Atranorin

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    479-20-9

    Molecular formula
    C19H18O8

    SMILES
    CC1=CC(=C(C(=C1C(=O)OC2=C(C(=C(C(=C2)C)C(=O)OC)O)C)O)C=O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Phenolic 45.6%
    Odorless 44.08%
    Woody 36.21%
    Sweet 35.94%
    Dry 27.87%
    Balsamic 26.35%
    Fruity 25.89%
    Spicy 25.86%
    Floral 24.97%
    Powdery 23.32%

    Scent© AI

  • Properties

    XLogP3-AA
    4.3

    pKa est.
    6.76 (neutral)

    Molecular weight
    374.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    901°C

    Flash point est.
    237.18 ˚C

  • Synonyms

    • Atranorin
    • 479-20-9
    • Atranoric acid
    • Atranorine
    • Parmelin
    • Usnarin
    • Antranoric acid
    • Parmelin acid
    • Usnarin acid
    • 3-Hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl 3-formyl-2,4-dihydroxy-6-methylbenzoate
    • NSC 249980
    • NSC 685591
    • NSC-685591
    • EINECS 207-527-7
    • UNII-450U2VJ2VG
    • 450U2VJ2VG
    • Benzoic acid,3-formyl-2,4-dihydroxy-6-methyl-,3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester
    • ATRANORIN [MI]
    • NSC-249980
    • 3-formyl-2,4-dihydroxy-6-methylbenzoic acid 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester
    • CHEMBL173395
    • Benzoic acid, 3-formyl-2,4-dihydroxy-6-methyl-, 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester
    • DTXSID10197319
    • NSC685591
    • Isophthalaldehydic acid, 2,4-dihydroxy-6-methyl-, 4-ester with methyl 3,6-dimethyl-beta-resorcylate
    • Isophthalaldehydic acid, 2,4-dihydroxy-6-methyl-, 4-ester with methyl 3,6-dimethyl-.beta.-resorcylate
    • Benzoic acid,4-dihydroxy-6-methyl-, 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester
    • Isophthalaldehydic acid,4-dihydroxy-6-methyl-, 4-ester with methyl 3,6-dimethyl-.beta.-resorcylate
    • MFCD00016597
    • (3-hydroxy-4-methoxycarbonyl-2,5-dimethylphenyl) 3-formyl-2,4-dihydroxy-6-methylbenzoate
    • Atranorin (Standard)
    • Spectrum_000143
    • SpecPlus_000239
    • Atranoric acid; Parmelin
    • Spectrum2_001749
    • Spectrum3_001716
    • Spectrum4_001700
    • Spectrum5_000380
    • BSPBio_003332
    • KBioGR_002000
    • KBioSS_000623
    • SPECTRUM200034
    • DivK1c_006335
    • SPBio_001858
    • SCHEMBL1370191
    • HY-N2907R
    • KBio1_001279
    • KBio2_000623
    • KBio2_003191
    • KBio2_005759
    • KBio3_002552
    • DTXCID70119810
    • CHEBI:144119
    • HY-N2907
    • NSC87512
    • BDBM50056919
    • CCG-38801
    • NSC-87512
    • NSC249980
    • AKOS024319117
    • FA64948
    • SDCCGMLS-0066426.P001
    • NCGC00095465-01
    • NCGC00095465-02
    • DA-61304
    • MS-26044
    • CS-0023502
    • NS00031734
    • G12060
    • SR-05000002629
    • SR-05000002629-1
    • Q27258788
    • (3-hydroxy-4-methoxycarbonyl-2,5-dimethyl-phenyl) 3-formyl-2,4-dihydroxy-6-methyl-benzoate
    • 3-Hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl 3-formyl-2,4-dihydroxy-6-methylbenzoate #
    • Methyl 4-(3-formyl-2,4-dihydroxy-6-methyl-benzoyloxy)-2-hydroxy- 3,6-dimethyl-benzoate
    • Methyl 4-(3-formyl-2,4-dihydroxy-6-methyl-benzoyloxy)-2-hydroxy-3,6-dimethyl-benzoate
    • 3-Hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl 3-formyl-2,4-dihydroxy-6-methylbenzoic acid
    • 4-Hydroxy-3-(methoxycarbonyl)-2,5-dimethylphenyl 3-formyl-2,4-dihydroxy-6-methylbenzoic acid
    • Benzoic acid, 3-formyl-2,4-dihydroxy-6-methyl-, 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester (9CI)
    • Isophthalaldehydic acid, 2,4-dihydroxy-6-methyl-, 4-ester with methyl 3,6-dimethyl-beta-resorcylate (8CI)
    • methyl 1-(3-formyl-2,4-dihydroxy-6-methylphenylcarbonyloxy)-3-hydroxy-2,5-dimethyl-4-benzenecarboxylate

