Marrubiin

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  • Identifiers

    CAS number
    465-92-9

    Molecular formula
    C20H28O4

    SMILES
    C[C@@H]1C[C@@H]2[C@H]3[C@](CCC[C@@]3([C@]1(CCC4=COC=C4)O)C)(C(=O)O2)C

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Woody 50.85%
    Spicy 32.47%
    Herbal 30.63%
    Earthy 29.5%
    Fresh 28.53%
    Green 27.4%
    Balsamic 26.67%
    Mint 25.45%
    Sweet 24.06%
    Floral 23.61%

     

    Flavor
    Bitter 76.1%
    Earthy 24.62%
    Cedarleaf 23.4%
    Ripe apricot 21.54%
    Patchouli 21.48%
    Beet 21.31%
    Sweet-like 21.22%
    Parsley 21.21%
    Soil 21.2%
    Red fruit 21.07%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.7

    pKa est.
    5.62 (weak acid)

    Molecular weight
    332.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    611°C

    Flash point

    • 224.14 ˚C est.

  • Synonyms

    • Marrubiin
    • 465-92-9
    • DTXSID50963595
    • AP086P88M4
    • NSC-36693
    • (1R,4S,8S,9R,10R,12R)-9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-2-oxatricyclo[6.3.1.04,12]dodecan-3-one
    • (1R,4S,8S,9R,10R,12R)-9-(2-(furan-3-yl)ethyl)-9-hydroxy-4,8,10-trimethyl-2-oxatricyclo(6.3.1.04,12)dodecan-3-one
    • RefChem:810635
    • DTXCID501764789
    • MFCD08461003
    • MARRUBIN
    • NSC36693
    • MLS000738128
    • UNII-AP086P88M4
    • Marrubiin CRS
    • NSC 36693
    • Marrubiin (Standard)
    • MARRUBIIN [MI]
    • Marrubiin (Marrubium bitter).
    • CHEBI:6696
    • SCHEMBL2784576
    • CHEMBL1999372
    • HY-N6995R
    • HY-N6995
    • AKOS040760545
    • ND-1214
    • XM36381
    • DA-75323
    • MS-25009
    • 2-(3-furyl)ethyl-hydroxy-trimethyl-[?]one
    • CS-0101468
    • NS00093865
    • C09128
    • G13500
    • AO-222/41148796
    • Q11770828
    • 8.beta.H-Labda-13(16), 15,16-epoxy-6.beta.,9-dihydroxy-, .gamma.-lactone
    • (1R,4S,8S,9R,10R,12R)-9-[2-(3-furyl)ethyl]-9-hydroxy-4,8,10-trimethyl-2-oxatricyclo[6.3.1.04,12]dodecan-3-one
    • (2AS,5AS,6R,7R,8AR,8BR)-6-(2-(3-FURANYL)ETHYL)DECAHYDRO-6-HYDROXY-2A,5A,7-TRIMETHYL-2H-NAPHTHO(1,8-BC)FURAN-2-ONE
    • (2aS,5aS,6R,7R,8aR,8bR)-6-[2-(Furan-3-yl)ethyl]-6-hydroxy-2a,5a,7-trimethyldecahydro-2H-naphtho[1,8-bc]furan-2-one
    • 2H-Naphtho(1,8-bc)furan-2-one, 6-(2-(3-furanyl)ethyl)decahydro-6-hydroxy-2a,5a,7-trimethyl-, (2aS-(2aalpha,5abeta,6alpha,7alpha,8aalpha,8balpha))-
    • 2H-Naphtho[1, 6-[2-(3-furanyl)ethyl]decahydro-6-hydroxy-2a,5a,7-trimethyl-, [2aS-(2a.alpha.,5a.beta.,6.alpha.,7.alpha.,8a.alpha.,8b.alpha.)]-
    • 2H-Naphtho[1,8-bc]furan-2-one, 6-[2-(3-furanyl)ethyl]decahydro-6-hydroxy-2a,5a,7-trimethyl-, (2aS,5aS,6R,7R,8aR,8bR)-
    • 465-92-9

