound to study sesquiterpene biosynthesis, spectral characterization, and stereochemical rearrangements of bicyclic frameworks; as a substrate in studies of stability, matrix interactions, and odor release in microencapsulation systems; and it is often evaluated in vitro for exploratory bioactivities (e.g., antimicrobial, antioxidant) as an early screening lead, without implying therapeutic use.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 73.95
    methanol 69.55
    isopropanol 83.5
    water 0.67
    ethyl acetate 119.59
    n-propanol 80.67
    acetone 162.35
    n-butanol 78.82
    acetonitrile 115.31
    DMF 214.1
    toluene 182.29
    isobutanol 66.69
    1,4-dioxane 260.8
    methyl acetate 127.66
    THF 459.65
    2-butanone 149.7
    n-pentanol 48.13
    sec-butanol 60.79
    n-hexane 8.54
    ethylene glycol 25.71
    NMP 202.97
    cyclohexane 25.17
    DMSO 91.67
    n-butyl acetate 95.94
    n-octanol 42.54
    chloroform 368.53
    n-propyl acetate 71.33
    acetic acid 61.83
    dichloromethane 300.35
    cyclohexanone 247.04
    propylene glycol 32.72
    isopropyl acetate 94.06
    DMAc 158.72
    2-ethoxyethanol 68.77
    isopentanol 66.65
    n-heptane 11.17
    ethyl formate 73.5
    1,2-dichloroethane 174.1
    n-hexanol 84.97
    2-methoxyethanol 119.54
    isobutyl acetate 64.25
    tetrachloromethane 66.45
    n-pentyl acetate 80.87
    transcutol 115.9
    n-heptanol 50.93
    ethylbenzene 75.62
    MIBK 97.85
    2-propoxyethanol 148.83
    tert-butanol 84.51
    MTBE 92.02
    2-butoxyethanol 85.24
    propionic acid 68.97
    o-xylene 103.88
    formic acid 21.98
    diethyl ether 99.1
    m-xylene 130.87
    p-xylene 99.37
    chlorobenzene 170.64
    dimethyl carbonate 72.56
    n-octane 6.1
    formamide 42.87
    cyclopentanone 324.2
    2-pentanone 127.99
    anisole 117.75
    cyclopentyl methyl ether 173.07
    gamma-butyrolactone 288.58
    1-methoxy-2-propanol 114.85
    pyridine 254.45
    3-pentanone 106.25
    furfural 208.61
    n-dodecane 5.88
    diethylene glycol 103.81
    diisopropyl ether 42.42
    tert-amyl alcohol 59.25
    acetylacetone 150.41
    n-hexadecane 6.98
    acetophenone 112.11
    methyl propionate 112.56
    isopentyl acetate 102.92
    trichloroethylene 325.27
    n-nonanol 42.32
    cyclohexanol 90.32
    benzyl alcohol 90.8
    2-ethylhexanol 56.07
    isooctanol 44.51
    dipropyl ether 53.75
    1,2-dichlorobenzene 146.69
    ethyl lactate 47.92
    propylene carbonate 146.94
    n-methylformamide 95.47
    2-pentanol 58.11
    n-pentane 12.91
    1-propoxy-2-propanol 96.25
    1-methoxy-2-propyl acetate 128.39
    2-(2-methoxypropoxy) propanol 78.34
    mesitylene 76.57
    ε-caprolactone 179.94
    p-cymene 52.67
    epichlorohydrin 298.42
    1,1,1-trichloroethane 180.68
    2-aminoethanol 45.99
    morpholine-4-carbaldehyde 210.25
    sulfolane 219.29
    2,2,4-trimethylpentane 8.45
    2-methyltetrahydrofuran 228.49
    n-hexyl acetate 100.54
    isooctane 9.43
    2-(2-butoxyethoxy)ethanol 86.74
    sec-butyl acetate 61.27
    tert-butyl acetate 97.85
    decalin 15.61
    glycerin 44.61
    diglyme 155.27
