Vulpinic Acid

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  • Identifiers

    CAS number
    521-52-8

    Molecular formula
    C19H14O5

    SMILES
    COC(=O)/C(=C/1\C(=C(C(=O)O1)C2=CC=CC=C2)O)/C3=CC=CC=C3

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sweet 52.53%
    Fruity 49.15%
    Balsamic 47.38%
    Honey 42.23%
    Green 37.69%
    Spicy 36.68%
    Floral 31.88%
    Phenolic 30.58%
    Caramellic 29.88%
    Powdery 28.64%

     

    Flavor
    Bitter 68.0%
    Odorless 25.35%
    Lovage 20.53%
    Nitrile 19.79%
    Heather 19.48%
    Broom 19.44%
    Genet 19.38%
    Aniseed 19.06%
    Ethyl benzoate 19.05%
    Balsam 18.96%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.0

    pKa est.
    5.09 (weak acid)

    Molecular weight
    322.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    609°C

    Flash point

    • 203.31 ˚C est.

  • Synonyms

    • vulpinic acid
    • 521-52-8
    • methyl (2E)-2-(3-hydroxy-5-oxo-4-phenylfuran-2-ylidene)-2-phenylacetate
    • DTXSID601027308
    • NSC-5897
    • RefChem:194707
    • DTXCID001511575
    • methyl (2E)-(5-hydroxy-3-oxo-4-phenyl-2(3H)-furanylidene)(phenyl)acetate
    • 208-314-1
    • Benzeneacetic acid, alpha-(3-hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)-, methyl ester, (alphaE)-
    • 13N7RF6M84
    • Vulpic acid
    • MFCD00075804
    • 73622-57-8
    • NSC5897
    • methyl (E)-2-(3-hydroxy-5-oxo-4-phenylfuran-2(5H)-ylidene)-2-phenylacetate
    • BRN 1437166
    • NSC 5897
    • methyl (Z)-2-(3-hydroxy-5-oxo-4-phenylfuran-2(5H)-ylidene)-2-phenylacetate
    • Acetic acid, (3-hydroxy-5-oxo-4-phenyl-2(5H)-furylidene)phenyl-, methyl ester
    • SR-05000002200
    • Methylpulvinsaure
    • 2-(2,5-Dihydro-3-hydroxy-5-oxo-4-phenyl-2-furanylidene)-2-phenylacetic acid methyl ester
    • SCHEMBL559924
    • SCHEMBL559925
    • CHEMBL463212
    • orb1303479
    • CHEBI:144250
    • NLQPTDHMZUGQCX-BMRADRMJSA-N
    • OMZRMXULWNMRAE-BMRADRMJSA-N
    • BDBM50478424
    • WLN: T5VOYJ CUYR&VO1 DQ ER
    • 3,4-Dihydroxy-2,5-Diphenyl-2,4-hexadienedioic Acid Methyl Ester 3,6-Lactone
    • AKOS030632335
    • CCG-208551
    • EBC-617599
    • FV28725
    • Benzeneacetic acid, .alpha.-(3-hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)-, methyl ester
    • methyl 2-[(2E)-3-hydroxy-5-oxo-4-phenyl-2,5-dihydrofuran-2-ylidene]-2-phenylacetate
    • Benzeneacetic acid, methyl ester, (E)-
    • NCGC00160145-01
    • Acetic acid, 2-(2,5-dihydro-3-hydroxy-5-oxo-4-phenyl-2-furanylidene)-2-phenyl-, methyl ester
    • DA-68664
    • HY-125919
    • CS-0103068
    • SR-05000002200-2
    • SR-05000002200-3
    • .DELTA.2(5H), 3-hydroxy-5-oxo-.alpha.,4-diphenyl-, methyl ester
    • .delta.(sup 2(5H), 3-hydroxy-5-oxo-.alpha.,4-diphenyl-, methyl ester
    • 2, 3,4-dihydroxy-2,5-diphenyl-, mono-.gamma.-lactone, methyl ester
    • methyl (2E)-2-(3-hydroxy-5-oxo-4-phenyl-2-furylidene)-2-phenyl-acetate
    • (?E)-?-(3-Hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)benzeneacetic acid methyl ester
    • .delta.2(5H),.alpha.-Furanacetic acid, 3-hydroxy-5-oxo-.alpha.,4-diphenyl-, methyl ester
    • 2,4-Hexadienedioic acid, 3,4-dihydroxy-2,5-diphenyl-, mono-.gamma.-lactone, methyl ester
    • Methyl (2E)-(3-hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)(phenyl)ethanoate
    • Methyl (2E)-(3-hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)(phenyl)ethanoate #
    • (alphaE)-alpha-(3-Hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)benzeneacetic Acid Methyl Ester
    • .delta.(sup 2(5H),.alpha.)-Furanacetic acid, 3-hydroxy-5-oxo-.alpha.,4-diphenyl-, methyl ester
    • Benzeneacetic acid, .alpha.-(3-hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)-, methyl ester, (E)-
    • 521-52-8

