Amarogentin

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  • Identifiers

    CAS number
    21018-84-8

    Molecular formula
    C29H30O13

    SMILES
    C=C[C@@H]1[C@@H]2CCOC(=O)C2=CO[C@H]1O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC(=O)C4=C(C=C(C=C4O)O)C5=CC(=CC=C5)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 69.88%
    Spicy 25.28%
    Sweet 23.42%
    Vanilla 22.66%
    Phenolic 19.96%
    Bitter 19.22%
    Balsamic 19.06%
    Milky 18.18%
    Savory 17.29%
    Aromatic 16.0%

     

    Flavor
    Bitter 91.02%
    Bland 28.4%
    Odorless 25.58%
    Sweet-like 22.12%
    Cedarleaf 20.39%
    Lovage 19.59%
    Parsley 19.11%
    Nitrile 18.61%
    Ripe apricot 18.12%
    Ethyl benzoate 18.09%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.4

    pKa est.
    5.51 (weak acid)

    Molecular weight
    586.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    3945°C

    Flash point

    • 270.89 ˚C est.

  • Synonyms

    • Amarogentin
    • 21018-84-8
    • 5L82GT5I0W
    • DTXSID501029787
    • [(2S,3R,4S,5S,6R)-2-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate
    • CHEBI:2622
    • (4aR)-5t-ethenyl-6c-[O(2)-(3,5,3'-trihydroxybiphenyl-2-ylcarbonyl)-beta-D-glucopyranosyloxy]-4,4ar,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one
    • ((2S,3R,4S,5S,6R)-2-(((3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano(3,4-c)pyran-3-yl)oxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl) 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate
    • (4aR)-5t-ethenyl-6c-(O(2)-(3,5,3'-trihydroxybiphenyl-2-ylcarbonyl)-beta-D-glucopyranosyloxy)-4,4ar,5,6-tetrahydro-3H-pyrano(3,4-c)pyran-1-one
    • RefChem:111835
    • DTXCID401514995
    • sweroside-2'-(3'',5'',3'''-trihydroxydiphenyl)-2''-carboxylic acid ester
    • (2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-2-(((3S,4R,4aS)-8-oxo-4-vinyl-3,4,4a,5,6,8-hexahydropyrano[3,4-c]pyran-3-yl)oxy)tetrahydro-2H-pyran-3-yl 3,3',5-trihydroxy-[1,1'-biphenyl]-2-carboxylate
    • (4aS,5R,6S)-5-ethenyl-1-oxo-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl- 2-O-[(3,3',5-trihydroxybiphenyl-2-yl)carbonyl]-beta-D-glucopyranoside
    • DBOVHQOUSDWAPQ-WTONXPSSSA-N
    • Amarogentin (Standard)
    • AMAROGENTIN [MI]
    • C09767
    • UNII-5L82GT5I0W
    • SCHEMBL1031187
    • GTPL12459
    • HY-N2447R
    • HY-N2447
    • C29H30O13
    • s1273
    • AKOS015896722
    • EBC-618508
    • (2S,3R,4S,5S,6R)-2-{[(3S,4R,4aS)-4-ethenyl-8-oxo-3H,4H,4aH,5H,6H,8H-pyrano[3,4-c]pyran-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,3',5-trihydroxy-[1,1'-biphenyl]-2-carboxylate
    • DA-70749
    • FA146492
    • CS-0022673
    • NS00120927
    • Q3613679
    • 2-(4aS-(4aalpha,5beta,6alpha))-3,3',5-Trihydroxy-(1,1'-biphenyl)-2-carboxylate
    • (1,1'-Biphenyl)-2-carboxylic acid, 3,3',5-trihydroxy-, 2-ester with 5-ethenyl-6-(beta-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-1H,3H-pyrano(3,4-c)pyran-1-one, (4aS-(4aalpha,5beta,6alpha))-
    • [(2S,3R,4S,5S,6R)-2-[[(3S,4R,4aS)-8-oxo-4-vinyl-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate
    • 1H,3H-Pyrano(3,4-c)pyran-1-one, 5-ethenyl-4,4a,5,6-tetrahydro-6-((2-O-((3,3',5-trihydroxy(1,1'-biphenyl)-2-yl)carbonyl)-beta-D-glucopyranosyl)oxy)-, (4aS,5R,6S)-
    • 21018-84-8

