Marrubic acid

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  • Identifiers

    CAS number
    564-12-5

    Molecular formula
    C20H30O5

    SMILES
    C[C@@H]1C[C@H]([C@@H]2[C@H](CCC[C@@]2([C@]1(CCC3=COC=C3)O)C)C(=O)OC)O

    Safety labels

  • Odor profile

    Fragrance
    Woody 40.36%
    Floral 33.21%
    Mint 30.51%
    Herbal 29.86%
    Odorless 29.72%
    Sweet 28.49%
    Cooling 28.47%
    Fruity 27.58%
    Balsamic 26.73%
    Fresh 26.65%

     

    Flavor
    Bitter 65.12%
    Fruity 25.94%
    Cedarleaf 22.88%
    Sweet-like 22.48%
    Minty 22.44%
    Sweet 21.93%
    Pleasant 21.08%
    Metallic 21.01%
    Beet 20.81%
    Fatty 20.75%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.9

    pKa est.
    6.47 (neutral)

    Molecular weight
    350.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    614°C

    Flash point

    • 193.97 ˚C est.

  • Synonyms

    • 564-12-5
    • RefChem:1088867
    • Marrubic acid
    • Marrubinsaeure [German]
    • NSC 41312
    • Marrubinsaeure
    • 6-beta,9-Dihydroxy-15,16-epoxylabda-13(16),14-dien-19-oic acid
    • Labda-13(16),14-dien-19-oic acid, 6-beta,9-dihydroxy-15,16-epoxy-
    • 1-Naphthalenecarboxylic acid, 5-(2-(3-furanyl)ethyl)decahydro-5,8-dihydroxy-1,4a,6-trimethyl-, (1S-(1-alpha,4a-alpha,5-beta,6-beta,8-alpha,8a-beta)-
    • 564-12-5

