Usnic Acid

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  • Identifiers

    CAS number
    125-46-2

    Molecular formula
    C18H16O7

    SMILES
    CC1=C(C(=C2C(=C1O)C3(C(=CC(=O)C(C3=O)C(=O)C)O2)C)C(=O)C)O

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

    Environmental Hazard
    Environmental

  • Odor profile

    Caramellic 37.07%
    Fruity 35.34%
    Burnt 35.2%
    Sweet 35.12%
    Odorless 34.97%
    Dry 27.71%
    Woody 27.24%
    Spicy 25.68%
    Phenolic 23.46%
    Tobacco 20.74%

    Scent© AI

  • Properties

    XLogP3-AA
    1.4

    Molecular weight
    344.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1686°C

    Melting point expt.

    • 204 °C

    Flash point est.
    246.56 ˚C

    Solubility expt.

    • Solubility at 25 °C (g/100 ml): acetone, 0.77; ethyl acetate, 0.88; fural, 7.32; furfuryl alcohol, 1.21
    • Solubility at 25 °C (g/100 ml): water, <0.01

  • Synonyms

    • usnic acid
    • 125-46-2
    • Usno
    • Usninic acid
    • 1,3(2H,9bH)-Dibenzofurandione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-
    • (+-)-Uanic acid
    • Usninsaeure [German]
    • NSC 8517
    • CCRIS 5518
    • (+/-)-Usnic acid
    • usnic-acid
    • HSDB 7170
    • L-Usnic acid
    • EINECS 204-740-7
    • BRN 1299865
    • AI3-50457
    • NSC5890
    • 2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H,9bH)-dibenzofurandione
    • 7-Hydroxy-(S)-usnate
    • 2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bh)-dione
    • 2,6-Diacetyl-1,2,3,9b-tetrahydro-7,9-dihydroxy-8,9b-dimethyldibenzofuran-1,3-dione
    • CHEBI:2264
    • DTXSID0040123
    • NSC5889
    • NSC8517
    • 0W584PFJ77
    • NSC-8517
    • Usninsaeure (german)
    • 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzofuran-1,3-dione
    • 1,3-(2H,9bH)-Dibenzofurandione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-
    • 4,10-diacetyl-11,13-dihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),6,10,12-tetraene-3,5-dione
    • UNII-0W584PFJ77
    • Usinic acid
    • Uanic acid
    • Spectrum_000177
    • Spectrum2_000744
    • Spectrum3_001195
    • Spectrum4_001811
    • Spectrum5_000541
    • USNIC ACID [INCI]
    • USNIC ACID, (D)
    • USNIC ACID, (L)
    • (.+/-.)-Usnic acid
    • BSPBio_002869
    • KBioGR_002446
    • KBioSS_000657
    • DivK1c_001009
    • SCHEMBL177774
    • SPBio_000728
    • CHEMBL1375951
    • DTXCID8020123
    • HMS503I19
    • KBio1_001009
    • KBio2_000657
    • KBio2_003225
    • KBio2_005793
    • KBio3_002369
    • NINDS_001009
    • 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-dibenzofuran-1,3-dione
    • HY-N0656
    • BBL009902
    • CCG-40251
    • s4953
    • STK801335
    • AKOS005613032
    • FU32857
    • SDCCGMLS-0066516.P001
    • IDI1_001009
    • NCGC00094823-01
    • NCGC00094823-02
    • NCGC00094823-03
    • NCGC00094823-04
    • AS-18744
    • DA-48608
    • NCI60_004436
    • NCI60_004437
    • CS-0009679
    • NS00004156
    • U0023
    • EN300-7388062
    • BRD-A85739295-001-03-6
    • Q27105599
    • WLN: T B656 CV EV HO FU BHT & JB1 DV1 KQ L1 MQ
    • 1,3(2H,9bH)Dibenzofurandione, 2,6diacetyl7,9dihydroxy8,9bdimethyl
    • 2,6Diacetyl7,9dihydroxy8,9bdimethyl1,3(2H,9bH)dibenzofurandione
    • 1,9bH)-Dibenzofurandione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-
    • 2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H, 9bH)-dibenzofuradione
    • 2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H, 9bH-dibenzofurandione
    • Dibenzofuran-1,9bH)-dione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-
    • (+/-)-1,3(2H,9bH)-Dibenzofurandione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-
    • 2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bh)-dione #
    • 2,6-Diacetyl-1,2,3,9b-tetrahydro-7,9-dihydroxy-8,9b-dimethyldiben- zofuran-1,3-dione/ Usno
    • 4,10-diacetyl-11,13-dihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0,2,7]trideca-1(13),6,9,11-tetraene-3,5-dione

