Oosporein

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  • Identifiers

    CAS number
    475-54-7

    Molecular formula
    C14H10O8

    SMILES
    CC1=C(C(=O)C(=C(C1=O)O)C2=C(C(=O)C(=C(C2=O)O)C)O)O

    Safety labels

  • Odor profile

    Fragrance
    Caramellic 71.75%
    Burnt 55.65%
    Sweet 53.89%
    Odorless 29.49%
    Roasted 23.87%
    Sharp 23.12%
    Coffee 22.03%
    Buttery 19.82%
    Savory 19.15%
    Creamy 17.49%

     

    Flavor
    Bitter 34.15%
    Maple 26.05%
    Very mild 24.59%
    Odorless 24.34%
    Maple syrup 22.75%
    Seedy 22.61%
    Cotton candy 22.49%
    Fenugreek 22.37%
    Extremely sweet 22.28%
    Caramel 20.82%

     

    Odor impact est.
    Low

  • Properties

    pKa est.
    2.86 (strong acid)

    Molecular weight
    306.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    690°C

    Flash point

    • 240.67 ˚C est.

  • Synonyms

    • Oosporein
    • 475-54-7
    • Chaetomidin
    • 3,3',6,6'-Tetrahydroxy-5,5'-dimethyl-2,2'-bi-p-benzoquinone
    • 708AUK232A
    • NSC-88466
    • 2-(2,5-dihydroxy-4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-3,6-dihydroxy-5-methylcyclohexa-2,5-diene-1,4-dione
    • DTXSID80963861
    • 2,2',5,5'-Tetrahydroxy-4,4'-dimethyl(bi-1,4-cyclohexadien-1-yl)-3,3',6,6'-tetrone
    • RefChem:168316
    • DTXCID401391589
    • OOSPORIN
    • NSC88466
    • MLS002694850
    • 2,2'-Bi-p-benzoquinone, 3,3',6,6'-tetrahydroxy-5,5'-dimethyl-
    • (Bi-1,4-cyclohexadien-1-yl)-3,3',6,6'-tetrone, 2,2',5,5'-tetrahydroxy-4,4'-dimethyl-
    • [Bi-1,4-cyclohexadien-1-yl]-3,3',6,6'-tetrone, 2,2',5,5'-tetrahydroxy-4,4'-dimethyl-
    • NSC 88466
    • 2-(2,5-dihydroxy-4-methyl-3,6-dioxo-cyclohexa-1,4-dien-1-yl)-3,6-dihydroxy-5-methyl-1,4-benzoquinone
    • ISO-OOSPOREIN
    • BRN 1892735
    • UNII-708AUK232A
    • OOSPOREIN [MI]
    • 4-08-00-03742 (Beilstein Handbook Reference)
    • orb1694319
    • SCHEMBL1097952
    • CHEMBL1733061
    • CHEBI:215764
    • DHMPJEGFPQTNFX-UHFFFAOYSA-N
    • AAA47554
    • HY-N7719
    • AKOS040754830
    • BS-1604
    • NCGC00246895-01
    • DA-66350
    • NCI60_041960
    • CS-0135680
    • Oosporein; Isoosporin; Chaetomidin; NSC-88466
    • Q27265843
    • [Bi-1,3',6,6'-tetrone, 2,2',5,5'-tetrahydroxy-4,4'-dimethyl-
    • Dicyclohexyl-2,2',3,3',5,5',6,6'-octaone, 4,4'-dimethyl-
    • 2,2',5,5'-Tetrahydroxy-4,4'-dimethyl[1,1'-bi(cyclohexa-1,4-diene)]-3,3',6,6'-tetrone
    • 3,3',6,6'-tetrahydroxy-4,4'-dimethyl-1,1'-bi(cyclohexa-3,6-diene)-2,2',5,5'- tetraone
    • 475-54-7