    acrylic acid 65.25
    isopropyl myristate 47.7
    n-butyric acid 90.0
    acetyl acetate 92.66
    di(2-ethylhexyl) phthalate 54.65
    ethyl propionate 76.12
    nitromethane 130.81
    1,2-diethoxyethane 67.91
    benzonitrile 146.47
    trioctyl phosphate 39.31
    1-bromopropane 109.85
    gamma-valerolactone 303.94
    n-decanol 33.44
    triethyl phosphate 45.2
    4-methyl-2-pentanol 45.8
    propionitrile 119.16
    vinylene carbonate 145.29
    1,1,2-trichlorotrifluoroethane 139.7
    DMS 110.94
    cumene 52.09
    2-octanol 35.91
    2-hexanone 77.34
    octyl acetate 56.23
    limonene 60.88
    1,2-dimethoxyethane 120.2
    ethyl orthosilicate 44.07
    tributyl phosphate 40.34
    diacetone alcohol 101.49
    N,N-dimethylaniline 77.19
    acrylonitrile 146.18
    aniline 128.46
    1,3-propanediol 66.14
    bromobenzene 191.61
    dibromomethane 197.82
    1,1,2,2-tetrachloroethane 218.19
    2-methyl-cyclohexyl acetate 82.57
    tetrabutyl urea 52.98
    diisobutyl methanol 37.13
    2-phenylethanol 125.3
    styrene 82.58
    dioctyl adipate 56.6
    dimethyl sulfate 98.31
    ethyl butyrate 72.98
    methyl lactate 61.89
    butyl lactate 62.32
    diethyl carbonate 53.76
    propanediol butyl ether 60.88
    triethyl orthoformate 56.53
    p-tert-butyltoluene 52.04
    methyl 4-tert-butylbenzoate 104.66
    morpholine 229.39
    tert-butylamine 57.48
    n-dodecanol 26.02
    dimethoxymethane 158.87
    ethylene carbonate 120.01
    cyrene 94.64
    2-ethoxyethyl acetate 111.09
    2-ethylhexyl acetate 86.2
    1,2,4-trichlorobenzene 166.49
    4-methylpyridine 238.31
    dibutyl ether 39.81
    2,6-dimethyl-4-heptanol 37.13
    DEF 111.19
    dimethyl isosorbide 148.93
    tetrachloroethylene 152.46
    eugenol 93.61
    triacetin 93.19
    span 80 69.38
    1,4-butanediol 31.3
    1,1-dichloroethane 176.22
    2-methyl-1-pentanol 47.01
    methyl formate 85.82
    2-methyl-1-butanol 61.13
    n-decane 9.59
    butyronitrile 102.76
    3,7-dimethyl-1-octanol 45.14
    1-chlorooctane 36.77
    1-chlorotetradecane 17.37
    n-nonane 8.23
    undecane 7.44
    tert-butylcyclohexane 14.22
    cyclooctane 10.77
    cyclopentanol 104.52
    tetrahydropyran 215.34
    tert-amyl methyl ether 63.41
    2,5,8-trioxanonane 109.79
    1-hexene 30.22
    2-isopropoxyethanol 61.4
    2,2,2-trifluoroethanol 40.7
    methyl butyrate 85.7

    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
Amomum muricarpum Amomum muricarpum Elm, fam. Zingiberaceae 3.0%
Spikenard 1 8022-22-8 Nardostachys jatamansi (Roxb.) DC., fam. Valerianaceae 1.0%
Snakeroot, Canadian 8016-69-1 Asarum canadense L., fam. Aristolochiaceae 0.79%
Patchouli (China) 1 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.85%
Psiadia viscosa Psiadia viscosa (Lam.) A.J. Scott, fam. Asteraceae (Compositae) 1.05%
Eugenia banderensis leaf (Cuba) Eugenia banderensis Urb., fam. Myrtaceae 0.92%
Patchouli (China) 2 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 1.17%
Patchouli (India) 2 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.01%
Cyperus maculatus rhizome Cyperus maculatus Boeck, fam. Cyperaceae 1.5%