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.91
    methanol 2.42
    isopropanol 1.09
    water 0.01
    ethyl acetate 9.2
    n-propanol 1.36
    acetone 10.26
    n-butanol 1.67
    acetonitrile 6.61
    DMF 44.21
    toluene 1.8
    isobutanol 1.38
    1,4-dioxane 20.82
    methyl acetate 11.76
    THF 49.51
    2-butanone 11.65
    n-pentanol 2.21
    sec-butanol 1.48
    n-hexane 0.23
    ethylene glycol 1.34
    NMP 87.08
    cyclohexane 0.25
    DMSO 84.16
    n-butyl acetate 11.94
    n-octanol 2.84
    chloroform 13.47
    n-propyl acetate 12.26
    acetic acid 5.6
    dichloromethane 12.87
    cyclohexanone 31.96
    propylene glycol 1.23
    isopropyl acetate 7.43
    DMAc 70.65
    2-ethoxyethanol 9.81
    isopentanol 2.45
    n-heptane 0.15
    ethyl formate 8.55
    1,2-dichloroethane 10.49
    n-hexanol 2.82
    2-methoxyethanol 13.87
    isobutyl acetate 8.75
    tetrachloromethane 1.51
    n-pentyl acetate 7.74
    transcutol 10.43
    n-heptanol 2.74
    ethylbenzene 2.32
    MIBK 8.26
    2-propoxyethanol 19.35
    tert-butanol 2.92
    MTBE 2.0
    2-butoxyethanol 9.72
    propionic acid 4.76
    o-xylene 2.05
    formic acid 4.52
    diethyl ether 2.48
    m-xylene 1.89
    p-xylene 3.83
    chlorobenzene 4.32
    dimethyl carbonate 15.8
    n-octane 0.13
    formamide 8.85
    cyclopentanone 47.39
    2-pentanone 9.12
    anisole 7.28
    cyclopentyl methyl ether 10.02
    gamma-butyrolactone 58.97
    1-methoxy-2-propanol 11.4
    pyridine 13.93
    3-pentanone 9.35
    furfural 39.27
    n-dodecane 0.18
    diethylene glycol 18.22
    diisopropyl ether 1.03
    tert-amyl alcohol 2.94
    acetylacetone 22.23
    n-hexadecane 0.23
    acetophenone 14.1
    methyl propionate 12.75
    isopentyl acetate 11.61
    trichloroethylene 23.5
    n-nonanol 3.19
    cyclohexanol 4.17
    benzyl alcohol 6.67
    2-ethylhexanol 3.14
    isooctanol 2.76
    dipropyl ether 3.44
    1,2-dichlorobenzene 6.46
    ethyl lactate 11.54
    propylene carbonate 25.87
    n-methylformamide 13.99
    2-pentanol 1.26
    n-pentane 0.09
    1-propoxy-2-propanol 11.73
    1-methoxy-2-propyl acetate 18.18
    2-(2-methoxypropoxy) propanol 14.17
    mesitylene 1.39
    ε-caprolactone 26.4
    p-cymene 2.09
    epichlorohydrin 44.94
    1,1,1-trichloroethane 7.38
    2-aminoethanol 1.69
    morpholine-4-carbaldehyde 58.49
    sulfolane 106.64
    2,2,4-trimethylpentane 0.1
    2-methyltetrahydrofuran 14.8
    n-hexyl acetate 9.26
    isooctane 0.09
    2-(2-butoxyethoxy)ethanol 10.92
    sec-butyl acetate 7.43
    tert-butyl acetate 9.15
    decalin 0.41
    glycerin 5.95
    diglyme 22.22
    acrylic acid 6.44
    isopropyl myristate 5.01
    n-butyric acid 6.4
    acetyl acetate 9.24
    di(2-ethylhexyl) phthalate 8.03
    ethyl propionate 13.61
    nitromethane 33.05
    1,2-diethoxyethane 5.92
    benzonitrile 10.01
    trioctyl phosphate 6.4
    1-bromopropane 3.1
    gamma-valerolactone 66.04
    n-decanol 2.48
    triethyl phosphate 10.5
    4-methyl-2-pentanol 1.63
    propionitrile 6.92
    vinylene carbonate 23.0
    1,1,2-trichlorotrifluoroethane 32.62
    DMS 16.05
    cumene 1.96
    2-octanol 2.17
    2-hexanone 13.61
    octyl acetate 6.63
    limonene 2.43
    1,2-dimethoxyethane 30.37
    ethyl orthosilicate 7.85
    tributyl phosphate 7.54
    diacetone alcohol 15.43
    N,N-dimethylaniline 6.22
    acrylonitrile 12.11
    aniline 3.63
    1,3-propanediol 3.47
    bromobenzene 4.05
    dibromomethane 7.06
    1,1,2,2-tetrachloroethane 19.27
    2-methyl-cyclohexyl acetate 12.68
    tetrabutyl urea 12.72
    diisobutyl methanol 2.51
    2-phenylethanol 9.28
    styrene 2.17
    dioctyl adipate 8.92
    dimethyl sulfate 42.71
    ethyl butyrate 10.45
    methyl lactate 14.23
    butyl lactate 8.28
    diethyl carbonate 9.49
    propanediol butyl ether 7.24
    triethyl orthoformate 8.81
    p-tert-butyltoluene 1.78
    methyl 4-tert-butylbenzoate 13.67
    morpholine 19.73
    tert-butylamine 1.03
    n-dodecanol 1.91
    dimethoxymethane 24.99
    ethylene carbonate 21.32
    cyrene 30.09
    2-ethoxyethyl acetate 10.64
    2-ethylhexyl acetate 9.94
    1,2,4-trichlorobenzene 9.08
    4-methylpyridine 12.79
    dibutyl ether 3.04
    2,6-dimethyl-4-heptanol 2.51
    DEF 18.5
    dimethyl isosorbide 35.32
    tetrachloroethylene 11.6
    eugenol 13.92
    triacetin 12.67
    span 80 10.3
    1,4-butanediol 2.13
    1,1-dichloroethane 5.19
    2-methyl-1-pentanol 2.96
    methyl formate 16.57
    2-methyl-1-butanol 2.1
    n-decane 0.28
    butyronitrile 5.48
    3,7-dimethyl-1-octanol 2.93
    1-chlorooctane 1.61
    1-chlorotetradecane 0.81
    n-nonane 0.22
    undecane 0.22
    tert-butylcyclohexane 0.29
    cyclooctane 0.12
    cyclopentanol 5.74
    tetrahydropyran 9.67
    tert-amyl methyl ether 2.87
    2,5,8-trioxanonane 20.71
    1-hexene 0.98
    2-isopropoxyethanol 7.93
    2,2,2-trifluoroethanol 6.64
    methyl butyrate 17.83

    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