  • Applications

    Marrubic acid (CAS 564-12-5) is primarily used as an intermediate in organic synthesis; it may serve as a building block for the preparation of more complex pharmaceuticals and agrochemicals. In addition, it is evaluated for fragrance and flavor work as a possible odorant or aroma component, and it can be considered for cosmetic and personal care formulations as a specialty ingredient under formulation limits. It may also find use in coatings and inks as a functional additive, and in cleaning formulations as an acidifier or chelating agent to aid metal complexation. Its exact utility depends on purity, regulatory status, and compatibility with other formulation components, and is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 38.98
    methanol 140.42
    isopropanol 17.8
    water 0.41
    ethyl acetate 29.42
    n-propanol 33.51
    acetone 51.31
    n-butanol 20.68
    acetonitrile 21.05
    DMF 373.51
    toluene 24.37
    isobutanol 15.25
    1,4-dioxane 127.1
    methyl acetate 28.32
    THF 283.34
    2-butanone 33.08
    n-pentanol 10.5
    sec-butanol 7.86
    n-hexane 0.19
    ethylene glycol 14.79
    NMP 155.7
    cyclohexane 0.86
    DMSO 226.47
    n-butyl acetate 13.61
    n-octanol 5.93
    chloroform 96.69
    n-propyl acetate 12.95
    acetic acid 81.35
    dichloromethane 84.25
    cyclohexanone 77.85
    propylene glycol 14.38
    isopropyl acetate 22.61
    DMAc 211.39
    2-ethoxyethanol 63.7
    isopentanol 15.76
    n-heptane 0.25
    ethyl formate 20.62
    1,2-dichloroethane 40.49
    n-hexanol 13.39
    2-methoxyethanol 161.28
    isobutyl acetate 10.14
    tetrachloromethane 7.33
    n-pentyl acetate 14.03
    transcutol 119.05
    n-heptanol 10.26
    ethylbenzene 7.07
    MIBK 22.93
    2-propoxyethanol 78.28
    tert-butanol 16.77
    MTBE 10.48
    2-butoxyethanol 40.57
    propionic acid 25.47
    o-xylene 12.77
    formic acid 80.43
    diethyl ether 15.27
    m-xylene 14.39
    p-xylene 8.96
    chlorobenzene 30.81
    dimethyl carbonate 42.54
    n-octane 0.16
    formamide 126.77
    cyclopentanone 125.21
    2-pentanone 29.39
    anisole 33.34
    cyclopentyl methyl ether 45.1
    gamma-butyrolactone 132.73
    1-methoxy-2-propanol 99.24
    pyridine 109.25
    3-pentanone 22.25
    furfural 138.75
    n-dodecane 0.12
    diethylene glycol 77.01
    diisopropyl ether 3.42
    tert-amyl alcohol 8.98
    acetylacetone 67.48
    n-hexadecane 0.16
    acetophenone 36.2
    methyl propionate 36.68
    isopentyl acetate 15.68
    trichloroethylene 122.62
    n-nonanol 6.79
    cyclohexanol 16.35
    benzyl alcohol 36.23
    2-ethylhexanol 6.08
    isooctanol 8.25
    dipropyl ether 6.54
    1,2-dichlorobenzene 27.48
    ethyl lactate 16.14
    propylene carbonate 47.56
    n-methylformamide 135.87
    2-pentanol 6.54
    n-pentane 0.23
    1-propoxy-2-propanol 36.15
    1-methoxy-2-propyl acetate 39.88
    2-(2-methoxypropoxy) propanol 32.36
    mesitylene 6.86
    ε-caprolactone 59.49
    p-cymene 4.31
    epichlorohydrin 161.38
    1,1,1-trichloroethane 23.45
    2-aminoethanol 37.57
    morpholine-4-carbaldehyde 194.93
    sulfolane 156.22
    2,2,4-trimethylpentane 0.31
    2-methyltetrahydrofuran 50.93
    n-hexyl acetate 16.23
    isooctane 0.27
    2-(2-butoxyethoxy)ethanol 45.93
    sec-butyl acetate 10.4
    tert-butyl acetate 26.69
    decalin 0.58
    glycerin 44.9
    diglyme 103.14
    acrylic acid 38.03
    isopropyl myristate 5.62
    n-butyric acid 36.91
    acetyl acetate 34.5
    di(2-ethylhexyl) phthalate 12.38
    ethyl propionate 14.3
    nitromethane 155.76
    1,2-diethoxyethane 20.59
    benzonitrile 31.66
    trioctyl phosphate 7.22
    1-bromopropane 9.39
    gamma-valerolactone 204.9
    n-decanol 4.02
    triethyl phosphate 10.26
    4-methyl-2-pentanol 6.82
    propionitrile 19.62
    vinylene carbonate 57.88
    1,1,2-trichlorotrifluoroethane 109.68
    DMS 25.56
    cumene 4.21
    2-octanol 4.42
    2-hexanone 13.86
    octyl acetate 8.09
    limonene 5.02
    1,2-dimethoxyethane 94.5
    ethyl orthosilicate 10.04
    tributyl phosphate 6.84
    diacetone alcohol 40.22
    N,N-dimethylaniline 20.27
    acrylonitrile 43.29
    aniline 45.05
    1,3-propanediol 54.16
    bromobenzene 26.61
    dibromomethane 32.13
    1,1,2,2-tetrachloroethane 74.67
    2-methyl-cyclohexyl acetate 14.93
    tetrabutyl urea 11.73
    diisobutyl methanol 4.05
    2-phenylethanol 33.11
    styrene 9.27
    dioctyl adipate 12.28
    dimethyl sulfate 78.91
    ethyl butyrate 12.18
    methyl lactate 39.94
    butyl lactate 18.07
    diethyl carbonate 9.81
    propanediol butyl ether 26.76
    triethyl orthoformate 12.64
    p-tert-butyltoluene 4.19
    methyl 4-tert-butylbenzoate 32.53
    morpholine 147.23
    tert-butylamine 5.1
    n-dodecanol 2.37
    dimethoxymethane 200.07
    ethylene carbonate 42.89
    cyrene 53.25
    2-ethoxyethyl acetate 32.56
    2-ethylhexyl acetate 10.72
    1,2,4-trichlorobenzene 37.89
    4-methylpyridine 72.02
    dibutyl ether 3.93
    2,6-dimethyl-4-heptanol 4.05
    DEF 50.04
    dimethyl isosorbide 67.48
    tetrachloroethylene 53.07
    eugenol 37.38
    triacetin 30.22
    span 80 25.68
    1,4-butanediol 15.4
    1,1-dichloroethane 23.94
    2-methyl-1-pentanol 9.12
    methyl formate 87.96
    2-methyl-1-butanol 11.59
    n-decane 0.29
    butyronitrile 16.76
    3,7-dimethyl-1-octanol 6.12
    1-chlorooctane 2.11
    1-chlorotetradecane 0.62
    n-nonane 0.22
    undecane 0.18
    tert-butylcyclohexane 0.42
    cyclooctane 0.34
    cyclopentanol 25.22
    tetrahydropyran 54.84
    tert-amyl methyl ether 8.41
    2,5,8-trioxanonane 65.63
    1-hexene 1.18
    2-isopropoxyethanol 32.76
    2,2,2-trifluoroethanol 37.45
    methyl butyrate 18.81

    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