  • Applications

    Marrubiin (CAS 465-92-9) is a naturally occurring diterpene lactone found in Horehound and related Lamiaceae. In industrial contexts, it is mainly encountered as a natural product constituent and can serve as an intermediate in synthetic transformations for diterpene chemistry. It is occasionally explored in fragrance and flavor research as a potential fragrance component or note modifier and may appear in botanical extracts used in cosmetics and personal care. In pharmaceutical and academic settings, Marrubiin is studied for bioactivity as a lead-like scaffold in natural product chemistry, though no therapeutic claims are made here and usage is subject to regulatory formulation limits. Its utility is largely in research and development as a reference compound for synthesis and structure-activity investigations rather than a broad commercial ingredient.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 31.43
    methanol 83.67
    isopropanol 26.4
    water 0.56
    ethyl acetate 50.3
    n-propanol 37.5
    acetone 95.66
    n-butanol 37.98
    acetonitrile 57.31
    DMF 371.92
    toluene 71.35
    isobutanol 25.29
    1,4-dioxane 141.96
    methyl acetate 48.85
    THF 343.95
    2-butanone 67.69
    n-pentanol 20.91
    sec-butanol 10.21
    n-hexane 0.49
    ethylene glycol 14.26
    NMP 160.24
    cyclohexane 1.76
    DMSO 138.3
    n-butyl acetate 34.17
    n-octanol 11.25
    chloroform 181.15
    n-propyl acetate 33.56
    acetic acid 70.21
    dichloromethane 135.11
    cyclohexanone 125.44
    propylene glycol 11.48
    isopropyl acetate 49.46
    DMAc 190.33
    2-ethoxyethanol 66.99
    isopentanol 32.08
    n-heptane 0.68
    ethyl formate 37.32
    1,2-dichloroethane 63.28
    n-hexanol 27.43
    2-methoxyethanol 138.01
    isobutyl acetate 32.87
    tetrachloromethane 14.78
    n-pentyl acetate 33.75
    transcutol 131.16
    n-heptanol 20.68
    ethylbenzene 19.59
    MIBK 51.39
    2-propoxyethanol 107.17
    tert-butanol 23.11
    MTBE 16.67
    2-butoxyethanol 62.35
    propionic acid 36.19
    o-xylene 28.22
    formic acid 54.21
    diethyl ether 26.63
    m-xylene 40.54
    p-xylene 27.09
    chlorobenzene 72.76
    dimethyl carbonate 66.05
    n-octane 0.38
    formamide 95.76
    cyclopentanone 190.54
    2-pentanone 64.99
    anisole 58.98
    cyclopentyl methyl ether 71.09
    gamma-butyrolactone 182.97
    1-methoxy-2-propanol 108.0
    pyridine 168.05
    3-pentanone 49.85
    furfural 192.27
    n-dodecane 0.45
    diethylene glycol 93.11
    diisopropyl ether 9.5
    tert-amyl alcohol 10.59
    acetylacetone 110.63
    n-hexadecane 0.57
    acetophenone 67.02
    methyl propionate 57.68
    isopentyl acetate 39.16
    trichloroethylene 171.33
    n-nonanol 13.72
    cyclohexanol 24.91
    benzyl alcohol 60.29
    2-ethylhexanol 15.14
    isooctanol 18.44
    dipropyl ether 15.63
    1,2-dichlorobenzene 65.08
    ethyl lactate 32.24
    propylene carbonate 79.9
    n-methylformamide 126.71
    2-pentanol 13.83
