Penta-O-galloyl-beta-D-glucose

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  • Identifiers

    CAS number
    14937-32-7

    Molecular formula
    C41H32O26

    SMILES
    C1=C(C=C(C(=C1O)O)O)C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC(=O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O)OC(=O)C6=CC(=C(C(=C6)O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 83.64%
    Phenolic 25.26%
    Balsamic 20.11%
    Burnt 19.3%
    Savory 15.46%
    Milky 13.62%
    Clean 13.37%
    Smoky 12.16%
    Bitter 12.15%
    Vanilla 11.84%

     

    Flavor
    Bitter 88.67%
    Odorless 42.79%
    Bland 38.32%
    Sweet-like 24.54%
    Very mild 22.93%
    Mild 20.1%
    Cedarleaf 19.52%
    Parsley 19.03%
    Lovage 18.82%
    Nitrile 18.8%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.6

    pKa est.
    5.78 (weak acid)

    Molecular weight
    940.7 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1972°C

    Flash point

    • 246.66 ˚C est.

  • Synonyms

    • Pentagalloylglucose
    • 14937-32-7
    • 1,2,3,4,6-Penta-O-galloyl-beta-D-glucose
    • GALLOTANNIN 15
    • Pentagalloyl-beta-D-glucose
    • 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose
    • Penta-O-galloyl-beta-D-glucose
    • beta-D-pentagalloylglucose
    • 1,2,3,4,6-Penta-O-galloylglucose
    • beta-D-Glucopyranose pentakis(3,4,5-trihydroxybenzoate)
    • Beta-1,2,3,4,6-Pentagalloylglucose
    • 3UI3K8W93I
    • 1,2,3,4,6-Penta-O-galloyl beta-glucopyranose
    • J277.746K
    • C04576
    • 1,2,3,4,6-pentagalloyl-beta-d-glucopyranoside
    • [(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
    • penta-o-galloyl-alpha-d-glucose
    • penta-O-galloyl-beta-D-glucoside
    • ((2R,3R,4S,5R,6S)-3,4,5,6-tetrakis((3,4,5-trihydroxybenzoyl)oxy)oxan-2-yl)methyl 3,4,5-trihydroxybenzoate
    • RefChem:44252
    • 1,2,3,4,6-penta-o-galloyl-beta-glucose
    • penta-1,2,3,4,6-O-galloyl-beta-D-glucose
    • beta-penta-O-galloyl-glucose, (D)-
    • PENTA-O-GALLOYL-beta-D-GLUCOPYRANOSE
    • 1,2,3,4,6-pentagalloyl-beta-D-glucopyranose
    • 1,2,3,4,6-pentagalloyl-D-glucose
    • 1,2,3,4,6-Pentagalloylglucose
    • Pentagalloyl glucose
    • 1,2,3,4,6-Pgg
    • 1,2,3,4,6-Pentakis-O-galloyl-beta-D-glucose
    • 1,2,3,4,6-o-Pentagalloylglucose
    • (2S,3R,4S,5R,6R)-6-(((3,4,5-Trihydroxybenzoyl)oxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetrakis(3,4,5-trihydroxybenzoate)
    • CHEMBL382408
    • PGG
    • MFCD03788860
    • 1,2,3,4,6-pentakis-O-(3,4,5-trihydroxybenzoyl)-beta-D-glucopyranose
    • beta-Penta-O-galloyl-glucose
    • [(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis[(3,4,5-trihydroxybenzoyl)oxy]tetrahydropyran-2-yl]methyl 3,4,5-trihydroxybenzoate
    • 5GG
    • penta-O-galloyl-beta-d-glucose hydrate
    • 1,2,3,4,6-Penta-O-galloyl-b-D-glucopyranose >90%
    • UNII-3UI3K8W93I
    • DB03208
    • 1,2,3,4,6-Pentagalloyl glucose
    • pentagalloyl-glucoside
    • 1,2,3,4,6-penta-O-galloyl-D-glucopyranose
    • 1,2,3,4,6-penta-o-galloyl-d-glucose
    • penta-o-galloyl glucose
    • pentagalloylglucopyranose
    • penta-O-galloyl-glucose
    • pentagalloylglucose [INN]
    • 1,2,3,4,6-penta-o-galloyl-beta-d-glucopyranoside
    • pentagalloy-HHDP-glucopyranose
    • Pentagalloylglucose (Standard)
    • SCHEMBL640108
    • Penta-O-galloyl-|A-D-glucose
    • MEGxp0_001051
    • orb1303737
    • ACon1_000145
    • CHEBI:18082
    • HY-N0527R
    • PENTAGALLOYLGLUCOSE [USAN]
    • DTXSID901029765
    • GLXC-15029
    • HY-N0527
    • BDBM50241052
    • beta-D-glucopyranose, 1,2,3,4,6-pentakis(3,4,5-trihydroxybenzoate)
    • MSK161011
    • s9399
    • 1,2,3,4,6-penta-o-galloyl-glucose
    • AKOS015896803
    • CCG-270584
    • CS-5018
    • EBC-441042
    • MP05328
    • Pentagalloylglucose - Bio-X trade mark
    • 1,2,3,4,6-beta-D-pentagalloylglucose
    • NCGC00180839-01
    • NCGC00180839-02
    • NCGC00180839-03
    • 1,2,3,4,6-Pentagalloyl beta-D-glucose
    • AC-34850
    • BP300150
    • BS-15460
    • DA-59773
    • 1,2,3,4,6-penta-O-galloyl beta-D-glucose
    • 1,2,3,4,6-penta-o-galloyl-beta-d-glucoside
    • 1,2,3,4,6-Penta-O-galloyl-?-D-glucopyranose
    • Q4545645
    • 1,2,3,4,6-Penta-O-galloyl- beta -D-glucopyranose
    • 1,2,3,4,6-Penta-O-galloyl-?-D-glucopyranose >90%
    • 1,2,3,4,6-Penta-O-galloyl-b-D-glucopyranose (>85%)
    • beta-D-Glucopyranose, pentakis(3,4,5-trihydroxybenzoate)
    • |_-D-Glucopyranose, 1,2,3,4,6-pentakis(3,4,5-trihydroxybenzoate)
    • 1,2,3,4,6-PENTAGALLOYL GLUCOSE (CONSTITUENT OF BANABA LEAF) [DSC]
    • (2S,3R,4S,5R,6R)-3,4,5-tris(3,4,5-trihydroxybenzoyloxy)-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl 3,4,5-trihydroxybenzoate
    • 1,2,3,4,6-O-PentagalloylglucosePentagalloyl glucose; 1,2,3,4,6-Penta-O-galloyl-beta-D-glucose; 1,2,3,4,6-Pentagalloylglucose
    • 14937-32-7

