Citrinin

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  • Identifiers

    CAS number
    518-75-2

    Molecular formula
    C13H14O5

    SMILES
    C[C@@H]1[C@H](OC=C2C1=C(C(=C(C2=O)C(=O)O)O)C)C

    Safety labels

  • Odor profile

    Fragrance
    Caramellic 41.61%
    Sweet 37.3%
    Odorless 35.89%
    Burnt 33.76%
    Roasted 27.05%
    Mint 25.65%
    Spicy 25.44%
    Nutty 23.55%
    Tobacco 21.22%
    Lactonic 20.91%

     

    Flavor
    Bitter 45.54%
    Odorless 26.21%
    Cotton candy 21.1%
    Seedy 21.05%
    Extremely sweet 20.91%
    Leaves 20.74%
    Fenugreek 20.58%
    Basil 20.51%
    Maple syrup 20.41%
    Lovage 20.28%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.7

    pKa est.
    6.0 (neutral)

    Molecular weight
    250.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    397°C

    Flash point

    • 193.97 ˚C est.

  • Synonyms

    • citrinin
    • 518-75-2
    • (-)-citrinin
    • Citriain
    • (3R,4S)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid
    • NSC186
    • (3R,4S)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydroisochromene-7-carboxylic acid
    • 4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid
    • NSC 186
    • 3S697X6SNZ
    • NSC-186
    • MFCD00006912
    • (3R-trans)-4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid
    • 3H-2-Benzopyran-7-carboxylic acid, 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-, (3R-trans)-
    • Citrinin 100 microg/mL in Acetonitrile
    • (3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid
    • 3H-2-Benzopyran-7-carboxylic acid, 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-, (3R,4S)-
    • (3R,4S)-8-Hdroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid
    • CCRIS 175
    • HSDB 3473
    • EINECS 208-257-2
    • BRN 0088597
    • UNII-3S697X6SNZ
    • 3H-2-Benzopyran-7-carboxylic acid, 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-, (3R-trans)-; Citrinin (6CI); (3R,4S)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid; (-)-Citrinin; 4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid; NSC 186
    • (-)-Citrini
    • Citrinin, 98%
    • Spectrum_000451
    • CITRININ [HSDB]
    • CITRININ [IARC]
    • CITRININ [MI]
    • Spectrum2_000734
    • Spectrum3_000240
    • Spectrum4_001804
    • Spectrum5_000507
    • 3,4-Dihydro-8-hydroxy-3,4,5-trimethyl-6H-6-oxobenzo(c)pyran-7-carboxylic acid
    • BSPBio_001919
    • KBioGR_002411
    • KBioSS_000931
    • SPECTRUM210186
    • 5-18-09-00061 (Beilstein Handbook Reference)
    • DivK1c_000646
    • SCHEMBL157775
    • SPBio_000688
    • orb1710040
    • orb3025763
    • DTXSID8020333
    • SCHEMBL24312832
    • SCHEMBL29407967
    • CHEBI:48707
    • HMS502A08
    • KBio1_000646
    • KBio2_000931
    • KBio2_003499
    • KBio2_006067
    • KBio3_001419
    • MSK7220
    • CBGDIJWINPWWJW-IYSWYEEDSA-N
    • NINDS_000646
    • HMS1923C05
    • CCG-39048
    • EX-A16387
    • HB3839
    • MSK7220-100A
    • AKOS030254668
    • FC20467
    • SDCCGMLS-0066537.P001
    • (3R,4S)-6-hydroxy-3,4,5-trimethyl-8-oxo-4,8-dihydro-3H-2-benzopyran-7-carboxylic acid
    • (3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-2-benzopyran-7-carboxylic acid
    • IDI1_000646
    • NCGC00160164-01
    • NCGC00160164-02
    • NCGC00160164-03
    • NCI60_001544
    • Citrinin solution in Acetonitrile, 100ug/mL
    • ST50405294
    • E80637
    • Q420354
    • SR-05000002496
    • WLN: T66 CO HV AUT&J D1 E1 G1 IVQ JQ
    • SR-05000002496-1
    • Citrinin, from Penicillium citrinum, >=98% (HPLC)
    • Q63392265
    • (4S,3R)-8-hydroxy-3,4,5-trimethyl-6-oxoisochromane-7-carboxylic acid
    • (3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-3,4-dihydroisochromene-7-carboxylic acid
    • 3H-2-Benzopyran-7-carboxylic acid, 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-
    • 8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid #
    • (-)-citrinin; 4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid
    • 3H-2-Benzopyran-7-carboxylic acid, 4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-,(3R,4S)-
    • 3H-2-Benzopyran-7-carboxylic acid,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-, (3R-trans)-
    • 4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo, (3R-trans)-3H-2-benzopyran-7-carboxylic acid
    • 518-75-2

