8-ethenyl-5-methylidene-4,4a,6,7,8,8a-hexahydro-3H-naphthalene-2-carboxylic acid

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  • Identifiers

    CAS number
    1451-36-1

    Molecular formula
    C14H18O2

    SMILES
    C=CC1CCC(=C)C2C1C=C(CC2)C(=O)O

  • Odor profile

    Green 74.92%
    Fruity 58.85%
    Woody 37.28%
    Spicy 36.94%
    Herbal 31.42%
    Fresh 27.8%
    Aldehydic 24.26%
    Sweet 23.82%
    Leafy 23.79%
    Fatty 23.65%

    Scent© AI

  • Properties

    XLogP3-AA
    3.0

    pKa est.
    8.12 (weak base)

    Molecular weight
    218.29 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    337°C

    Flash point est.
    157.95 ˚C

  • Synonyms

    • 1451-36-1
    • 8-ethenyl-5-methylidene-4,4a,6,7,8,8a-hexahydro-3H-naphthalene-2-carboxylic acid
    • Khusilic acid
    • Khusiloic acid
    • 2-Naphthoic acid, 3,4,4a,5,6,7,8,8a-octahydro-5-methylene-8-vinyl-
    • DTXSID00340195
    • OBKSUSLJGNFZDQ-UHFFFAOYSA-N
    • 2-Naphthalenecarboxylic acid, 8-ethenyl-3,4,4a,5,6,7,8,8a-octahydro-5-methylene-
    • 5-Methylene-8-vinyl-3,4,4a,5,6,7,8,8a-octahydro-2-naphthalenecarboxylic acid #