  • Applications

    Oosporein (CAS 475-54-7) is a fungal metabolite of interest as a natural pigment and potential colorant for coatings, inks, and personal care formulations in the form of a red to deep brown pigment; beyond coloration, it is studied for biological activities in vitro, such as antimicrobial effects and cytotoxicity, and is sometimes used as a research tool in natural products and chemical biology. It is also considered as a potential intermediate or building block in organic synthesis to access derivatives. In agriculture, oosporein has been investigated for bioactive properties related to plant protection or pest management, with potential as a biopesticide lead. In analytical contexts, it can serve as a reference standard or marker in mycotoxin detection methods (e.g., LC-MS), subject to local regulations and formulation constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.53
    methanol 2.72
    isopropanol 0.83
    water 0.06
    ethyl acetate 0.64
    n-propanol 1.25
    acetone 0.23
    n-butanol 0.7
    acetonitrile 0.12
    DMF 23.84
    toluene 0.12
    isobutanol 0.52
    1,4-dioxane 2.13
    methyl acetate 0.87
    THF 5.06
    2-butanone 0.97
    n-pentanol 0.39
    sec-butanol 1.2
    n-hexane 0.04
    ethylene glycol 2.25
    NMP 28.36
    cyclohexane 0.04
    DMSO 27.21
    n-butyl acetate 0.53
    n-octanol 0.53
    chloroform 0.18
    n-propyl acetate 0.27
    acetic acid 0.6
    dichloromethane 0.27
    cyclohexanone 0.75
    propylene glycol 1.83
    isopropyl acetate 0.41
    DMAc 29.64
    2-ethoxyethanol 4.84
    isopentanol 0.49
    n-heptane 0.05
    ethyl formate 0.34
    1,2-dichloroethane 0.28
    n-hexanol 0.59
    2-methoxyethanol 14.27
    isobutyl acetate 0.06
    tetrachloromethane 0.07
    n-pentyl acetate 0.57
    transcutol 5.85
    n-heptanol 0.83
    ethylbenzene 0.13
    MIBK 0.3
    2-propoxyethanol 6.58
    tert-butanol 1.14
    MTBE 0.72
    2-butoxyethanol 3.32
    propionic acid 1.27
    o-xylene 0.27
    formic acid 3.26
    diethyl ether 1.03
    m-xylene 0.11
    p-xylene 0.09
    chlorobenzene 0.04
    dimethyl carbonate 2.28
    n-octane 0.03
    formamide 9.98
    cyclopentanone 1.92
    2-pentanone 0.5
    anisole 0.53
    cyclopentyl methyl ether 1.6
    gamma-butyrolactone 3.34
    1-methoxy-2-propanol 10.57
    pyridine 1.38
    3-pentanone 0.82
    furfural 2.37
    n-dodecane 0.02
    diethylene glycol 6.75
    diisopropyl ether 0.21
    tert-amyl alcohol 1.74
    acetylacetone 0.58
    n-hexadecane 0.02
    acetophenone 0.64
    methyl propionate 2.17
    isopentyl acetate 0.4
    trichloroethylene 0.4
    n-nonanol 0.59
    cyclohexanol 0.63
    benzyl alcohol 0.49
    2-ethylhexanol 0.38
    isooctanol 0.48
    dipropyl ether 0.92
    1,2-dichlorobenzene 0.09
    ethyl lactate 1.06
    propylene carbonate 0.71
    n-methylformamide 6.52
    2-pentanol 0.64
    n-pentane 0.04
    1-propoxy-2-propanol 4.13
    1-methoxy-2-propyl acetate 2.06
    2-(2-methoxypropoxy) propanol 3.0
    mesitylene 0.09
    ε-caprolactone 1.32
    p-cymene 0.17
    epichlorohydrin 2.61
    1,1,1-trichloroethane 0.07
    2-aminoethanol 3.66
    morpholine-4-carbaldehyde 15.35
    sulfolane 13.11
    2,2,4-trimethylpentane 0.04
    2-methyltetrahydrofuran 1.89
    n-hexyl acetate 0.73
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 3.32
    sec-butyl acetate 0.21
    tert-butyl acetate 0.69
    decalin 0.03
    glycerin 7.22
    diglyme 7.31
    acrylic acid 1.63
    isopropyl myristate 0.27
    n-butyric acid 0.64
    acetyl acetate 0.22
    di(2-ethylhexyl) phthalate 0.46
    ethyl propionate 0.7
    nitromethane 1.62
    1,2-diethoxyethane 1.26
    benzonitrile 0.13
    trioctyl phosphate 0.4
    1-bromopropane 0.18
    gamma-valerolactone 4.25
    n-decanol 0.37
    triethyl phosphate 0.8
    4-methyl-2-pentanol 0.32
    propionitrile 0.29
    vinylene carbonate 0.56
    1,1,2-trichlorotrifluoroethane 5.11
    DMS 1.29
    cumene 0.1
    2-octanol 0.47
    2-hexanone 0.27
    octyl acetate 0.43
    limonene 0.28
    1,2-dimethoxyethane 5.69
    ethyl orthosilicate 0.76
    tributyl phosphate 0.36
    diacetone alcohol 2.3
    N,N-dimethylaniline 0.98
    acrylonitrile 0.57
    aniline 0.49
    1,3-propanediol 3.02
    bromobenzene 0.03
    dibromomethane 0.15
    1,1,2,2-tetrachloroethane 0.61
    2-methyl-cyclohexyl acetate 0.43
    tetrabutyl urea 0.95
    diisobutyl methanol 0.3
    2-phenylethanol 0.63
    styrene 0.1
    dioctyl adipate 0.46
    dimethyl sulfate 8.08
    ethyl butyrate 0.54
    methyl lactate 4.39
    butyl lactate 1.21
    diethyl carbonate 0.44
    propanediol butyl ether 2.1
    triethyl orthoformate 0.9
    p-tert-butyltoluene 0.2
    methyl 4-tert-butylbenzoate 1.91
    morpholine 5.42
    tert-butylamine 0.56
    n-dodecanol 0.22
    dimethoxymethane 11.15
    ethylene carbonate 0.39
    cyrene 3.42
    2-ethoxyethyl acetate 1.26
    2-ethylhexyl acetate 0.34
    1,2,4-trichlorobenzene 0.2
    4-methylpyridine 0.66
    dibutyl ether 0.36
    2,6-dimethyl-4-heptanol 0.3
    DEF 4.8
    dimethyl isosorbide 4.36
    tetrachloroethylene 0.58
    eugenol 1.88
    triacetin 1.07
    span 80 1.81
    1,4-butanediol 0.8
    1,1-dichloroethane 0.07
    2-methyl-1-pentanol 0.34
    methyl formate 2.01
    2-methyl-1-butanol 0.68
    n-decane 0.04
    butyronitrile 0.14
    3,7-dimethyl-1-octanol 0.35
    1-chlorooctane 0.15
    1-chlorotetradecane 0.05
    n-nonane 0.04
    undecane 0.02
    tert-butylcyclohexane 0.03
    cyclooctane 0.02
    cyclopentanol 1.0
    tetrahydropyran 0.87
    tert-amyl methyl ether 1.4
    2,5,8-trioxanonane 4.78
    1-hexene 0.11
    2-isopropoxyethanol 1.75
    2,2,2-trifluoroethanol 0.89
    methyl butyrate 0.67

    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