Fumarprotocetraric Acid

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  • Identifiers

    CAS number
    489-50-9

    Molecular formula
    C22H16O12

    SMILES
    CC1=CC(=C(C2=C1C(=O)OC3=C(O2)C(=C(C(=C3COC(=O)/C=C/C(=O)O)O)C(=O)O)C)C=O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 65.07%
    Phenolic 25.45%
    Burnt 24.37%
    Balsamic 22.56%
    Milky 20.3%
    Sweet 20.06%
    Clean 19.65%
    Sour 19.62%
    Dry 19.33%
    Caramellic 19.0%

     

    Flavor
    Bitter 57.71%
    Odorless 49.02%
    Very mild 29.61%
    Bland 26.78%
    Mild 24.79%
    Sweet-like 20.91%
    Seedy 20.22%
    Yeast 20.09%
    Nitrile 20.02%
    Faint 19.81%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.5

    pKa est.
    5.01 (weak acid)

    Molecular weight
    472.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1284°C

    Flash point

    • 314.53 ˚C est.

  • Synonyms

    • Fumarprotocetraric acid
    • 489-50-9
    • NSC-685588
    • Fumaroprotocetraric Acid
    • NSC-249984
    • 4-[[(E)-3-carboxyprop-2-enoyl]oxymethyl]-10-formyl-3,9-dihydroxy-1,7-dimethyl-6-oxobenzo[b][1,4]benzodioxepine-2-carboxylic acid
    • 5VJ6J3A960
    • DTXSID801313939
    • 4-[[(E)-3-carboxyprop-2-enoyl]oxymethyl]-10-formyl-3,9-dihydroxy-1,7-dimethyl-6-oxo-benzo[b][1,4]benzodioxepine-2-carboxylic acid
    • 4-(((E)-3-carboxyprop-2-enoyl)oxymethyl)-10-formyl-3,9-dihydroxy-1,7-dimethyl-6-oxo-benzo(b)(1,4)benzodioxepine-2-carboxylic acid
    • 4-(((E)-3-carboxyprop-2-enoyl)oxymethyl)-10-formyl-3,9-dihydroxy-1,7-dimethyl-6-oxobenzo(b)(1,4)benzodioxepine-2-carboxylic acid
    • RefChem:141657
    • DTXCID801743740
    • 207-698-8
    • CHEMBL366861
    • 4-(3-carboxyprop-2-enoyloxymethyl)-10-formyl-3,9-dihydroxy-1,7-dimethyl-6-oxobenzo[b][1,4]benzodioxepine-2-carboxylic acid
    • 9-({[(2E)-3-carboxyprop-2-enoyl]oxy}methyl)-4-formyl-3,8-dihydroxy-1,6-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepine-7-carboxylic acid
    • C22H16O12
    • Spectrum5_000885
    • FUMARPROTOCETRARICACID
    • BSPBio_002497
    • SPECTRUM200054
    • SCHEMBL717507
    • orb1991901
    • SCHEMBL29740177
    • CHEBI:144157
    • VEGGRTFDFMUBPD-ONEGZZNKSA-N
    • GLXC-23168
    • BDBM50056933
    • CCG-38658
    • HY-N15031
    • NSC249984
    • AKOS040734853
    • FF65418
    • NCGC00095467-01
    • NCGC00095467-02
    • NS00042897
    • SR-05000002702
    • SR-05000002702-1
    • Q27896597
    • (E)-2-BUTENEDIOIC ACID,8-DIHYDROXY-1,6-DIMETHYL-11-OXO-11H-DIBENZO[B,E][1,4]DIOXEPIN-9-YL)METHYL] ESTER
    • (E)-But-2-enedioic acid mono-(7-carboxy-4-formyl-3,8-dihydroxy-1,6-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepin-9-ylmethyl) ester
    • 10-formyl-3,9-dihydroxy-4-[[(E)-4-hydroxy-4-oxo-but-2-enoyl]oxymethyl]-1,7-dimethyl-6-oxo-benzo[b][1,4]benzodioxepine-2-carboxylic acid
    • 2-BUTENEDIOIC ACID (2E)-, 1-((7-CARBOXY-4-FORMYL-3,8-DIHYDROXY-1,6-DIMETHYL-11-OXO-11H-DIBENZO(B,E)(1,4)DIOXEPIN-9-YL)METHYL) ESTER
    • 2-butenedioic acid, mono[(7-carboxy-4-formyl-3,8-dihydroxy-1,6-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepin-9-yl)methyl] ester, (2E)-
    • 9-(3-Carboxy-acryloyloximethyl)-4-formyl-3,8-dihydroxy-1,6-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepin-7-carboxylic acid
    • 9-[((2E)-3-Carboxyprop-2-enoyloxy)methyl]-4-formyl-3,8-dihydroxy-1,6-dimethyl-11-oxodibenzo[b,e]1,4-dioxepin-7-carboxylic acid
    • But-2-enedioic acid mono-(7-carboxy-4-formyl-3,8-dihydroxy-1,6-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepin-9-ylmethyl) ester
    • FUMARIC ACID, 9-MONOESTER WITH 4-FORMYL-3,8-DIHYDROXY-9-(HYDROXYMETHYL)-1,6-DIMETHYL-11-OXO-11H-DIBENZO(B,E)(1,4)DIOXEPIN-7-CARBOXYLIC ACID
    • InChI=1/C22H16O12/c1-8-5-12(24)10(6-23)19-15(8)22(31)34-20-11(7-32-14(27)4-3-13(25)26)17(28)16(21(29)30)9(2)18(20)33-19/h3-6,24,28H,7H2,1-2H3,(H,25,26)(H,29,30)/b4-3
    • 489-50-9