  • Applications

    Vulpinic acid, CAS 521-52-8, is a natural compound found in certain lichens and is commonly regarded as a natural yellow pigment; in industry it is considered usable as a colorant for coatings, inks, plastics, and as a starting material for organic synthesis; it is also evaluated for cosmetic and personal care colorant applications under regulatory controls; additionally, it may serve as a reference reagent in pigment chemistry and related organic synthesis in R&D activities.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 6.87
    methanol 9.0
    isopropanol 3.92
    water 0.01
    ethyl acetate 25.21
    n-propanol 7.3
    acetone 58.73
    n-butanol 6.35
    acetonitrile 25.73
    DMF 263.08
    toluene 47.7
    isobutanol 4.87
    1,4-dioxane 50.99
    methyl acetate 39.99
    THF 195.09
    2-butanone 63.09
    n-pentanol 5.33
    sec-butanol 5.57
    n-hexane 0.29
    ethylene glycol 4.26
    NMP 329.5
    cyclohexane 0.94
    DMSO 152.13
    n-butyl acetate 16.75
    n-octanol 3.01
    chloroform 135.82
    n-propyl acetate 15.75
    acetic acid 22.81
    dichloromethane 149.14
    cyclohexanone 110.33
    propylene glycol 4.59
    isopropyl acetate 18.27
    DMAc 306.59
    2-ethoxyethanol 15.8
    isopentanol 7.05
    n-heptane 0.34
    ethyl formate 16.26
    1,2-dichloroethane 122.67
    n-hexanol 6.8
    2-methoxyethanol 41.72
    isobutyl acetate 9.99
    tetrachloromethane 6.28
    n-pentyl acetate 11.32
    transcutol 19.44
    n-heptanol 5.09
    ethylbenzene 12.55
    MIBK 21.62
    2-propoxyethanol 27.05
    tert-butanol 7.55
    MTBE 8.73
    2-butoxyethanol 15.0
    propionic acid 16.48
    o-xylene 18.65
    formic acid 10.74
    diethyl ether 10.96
    m-xylene 16.72
    p-xylene 14.74
    chlorobenzene 51.3
    dimethyl carbonate 52.54
    n-octane 0.23
    formamide 31.69
    cyclopentanone 200.2
    2-pentanone 41.17
    anisole 26.01
    cyclopentyl methyl ether 46.61
    gamma-butyrolactone 172.8
    1-methoxy-2-propanol 28.29
    pyridine 134.43
    3-pentanone 41.73
    furfural 119.9
    n-dodecane 0.33
    diethylene glycol 21.6
    diisopropyl ether 3.22
    tert-amyl alcohol 8.11
    acetylacetone 58.93
    n-hexadecane 0.42
    acetophenone 37.68
    methyl propionate 49.01
    isopentyl acetate 17.22
    trichloroethylene 269.72
    n-nonanol 3.72
    cyclohexanol 14.75
    benzyl alcohol 25.04
    2-ethylhexanol 6.36
    isooctanol 4.82
    dipropyl ether 7.84
    1,2-dichlorobenzene 43.58
    ethyl lactate 14.92
    propylene carbonate 60.48
    n-methylformamide 62.98
    2-pentanol 4.29
    n-pentane 0.28
    1-propoxy-2-propanol 16.45
    1-methoxy-2-propyl acetate 30.82
    2-(2-methoxypropoxy) propanol 17.43
    mesitylene 7.56
    ε-caprolactone 72.41
    p-cymene 7.22
