(2R,4aR,5S,8aS)-1,2,3,4,4a,5,8,8a-Octahydro-5-hydroxy-4a-methyl-alpha,8-bis(methylene)-2-naphthaleneacetic acid

Overview IFRA Request a quote

  • Identifiers

    CAS number
    135594-81-9

    Molecular formula
    C15H20O3

    SMILES
    C[C@@]12CC[C@H](C[C@H]1C(=C)C=C[C@@H]2O)C(=C)C(=O)O

    Safety labels

  • Odor profile

    Fragrance
    Mint 40.62%
    Green 36.27%
    Woody 34.75%
    Spicy 34.25%
    Fruity 33.42%
    Herbal 30.03%
    Odorless 28.45%
    Sweet 26.76%
    Cooling 26.59%
    Camphoreous 24.37%

     

    Flavor
    Bitter 60.34%
    Odorless 26.68%
    Basil 21.2%
    Nitrile 20.77%
    Cedarleaf 20.62%
    Leaves 20.43%
    Fenugreek 20.4%
    Lovage 20.14%
    Maple syrup 19.73%
    Seedy 19.55%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.5

    pKa est.
    7.49 (neutral)

    Molecular weight
    248.32 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    426°C

    Flash point

    • 190.09 ˚C est.

  • Synonyms

    • 135594-81-9
    • RefChem:68895
    • (2R,4aR,5S,8aS)-1,2,3,4,4a,5,8,8a-Octahydro-5-hydroxy-4a-methyl-alpha,8-bis(methylene)-2-naphthaleneacetic acid
    • DTXSID501109539
    • (2R,4aR,5S,8aS)-1,2,3,4,4a,5,8,8a-Octahydro-5-hydroxy-4a-methyl-I+/-,8-bis(methylene)-2-naphthaleneacetic acid
    • 135594-81-9