  • Applications

    8-ethenyl-5-methylidene-4,4a,6,7,8,8a-hexahydro-3H-naphthalene-2-carboxylic acid (CAS 1451-36-1) is employed as a rigid terpenoid building block in organic and medicinal synthesis, where the carboxylic acid and exocyclic double bonds enable selective, stereocontrolled derivatization (esterification for fragrance esters, amidation for bioactive precursors, and halogenation/epoxidation/hydroxylation to expand derivative libraries); in flavor–fragrance and cosmetics it serves as a precursor to esters, lactones and anhydrides with woody–resinous notes or as an odor modulator, while rosin-like derivatives contribute to improved tack, compatibility and film integrity in adhesives, coatings and printing inks; in materials and polymers its hydrophobic decalin scaffold underpins monomers/additives with high rigidity and thermal stability (e.g., acrylate or maleate attachment for copolymerization), enhancing mechanical strength and chemical resistance; in research it functions as a reference/model compound to study resin-acid metabolism, surface hydrophobicity, self-assembly and protein–membrane interactions, and as a precursor to bio-based surfactants and organic ligands; additionally, its salts or complexes can act as structuring agents, compatibilizers or pH-modifying components in emulsions and technical formulations, with terpene-derived credentials supporting more sustainable application routes.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 142.14
    methanol 220.81
    isopropanol 98.66
    water 0.17
    ethyl acetate 177.16
    n-propanol 144.56
    acetone 190.55
    n-butanol 114.76
    acetonitrile 63.36
    DMF 345.8
    toluene 144.62
    isobutanol 87.97
    1,4-dioxane 284.19
    methyl acetate 127.59
    THF 598.61
    2-butanone 218.25
    n-pentanol 66.47
    sec-butanol 85.49
    n-hexane 3.0
    ethylene glycol 33.41
    NMP 423.19
    cyclohexane 4.93
    DMSO 627.43
    n-butyl acetate 119.31
    n-octanol 18.61
    chloroform 247.25
    n-propyl acetate 84.6
    acetic acid 92.96
    dichloromethane 283.21
    cyclohexanone 282.88
    propylene glycol 47.33
    isopropyl acetate 113.41
    DMAc 292.01
    2-ethoxyethanol 170.7
    isopentanol 116.49
    n-heptane 1.54
    ethyl formate 80.83
    1,2-dichloroethane 280.78
    n-hexanol 80.92
    2-methoxyethanol 329.62
    isobutyl acetate 45.41
    tetrachloromethane 38.23
    n-pentyl acetate 63.14
    transcutol 1149.23
    n-heptanol 35.95
    ethylbenzene 48.41
    MIBK 119.24
    2-propoxyethanol 231.24
    tert-butanol 124.86
    MTBE 107.09
    2-butoxyethanol 118.47
    propionic acid 99.87
    o-xylene 75.63
    formic acid 76.33
    diethyl ether 118.01
    m-xylene 92.57
    p-xylene 45.55
    chlorobenzene 130.5
    dimethyl carbonate 100.32
    n-octane 0.57
    formamide 171.58
    cyclopentanone 439.49
    2-pentanone 200.92
    anisole 132.76
    cyclopentyl methyl ether 231.74
    gamma-butyrolactone 469.8
    1-methoxy-2-propanol 277.33
    pyridine 281.34
    3-pentanone 142.69
    furfural 359.99
    n-dodecane 0.38
    diethylene glycol 177.79
    diisopropyl ether 32.77
    tert-amyl alcohol 104.28
    acetylacetone 213.52
    n-hexadecane 0.47
    acetophenone 122.95
    methyl propionate 178.13
    isopentyl acetate 110.33
    trichloroethylene 553.09
    n-nonanol 18.08
    cyclohexanol 99.69
    benzyl alcohol 125.28
    2-ethylhexanol 39.34
    isooctanol 30.02
    dipropyl ether 40.8
    1,2-dichlorobenzene 120.78
    ethyl lactate 51.76
    propylene carbonate 172.32
    n-methylformamide 247.61
    2-pentanol 71.26
    n-pentane 3.1
    1-propoxy-2-propanol 151.38
    1-methoxy-2-propyl acetate 187.06
    2-(2-methoxypropoxy) propanol 129.41
    mesitylene 44.6
    ε-caprolactone 242.16
    p-cymene 23.53
    epichlorohydrin 621.36
    1,1,1-trichloroethane 144.36
    2-aminoethanol 84.55
    morpholine-4-carbaldehyde 375.47
    sulfolane 588.9
    2,2,4-trimethylpentane 2.89
    2-methyltetrahydrofuran 329.14
    n-hexyl acetate 75.87
    isooctane 3.0
    2-(2-butoxyethoxy)ethanol 219.92
    sec-butyl acetate 64.16
    tert-butyl acetate 138.65
    decalin 4.18
    glycerin 90.96
    diglyme 385.91
    acrylic acid 94.77
    isopropyl myristate 21.79
    n-butyric acid 140.76
    acetyl acetate 75.89
    di(2-ethylhexyl) phthalate 38.39
    ethyl propionate 80.59
    nitromethane 218.53
    1,2-diethoxyethane 167.61
    benzonitrile 104.52
    trioctyl phosphate 22.97
    1-bromopropane 81.95
    gamma-valerolactone 532.46
    n-decanol 12.02
    triethyl phosphate 37.14
    4-methyl-2-pentanol 50.4
    propionitrile 84.83
    vinylene carbonate 145.1
    1,1,2-trichlorotrifluoroethane 311.14
    DMS 97.29
    cumene 28.33
    2-octanol 16.93
    2-hexanone 92.27
    octyl acetate 30.18
    limonene 28.33
    1,2-dimethoxyethane 231.71
    ethyl orthosilicate 35.74
    tributyl phosphate 30.71
    diacetone alcohol 197.21
    N,N-dimethylaniline 76.18
    acrylonitrile 121.48
    aniline 205.68
    1,3-propanediol 143.37
    bromobenzene 114.66
    dibromomethane 147.36
    1,1,2,2-tetrachloroethane 391.12
    2-methyl-cyclohexyl acetate 59.72
    tetrabutyl urea 37.49
    diisobutyl methanol 25.03
    2-phenylethanol 113.67
    styrene 56.27
    dioctyl adipate 43.34
    dimethyl sulfate 181.06
    ethyl butyrate 69.67
    methyl lactate 100.07
    butyl lactate 73.89
    diethyl carbonate 43.33
    propanediol butyl ether 120.58
    triethyl orthoformate 50.54
    p-tert-butyltoluene 23.47
    methyl 4-tert-butylbenzoate 93.13
    morpholine 401.83
    tert-butylamine 53.89
    n-dodecanol 7.67
    dimethoxymethane 330.32
    ethylene carbonate 111.53
    cyrene 126.75
    2-ethoxyethyl acetate 144.9
    2-ethylhexyl acetate 78.25
    1,2,4-trichlorobenzene 160.56
    4-methylpyridine 288.33
    dibutyl ether 23.53
    2,6-dimethyl-4-heptanol 25.03
    DEF 209.17
    dimethyl isosorbide 231.16
    tetrachloroethylene 252.42
    eugenol 99.8
    triacetin 93.77
    span 80 91.56
    1,4-butanediol 41.38
    1,1-dichloroethane 162.67
    2-methyl-1-pentanol 70.72
    methyl formate 155.56
    2-methyl-1-butanol 96.11
    n-decane 0.76
    butyronitrile 72.65
    3,7-dimethyl-1-octanol 29.25
    1-chlorooctane 8.84
    1-chlorotetradecane 2.42
    n-nonane 0.65
    undecane 0.52
    tert-butylcyclohexane 3.96
    cyclooctane 2.17
    cyclopentanol 125.74
    tetrahydropyran 245.81
    tert-amyl methyl ether 82.36
    2,5,8-trioxanonane 226.2
    1-hexene 17.36
    2-isopropoxyethanol 115.65
    2,2,2-trifluoroethanol 51.99
    methyl butyrate 97.58

    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 1.2%