  • Applications

    Amarogentin is a natural, highly potent bitter-tasting compound from the Gentianaceae family (CAS 21018-84-8). It is used as a natural bittering agent in flavor formulations for foods and beverages; in pharmaceutical and dietary supplement formulations to characterize or manage bitterness during product development and testing; in sensory science as a reference standard for bitterness evaluation and for studies of bitter taste receptors; and in natural products research and flavor development where bitterness profiles are relevant; subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 19.28
    methanol 59.25
    isopropanol 7.18
    water 0.05
    ethyl acetate 6.41
    n-propanol 19.26
    acetone 28.39
    n-butanol 12.45
    acetonitrile 4.14
    DMF 108.72
    toluene 0.74
    isobutanol 4.96
    1,4-dioxane 23.79
    methyl acetate 9.93
    THF 62.79
    2-butanone 25.09
    n-pentanol 3.94
    sec-butanol 6.76
    n-hexane 0.02
    ethylene glycol 17.38
    NMP 99.69
    cyclohexane 0.05
    DMSO 259.69
    n-butyl acetate 1.37
    n-octanol 1.52
    chloroform 3.8
    n-propyl acetate 2.05
    acetic acid 71.69
    dichloromethane 5.09
    cyclohexanone 26.0
    propylene glycol 26.68
    isopropyl acetate 2.23
    DMAc 110.9
    2-ethoxyethanol 36.55
    isopentanol 3.76
    n-heptane 0.03
    ethyl formate 12.75
    1,2-dichloroethane 4.05
    n-hexanol 1.31
    2-methoxyethanol 113.57
    isobutyl acetate 0.54
    tetrachloromethane 0.37
    n-pentyl acetate 2.07
    transcutol 27.27
    n-heptanol 1.66
    ethylbenzene 0.16
    MIBK 2.69
    2-propoxyethanol 18.38
    tert-butanol 2.99
    MTBE 1.24
    2-butoxyethanol 10.66
    propionic acid 18.27
    o-xylene 0.36
    formic acid 57.99
    diethyl ether 3.05
    m-xylene 0.29
    p-xylene 0.16
    chlorobenzene 0.66
    dimethyl carbonate 8.18
    n-octane 0.02
    formamide 60.82
    cyclopentanone 53.16
    2-pentanone 12.93
    anisole 1.32
    cyclopentyl methyl ether 4.24
    gamma-butyrolactone 49.72
    1-methoxy-2-propanol 49.78
    pyridine 14.03
    3-pentanone 7.05
    furfural 33.96
    n-dodecane 0.02
    diethylene glycol 21.59
    diisopropyl ether 0.2
    tert-amyl alcohol 3.15
    acetylacetone 16.57
    n-hexadecane 0.02
    acetophenone 2.34
    methyl propionate 10.55
    isopentyl acetate 0.9
    trichloroethylene 9.49
    n-nonanol 1.57
    cyclohexanol 3.8
    benzyl alcohol 3.39
    2-ethylhexanol 0.51
    isooctanol 0.92
    dipropyl ether 0.99
    1,2-dichlorobenzene 0.51
    ethyl lactate 4.44
    propylene carbonate 10.03
    n-methylformamide 62.43
    2-pentanol 2.64
    n-pentane 0.05
    1-propoxy-2-propanol 8.29
    1-methoxy-2-propyl acetate 4.37
    2-(2-methoxypropoxy) propanol 8.55
    mesitylene 0.11
    ε-caprolactone 20.52
    p-cymene 0.11
    epichlorohydrin 44.1
    1,1,1-trichloroethane 1.02
    2-aminoethanol 30.73
    morpholine-4-carbaldehyde 72.02
    sulfolane 90.0
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 11.48
    n-hexyl acetate 2.4
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 14.1
    sec-butyl acetate 0.86
    tert-butyl acetate 1.78
    decalin 0.01
    glycerin 55.15
    diglyme 22.62
    acrylic acid 24.54
    isopropyl myristate 0.65
    n-butyric acid 19.77
    acetyl acetate 3.54
    di(2-ethylhexyl) phthalate 1.33
    ethyl propionate 2.24
    nitromethane 85.24
    1,2-diethoxyethane 3.38
    benzonitrile 1.49
    trioctyl phosphate 1.13
    1-bromopropane 1.27
    gamma-valerolactone 119.13
    n-decanol 0.97
    triethyl phosphate 0.93
    4-methyl-2-pentanol 0.72
    propionitrile 4.09
    vinylene carbonate 10.97
    1,1,2-trichlorotrifluoroethane 48.67
    DMS 2.29
    cumene 0.08
    2-octanol 0.77
    2-hexanone 3.44
    octyl acetate 1.48
    limonene 0.23
    1,2-dimethoxyethane 27.75
    ethyl orthosilicate 0.76
    tributyl phosphate 1.01
    diacetone alcohol 9.63
    N,N-dimethylaniline 0.76
    acrylonitrile 8.13
    aniline 2.99
    1,3-propanediol 42.82
    bromobenzene 0.36
    dibromomethane 1.87
    1,1,2,2-tetrachloroethane 6.13
    2-methyl-cyclohexyl acetate 1.01
    tetrabutyl urea 2.02
    diisobutyl methanol 0.24
    2-phenylethanol 1.66
    styrene 0.23
    dioctyl adipate 1.94
    dimethyl sulfate 17.47
    ethyl butyrate 1.55
    methyl lactate 20.78
    butyl lactate 3.92
    diethyl carbonate 0.91
    propanediol butyl ether 11.68
    triethyl orthoformate 1.4
    p-tert-butyltoluene 0.1
    methyl 4-tert-butylbenzoate 3.28
    morpholine 43.69
    tert-butylamine 0.57
    n-dodecanol 0.58
    dimethoxymethane 42.55
    ethylene carbonate 7.91
    cyrene 14.18
    2-ethoxyethyl acetate 5.32
    2-ethylhexyl acetate 0.59
    1,2,4-trichlorobenzene 0.92
    4-methylpyridine 5.99
    dibutyl ether 0.8
    2,6-dimethyl-4-heptanol 0.24
    DEF 17.92
    dimethyl isosorbide 9.87
    tetrachloroethylene 3.93
    eugenol 3.89
    triacetin 4.28
    span 80 7.67
    1,4-butanediol 9.9
    1,1-dichloroethane 1.77
    2-methyl-1-pentanol 1.76
    methyl formate 40.19
    2-methyl-1-butanol 4.8
    n-decane 0.04
    butyronitrile 3.54
    3,7-dimethyl-1-octanol 0.74
    1-chlorooctane 0.27
    1-chlorotetradecane 0.09
    n-nonane 0.03
    undecane 0.03
    tert-butylcyclohexane 0.01
    cyclooctane 0.02
    cyclopentanol 8.33
    tetrahydropyran 9.81
    tert-amyl methyl ether 1.45
    2,5,8-trioxanonane 15.56
    1-hexene 0.12
    2-isopropoxyethanol 9.57
    2,2,2-trifluoroethanol 16.91
    methyl butyrate 4.19

    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