Roquefortine

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  • Identifiers

    CAS number
    58735-64-1

    Molecular formula
    C22H23N5O2

    SMILES
    CC(C)(C=C)[C@@]12C[C@H]3C(=O)N/C(=C/C4=CN=CN4)/C(=O)N3[C@@H]1NC5=CC=CC=C25

    Safety labels

  • Odor profile

    Fragrance
    Odorless 47.06%
    Nutty 23.89%
    Roasted 22.17%
    Green 21.27%
    Bitter 19.94%
    Burnt 18.87%
    Cooked 18.04%
    Popcorn 17.87%
    Cooling 17.73%
    Spicy 17.26%

     

    Flavor
    Bitter 96.23%
    Odorless 19.36%
    Cedarleaf 18.7%
    Nitrile 17.55%
    Bland 17.25%
    Lovage 17.05%
    Sweet-like 16.95%
    Very strong 16.55%
    Heather 16.43%
    Broom 16.41%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.0

    pKa est.
    7.2 (neutral)

    Molecular weight
    389.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    1132°C

    Melting point expt.

    • 202-205 °C

    Flash point

    • 302.73 ˚C est.

  • Synonyms

    • Roquefortine C
    • 58735-64-1
    • Roquefortine
    • roquefortin
    • 4VW6U94XFK
    • (1S,4E,7S,9R)-4-(1H-imidazol-5-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-triene-3,6-dione
    • DTXSID20891816
    • NSC-292134
    • 2H-Pyrazino(1',2':1,5)pyrrolo(2,3-b)indole-1,4(3H,5aH)-dione, 10b-(1,1-dimethyl-2-propenyl)-6,10b,11,11a-tetrahydro-3-(1H-imidazol-4-ylmethylene)-
    • (1S,4E,7S,9R)-4-(1H-imidazol-5-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo(7.7.0.02,7.010,15)hexadeca-10,12,14-triene-3,6-dione
    • RefChem:179817
    • DTXCID201031054
    • (4Z)-6-hydroxy-4-(1H-imidazol-5-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo(7.7.0.02,7.010,15)hexadeca-5,10,12,14-tetraen-3-one
    • Isoroquefortine C
    • (1S,4Z,7S,9R)-4-(1H-Imidazol-5-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-triene-3,6-dione
    • C22H23N5O2
    • NSC 292134
    • UNII-4VW6U94XFK
    • HSDB 7246
    • BRN 1231991
    • ROQUEFORTINE [HSDB]
    • (-)-ROQUEFORTINE C
    • CHEMBL517788
    • orb1989656
    • SCHEMBL29915259
    • CHEBI:183713
    • 2H-PYRAZINO(1',2':1,5)PYRROLO(2,3-B)INDOLE-1,4(3H,5AH)-DIONE, 10B-(1,1-DIMETHYL-2-PROPENYL)-6,10B,11,11A-TETRAHYDRO-3-(1H-IMIDAZOL-4-YLMETHYLENE)-, (3E,5AS,10BR,11AS)-
    • HY-N6748
    • MSK001587
    • AKOS040740902
    • NCGC00489127-01
    • BR162745
    • CS-0099780
    • NS00018320
    • G91402
    • (1S,4E,7S,9R)-9-(1,1-dimethylallyl)-4-(1H-imidazol-5-ylmethylene)-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-triene-3,6-dione
    • (3E,5aS,10bR,11aS)-3-[(1H-Imidazol-4-yl)methylidene]-10b-(2-methylbut-3-en-2-yl)-6,10b,11,11a-tetrahydro-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione
    • 2H-PYRAZINO(1',2':1,5)PYRROLO(2,3-B)INDOLE-1,4(3H,5AH)-DIONE, 10B-(1,1-DIMETHYL-2-PROPEN-1-YL)-6,10B,11,11A-TETRAHYDRO-3-(1H-IMIDAZOL-5-YLMETHYLENE)-, (3E,5AS,10BR,11AS)-
    • 68628-81-9
    • 58735-64-1