  • Applications

    Atranorin (CAS 479-20-9) is a lichen-derived natural depside applied and investigated for: (1) analytical and chemotaxonomic uses as a reference marker in lichen studies and quality control of lichen extracts (TLC/HPLC/LC–MS); (2) natural photoprotection and UV absorption in cosmetics and materials, serving as a prototype ingredient for sunscreens/anti-photoaging skincare and as a UV-stabilizing/antioxidant additive in polymers and coatings; (3) a medicinal-chemistry scaffold with studied antioxidant, anti-inflammatory, antibacterial/antifungal and antibiofilm activities, supporting prospects in skin care, antisepsis, wound-healing support, and cancer research via apoptosis induction and modulation of NF-kB and redox pathways; (4) ecological roles as a defensive allelopathic/anti-herbivory agent and as a marker to monitor lichen responses to pollution; note its poor water solubility (commonly formulated in DMSO, ethanol, or acetone) and photosensitivity, which require control during formulation and storage.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 5.84
    methanol 7.76
    isopropanol 5.08
    water 0.0
    ethyl acetate 13.95
    n-propanol 8.0
    acetone 27.19
    n-butanol 6.42
    acetonitrile 7.21
    DMF 142.63
    toluene 1.58
    isobutanol 4.98
    1,4-dioxane 25.06
    methyl acetate 14.72
    THF 192.72
    2-butanone 26.05
    n-pentanol 7.17
    sec-butanol 6.44
    n-hexane 0.24
    ethylene glycol 4.2
    NMP 137.67
    cyclohexane 0.11
    DMSO 313.99
    n-butyl acetate 9.62
    n-octanol 2.39
    chloroform 10.3
    n-propyl acetate 11.02
    acetic acid 12.9
    dichloromethane 11.06
    cyclohexanone 33.33
    propylene glycol 8.13
    isopropyl acetate 9.0
    DMAc 100.29
    2-ethoxyethanol 30.89
    isopentanol 5.46
    n-heptane 0.19
    ethyl formate 8.64
    1,2-dichloroethane 11.49
    n-hexanol 4.76
    2-methoxyethanol 68.2
    isobutyl acetate 5.39
    tetrachloromethane 0.79
    n-pentyl acetate 6.5
    transcutol 29.24
    n-heptanol 3.25
    ethylbenzene 1.26
    MIBK 11.2
    2-propoxyethanol 42.67
    tert-butanol 8.54
    MTBE 5.19
    2-butoxyethanol 14.88
    propionic acid 11.42
    o-xylene 1.21
    formic acid 9.61
    diethyl ether 5.88
    m-xylene 1.45
    p-xylene 1.64
    chlorobenzene 2.57
    dimethyl carbonate 19.15
    n-octane 0.11
    formamide 22.27
    cyclopentanone 96.08
    2-pentanone 20.65
    anisole 6.12
    cyclopentyl methyl ether 19.48
    gamma-butyrolactone 111.2
    1-methoxy-2-propanol 56.13
    pyridine 14.53
    3-pentanone 14.84
    furfural 48.49
    n-dodecane 0.1
    diethylene glycol 34.4
    diisopropyl ether 1.29
    tert-amyl alcohol 7.82
    acetylacetone 33.59
    n-hexadecane 0.12
    acetophenone 9.62
    methyl propionate 22.74
    isopentyl acetate 8.34
    trichloroethylene 25.13
    n-nonanol 2.7
    cyclohexanol 5.4
    benzyl alcohol 6.92
    2-ethylhexanol 3.11
    isooctanol 2.72
    dipropyl ether 5.7
    1,2-dichlorobenzene 3.11
    ethyl lactate 11.89
    propylene carbonate 25.82
    n-methylformamide 41.07
    2-pentanol 4.26
    n-pentane 0.14
    1-propoxy-2-propanol 26.53
    1-methoxy-2-propyl acetate 25.0
