Gentiopicroside

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  • Identifiers

    CAS number
    20831-76-9

    Molecular formula
    C16H20O9

    SMILES
    C=C[C@H]1[C@@H](OC=C2C1=CCOC2=O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 57.25%
    Spicy 30.52%
    Sweet 27.0%
    Caramellic 19.62%
    Roasted 19.2%
    Nutty 18.24%
    Burnt 17.89%
    Savory 16.88%
    Vanilla 14.94%
    Milky 14.5%

     

    Flavor
    Bitter 85.91%
    Sweet-like 22.76%
    Bland 22.22%
    Odorless 21.27%
    Cedarleaf 20.17%
    Lovage 19.04%
    Alkaline 18.93%
    Shrimp 18.76%
    Parsley 18.73%
    Leaves 18.62%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.2

    pKa est.
    5.23 (weak acid)

    Molecular weight
    356.32 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2241°C

    Flash point

    • 225.03 ˚C est.

  • Synonyms

    • Gentiopicroside
    • Gentiopicrin
    • 20831-76-9
    • 0WE09Z21RC
    • DTXSID40878043
    • NSC-606402
    • (3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one
    • 1H,3H-Pyrano(3,4-c)pyran-1-one, 5-ethenyl-6-(beta-D-glucopyranosyloxy)-5,6-dihydro-, (5R-trans)-
    • (3S,4R)-4-ethenyl-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-4,6-dihydro-3H-pyrano(3,4-c)pyran-8-one
    • RefChem:37451
    • DTXCID501016106
    • 244-070-2
    • MFCD00075700
    • C16H20O9
    • (5R,6S)-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-vinyl-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one
    • 1H,3H-Pyrano[3,4-c]pyran-1-one, 5-ethenyl-6-(beta-D-glucopyranosyloxy)-5,6-dihydro-, (5R,6S)-
    • Gentiopicroside, >=98% (HPLC)
    • (5R,6S)-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-vinyl-5,6-dihydropyrano[3,4-c]pyran-1(3H)-one
    • gentiopicorside
    • Gentiopicroside?
    • DUAGQYUORDTXOR-GPQRQXLASA-N
    • 1H,3H-Pyrano[3,4-c]pyran-1-one, 5-ethenyl-6-(ss-D-glucopyranosyloxy)-5,6-dihydro-, (5R,6S)-; 1H,3H-Pyrano[3,4-c]pyran-1-one, 5-ethenyl-6-(ss-D-glucopyranosyloxy)-5,6-dihydro-, (5R-trans)-; Gentiopicrin (6CI); Gentiopicroside (7CI,8CI); (5R,6S)-5-Ethenyl-6-(ss-D-glucopyranosyloxy)-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one; NSC 606402
    • GENTIOPICRIN [MI]
    • UNII-0WE09Z21RC
    • MLS002473254
    • SCHEMBL154304
    • CHEBI:5321
    • CHEMBL508320
    • MEGxp0_000872
    • orb1305041
    • ACon1_001284
    • HMS2198G10
    • EX-A6716
    • HY-N0494
    • MSK40190
    • EINECS 244-070-2
    • s3777
    • ZB1867
    • AKOS015896721
    • CCG-268110
    • EBC-157187
    • LMPR0102070009
    • MG09586
    • NSC 606402
    • NCGC00180669-01
    • (5R,6S)-5-ethenyl-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,3H,5H,6H-pyrano[3,4-c]pyran-1-one
    • AC-20248
    • AC-33960
    • AS-74360
    • SMR001397341
    • SY068964
    • CS-0009015
    • G0576
    • C09782
    • 831G769
    • BRD-K33131085-001-01-5
    • BRD-K33131085-001-07-2
    • Q27106718
    • 1H,3H-Pyrano[3,4-c]pyran-1-one,5-ethenyl-6-(|A-D-
    • (5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl beta-D-glucopyranoside
    • (3S,4R)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-4-vinyl-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one
    • (5R,6S)-5-ETHENYL-6-(.BETA.-D-GLUCOPYRANOSYLOXY)-5,6-DIHYDRO-1H,3H-PYRANO(3,4-C)PYRAN-1-ONE
    • (5R-trans)-6-(beta-D-Glucopyranosyloxy)-5,6-dihydro-5-vinyl-1H,3H-pyrano(3,4-c)pyran-1-one
    • 1H,3H-Pyrano[3,4-c]pyran-1-one, 5-ethenyl-6-(|A-D-glucopyranosyloxy)-5,6-dihydro-, (5R,6S)-
    • 20831-76-9