    epichlorohydrin 225.88
    1,1,1-trichloroethane 53.29
    2-aminoethanol 6.95
    morpholine-4-carbaldehyde 127.77
    sulfolane 254.07
    2,2,4-trimethylpentane 0.44
    2-methyltetrahydrofuran 68.98
    n-hexyl acetate 12.06
    isooctane 0.25
    2-(2-butoxyethoxy)ethanol 15.92
    sec-butyl acetate 12.93
    tert-butyl acetate 21.92
    decalin 1.07
    glycerin 14.2
    diglyme 39.93
    acrylic acid 25.02
    isopropyl myristate 6.63
    n-butyric acid 20.39
    acetyl acetate 22.93
    di(2-ethylhexyl) phthalate 10.11
    ethyl propionate 18.58
    nitromethane 85.4
    1,2-diethoxyethane 10.9
    benzonitrile 34.12
    trioctyl phosphate 6.41
    1-bromopropane 26.85
    gamma-valerolactone 162.97
    n-decanol 3.01
    triethyl phosphate 12.89
    4-methyl-2-pentanol 4.09
    propionitrile 24.52
    vinylene carbonate 56.24
    1,1,2-trichlorotrifluoroethane 104.7
    DMS 28.27
    cumene 6.88
    2-octanol 2.93
    2-hexanone 22.3
    octyl acetate 8.32
    limonene 9.32
    1,2-dimethoxyethane 40.62
    ethyl orthosilicate 10.51
    tributyl phosphate 7.34
    diacetone alcohol 32.28
    N,N-dimethylaniline 19.49
    acrylonitrile 53.28
    aniline 45.28
    1,3-propanediol 10.77
    bromobenzene 58.54
    dibromomethane 76.13
    1,1,2,2-tetrachloroethane 170.82
    2-methyl-cyclohexyl acetate 17.69
    tetrabutyl urea 13.73
    diisobutyl methanol 4.69
    2-phenylethanol 24.38
    styrene 17.36
    dioctyl adipate 12.21
    dimethyl sulfate 108.24
    ethyl butyrate 14.55
    methyl lactate 34.6
    butyl lactate 11.41
    diethyl carbonate 11.92
    propanediol butyl ether 8.2
    triethyl orthoformate 12.05
    p-tert-butyltoluene 6.46
    methyl 4-tert-butylbenzoate 27.07
    morpholine 67.04
    tert-butylamine 3.71
    n-dodecanol 2.51
    dimethoxymethane 80.59
    ethylene carbonate 38.71
    cyrene 39.18
    2-ethoxyethyl acetate 17.56
    2-ethylhexyl acetate 14.43
    1,2,4-trichlorobenzene 62.22
    4-methylpyridine 105.43
    dibutyl ether 4.63
    2,6-dimethyl-4-heptanol 4.69
    DEF 69.94
    dimethyl isosorbide 48.03
    tetrachloroethylene 85.27
    eugenol 25.24
    triacetin 18.67
    span 80 13.17
    1,4-butanediol 3.78
    1,1-dichloroethane 60.86
    2-methyl-1-pentanol 7.32
    methyl formate 49.62
    2-methyl-1-butanol 7.54
    n-decane 0.46
    butyronitrile 17.48
    3,7-dimethyl-1-octanol 4.32
    1-chlorooctane 3.17
    1-chlorotetradecane 1.8
    n-nonane 0.33
    undecane 0.38
    tert-butylcyclohexane 0.7
    cyclooctane 0.35
    cyclopentanol 23.27
    tetrahydropyran 41.36
    tert-amyl methyl ether 11.34
    2,5,8-trioxanonane 30.7
    1-hexene 2.48
    2-isopropoxyethanol 11.62
    2,2,2-trifluoroethanol 13.28
    methyl butyrate 23.72

    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