  • Applications

    Fumarprotocetraric acid (CAS 489-50-9) is a natural product metabolite frequently used as an analytical standard and reference material in natural product chemistry and chromatographic analysis; in pharmaceutical and microbiological research it is evaluated for antimicrobial and antifungal activity and can serve as a scaffold for the synthesis of depsidone derivatives; it is also explored as a potential bioactive ingredient for cosmetic and personal-care formulations under appropriate formulation controls.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 9.99
    methanol 17.45
    isopropanol 4.98
    water 0.12
    ethyl acetate 11.2
    n-propanol 8.84
    acetone 23.33
    n-butanol 4.02
    acetonitrile 6.88
    DMF 238.05
    toluene 0.77
    isobutanol 3.51
    1,4-dioxane 24.43
    methyl acetate 21.31
    THF 67.06
    2-butanone 22.81
    n-pentanol 2.48
    sec-butanol 4.73
    n-hexane 0.07
    ethylene glycol 18.88
    NMP 278.57
    cyclohexane 0.07
    DMSO 365.81
    n-butyl acetate 3.61
    n-octanol 0.95
    chloroform 3.06
    n-propyl acetate 6.39
    acetic acid 36.36
    dichloromethane 4.55
    cyclohexanone 17.3
    propylene glycol 22.47
    isopropyl acetate 4.02
    DMAc 243.43
    2-ethoxyethanol 38.25
    isopentanol 2.07
    n-heptane 0.06
    ethyl formate 10.06
    1,2-dichloroethane 4.68
    n-hexanol 1.03
    2-methoxyethanol 97.22
    isobutyl acetate 1.77
    tetrachloromethane 0.26
    n-pentyl acetate 2.64
    transcutol 34.68
    n-heptanol 1.18
    ethylbenzene 0.38
    MIBK 2.98
    2-propoxyethanol 30.91
    tert-butanol 3.69
    MTBE 2.07
    2-butoxyethanol 11.23
    propionic acid 22.54
    o-xylene 0.54
    formic acid 48.53
    diethyl ether 4.12
    m-xylene 0.4
    p-xylene 0.46
    chlorobenzene 0.6
    dimethyl carbonate 31.37
    n-octane 0.04
    formamide 86.61
    cyclopentanone 57.11
    2-pentanone 9.63
    anisole 2.94
    cyclopentyl methyl ether 6.81
    gamma-butyrolactone 103.92
    1-methoxy-2-propanol 60.75
    pyridine 15.53
    3-pentanone 9.8
    furfural 45.52
    n-dodecane 0.03
    diethylene glycol 43.44
    diisopropyl ether 0.45
    tert-amyl alcohol 4.09
    acetylacetone 19.28
    n-hexadecane 0.04
    acetophenone 5.22
    methyl propionate 27.41
    isopentyl acetate 2.25
    trichloroethylene 9.75
    n-nonanol 1.09
    cyclohexanol 2.56
    benzyl alcohol 3.76
    2-ethylhexanol 0.62
    isooctanol 0.87
    dipropyl ether 2.58
    1,2-dichlorobenzene 0.68
    ethyl lactate 11.26
    propylene carbonate 18.45
    n-methylformamide 89.69
    2-pentanol 1.83
    n-pentane 0.07
    1-propoxy-2-propanol 17.54
    1-methoxy-2-propyl acetate 12.78
    2-(2-methoxypropoxy) propanol 13.62
    mesitylene 0.19
    ε-caprolactone 20.74