  • Applications

    Citrinin (CAS 518-75-2) is a mycotoxin commonly encountered as a contamination in foods and animal feeds, so its practical applications focus on food safety surveillance and risk assessment along cereal processing and fermentation streams; it is used as a reference standard and analyte in analytical methods such as LC-MS/MS and HPLC for detecting and quantifying mycotoxins. In laboratory settings, Citrinin is employed in toxicology research to understand nephrotoxic mechanisms and the biological impact of mycotoxins. It also serves as a subject in fungal secondary metabolite studies and the biosynthesis pathways of Penicillium/Aspergillus, enhancing knowledge of fungal metabolite chemistry. Studies on decontamination and mitigation strategies to reduce Citrinin levels in food products are conducted to develop control measures and ensure food safety.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.5
    methanol 8.37
    isopropanol 3.22
    water 0.05
    ethyl acetate 11.12
    n-propanol 3.79
    acetone 15.79
    n-butanol 4.51
    acetonitrile 9.51
    DMF 54.71
    toluene 3.16
    isobutanol 3.37
    1,4-dioxane 14.13
    methyl acetate 12.49
    THF 91.45
    2-butanone 15.32
    n-pentanol 2.94
    sec-butanol 2.99
    n-hexane 0.11
    ethylene glycol 3.85
    NMP 95.0
    cyclohexane 0.12
    DMSO 132.26
    n-butyl acetate 9.35
    n-octanol 1.57
    chloroform 15.08
    n-propyl acetate 6.56
    acetic acid 7.82
    dichloromethane 20.01
    cyclohexanone 25.28
    propylene glycol 3.36
    isopropyl acetate 7.1
    DMAc 69.6
    2-ethoxyethanol 12.23
    isopentanol 5.4
    n-heptane 0.09
    ethyl formate 8.8
    1,2-dichloroethane 18.88
    n-hexanol 4.02
    2-methoxyethanol 32.45
    isobutyl acetate 3.98
    tetrachloromethane 2.45
    n-pentyl acetate 5.39
    transcutol 17.48
    n-heptanol 2.59
    ethylbenzene 2.17
    MIBK 9.58
    2-propoxyethanol 23.84
    tert-butanol 6.24
    MTBE 2.98
    2-butoxyethanol 11.13
    propionic acid 6.45
    o-xylene 2.93
    formic acid 9.63
    diethyl ether 3.18
    m-xylene 3.5
    p-xylene 2.74
    chlorobenzene 6.27
    dimethyl carbonate 14.12
    n-octane 0.05
    formamide 18.95
    cyclopentanone 60.09
    2-pentanone 14.4
    anisole 7.82
    cyclopentyl methyl ether 15.05
    gamma-butyrolactone 69.93
    1-methoxy-2-propanol 24.1
    pyridine 15.98
    3-pentanone 10.37
    furfural 47.77
    n-dodecane 0.06
    diethylene glycol 24.49
    diisopropyl ether 1.08
    tert-amyl alcohol 5.15
    acetylacetone 21.91
    n-hexadecane 0.07
    acetophenone 11.95
    methyl propionate 15.9
    isopentyl acetate 9.54
    trichloroethylene 38.93
    n-nonanol 1.74
    cyclohexanol 4.63
    benzyl alcohol 8.33
    2-ethylhexanol 3.01
    isooctanol 2.4
    dipropyl ether 2.72
    1,2-dichlorobenzene 7.59
    ethyl lactate 7.87
    propylene carbonate 21.34
    n-methylformamide 27.87
    2-pentanol 2.78