    2-(2-methoxypropoxy) propanol 16.98
    mesitylene 0.85
    ε-caprolactone 27.4
    p-cymene 1.11
    epichlorohydrin 111.24
    1,1,1-trichloroethane 5.93
    2-aminoethanol 8.8
    morpholine-4-carbaldehyde 84.27
    sulfolane 227.98
    2,2,4-trimethylpentane 0.12
    2-methyltetrahydrofuran 32.97
    n-hexyl acetate 7.41
    isooctane 0.09
    2-(2-butoxyethoxy)ethanol 19.23
    sec-butyl acetate 6.32
    tert-butyl acetate 13.17
    decalin 0.17
    glycerin 24.25
    diglyme 35.33
    acrylic acid 12.85
    isopropyl myristate 3.26
    n-butyric acid 12.57
    acetyl acetate 7.86
    di(2-ethylhexyl) phthalate 4.67
    ethyl propionate 12.0
    nitromethane 60.09
    1,2-diethoxyethane 10.59
    benzonitrile 4.98
    trioctyl phosphate 3.8
    1-bromopropane 4.29
    gamma-valerolactone 109.51
    n-decanol 2.01
    triethyl phosphate 6.36
    4-methyl-2-pentanol 2.73
    propionitrile 8.71
    vinylene carbonate 18.03
    1,1,2-trichlorotrifluoroethane 55.04
    DMS 10.66
    cumene 0.94
    2-octanol 2.25
    2-hexanone 16.28
    octyl acetate 4.47
    limonene 1.61
    1,2-dimethoxyethane 50.9
    ethyl orthosilicate 5.22
    tributyl phosphate 4.35
    diacetone alcohol 29.52
    N,N-dimethylaniline 4.67
    acrylonitrile 14.58
    aniline 4.43
    1,3-propanediol 15.59
    bromobenzene 2.21
    dibromomethane 6.14
    1,1,2,2-tetrachloroethane 20.6
    2-methyl-cyclohexyl acetate 7.51
    tetrabutyl urea 7.59
    diisobutyl methanol 2.28
    2-phenylethanol 7.54
    styrene 1.31
    dioctyl adipate 6.22
    dimethyl sulfate 57.19
    ethyl butyrate 8.66
    methyl lactate 26.92
    butyl lactate 8.41
    diethyl carbonate 5.45
    propanediol butyl ether 11.51
    triethyl orthoformate 7.35
    p-tert-butyltoluene 1.18
    methyl 4-tert-butylbenzoate 11.84
    morpholine 43.08
    tert-butylamine 2.22
    n-dodecanol 1.42
    dimethoxymethane 77.45
    ethylene carbonate 13.43
    cyrene 31.52
    2-ethoxyethyl acetate 12.15
    2-ethylhexyl acetate 6.03
    1,2,4-trichlorobenzene 4.69
    4-methylpyridine 12.07
    dibutyl ether 3.25
    2,6-dimethyl-4-heptanol 2.28
    DEF 28.8
    dimethyl isosorbide 45.16
    tetrachloroethylene 8.78
    eugenol 12.31
    triacetin 11.23
    span 80 12.33
    1,4-butanediol 6.08
    1,1-dichloroethane 6.42
    2-methyl-1-pentanol 5.94
    methyl formate 28.81
    2-methyl-1-butanol 5.67
    n-decane 0.18
    butyronitrile 7.1
    3,7-dimethyl-1-octanol 2.5
    1-chlorooctane 1.21
    1-chlorotetradecane 0.48
    n-nonane 0.15
    undecane 0.13
    tert-butylcyclohexane 0.18
    cyclooctane 0.06
    cyclopentanol 12.26
    tetrahydropyran 13.92
    tert-amyl methyl ether 6.19
    2,5,8-trioxanonane 26.34
    1-hexene 1.31
    2-isopropoxyethanol 17.22
    2,2,2-trifluoroethanol 7.84
    methyl butyrate 15.48

    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

Botanical

Name CAS Botanical Proportion
Oakmoss absolute (Morocco) 9000-50-4 Evernia prunastri (L.) Ach., fam. Usneaceae 0.01%
Oakmoss (Yugoslavia) 1 9000-50-4 Evernia prunastri (L.) Ach., fam. Usneaceae 0.3%
Oakmoss (Yugoslavia) 2 9000-50-4 Evernia prunastri (L.) Ach., fam. Usneaceae 0.01%
Treemoss concrete 9000-50-4 Evernia ssp., fam. Usneaceae 0.01%