  • Applications

    Roquefortine (CAS 58735-64-1) is a fungal alkaloid produced by Penicillium roqueforti and related species. In practice, its industrial applications are limited and largely confined to research and food-safety contexts: it is employed as an analytical reference and research tool in mycotoxin detection and in monitoring mold contamination of foods, especially fermented dairy products such as cheese; it is studied as a lead-like scaffold for medicinal chemistry and biochemistry to explore enzyme inhibition mechanisms and drug-discovery concepts; it can serve as a reference compound in academic investigations of fungal toxins and quality control of processed foods. It is not used as a consumer additive in cosmetics, fragrances, flavors, or foods, and any use must comply with local regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.62
    methanol 4.09
    isopropanol 1.12
    water 0.03
    ethyl acetate 3.76
    n-propanol 1.68
    acetone 4.86
    n-butanol 1.61
    acetonitrile 3.02
    DMF 48.51
    toluene 0.56
    isobutanol 1.17
    1,4-dioxane 5.81
    methyl acetate 5.54
    THF 14.69
    2-butanone 8.43
    n-pentanol 1.24
    sec-butanol 1.04
    n-hexane 0.02
    ethylene glycol 2.27
    NMP 50.45
    cyclohexane 0.03
    DMSO 18.59
    n-butyl acetate 3.58
    n-octanol 0.55
    chloroform 17.29
    n-propyl acetate 3.43
    acetic acid 14.16
    dichloromethane 11.44
    cyclohexanone 12.77
    propylene glycol 2.53
    isopropyl acetate 2.27
    DMAc 70.7
    2-ethoxyethanol 8.39
    isopentanol 1.59
    n-heptane 0.02
    ethyl formate 4.74
    1,2-dichloroethane 4.21
    n-hexanol 1.26
    2-methoxyethanol 17.61
    isobutyl acetate 2.19
    tetrachloromethane 0.91
    n-pentyl acetate 3.59
    transcutol 10.82
    n-heptanol 1.18
    ethylbenzene 0.29
    MIBK 2.49
    2-propoxyethanol 14.88
    tert-butanol 0.89
    MTBE 0.49
    2-butoxyethanol 9.07
    propionic acid 6.18
    o-xylene 0.38
    formic acid 14.66
    diethyl ether 0.72
    m-xylene 0.4
    p-xylene 0.53
    chlorobenzene 1.89
    dimethyl carbonate 8.47
    n-octane 0.01
    formamide 20.12
    cyclopentanone 22.56
    2-pentanone 4.64
    anisole 1.4
    cyclopentyl methyl ether 2.04
    gamma-butyrolactone 30.51
    1-methoxy-2-propanol 12.14
    pyridine 11.19
    3-pentanone 3.61
    furfural 30.95
    n-dodecane 0.01
    diethylene glycol 14.52
    diisopropyl ether 0.17
    tert-amyl alcohol 0.93
    acetylacetone 7.43
    n-hexadecane 0.02
    acetophenone 4.1
    methyl propionate 6.04
    isopentyl acetate 3.66
    trichloroethylene 22.68
    n-nonanol 0.72
    cyclohexanol 1.26
    benzyl alcohol 3.47
    2-ethylhexanol 0.72
    isooctanol 1.0
    dipropyl ether 0.65
    1,2-dichlorobenzene 2.3
    ethyl lactate 5.36
    propylene carbonate 12.38
    n-methylformamide 18.67
    2-pentanol 0.74
    n-pentane 0.02
    1-propoxy-2-propanol 7.3
    1-methoxy-2-propyl acetate 7.68
    2-(2-methoxypropoxy) propanol 7.04
    mesitylene 0.22
    ε-caprolactone 12.64
    p-cymene 0.35
    epichlorohydrin 27.04
    1,1,1-trichloroethane 3.31
    2-aminoethanol 3.67
    morpholine-4-carbaldehyde 40.65
    sulfolane 40.87
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 3.83
    n-hexyl acetate 2.89
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 7.89
    sec-butyl acetate 1.94
    tert-butyl acetate 1.92
    decalin 0.02
    glycerin 10.4
    diglyme 15.79
    acrylic acid 10.57
    isopropyl myristate 0.91
    n-butyric acid 7.81
    acetyl acetate 3.5
    di(2-ethylhexyl) phthalate 2.94
    ethyl propionate 3.09
    nitromethane 33.97
    1,2-diethoxyethane 2.03
    benzonitrile 4.6
    trioctyl phosphate 1.65
    1-bromopropane 0.98
    gamma-valerolactone 48.43
    n-decanol 0.47
    triethyl phosphate 2.47
    4-methyl-2-pentanol 0.64
    propionitrile 3.33
    vinylene carbonate 16.33
    1,1,2-trichlorotrifluoroethane 43.87
    DMS 5.69
    cumene 0.23
    2-octanol 0.52
    2-hexanone 3.52
    octyl acetate 1.53
    limonene 0.37
    1,2-dimethoxyethane 11.33
    ethyl orthosilicate 1.9
    tributyl phosphate 1.81
    diacetone alcohol 6.07
    N,N-dimethylaniline 1.14
    acrylonitrile 8.52
    aniline 2.32
    1,3-propanediol 5.88
    bromobenzene 1.57
    dibromomethane 3.61
    1,1,2,2-tetrachloroethane 14.51
    2-methyl-cyclohexyl acetate 2.84
    tetrabutyl urea 3.0
    diisobutyl methanol 0.41
    2-phenylethanol 4.08
    styrene 0.38
    dioctyl adipate 2.34
    dimethyl sulfate 19.0
    ethyl butyrate 2.72
    methyl lactate 12.04
    butyl lactate 6.01
    diethyl carbonate 2.56
    propanediol butyl ether 6.01
    triethyl orthoformate 2.44
    p-tert-butyltoluene 0.3
    methyl 4-tert-butylbenzoate 5.06
    morpholine 9.22
    tert-butylamine 0.25
    n-dodecanol 0.3
    dimethoxymethane 12.67
    ethylene carbonate 10.83
    cyrene 13.93
    2-ethoxyethyl acetate 6.98
    2-ethylhexyl acetate 2.71
    1,2,4-trichlorobenzene 4.13
    4-methylpyridine 6.82
    dibutyl ether 0.43
    2,6-dimethyl-4-heptanol 0.41
    DEF 9.08
    dimethyl isosorbide 13.9
    tetrachloroethylene 7.95
    eugenol 8.03
    triacetin 5.71
    span 80 5.54
    1,4-butanediol 2.45
    1,1-dichloroethane 3.35
    2-methyl-1-pentanol 1.24
    methyl formate 13.55
    2-methyl-1-butanol 1.39
    n-decane 0.02
    butyronitrile 2.81
    3,7-dimethyl-1-octanol 0.65
    1-chlorooctane 0.18
    1-chlorotetradecane 0.08
    n-nonane 0.02
    undecane 0.02
    tert-butylcyclohexane 0.02
    cyclooctane 0.01
    cyclopentanol 2.42
    tetrahydropyran 2.43
    tert-amyl methyl ether 0.56
    2,5,8-trioxanonane 9.86
    1-hexene 0.13
    2-isopropoxyethanol 4.97
    2,2,2-trifluoroethanol 8.41
    methyl butyrate 4.91

    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