  • Applications

    For reference, the chemical name is (2R,4aR,5S,8aS)-1,2,3,4,4a,5,8,8a-Octahydro-5-hydroxy-4a-methyl-alpha,8-bis(methylene)-2-naphthaleneacetic acid (CAS 135594-81-9). Owing to its chiral naphthaleneacetic acid framework, the compound is typically considered as a plant growth regulator (auxin analogue) used to promote rooting and shoot development in cuttings and tissue-culture systems; it may also serve as a chiral building block or intermediate in the synthesis of pharmaceutical and agrochemical compounds, enabling asymmetric synthesis and SAR exploration; in chemical research and development it can function as a scaffold for designing related fine chemicals and specialized intermediates, including use as a precursor for chiral ligands or catalysts in asymmetric synthesis.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 54.75
    methanol 93.03
    isopropanol 36.12
    water 0.2
    ethyl acetate 53.52
    n-propanol 45.6
    acetone 26.49
    n-butanol 41.33
    acetonitrile 8.23
    DMF 65.5
    toluene 38.15
    isobutanol 25.11
    1,4-dioxane 128.72
    methyl acetate 30.24
    THF 233.73
    2-butanone 46.15
    n-pentanol 19.52
    sec-butanol 26.42
    n-hexane 0.76
    ethylene glycol 9.95
    NMP 60.56
    cyclohexane 1.34
    DMSO 92.55
    n-butyl acetate 35.77
    n-octanol 8.48
    chloroform 33.94
    n-propyl acetate 20.64
    acetic acid 28.57
    dichloromethane 25.99
    cyclohexanone 60.54
    propylene glycol 14.06
    isopropyl acetate 41.32
    DMAc 104.02
    2-ethoxyethanol 81.96
    isopentanol 41.12
    n-heptane 0.7
    ethyl formate 16.5
    1,2-dichloroethane 28.86
    n-hexanol 40.8
    2-methoxyethanol 152.82
    isobutyl acetate 12.22
    tetrachloromethane 7.78
    n-pentyl acetate 21.73
    transcutol 303.02
    n-heptanol 20.5
    ethylbenzene 13.7
    MIBK 42.5
    2-propoxyethanol 131.03
    tert-butanol 67.59
    MTBE 44.41
    2-butoxyethanol 61.38
    propionic acid 22.01
    o-xylene 25.44
    formic acid 34.85
    diethyl ether 42.02
    m-xylene 34.25
    p-xylene 13.6
    chlorobenzene 21.57
    dimethyl carbonate 30.29
    n-octane 0.37
    formamide 64.99
    cyclopentanone 85.34
    2-pentanone 50.98
    anisole 42.23
    cyclopentyl methyl ether 71.58
    gamma-butyrolactone 88.89
    1-methoxy-2-propanol 127.71
    pyridine 61.28
    3-pentanone 31.9
    furfural 75.0
    n-dodecane 0.26
    diethylene glycol 100.0
    diisopropyl ether 12.82
    tert-amyl alcohol 48.6
    acetylacetone 59.05
    n-hexadecane 0.3
    acetophenone 33.99
    methyl propionate 47.12
    isopentyl acetate 39.57
    trichloroethylene 65.33
    n-nonanol 9.15
    cyclohexanol 30.56
    benzyl alcohol 36.34
    2-ethylhexanol 17.78
    isooctanol 16.46
    dipropyl ether 16.09
    1,2-dichlorobenzene 20.82
    ethyl lactate 19.83
    propylene carbonate 37.67
    n-methylformamide 52.87
    2-pentanol 25.48
    n-pentane 0.96
    1-propoxy-2-propanol 80.67
    1-methoxy-2-propyl acetate 80.66
    2-(2-methoxypropoxy) propanol 56.93
    mesitylene 18.44
    ε-caprolactone 56.15
    p-cymene 10.18
    epichlorohydrin 134.79
    1,1,1-trichloroethane 22.18
    2-aminoethanol 30.54
    morpholine-4-carbaldehyde 108.42
    sulfolane 97.69
    2,2,4-trimethylpentane 1.2
    2-methyltetrahydrofuran 85.48
    n-hexyl acetate 23.65
    isooctane 1.47
    2-(2-butoxyethoxy)ethanol 88.95
    sec-butyl acetate 20.33
    tert-butyl acetate 63.06
    decalin 1.21
    glycerin 37.52
    diglyme 154.74
    acrylic acid 20.65
    isopropyl myristate 8.65
    n-butyric acid 43.23
    acetyl acetate 23.15
    di(2-ethylhexyl) phthalate 13.88
    ethyl propionate 23.36
    nitromethane 44.48
    1,2-diethoxyethane 55.88
    benzonitrile 20.28
    trioctyl phosphate 9.58
    1-bromopropane 11.53
    gamma-valerolactone 131.21
    n-decanol 6.54
    triethyl phosphate 15.7
    4-methyl-2-pentanol 24.17
    propionitrile 13.95
    vinylene carbonate 30.64
    1,1,2-trichlorotrifluoroethane 75.81
    DMS 27.87
    cumene 9.86
    2-octanol 8.86
    2-hexanone 21.81
    octyl acetate 11.23
    limonene 10.9
    1,2-dimethoxyethane 103.94
    ethyl orthosilicate 16.26
    tributyl phosphate 10.22
    diacetone alcohol 91.79
    N,N-dimethylaniline 28.08
    acrylonitrile 19.25
    aniline 55.37
    1,3-propanediol 65.01
    bromobenzene 18.6
    dibromomethane 16.02
    1,1,2,2-tetrachloroethane 57.03
    2-methyl-cyclohexyl acetate 22.95
    tetrabutyl urea 14.48
    diisobutyl methanol 12.82
    2-phenylethanol 48.66
    styrene 12.55
    dioctyl adipate 14.27
    dimethyl sulfate 50.95
    ethyl butyrate 23.01
    methyl lactate 34.9
    butyl lactate 26.37
    diethyl carbonate 14.96
    propanediol butyl ether 44.54
    triethyl orthoformate 20.7
    p-tert-butyltoluene 11.35
    methyl 4-tert-butylbenzoate 39.21
    morpholine 148.9
    tert-butylamine 25.94
    n-dodecanol 4.34
    dimethoxymethane 135.77
    ethylene carbonate 26.87
    cyrene 51.73
    2-ethoxyethyl acetate 49.48
    2-ethylhexyl acetate 25.17
    1,2,4-trichlorobenzene 27.31
    4-methylpyridine 60.41
    dibutyl ether 8.08
    2,6-dimethyl-4-heptanol 12.82
    DEF 45.95
    dimethyl isosorbide 105.0
    tetrachloroethylene 42.95
    eugenol 43.24
    triacetin 29.74
    span 80 37.58
    1,4-butanediol 14.87
    1,1-dichloroethane 20.67
    2-methyl-1-pentanol 22.19
    methyl formate 36.7
    2-methyl-1-butanol 29.22
    n-decane 0.46
    butyronitrile 14.8
    3,7-dimethyl-1-octanol 13.03
    1-chlorooctane 3.11
    1-chlorotetradecane 1.15
    n-nonane 0.36
    undecane 0.33
    tert-butylcyclohexane 1.48
    cyclooctane 0.76
    cyclopentanol 32.59
    tetrahydropyran 79.34
    tert-amyl methyl ether 33.62
    2,5,8-trioxanonane 101.64
    1-hexene 3.85
    2-isopropoxyethanol 55.23
    2,2,2-trifluoroethanol 16.4
    methyl butyrate 26.17

    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