(2R,4aR,8aR)-1,2,3,4,4a,5,6,8a-Octahydro-4a,8-dimethyl-alpha-methylene-2-naphthaleneacetic acid

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  • Identifiers

    CAS number
    28399-17-9

    Molecular formula
    C15H22O2

    SMILES
    CC1=CCC[C@]2([C@H]1C[C@@H](CC2)C(=C)C(=O)O)C

    Safety labels

  • Odor profile

    Fragrance
    Woody 58.65%
    Sweet 45.67%
    Fruity 43.95%
    Green 43.91%
    Balsamic 39.14%
    Herbal 34.86%
    Spicy 34.05%
    Dry 33.55%
    Amber 30.57%
    Mint 29.57%

     

    Flavor
    Woody 25.63%
    Sweet 22.42%
    Odorless 22.41%
    Balsam 22.3%
    Minty 22.13%
    Herbal 21.66%
    Spicy 20.92%
    Basil 20.78%
    Ethyl benzoate 20.39%
    Spice 20.2%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.9

    pKa est.
    8.57 (weak base)

    Molecular weight
    234.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    354°C

    Flash point

    • 164.79 ˚C est.

  • Synonyms

    • 28399-17-9
    • RefChem:1049898
    • (2R,4aR,8aR)-1,2,3,4,4a,5,6,8a-Octahydro-4a,8-dimethyl-alpha-methylene-2-naphthaleneacetic acid
    • 12-Carboxyeudesma-3,11(13)-diene
    • 2-[(2R,4aR,8aR)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]prop-2-enoic acid
    • 2-[(2r,4ar,8ar)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-2-yl]prop-2-enoic acid
    • 2-Naphthaleneaceticacid, 1,2,3,4,4a,5,6,8a-octahydro-4a,8-dimethyl-a-methylene-, (2R,4aR,8aR)-
    • BRN 4184260
    • Eudesma-3,11(13)-dien-12-oic acid
    • MEGxp0_001523
    • orb1991613
    • SCHEMBL17689577
    • ACon0_000576
    • ACon1_002195
    • DTXSID60951064
    • AKOS040735144
    • NCGC00179735-01
    • BRD-K88821347-001-01-9
    • 2-(4a,8-Dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-2-yl)prop-2-enoic acid
    • 28399-17-9

