Chloroatranorin

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  • Identifiers

    CAS number
    479-16-3

    Molecular formula
    C19H17ClO8

    SMILES
    CC1=CC(=C(C(=C1C(=O)OC)O)C)OC(=O)C2=C(C(=C(C(=C2O)C=O)O)Cl)C

  • Odor profile

    Odorless 46.29%
    Phenolic 42.63%
    Sweet 31.83%
    Woody 31.34%
    Dry 28.55%
    Balsamic 25.15%
    Spicy 25.0%
    Fruity 24.23%
    Burnt 24.23%
    Powdery 23.8%

    Scent© AI

  • Properties

    XLogP3-AA
    5.0

    pKa est.
    6.15 (neutral)

    Molecular weight
    408.8 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1090°C

    Flash point est.
    238.1 ˚C

  • Synonyms

    • Chloratranorin
    • Chloroatranorin
    • 479-16-3
    • Benzoic acid, 3-chloro-5-formyl-4,6-dihydroxy-2-methyl-, 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester
    • UNII-433PEB1G7C
    • 433PEB1G7C
    • 5-CHLOROATRANORIN
    • (3-hydroxy-4-methoxycarbonyl-2,5-dimethylphenyl) 5-chloro-3-formyl-2,4-dihydroxy-6-methylbenzoate
    • DTXSID50197318
    • 4-[(3-Chloro-5-formyl-4,6-dihydroxy-2-methylbenzoyl)oxy]-2-hydroxy-3,6-dimethylbenzoic acid methyl ester
    • Isophthalaldehydic acid, 5-chloro-2,4-dihydroxy-6-methyl-, 4-ester with methyl 3,6-dimethyl-.beta.-resorcylate
    • .BETA.-RESORCYLIC ACID, 3,6-DIMETHYL-, METHYL ESTER, 4-(5-CHLORO-2,4-DIHYDROXY-6-METHYLISOPHTHALALDEHYDATE)
    • .beta.-Resorcylic acid, 3,6-dimethyl-,methyl ester, 4-(5-chloro-2,4-dihydroxy-6-methylisophthalaldehydate)
    • Spectrum5_002072
    • SCHEMBL21369176
    • DTXCID60119809
    • CHEBI:144138
    • AAA47916
    • NS00134223
    • Q27258607
    • 3-Hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl 3-chloro-5-formyl-4,6-dihydroxy-2-methylbenzoate
    • 3-Hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl 3-chloro-5-formyl-4,6-dihydroxy-2-methylbenzoate #
    • 3-Hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl 3-chloro-5-formyl-4,6-dihydroxy-2-methylbenzoic acid
    • BETA-RESORCYLIC ACID, 3,6-DIMETHYL-, METHYL ESTER, 4-(5-CHLORO-2,4-DIHYDROXY-6-METHYLISOPHTHALALDEHYDATE)
    • beta-Resorcylic acid, 3,6-dimethyl-,methyl ester, 4-(5-chloro-2,4-dihydroxy-6-methylisophthalaldehydate)
    • Isophthalaldehydic acid, 5-chloro-2,4-dihydroxy-6-methyl-, 4-ester with methyl 3,6-dimethyl-beta-resorcylate