  • Applications

    Gentiopicroside (CAS 20831-76-9) is a natural iridoid glycoside predominantly found in Gentiana species. In industry, it is primarily used as a phytochemical constituent in Gentiana-based herbal medicines and in nutraceuticals, often as a marker compound for quality control and standardization of botanical extracts. It is employed in analytical chemistry as a chemical marker to authenticate Gentiana raw materials and finished products. The compound is also studied in natural product research and pharmacology for its biological activities, contributing to exploratory work in herbal product development. Its use is typically limited to research, quality assessment, and formulation support rather than direct consumer applications.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 6.97
    methanol 34.91
    isopropanol 4.53
    water 1.85
    ethyl acetate 3.98
    n-propanol 6.83
    acetone 14.2
    n-butanol 7.29
    acetonitrile 5.18
    DMF 96.77
    toluene 1.23
    isobutanol 2.8
    1,4-dioxane 14.52
    methyl acetate 4.37
    THF 27.53
    2-butanone 7.33
    n-pentanol 2.54
    sec-butanol 3.44
    n-hexane 0.05
    ethylene glycol 22.42
    NMP 69.84
    cyclohexane 0.29
    DMSO 288.05
    n-butyl acetate 1.0
    n-octanol 2.12
    chloroform 1.13
    n-propyl acetate 1.23
    acetic acid 40.32
    dichloromethane 1.79
    cyclohexanone 15.53
    propylene glycol 16.45
    isopropyl acetate 2.19
    DMAc 96.99
    2-ethoxyethanol 30.75
    isopentanol 4.1
    n-heptane 0.2
    ethyl formate 6.04
    1,2-dichloroethane 2.6
    n-hexanol 1.71
    2-methoxyethanol 86.17
    isobutyl acetate 0.56
    tetrachloromethane 0.28
    n-pentyl acetate 1.68
    transcutol 44.03
    n-heptanol 2.31
    ethylbenzene 0.41
    MIBK 3.44
    2-propoxyethanol 16.73
    tert-butanol 3.67
    MTBE 1.24
    2-butoxyethanol 10.39
    propionic acid 8.22
    o-xylene 1.05
    formic acid 95.47
    diethyl ether 3.04
    m-xylene 0.89
    p-xylene 0.47
    chlorobenzene 0.68
    dimethyl carbonate 8.41
    n-octane 0.13
    formamide 101.13
    cyclopentanone 21.7
    2-pentanone 8.14
    anisole 1.73
    cyclopentyl methyl ether 5.76
    gamma-butyrolactone 23.88
    1-methoxy-2-propanol 40.95
    pyridine 8.14
    3-pentanone 5.13
    furfural 23.88
    n-dodecane 0.1
    diethylene glycol 33.67
    diisopropyl ether 0.59
    tert-amyl alcohol 2.85
    acetylacetone 12.83
    n-hexadecane 0.12
    acetophenone 3.28
    methyl propionate 7.5
    isopentyl acetate 1.14
    trichloroethylene 3.91
    n-nonanol 2.3
    cyclohexanol 5.28
    benzyl alcohol 4.42
    2-ethylhexanol 1.1
    isooctanol 1.66
    dipropyl ether 1.76
    1,2-dichlorobenzene 0.74
    ethyl lactate 4.92
    propylene carbonate 6.41
    n-methylformamide 44.87
    2-pentanol 2.86
    n-pentane 0.14
    1-propoxy-2-propanol 8.82