  • Applications

    Applications of (2R,4aR,8aR)-1,2,3,4,4a,5,6,8a-Octahydro-4a,8-dimethyl-alpha-methylene-2-naphthaleneacetic acid (CAS 28399-17-9) are primarily in the agrochemical and specialty chemical sectors. It is commonly used as a chiral building block and intermediate for the synthesis of auxin-type plant growth regulators and related agrochemicals, including rooting-hormone formulations. In addition, it may serve as a precursor in pharmaceutical or fine-chemical research for developing chiral compounds, and it can be employed in academic or industrial R&D as a reference or synthetic intermediate for stereoselective methods. Subject to local regulations and formulation constraints, its use is typically limited to specified applications.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 325.92
    methanol 314.44
    isopropanol 265.23
    water 0.19
    ethyl acetate 406.55
    n-propanol 391.47
    acetone 248.47
    n-butanol 331.3
    acetonitrile 101.67
    DMF 550.06
    toluene 359.52
    isobutanol 224.91
    1,4-dioxane 681.79
    methyl acetate 255.6
    THF 1112.27
    2-butanone 399.26
    n-pentanol 144.92
    sec-butanol 235.24
    n-hexane 14.64
    ethylene glycol 29.74
    NMP 357.18
    cyclohexane 27.23
    DMSO 354.08
    n-butyl acetate 259.26
    n-octanol 44.22
    chloroform 521.62
    n-propyl acetate 157.43
    acetic acid 88.34
    dichloromethane 393.01
    cyclohexanone 452.65
    propylene glycol 62.03
    isopropyl acetate 288.54
    DMAc 454.07
    2-ethoxyethanol 265.38
    isopentanol 274.35
    n-heptane 6.11
    ethyl formate 123.25
    1,2-dichloroethane 363.15
    n-hexanol 223.11
    2-methoxyethanol 531.89
    isobutyl acetate 102.01
    tetrachloromethane 82.53
    n-pentyl acetate 120.43
    transcutol 1514.3
    n-heptanol 82.81
    ethylbenzene 109.3
    MIBK 248.98
    2-propoxyethanol 480.08
    tert-butanol 331.15
    MTBE 472.06
    2-butoxyethanol 227.16
    propionic acid 147.29
    o-xylene 178.51
    formic acid 61.36
    diethyl ether 513.66
    m-xylene 242.74
    p-xylene 103.15
    chlorobenzene 250.89
    dimethyl carbonate 142.19
    n-octane 2.06
    formamide 141.19
    cyclopentanone 531.56
    2-pentanone 409.7
    anisole 261.27
    cyclopentyl methyl ether 525.8
    gamma-butyrolactone 472.77
    1-methoxy-2-propanol 506.89
    pyridine 469.86
    3-pentanone 300.13
    furfural 350.62
    n-dodecane 1.14
    diethylene glycol 249.0
    diisopropyl ether 125.92
    tert-amyl alcohol 283.77
    acetylacetone 307.87
    n-hexadecane 1.44
    acetophenone 177.31
    methyl propionate 369.56
    isopentyl acetate 245.04
    trichloroethylene 634.69
    n-nonanol 43.44
    cyclohexanol 246.96
    benzyl alcohol 177.93
    2-ethylhexanol 97.38
    isooctanol 68.24
    dipropyl ether 128.19
    1,2-dichlorobenzene 193.59
    ethyl lactate 79.12
    propylene carbonate 198.27
    n-methylformamide 304.14
    2-pentanol 216.33
    n-pentane 19.85
    1-propoxy-2-propanol 325.66
    1-methoxy-2-propyl acetate 407.88
    2-(2-methoxypropoxy) propanol 210.83
    mesitylene 122.47
    ε-caprolactone 378.2
    p-cymene 53.97
    epichlorohydrin 742.62
    1,1,1-trichloroethane 278.71
    2-aminoethanol 115.12
    morpholine-4-carbaldehyde 491.31
    sulfolane 432.97
    2,2,4-trimethylpentane 11.68
    2-methyltetrahydrofuran 648.28
    n-hexyl acetate 138.81
    isooctane 12.87
    2-(2-butoxyethoxy)ethanol 352.52
    sec-butyl acetate 143.76
    tert-butyl acetate 347.45
    decalin 13.98
    glycerin 94.8
    diglyme 585.08
    acrylic acid 98.96
    isopropyl myristate 46.47
    n-butyric acid 261.6
    acetyl acetate 132.83
    di(2-ethylhexyl) phthalate 57.86
    ethyl propionate 173.62
    nitromethane 195.68
    1,2-diethoxyethane 380.74
    benzonitrile 158.55
    trioctyl phosphate 37.75
    1-bromopropane 219.94
    gamma-valerolactone 682.65
    n-decanol 28.87
    triethyl phosphate 66.14
    4-methyl-2-pentanol 138.82
    propionitrile 182.34
    vinylene carbonate 180.5
    1,1,2-trichlorotrifluoroethane 317.95
    DMS 166.29
    cumene 66.95
    2-octanol 40.16
    2-hexanone 165.81
    octyl acetate 60.42
    limonene 67.51
    1,2-dimethoxyethane 416.16
    ethyl orthosilicate 70.14
    tributyl phosphate 49.51
    diacetone alcohol 341.46
    N,N-dimethylaniline 161.49
    acrylonitrile 193.54
    aniline 390.67
    1,3-propanediol 228.74
    bromobenzene 237.18
    dibromomethane 267.7
    1,1,2,2-tetrachloroethane 562.05
    2-methyl-cyclohexyl acetate 110.57
    tetrabutyl urea 59.94
    diisobutyl methanol 61.09
    2-phenylethanol 216.75
    styrene 123.23
    dioctyl adipate 72.24
    dimethyl sulfate 202.37
    ethyl butyrate 143.54
    methyl lactate 137.58
    butyl lactate 123.91
    diethyl carbonate 84.0
    propanediol butyl ether 174.71
    triethyl orthoformate 112.36
    p-tert-butyltoluene 61.56
    methyl 4-tert-butylbenzoate 148.85
    morpholine 933.77
    tert-butylamine 199.59
    n-dodecanol 18.61
    dimethoxymethane 642.44
    ethylene carbonate 164.18
    cyrene 157.25
    2-ethoxyethyl acetate 257.76
    2-ethylhexyl acetate 180.24
    1,2,4-trichlorobenzene 242.85
    4-methylpyridine 539.4
    dibutyl ether 67.77
    2,6-dimethyl-4-heptanol 61.09
    DEF 404.35
    dimethyl isosorbide 355.97
    tetrachloroethylene 336.03
    eugenol 158.35
    triacetin 138.04
    span 80 147.89
    1,4-butanediol 54.71
    1,1-dichloroethane 341.58
    2-methyl-1-pentanol 146.1
    methyl formate 158.05
    2-methyl-1-butanol 237.52
    n-decane 2.51
    butyronitrile 193.14
    3,7-dimethyl-1-octanol 66.76
    1-chlorooctane 23.33
    1-chlorotetradecane 6.14
    n-nonane 2.22
    undecane 1.63
    tert-butylcyclohexane 14.53
    cyclooctane 10.17
    cyclopentanol 217.74
    tetrahydropyran 780.92
    tert-amyl methyl ether 296.6
    2,5,8-trioxanonane 351.83
    1-hexene 63.93
    2-isopropoxyethanol 191.85
    2,2,2-trifluoroethanol 44.6
    methyl butyrate 187.04

    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