  • Applications

    Penta-O-galloyl-beta-D-glucose (CAS 14937-32-7) is a hydrolyzable tannin with five galloyl esters on a glucose core. In industrial and product formulations, it is commonly evaluated as a tanning agent in leather processing, as an antioxidant and stabilizer in cosmetics and personal-care formulations, and as a polyphenolic intermediate or building block in ellagitannin synthesis for pharmaceutical or natural products research; it can also serve as a chelating/antioxidant additive in polymer formulations and as a colorant or protective additive in coatings and inks, with performance dependent on formulation and local regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.43
    methanol 1.76
    isopropanol 1.01
    water 0.13
    ethyl acetate 1.21
    n-propanol 1.27
    acetone 2.58
    n-butanol 0.58
    acetonitrile 0.79
    DMF 38.07
    toluene 0.26
    isobutanol 0.46
    1,4-dioxane 8.11
    methyl acetate 2.62
    THF 17.1
    2-butanone 2.43
    n-pentanol 0.36
    sec-butanol 0.92
    n-hexane 0.01
    ethylene glycol 4.08
    NMP 26.46
    cyclohexane 0.02
    DMSO 35.43
    n-butyl acetate 0.3
    n-octanol 0.55
    chloroform 0.53
    n-propyl acetate 0.47
    acetic acid 6.67
    dichloromethane 0.63
    cyclohexanone 1.35
    propylene glycol 5.31
    isopropyl acetate 0.66
    DMAc 32.93
    2-ethoxyethanol 9.03
    isopentanol 0.26
    n-heptane 0.03
    ethyl formate 0.92
    1,2-dichloroethane 0.44
    n-hexanol 0.15
    2-methoxyethanol 20.77
    isobutyl acetate 0.12
    tetrachloromethane 0.06
    n-pentyl acetate 0.69
    transcutol 13.38
    n-heptanol 0.43
    ethylbenzene 0.08
    MIBK 0.33
    2-propoxyethanol 4.52
    tert-butanol 0.77
    MTBE 0.81
    2-butoxyethanol 4.14
    propionic acid 2.62
    o-xylene 0.18
    formic acid 7.78
    diethyl ether 0.99
    m-xylene 0.12
    p-xylene 0.07
    chlorobenzene 0.08
    dimethyl carbonate 3.65
    n-octane 0.03
    formamide 11.86
    cyclopentanone 5.23
    2-pentanone 1.12
    anisole 0.67
    cyclopentyl methyl ether 2.03
    gamma-butyrolactone 9.07
    1-methoxy-2-propanol 14.06
    pyridine 3.39
    3-pentanone 1.04
    furfural 5.99
    n-dodecane 0.02
    diethylene glycol 5.4
    diisopropyl ether 0.14
    tert-amyl alcohol 0.79
    acetylacetone 2.63
    n-hexadecane 0.02
    acetophenone 0.59
    methyl propionate 2.67
    isopentyl acetate 0.17
    trichloroethylene 1.18
    n-nonanol 0.57
    cyclohexanol 0.46
    benzyl alcohol 0.67
    2-ethylhexanol 0.09
    isooctanol 0.26
    dipropyl ether 0.7
    1,2-dichlorobenzene 0.07
    ethyl lactate 1.22
    propylene carbonate 1.27
    n-methylformamide 9.37
    2-pentanol 0.38
    n-pentane 0.02
    1-propoxy-2-propanol 3.45
    1-methoxy-2-propyl acetate 1.52
    2-(2-methoxypropoxy) propanol 3.13