    n-pentane 0.63
    1-propoxy-2-propanol 58.32
    1-methoxy-2-propyl acetate 73.69
    2-(2-methoxypropoxy) propanol 49.71
    mesitylene 19.14
    ε-caprolactone 94.24
    p-cymene 12.41
    epichlorohydrin 198.69
    1,1,1-trichloroethane 49.6
    2-aminoethanol 29.24
    morpholine-4-carbaldehyde 225.67
    sulfolane 166.61
    2,2,4-trimethylpentane 0.66
    2-methyltetrahydrofuran 73.16
    n-hexyl acetate 35.66
    isooctane 0.84
    2-(2-butoxyethoxy)ethanol 62.22
    sec-butyl acetate 28.62
    tert-butyl acetate 51.8
    decalin 1.52
    glycerin 37.92
    diglyme 131.11
    acrylic acid 48.02
    isopropyl myristate 16.01
    n-butyric acid 63.56
    acetyl acetate 60.19
    di(2-ethylhexyl) phthalate 26.35
    ethyl propionate 35.95
    nitromethane 171.04
    1,2-diethoxyethane 35.94
    benzonitrile 77.97
    trioctyl phosphate 16.88
    1-bromopropane 20.34
    gamma-valerolactone 282.63
    n-decanol 9.13
    triethyl phosphate 21.34
    4-methyl-2-pentanol 15.72
    propionitrile 52.82
    vinylene carbonate 101.08
    1,1,2-trichlorotrifluoroethane 115.83
    DMS 50.34
    cumene 12.49
    2-octanol 9.54
    2-hexanone 34.89
    octyl acetate 19.67
    limonene 12.73
    1,2-dimethoxyethane 115.93
    ethyl orthosilicate 20.38
    tributyl phosphate 16.82
    diacetone alcohol 60.49
    N,N-dimethylaniline 37.62
    acrylonitrile 93.47
    aniline 71.41
    1,3-propanediol 55.24
    bromobenzene 73.62
    dibromomethane 62.46
    1,1,2,2-tetrachloroethane 107.54
    2-methyl-cyclohexyl acetate 34.68
    tetrabutyl urea 25.91
    diisobutyl methanol 10.28
    2-phenylethanol 60.21
    styrene 26.79
    dioctyl adipate 28.48
    dimethyl sulfate 94.55
    ethyl butyrate 30.37
    methyl lactate 51.6
    butyl lactate 34.83
    diethyl carbonate 24.29
    propanediol butyl ether 36.97
    triethyl orthoformate 27.65
    p-tert-butyltoluene 11.63
    methyl 4-tert-butylbenzoate 57.38
    morpholine 143.37
    tert-butylamine 9.69
    n-dodecanol 6.15
    dimethoxymethane 219.54
    ethylene carbonate 77.12
    cyrene 79.07
    2-ethoxyethyl acetate 60.67
    2-ethylhexyl acetate 29.43
    1,2,4-trichlorobenzene 74.7
    4-methylpyridine 141.44
    dibutyl ether 9.25
    2,6-dimethyl-4-heptanol 10.28
    DEF 69.7
    dimethyl isosorbide 101.96
    tetrachloroethylene 75.35
    eugenol 62.18
    triacetin 54.1
    span 80 38.3
    1,4-butanediol 20.37
    1,1-dichloroethane 50.15
    2-methyl-1-pentanol 18.48
    methyl formate 93.37
    2-methyl-1-butanol 21.04
    n-decane 0.87
    butyronitrile 46.4
    3,7-dimethyl-1-octanol 13.75
    1-chlorooctane 5.5
    1-chlorotetradecane 2.25
    n-nonane 0.61
    undecane 0.6
    tert-butylcyclohexane 1.27
    cyclooctane 0.77
    cyclopentanol 32.81
    tetrahydropyran 77.43
    tert-amyl methyl ether 12.91
    2,5,8-trioxanonane 86.83
    1-hexene 3.12
    2-isopropoxyethanol 44.19
    2,2,2-trifluoroethanol 42.39
    methyl butyrate 42.96

    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