Frangulin A

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  • Identifiers

    CAS number
    521-62-0

    Molecular formula
    C21H20O9

    SMILES
    C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=CC3=C(C(=C2)O)C(=O)C4=C(C3=O)C=C(C=C4O)C)O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 72.32%
    Phenolic 30.98%
    Vanilla 27.8%
    Sweet 22.7%
    Spicy 22.6%
    Milky 21.75%
    Burnt 20.86%
    Bitter 20.02%
    Savory 19.67%
    Balsamic 18.43%

     

    Flavor
    Bitter 92.51%
    Bland 28.19%
    Odorless 27.27%
    Sweet-like 22.26%
    Cedarleaf 20.35%
    Lovage 19.29%
    Parsley 19.23%
    Nitrile 18.76%
    Ripe apricot 18.35%
    Red fruit 18.21%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.4

    pKa est.
    7.37 (neutral)

    Molecular weight
    416.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1780°C

    Flash point

    • 285.39 ˚C est.

  • Synonyms

    • Frangulin A
    • 521-62-0
    • HXU301W02A
    • 1,8-dihydroxy-3-methyl-6-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyanthracene-9,10-dione
    • 1,8-dihydroxy-3-methyl-6-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-anthracene-9,10-dione
    • DTXSID401031905
    • 1,8-dihydroxy-3-methyl-6-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-anthracene-9,10-dione
    • 1,8-dihydroxy-3-methyl-6-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyanthracene-9,10-dione
    • RefChem:141509
    • DTXCID101516904
    • 208-316-2
    • 274-082-3
    • EINECS 208-316-2
    • BRN 0059993
    • CHEMBL1172006
    • MFCD00016363
    • 1,8-Dihydroxy-3-methyl-6-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)anthracene-9,10-dione
    • UNII-HXU301W02A
    • Rhamnoxanthin
    • Emodin-L-rhamnoside
    • FRANGULIN A [MI]
    • Anthraquinone, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-1,8-dihydroxy-6-methyl-
    • 3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-1,8-dihydroxy-6-methyl-9,10-anthracenedione
    • Frangulin A (Rhamnoxanthin)
    • 5-17-06-00267 (Beilstein Handbook Reference)
    • CHEBI:5167
    • SCHEMBL1426460
    • Frangulin A, analytical standard
    • SCHEMBL29705160
    • DTXSID40966459
    • HY-N8344
    • BDBM50333878
    • 3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-1,8-dihydroxy-6-methylanthraquinone
    • AKOS040760401
    • FF65554
    • 9,10-Anthracenedione, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-1,8-dihydroxy-6-methyl-
    • FS-10669
    • CS-0143373
    • NS00042806
    • A828950
    • Q27106673
    • 4,5-Dihydroxy-7-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl 6-deoxyhexopyranoside
    • 4,5-dihydroxy-7-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl 6-deoxy-alpha-L-mannopyranoside
    • 521-62-0