    n-pentane 0.09
    1-propoxy-2-propanol 14.53
    1-methoxy-2-propyl acetate 17.5
    2-(2-methoxypropoxy) propanol 13.31
    mesitylene 2.06
    ε-caprolactone 21.78
    p-cymene 2.43
    epichlorohydrin 85.87
    1,1,1-trichloroethane 11.68
    2-aminoethanol 5.4
    morpholine-4-carbaldehyde 54.17
    sulfolane 113.33
    2,2,4-trimethylpentane 0.14
    2-methyltetrahydrofuran 25.59
    n-hexyl acetate 6.09
    isooctane 0.11
    2-(2-butoxyethoxy)ethanol 12.45
    sec-butyl acetate 4.89
    tert-butyl acetate 9.47
    decalin 0.25
    glycerin 13.04
    diglyme 26.47
    acrylic acid 8.0
    isopropyl myristate 2.45
    n-butyric acid 10.13
    acetyl acetate 7.25
    di(2-ethylhexyl) phthalate 5.39
    ethyl propionate 8.93
    nitromethane 33.7
    1,2-diethoxyethane 4.73
    benzonitrile 9.28
    trioctyl phosphate 3.72
    1-bromopropane 4.73
    gamma-valerolactone 64.5
    n-decanol 1.26
    triethyl phosphate 7.1
    4-methyl-2-pentanol 2.56
    propionitrile 8.16
    vinylene carbonate 17.7
    1,1,2-trichlorotrifluoroethane 43.3
    DMS 10.6
    cumene 1.93
    2-octanol 1.37
    2-hexanone 7.96
    octyl acetate 3.62
    limonene 2.66
    1,2-dimethoxyethane 25.8
    ethyl orthosilicate 5.86
    tributyl phosphate 4.29
    diacetone alcohol 20.94
    N,N-dimethylaniline 6.52
    acrylonitrile 16.08
    aniline 7.33
    1,3-propanediol 10.29
    bromobenzene 5.52
    dibromomethane 9.69
    1,1,2,2-tetrachloroethane 27.26
    2-methyl-cyclohexyl acetate 8.42
    tetrabutyl urea 6.99
    diisobutyl methanol 2.12
    2-phenylethanol 10.36
    styrene 2.1
    dioctyl adipate 5.13
    dimethyl sulfate 41.65
    ethyl butyrate 7.77
    methyl lactate 16.18
    butyl lactate 7.1
    diethyl carbonate 5.99
    propanediol butyl ether 7.29
    triethyl orthoformate 6.05
    p-tert-butyltoluene 2.22
    methyl 4-tert-butylbenzoate 13.05
    morpholine 21.87
    tert-butylamine 1.96
    n-dodecanol 0.87
    dimethoxymethane 34.9
    ethylene carbonate 14.22
    cyrene 24.49
    2-ethoxyethyl acetate 9.56
    2-ethylhexyl acetate 6.99
    1,2,4-trichlorobenzene 11.26
    4-methylpyridine 17.46
    dibutyl ether 1.37
    2,6-dimethyl-4-heptanol 2.12
    DEF 19.69
    dimethyl isosorbide 34.78
    tetrachloroethylene 15.24
    eugenol 14.07
    triacetin 8.46
    span 80 8.49
    1,4-butanediol 3.4
    1,1-dichloroethane 9.89
    2-methyl-1-pentanol 3.97
    methyl formate 25.16
    2-methyl-1-butanol 4.45
    n-decane 0.08
    butyronitrile 7.78
    3,7-dimethyl-1-octanol 2.2
    1-chlorooctane 0.82
    1-chlorotetradecane 0.36
    n-nonane 0.06
    undecane 0.07
    tert-butylcyclohexane 0.24
    cyclooctane 0.08
    cyclopentanol 9.45
    tetrahydropyran 9.02
    tert-amyl methyl ether 3.79
    2,5,8-trioxanonane 20.41
    1-hexene 0.67
    2-isopropoxyethanol 8.27
    2,2,2-trifluoroethanol 8.16
    methyl butyrate 11.19

    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