    p-cymene 0.22
    epichlorohydrin 56.64
    1,1,1-trichloroethane 1.16
    2-aminoethanol 23.21
    morpholine-4-carbaldehyde 143.26
    sulfolane 192.3
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 13.69
    n-hexyl acetate 2.71
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 15.93
    sec-butyl acetate 2.65
    tert-butyl acetate 3.81
    decalin 0.05
    glycerin 67.31
    diglyme 29.32
    acrylic acid 31.42
    isopropyl myristate 1.13
    n-butyric acid 11.32
    acetyl acetate 5.7
    di(2-ethylhexyl) phthalate 2.08
    ethyl propionate 8.32
    nitromethane 128.26
    1,2-diethoxyethane 6.15
    benzonitrile 2.2
    trioctyl phosphate 1.55
    1-bromopropane 1.55
    gamma-valerolactone 109.85
    n-decanol 0.82
    triethyl phosphate 3.45
    4-methyl-2-pentanol 0.73
    propionitrile 6.22
    vinylene carbonate 17.53
    1,1,2-trichlorotrifluoroethane 57.55
    DMS 8.3
    cumene 0.22
    2-octanol 0.7
    2-hexanone 5.2
    octyl acetate 1.93
    limonene 0.37
    1,2-dimethoxyethane 46.04
    ethyl orthosilicate 2.56
    tributyl phosphate 1.85
    diacetone alcohol 13.06
    N,N-dimethylaniline 2.05
    acrylonitrile 14.61
    aniline 2.73
    1,3-propanediol 21.38
    bromobenzene 0.44
    dibromomethane 1.97
    1,1,2,2-tetrachloroethane 7.68
    2-methyl-cyclohexyl acetate 2.69
    tetrabutyl urea 4.27
    diisobutyl methanol 0.48
    2-phenylethanol 2.2
    styrene 0.45
    dioctyl adipate 3.3
    dimethyl sulfate 86.6
    ethyl butyrate 4.28
    methyl lactate 43.28
    butyl lactate 5.52
    diethyl carbonate 3.4
    propanediol butyl ether 10.2
    triethyl orthoformate 4.45
    p-tert-butyltoluene 0.21
    methyl 4-tert-butylbenzoate 5.73
    morpholine 45.49
    tert-butylamine 0.83
    n-dodecanol 0.58
    dimethoxymethane 83.86
    ethylene carbonate 12.05
    cyrene 30.33
    2-ethoxyethyl acetate 7.65
    2-ethylhexyl acetate 1.66
    1,2,4-trichlorobenzene 1.47
    4-methylpyridine 7.11
    dibutyl ether 1.23
    2,6-dimethyl-4-heptanol 0.48
    DEF 28.17
    dimethyl isosorbide 25.06
    tetrachloroethylene 3.65
    eugenol 7.37
    triacetin 8.67
    span 80 9.1
    1,4-butanediol 7.99
    1,1-dichloroethane 1.79
    2-methyl-1-pentanol 1.53
    methyl formate 59.11
    2-methyl-1-butanol 2.78
    n-decane 0.06
    butyronitrile 2.71
    3,7-dimethyl-1-octanol 0.67
    1-chlorooctane 0.27
    1-chlorotetradecane 0.13
    n-nonane 0.05
    undecane 0.04
    tert-butylcyclohexane 0.03
    cyclooctane 0.03
    cyclopentanol 6.46
    tetrahydropyran 7.66
    tert-amyl methyl ether 2.68
    2,5,8-trioxanonane 22.97
    1-hexene 0.34
    2-isopropoxyethanol 14.53
    2,2,2-trifluoroethanol 19.06
    methyl butyrate 9.97

    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