Averufin

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  • Identifiers

    CAS number
    14016-29-6

    Molecular formula
    C20H16O7

    SMILES
    C[C@]12CCC[C@H](O1)C3=C(O2)C=C4C(=C3O)C(=O)C5=C(C4=O)C=C(C=C5O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 54.6%
    Phenolic 36.77%
    Sweet 28.17%
    Spicy 27.16%
    Balsamic 22.52%
    Vanilla 21.3%
    Creamy 19.6%
    Woody 19.48%
    Coconut 19.23%
    Powdery 18.91%

     

    Flavor
    Bitter 95.29%
    Bland 20.9%
    Odorless 20.04%
    Cedarleaf 19.88%
    Sweet-like 19.33%
    Lovage 19.19%
    Parsley 18.81%
    Ripe apricot 18.32%
    Red fruit 18.06%
    Nitrile 17.94%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.0

    pKa est.
    8.52 (weak base)

    Molecular weight
    368.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1026°C

    Flash point

    • 267.06 ˚C est.

  • Synonyms

    • Averufin
    • 14016-29-6
    • Averufine
    • 7R1N64C5MZ
    • (1S,17S)-3,7,9-trihydroxy-17-methyl-16,21-dioxapentacyclo[15.3.1.02,15.04,13.06,11]henicosa-2(15),3,6(11),7,9,13-hexaene-5,12-dione
    • DTXSID10891789
    • 2-Methyl-7,9,11-trihydroxy-3,4,5,6-tetrahydro-2,6-epoxy-2H-anthra(2,3-b)oxocin-8,13-dione
    • 3,4,5,6-Tetrahydro-7,9,11-trihydroxy-2-methyl-2,6-epoxy-2H-anthra(2,3-b)oxocin-8,13-dione
    • CHEBI:71537
    • (1S,17S)-3,7,9-trihydroxy-17-methyl-16,21-dioxapentacyclo(15.3.1.02,15.04,13.06,11)henicosa-2(15),3,6(11),7,9,13-hexaene-5,12-dione
    • RefChem:115769
    • DTXCID801031040
    • (2S,6S)-7,9,11-trihydroxy-2-methyl-3,4,5,6-tetrahydro-2H-2,6-epoxyanthra(2,3-b)oxocine-8,13-dione
    • (2S,6S)-7,9,11-trihydroxy-2-methyl-3,4,5,6-tetrahydro-2H-2,6-epoxyanthra[2,3-b]oxocine-8,13-dione
    • (1'S,5'S)-Averufin
    • 2,6-Epoxy-2H-anthra(2,3-b)oxocin-8,13-dione, 3,4,5,6-tetrahydro-7,9,11-trihydroxy-2-methyl-
    • MLS000563186
    • SMR000470849
    • 2'-DEOXYNIDURUFIN
    • UNII-7R1N64C5MZ
    • cid_638296
    • orb1990957
    • CHEMBL1706207
    • BDBM88955
    • HMS2268O21
    • 2,6-Epoxy-2H-anthra(2,3-b)oxocin-8,13-dione, 3,4,5,6-tetrahydro-2-methyl-7,9,11-trihydroxy-
    • AKOS040735878
    • BRN 1299991
    • NCGC00247578-01
    • HY-117915
    • NS00094876
    • Q27139693
    • (2S)-3,4,5,6-Tetrahydro-7,9,11-trihydroxy-2-methyl-2,6-epoxy-2H-anthra(2,3-b)oxocin-8,13-dione
    • 2,6-Epoxy-2H-anthra(2,3-b)oxocin-8,13-dione, 3,4,5,6-tetrahydro-7,9,11-trihydroxy-2-methyl-, (2S)-
    • 2,6-EPOXY-2H-ANTHRA(2,3-B)OXOCIN-8,13-DIONE, 3,4,5,6-TETRAHYDRO-7,9,11-TRIHYDROXY-2-METHYL-, (2S,6S)-
    • 14016-29-6