    mesitylene 0.05
    ε-caprolactone 2.03
    p-cymene 0.05
    epichlorohydrin 6.5
    1,1,1-trichloroethane 0.15
    2-aminoethanol 4.39
    morpholine-4-carbaldehyde 32.83
    sulfolane 14.73
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 2.99
    n-hexyl acetate 0.73
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 5.29
    sec-butyl acetate 0.25
    tert-butyl acetate 0.7
    decalin 0.01
    glycerin 16.17
    diglyme 11.47
    acrylic acid 3.82
    isopropyl myristate 0.25
    n-butyric acid 1.26
    acetyl acetate 0.69
    di(2-ethylhexyl) phthalate 0.22
    ethyl propionate 0.63
    nitromethane 14.45
    1,2-diethoxyethane 1.97
    benzonitrile 0.23
    trioctyl phosphate 0.22
    1-bromopropane 0.16
    gamma-valerolactone 17.82
    n-decanol 0.35
    triethyl phosphate 0.3
    4-methyl-2-pentanol 0.12
    propionitrile 0.5
    vinylene carbonate 1.29
    1,1,2-trichlorotrifluoroethane 9.68
    DMS 1.0
    cumene 0.04
    2-octanol 0.33
    2-hexanone 0.45
    octyl acetate 0.46
    limonene 0.07
    1,2-dimethoxyethane 9.81
    ethyl orthosilicate 0.31
    tributyl phosphate 0.16
    diacetone alcohol 2.13
    N,N-dimethylaniline 0.59
    acrylonitrile 1.15
    aniline 0.71
    1,3-propanediol 3.96
    bromobenzene 0.06
    dibromomethane 0.22
    1,1,2,2-tetrachloroethane 1.03
    2-methyl-cyclohexyl acetate 0.17
    tetrabutyl urea 0.54
    diisobutyl methanol 0.07
    2-phenylethanol 0.29
    styrene 0.1
    dioctyl adipate 0.46
    dimethyl sulfate 9.04
    ethyl butyrate 0.39
    methyl lactate 5.78
    butyl lactate 1.2
    diethyl carbonate 0.26
    propanediol butyl ether 4.77
    triethyl orthoformate 0.69
    p-tert-butyltoluene 0.06
    methyl 4-tert-butylbenzoate 1.33
    morpholine 12.83
    tert-butylamine 0.22
    n-dodecanol 0.22
    dimethoxymethane 15.54
    ethylene carbonate 0.84
    cyrene 3.55
    2-ethoxyethyl acetate 1.9
    2-ethylhexyl acetate 0.14
    1,2,4-trichlorobenzene 0.17
    4-methylpyridine 1.38
    dibutyl ether 0.51
    2,6-dimethyl-4-heptanol 0.07
    DEF 3.54
    dimethyl isosorbide 3.39
    tetrachloroethylene 0.52
    eugenol 1.24
    triacetin 1.95
    span 80 2.82
    1,4-butanediol 1.4
    1,1-dichloroethane 0.24
    2-methyl-1-pentanol 0.16
    methyl formate 6.35
    2-methyl-1-butanol 0.35
    n-decane 0.04
    butyronitrile 0.3
    3,7-dimethyl-1-octanol 0.18
    1-chlorooctane 0.12
    1-chlorotetradecane 0.04
    n-nonane 0.04
    undecane 0.03
    tert-butylcyclohexane 0.01
    cyclooctane 0.02
    cyclopentanol 1.3
    tetrahydropyran 2.04
    tert-amyl methyl ether 0.85
    2,5,8-trioxanonane 7.03
    1-hexene 0.05
    2-isopropoxyethanol 3.33
    2,2,2-trifluoroethanol 3.42
    methyl butyrate 0.71

    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