    1-methoxy-2-propyl acetate 5.1
    2-(2-methoxypropoxy) propanol 11.91
    mesitylene 0.62
    ε-caprolactone 11.59
    p-cymene 0.54
    epichlorohydrin 18.93
    1,1,1-trichloroethane 0.7
    2-aminoethanol 24.05
    morpholine-4-carbaldehyde 57.6
    sulfolane 64.98
    2,2,4-trimethylpentane 0.07
    2-methyltetrahydrofuran 6.96
    n-hexyl acetate 2.35
    isooctane 0.05
    2-(2-butoxyethoxy)ethanol 17.77
    sec-butyl acetate 0.82
    tert-butyl acetate 2.46
    decalin 0.1
    glycerin 50.74
    diglyme 30.31
    acrylic acid 14.25
    isopropyl myristate 1.15
    n-butyric acid 9.59
    acetyl acetate 3.57
    di(2-ethylhexyl) phthalate 2.18
    ethyl propionate 1.88
    nitromethane 57.74
    1,2-diethoxyethane 4.95
    benzonitrile 2.23
    trioctyl phosphate 1.7
    1-bromopropane 0.81
    gamma-valerolactone 49.68
    n-decanol 1.72
    triethyl phosphate 1.89
    4-methyl-2-pentanol 1.4
    propionitrile 2.99
    vinylene carbonate 7.2
    1,1,2-trichlorotrifluoroethane 29.36
    DMS 3.17
    cumene 0.32
    2-octanol 1.24
    2-hexanone 2.06
    octyl acetate 1.82
    limonene 0.91
    1,2-dimethoxyethane 25.13
    ethyl orthosilicate 1.68
    tributyl phosphate 1.63
    diacetone alcohol 10.97
    N,N-dimethylaniline 1.76
    acrylonitrile 6.23
    aniline 3.74
    1,3-propanediol 34.32
    bromobenzene 0.45
    dibromomethane 0.91
    1,1,2,2-tetrachloroethane 3.44
    2-methyl-cyclohexyl acetate 1.7
    tetrabutyl urea 3.57
    diisobutyl methanol 0.91
    2-phenylethanol 3.04
    styrene 0.46
    dioctyl adipate 2.69
    dimethyl sulfate 20.15
    ethyl butyrate 1.79
    methyl lactate 17.69
    butyl lactate 3.79
    diethyl carbonate 1.32
    propanediol butyl ether 11.89
    triethyl orthoformate 2.2
    p-tert-butyltoluene 0.53
    methyl 4-tert-butylbenzoate 5.7
    morpholine 23.33
    tert-butylamine 0.96
    n-dodecanol 1.23
    dimethoxymethane 40.22
    ethylene carbonate 5.51
    cyrene 18.11
    2-ethoxyethyl acetate 4.28
    2-ethylhexyl acetate 0.77
    1,2,4-trichlorobenzene 1.18
    4-methylpyridine 5.28
    dibutyl ether 1.33
    2,6-dimethyl-4-heptanol 0.91
    DEF 15.93
    dimethyl isosorbide 16.4
    tetrachloroethylene 2.66
    eugenol 6.67
    triacetin 5.44
    span 80 8.47
    1,4-butanediol 10.04
    1,1-dichloroethane 0.79
    2-methyl-1-pentanol 1.89
    methyl formate 30.85
    2-methyl-1-butanol 3.6
    n-decane 0.19
    butyronitrile 3.07
    3,7-dimethyl-1-octanol 1.53
    1-chlorooctane 0.58
    1-chlorotetradecane 0.26
    n-nonane 0.16
    undecane 0.14
    tert-butylcyclohexane 0.05
    cyclooctane 0.18
    cyclopentanol 6.9
    tetrahydropyran 6.36
    tert-amyl methyl ether 1.8
    2,5,8-trioxanonane 26.13
    1-hexene 0.2
    2-isopropoxyethanol 10.6
    2,2,2-trifluoroethanol 17.87
    methyl butyrate 2.8

    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