  • Applications

    Chloroatranorin (CAS 479-16-3) is a lichen-derived depside used primarily as a reference standard in phytochemistry and LC-MS/HPLC/TLC for identification, quantification, and chemotaxonomic profiling of lichens; as a scaffold for semisynthesis and structure–activity comparisons with atranorin derivatives; frequently evaluated in vitro for antimicrobial and antifungal activities, biofilm inhibition, antioxidant and anti-inflammatory properties, and cancer-oriented cytotoxicity; investigated for UV absorption and the photoprotective role of lichens (suggesting potential as a nature-based UV filter); and applied in quality control of lichen raw materials, extract standardization, analytical method development, and as a control when assessing toxicity and contact-allergy risk of lichen-containing preparations.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 4.33
    methanol 5.33
    isopropanol 3.93
    water 0.0
    ethyl acetate 12.04
    n-propanol 6.51
    acetone 18.19
    n-butanol 5.03
    acetonitrile 3.84
    DMF 115.27
    toluene 1.67
    isobutanol 4.08
    1,4-dioxane 22.83
    methyl acetate 11.36
    THF 157.01
    2-butanone 20.96
    n-pentanol 5.44
    sec-butanol 5.49
    n-hexane 0.18
    ethylene glycol 2.99
    NMP 111.6
    cyclohexane 0.1
    DMSO 157.95
    n-butyl acetate 8.47
    n-octanol 1.69
    chloroform 10.07
    n-propyl acetate 9.38
    acetic acid 8.15
    dichloromethane 10.45
    cyclohexanone 27.81
    propylene glycol 6.08
    isopropyl acetate 8.01
    DMAc 87.86
    2-ethoxyethanol 24.49
    isopentanol 4.2
    n-heptane 0.17
    ethyl formate 6.69
    1,2-dichloroethane 9.51
    n-hexanol 3.8
    2-methoxyethanol 48.95
    isobutyl acetate 4.61
    tetrachloromethane 0.73
    n-pentyl acetate 5.99
    transcutol 22.36
    n-heptanol 2.57
    ethylbenzene 1.21
    MIBK 8.95
    2-propoxyethanol 35.52
    tert-butanol 6.21
    MTBE 4.91
    2-butoxyethanol 12.76
    propionic acid 8.38
    o-xylene 1.23
    formic acid 5.65
    diethyl ether 5.69
    m-xylene 1.33
    p-xylene 1.52
    chlorobenzene 2.29
    dimethyl carbonate 16.8
    n-octane 0.1
    formamide 13.61
    cyclopentanone 77.05
    2-pentanone 17.12
    anisole 5.95
    cyclopentyl methyl ether 17.18
    gamma-butyrolactone 86.35
    1-methoxy-2-propanol 39.09
    pyridine 14.3
    3-pentanone 13.06
    furfural 42.58
    n-dodecane 0.08
    diethylene glycol 27.73
    diisopropyl ether 1.17
    tert-amyl alcohol 6.69
    acetylacetone 26.96
    n-hexadecane 0.1
    acetophenone 8.56
    methyl propionate 19.69
    isopentyl acetate 7.13
    trichloroethylene 21.41
    n-nonanol 2.0
    cyclohexanol 4.71
    benzyl alcohol 6.3
    2-ethylhexanol 2.5
    isooctanol 2.22
    dipropyl ether 5.49
    1,2-dichlorobenzene 2.8
    ethyl lactate 10.04
    propylene carbonate 20.52
    n-methylformamide 29.64
    2-pentanol 3.49
    n-pentane 0.12
    1-propoxy-2-propanol 22.52
    1-methoxy-2-propyl acetate 22.97
    2-(2-methoxypropoxy) propanol 14.54
    mesitylene 0.74
    ε-caprolactone 24.07
    p-cymene 1.07
    epichlorohydrin 88.05
    1,1,1-trichloroethane 4.89
    2-aminoethanol 6.67
    morpholine-4-carbaldehyde 72.85
    sulfolane 162.16
    2,2,4-trimethylpentane 0.11
    2-methyltetrahydrofuran 28.34
    n-hexyl acetate 6.05
    isooctane 0.08
    2-(2-butoxyethoxy)ethanol 15.58
    sec-butyl acetate 5.66
    tert-butyl acetate 11.34
    decalin 0.15
    glycerin 17.62
    diglyme 28.86
    acrylic acid 9.43
    isopropyl myristate 2.9
    n-butyric acid 9.4
    acetyl acetate 6.59
    di(2-ethylhexyl) phthalate 4.09
    ethyl propionate 10.53
    nitromethane 37.84
    1,2-diethoxyethane 9.8
    benzonitrile 4.04
    trioctyl phosphate 3.25
    1-bromopropane 3.8
    gamma-valerolactone 90.79
    n-decanol 1.52
    triethyl phosphate 5.4
    4-methyl-2-pentanol 2.12
    propionitrile 5.94
    vinylene carbonate 15.26
    1,1,2-trichlorotrifluoroethane 47.39
    DMS 9.76
    cumene 0.85
    2-octanol 1.82
    2-hexanone 13.22
    octyl acetate 3.81
    limonene 1.52
    1,2-dimethoxyethane 41.91
    ethyl orthosilicate 4.53
    tributyl phosphate 3.58
    diacetone alcohol 22.85
    N,N-dimethylaniline 4.45
    acrylonitrile 10.51
    aniline 4.36
    1,3-propanediol 10.74
    bromobenzene 2.02
    dibromomethane 5.52
    1,1,2,2-tetrachloroethane 17.81
    2-methyl-cyclohexyl acetate 6.55
    tetrabutyl urea 6.54
    diisobutyl methanol 1.91
    2-phenylethanol 6.91
    styrene 1.3
    dioctyl adipate 5.66
    dimethyl sulfate 44.45
    ethyl butyrate 8.08
    methyl lactate 22.53
    butyl lactate 7.79
    diethyl carbonate 5.06
    propanediol butyl ether 9.57
    triethyl orthoformate 6.7
    p-tert-butyltoluene 1.19
    methyl 4-tert-butylbenzoate 10.75
    morpholine 37.44
    tert-butylamine 1.75
    n-dodecanol 1.07
    dimethoxymethane 59.91
    ethylene carbonate 10.96
    cyrene 28.56
    2-ethoxyethyl acetate 11.74
    2-ethylhexyl acetate 5.42
    1,2,4-trichlorobenzene 4.34
    4-methylpyridine 11.19
    dibutyl ether 2.77
    2,6-dimethyl-4-heptanol 1.91
    DEF 26.67
    dimethyl isosorbide 38.1
    tetrachloroethylene 8.16
    eugenol 11.5
    triacetin 10.05
    span 80 11.09
    1,4-butanediol 4.61
    1,1-dichloroethane 5.15
    2-methyl-1-pentanol 4.7
    methyl formate 20.49
    2-methyl-1-butanol 4.62
    n-decane 0.15
    butyronitrile 5.03
    3,7-dimethyl-1-octanol 1.9
    1-chlorooctane 0.93
    1-chlorotetradecane 0.39
    n-nonane 0.13
    undecane 0.11
    tert-butylcyclohexane 0.16
    cyclooctane 0.06
    cyclopentanol 10.36
    tetrahydropyran 12.91
    tert-amyl methyl ether 5.87
    2,5,8-trioxanonane 22.05
    1-hexene 1.05
    2-isopropoxyethanol 14.15
    2,2,2-trifluoroethanol 5.11
    methyl butyrate 12.77

    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 0.7%
Oakmoss (Yugoslavia) 2 9000-50-4 Evernia prunastri (L.) Ach., fam. Usneaceae 0.1%
Treemoss concrete 9000-50-4 Evernia ssp., fam. Usneaceae 0.3%