  • Applications

    Frangulin A (CAS 521-62-0) is typically encountered as an anthraquinone glycoside derived from plant materials and is commonly used as an intermediate in organic synthesis. It may be employed as a starting material for the preparation of related anthraquinone derivatives, including dye and pigment precursors, and can serve as a scaffold in pharmaceutical or medicinal-chemistry research. In analytical workflows, it is sometimes used as a marker compound for quality control and characterization of plant extracts containing frangulin glycosides. Depending on formulation and regulatory allowances, it may be evaluated for use as a colorant or dye precursor in cosmetics, coatings, or inks, and could find roles in polymer formulations as a dye-related additive after appropriate processing.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 4.29
    methanol 5.14
    isopropanol 3.09
    water 0.1
    ethyl acetate 1.99
    n-propanol 4.29
    acetone 12.84
    n-butanol 1.94
    acetonitrile 2.41
    DMF 52.15
    toluene 0.46
    isobutanol 1.43
    1,4-dioxane 12.49
    methyl acetate 3.25
    THF 33.01
    2-butanone 6.47
    n-pentanol 1.86
    sec-butanol 1.84
    n-hexane 0.05
    ethylene glycol 11.97
    NMP 39.43
    cyclohexane 0.08
    DMSO 125.06
    n-butyl acetate 0.92
    n-octanol 1.39
    chloroform 0.39
    n-propyl acetate 1.48
    acetic acid 23.3
    dichloromethane 0.44
    cyclohexanone 8.34
    propylene glycol 11.23
    isopropyl acetate 1.21
    DMAc 67.88
    2-ethoxyethanol 23.93
    isopentanol 1.22
    n-heptane 0.09
    ethyl formate 2.17
    1,2-dichloroethane 0.71
    n-hexanol 1.0
    2-methoxyethanol 47.15
    isobutyl acetate 0.63
    tetrachloromethane 0.09
    n-pentyl acetate 1.43
    transcutol 20.97
    n-heptanol 1.66
    ethylbenzene 0.27
    MIBK 1.54
    2-propoxyethanol 17.83
    tert-butanol 2.46
    MTBE 0.66
    2-butoxyethanol 9.05
    propionic acid 5.55
    o-xylene 0.33
    formic acid 28.99
    diethyl ether 1.59
    m-xylene 0.32
    p-xylene 0.34
    chlorobenzene 0.22
    dimethyl carbonate 4.61
    n-octane 0.07
    formamide 36.73
    cyclopentanone 16.63
    2-pentanone 3.54
    anisole 1.06
    cyclopentyl methyl ether 2.94
    gamma-butyrolactone 18.1
    1-methoxy-2-propanol 24.55
    pyridine 6.21
    3-pentanone 2.51
    furfural 10.85
    n-dodecane 0.06
    diethylene glycol 29.05
    diisopropyl ether 0.25
    tert-amyl alcohol 1.48
    acetylacetone 7.68
    n-hexadecane 0.07
    acetophenone 2.08
    methyl propionate 4.07
    isopentyl acetate 0.85
    trichloroethylene 1.18
    n-nonanol 1.55
    cyclohexanol 1.64
    benzyl alcohol 2.51
    2-ethylhexanol 0.59
    isooctanol 1.08
    dipropyl ether 1.48
    1,2-dichlorobenzene 0.22
    ethyl lactate 3.58
    propylene carbonate 3.33
    n-methylformamide 19.89
    2-pentanol 0.94
    n-pentane 0.05
    1-propoxy-2-propanol 8.11
    1-methoxy-2-propyl acetate 3.96
    2-(2-methoxypropoxy) propanol 7.76
    mesitylene 0.21
    ε-caprolactone 6.39
    p-cymene 0.22
    epichlorohydrin 12.7
    1,1,1-trichloroethane 0.2
    2-aminoethanol 13.23
    morpholine-4-carbaldehyde 38.53
    sulfolane 39.19
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 4.88
    n-hexyl acetate 1.66
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 10.92
    sec-butyl acetate 0.71
    tert-butyl acetate 1.5
    decalin 0.04
    glycerin 33.67
    diglyme 17.93
    acrylic acid 8.29
    isopropyl myristate 0.79
    n-butyric acid 3.44
    acetyl acetate 1.53
    di(2-ethylhexyl) phthalate 1.34
    ethyl propionate 1.3
    nitromethane 32.82
    1,2-diethoxyethane 3.58
    benzonitrile 1.17
    trioctyl phosphate 1.15
    1-bromopropane 0.32
    gamma-valerolactone 36.98
    n-decanol 1.12
    triethyl phosphate 1.04
    4-methyl-2-pentanol 0.53
    propionitrile 1.82
    vinylene carbonate 3.06
    1,1,2-trichlorotrifluoroethane 17.86
    DMS 2.49
    cumene 0.17
    2-octanol 0.86
    2-hexanone 2.4
    octyl acetate 1.31
    limonene 0.31
    1,2-dimethoxyethane 20.97
    ethyl orthosilicate 0.95
    tributyl phosphate 1.04
    diacetone alcohol 7.56
    N,N-dimethylaniline 1.07
    acrylonitrile 3.65
    aniline 1.5
    1,3-propanediol 13.6
    bromobenzene 0.14
    dibromomethane 0.27
    1,1,2,2-tetrachloroethane 1.22
    2-methyl-cyclohexyl acetate 1.3
    tetrabutyl urea 2.49
    diisobutyl methanol 0.42
    2-phenylethanol 1.93
    styrene 0.28
    dioctyl adipate 1.75
    dimethyl sulfate 9.94
    ethyl butyrate 1.12
    methyl lactate 9.8
    butyl lactate 3.01
    diethyl carbonate 0.8
    propanediol butyl ether 8.64
    triethyl orthoformate 1.41
    p-tert-butyltoluene 0.22
    methyl 4-tert-butylbenzoate 3.26
    morpholine 19.91
    tert-butylamine 0.52
    n-dodecanol 0.78
    dimethoxymethane 24.49
    ethylene carbonate 2.51
    cyrene 12.2
    2-ethoxyethyl acetate 3.39
    2-ethylhexyl acetate 0.62
    1,2,4-trichlorobenzene 0.42
    4-methylpyridine 2.6
    dibutyl ether 1.01
    2,6-dimethyl-4-heptanol 0.42
    DEF 6.86
    dimethyl isosorbide 11.27
    tetrachloroethylene 0.95
    eugenol 4.46
    triacetin 3.78
    span 80 5.87
    1,4-butanediol 6.14
    1,1-dichloroethane 0.26
    2-methyl-1-pentanol 1.09
    methyl formate 12.24
    2-methyl-1-butanol 1.16
    n-decane 0.12
    butyronitrile 1.15
    3,7-dimethyl-1-octanol 0.79
    1-chlorooctane 0.33
    1-chlorotetradecane 0.15
    n-nonane 0.1
    undecane 0.08
    tert-butylcyclohexane 0.02
    cyclooctane 0.04
    cyclopentanol 3.68
    tetrahydropyran 4.31
    tert-amyl methyl ether 0.77
    2,5,8-trioxanonane 13.88
    1-hexene 0.24
    2-isopropoxyethanol 9.52
    2,2,2-trifluoroethanol 7.97
    methyl butyrate 1.87

    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