  • Applications

    Averufin is predominantly encountered as an intermediate in the aflatoxin biosynthetic pathway in Aspergillus species; in industrial and research settings it is mainly used to study fungal secondary metabolism and pathway regulation. It also serves as an analytical reference compound for method development and quality control in LC–MS and HPLC workflows to detect and quantify pathway intermediates. The compound is used in enzymology and biochemistry experiments to characterize enzymes involved in aflatoxin biosynthesis and to probe reaction mechanisms. It may be employed in metabolic engineering research to trace flux through the pathway and to evaluate genetic or regulatory controls. Handling and use are subject to safety considerations and local regulations due to the association with mycotoxins, and Averufin is not a material intended for consumer products.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.74
    methanol 1.95
    isopropanol 0.88
    water 0.04
    ethyl acetate 9.34
    n-propanol 1.16
    acetone 10.64
    n-butanol 0.85
    acetonitrile 8.87
    DMF 95.56
    toluene 0.69
    isobutanol 0.76
    1,4-dioxane 22.6
    methyl acetate 16.32
    THF 38.41
    2-butanone 9.76
    n-pentanol 0.83
    sec-butanol 0.59
    n-hexane 0.02
    ethylene glycol 5.15
    NMP 120.2
    cyclohexane 0.03
    DMSO 139.26
    n-butyl acetate 7.4
    n-octanol 1.06
    chloroform 3.57
    n-propyl acetate 8.91
    acetic acid 25.06
    dichloromethane 4.03
    cyclohexanone 16.68
    propylene glycol 3.28
    isopropyl acetate 5.55
    DMAc 117.45
    2-ethoxyethanol 15.34
    isopentanol 1.03
    n-heptane 0.03
    ethyl formate 8.46
    1,2-dichloroethane 3.77
    n-hexanol 0.57
    2-methoxyethanol 32.05
    isobutyl acetate 5.43
    tetrachloromethane 0.29
    n-pentyl acetate 4.94
    transcutol 50.53
    n-heptanol 0.97
    ethylbenzene 0.41
    MIBK 4.07
    2-propoxyethanol 25.24
    tert-butanol 1.46
    MTBE 0.73
    2-butoxyethanol 11.99
    propionic acid 10.02
    o-xylene 0.58
    formic acid 21.45
    diethyl ether 1.07
    m-xylene 0.61
    p-xylene 0.77
    chlorobenzene 1.35
    dimethyl carbonate 27.81
    n-octane 0.02
    formamide 37.36
    cyclopentanone 40.68
    2-pentanone 5.37
    anisole 3.8
    cyclopentyl methyl ether 5.0
    gamma-butyrolactone 91.58
    1-methoxy-2-propanol 21.83
    pyridine 14.42
    3-pentanone 4.96
    furfural 50.48
    n-dodecane 0.05
    diethylene glycol 37.03
    diisopropyl ether 0.36
    tert-amyl alcohol 0.84
    acetylacetone 23.39
    n-hexadecane 0.06
    acetophenone 8.75
    methyl propionate 17.57
    isopentyl acetate 6.83
    trichloroethylene 12.4
    n-nonanol 1.32
    cyclohexanol 1.26
    benzyl alcohol 4.46
    2-ethylhexanol 0.78
    isooctanol 1.06
    dipropyl ether 1.97
    1,2-dichlorobenzene 1.91
    ethyl lactate 12.64
    propylene carbonate 26.75
    n-methylformamide 37.71
    2-pentanol 0.49
    n-pentane 0.01
    1-propoxy-2-propanol 15.44
    1-methoxy-2-propyl acetate 21.37
    2-(2-methoxypropoxy) propanol 18.76
    mesitylene 0.44
    ε-caprolactone 24.06
    p-cymene 0.65
    epichlorohydrin 54.53
    1,1,1-trichloroethane 2.32
    2-aminoethanol 4.46
    morpholine-4-carbaldehyde 104.84
    sulfolane 124.06
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 7.45
    n-hexyl acetate 5.52
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 21.94
    sec-butyl acetate 4.58
    tert-butyl acetate 6.24
    decalin 0.05
    glycerin 19.32
    diglyme 44.61
    acrylic acid 19.58
    isopropyl myristate 2.92
    n-butyric acid 8.5
    acetyl acetate 12.8
    di(2-ethylhexyl) phthalate 5.73
    ethyl propionate 8.75
    nitromethane 114.9
    1,2-diethoxyethane 9.3
    benzonitrile 6.6
    trioctyl phosphate 3.58
    1-bromopropane 0.63
    gamma-valerolactone 102.03
    n-decanol 1.05
    triethyl phosphate 7.21
    4-methyl-2-pentanol 0.58
    propionitrile 5.94
    vinylene carbonate 29.3
    1,1,2-trichlorotrifluoroethane 53.07
    DMS 18.88
    cumene 0.35
    2-octanol 0.65
    2-hexanone 5.5
    octyl acetate 4.04
    limonene 0.67
    1,2-dimethoxyethane 32.47
    ethyl orthosilicate 5.28
    tributyl phosphate 4.69
    diacetone alcohol 13.58
    N,N-dimethylaniline 2.78
    acrylonitrile 17.37
    aniline 2.74
    1,3-propanediol 6.5
    bromobenzene 1.05
    dibromomethane 1.39
    1,1,2,2-tetrachloroethane 9.34
    2-methyl-cyclohexyl acetate 7.24
    tetrabutyl urea 7.87
    diisobutyl methanol 0.91
    2-phenylethanol 4.7
    styrene 0.53
    dioctyl adipate 7.52
    dimethyl sulfate 60.12
    ethyl butyrate 7.22
    methyl lactate 27.79
    butyl lactate 8.65
    diethyl carbonate 7.41
    propanediol butyl ether 10.69
    triethyl orthoformate 7.79
    p-tert-butyltoluene 0.62
    methyl 4-tert-butylbenzoate 10.82
    morpholine 25.27
    tert-butylamine 0.33
    n-dodecanol 0.84
    dimethoxymethane 39.77
    ethylene carbonate 22.25
    cyrene 30.87
    2-ethoxyethyl acetate 14.83
    2-ethylhexyl acetate 5.11
    1,2,4-trichlorobenzene 4.3
    4-methylpyridine 9.31
    dibutyl ether 1.72
    2,6-dimethyl-4-heptanol 0.91
    DEF 15.42
    dimethyl isosorbide 44.49
    tetrachloroethylene 3.87
    eugenol 13.55
    triacetin 18.04
    span 80 11.37
    1,4-butanediol 3.06
    1,1-dichloroethane 1.73
    2-methyl-1-pentanol 0.94
    methyl formate 36.74
    2-methyl-1-butanol 0.82
    n-decane 0.06
    butyronitrile 2.91
    3,7-dimethyl-1-octanol 1.3
    1-chlorooctane 0.38
    1-chlorotetradecane 0.25
    n-nonane 0.04
    undecane 0.05
    tert-butylcyclohexane 0.03
    cyclooctane 0.02
    cyclopentanol 2.63
    tetrahydropyran 4.29
    tert-amyl methyl ether 0.91
    2,5,8-trioxanonane 36.88
    1-hexene 0.1
    2-isopropoxyethanol 9.25
    2,2,2-trifluoroethanol 14.81
    methyl butyrate 11.08

    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