(-)-Gallocatechin gallate

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  • Identifiers

    CAS number
    4233-96-9

    Molecular formula
    C22H18O11

    SMILES
    C1[C@H]([C@@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 78.33%
    Phenolic 43.08%
    Burnt 25.73%
    Smoky 19.7%
    Balsamic 18.16%
    Spicy 17.19%
    Savory 16.99%
    Medicinal 15.75%
    Vanilla 14.28%
    Bitter 13.55%

     

    Flavor
    Bitter 92.49%
    Odorless 33.25%
    Bland 31.44%
    Sweet-like 23.85%
    Cedarleaf 20.46%
    Eugenol 19.71%
    Parsley 19.52%
    Lovage 19.25%
    Nitrile 19.18%
    Rotten 18.94%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.2

    pKa est.
    9.98 (weak base)

    Molecular weight
    458.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1512°C

    Flash point

    • 299.06 ˚C est.

  • Synonyms

    • (-)-Gallocatechin gallate
    • 4233-96-9
    • (-)-Gallocatechol gallate
    • Gallocatechin gallate, (-)-
    • (-)-gallocatechin-3-O-gallate
    • IRW3C4Y31Q
    • NVP-XAA 225
    • CHEBI:156271
    • DTXSID20195144
    • RefChem:390964
    • GlyTouCan:G97470JO
    • DTXCID30117635
    • G97470JO
    • 636-979-1
    • (2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate
    • MFCD00214298
    • (-)-Gallocatechin 3-gallate
    • CHEMBL264938
    • (2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-(3,4,5-trihydroxybenzoate)
    • (2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
    • (-)-Gallocatechin 3-O-gallate
    • C22H18O11
    • (2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate
    • Gallocatechol, 3-gallate, (-)-
    • GCG
    • UNII-IRW3C4Y31Q
    • CCRIS 9286
    • L-GCG
    • ent-Gallocatechin 3-gallate
    • SCHEMBL49461
    • Benzoic acid, 3,4,5-trihydroxy-, 3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester, (2S-trans)-
    • orb1303722
    • SCHEMBL30977114
    • CHEBI:95002
    • HY-N0522R
    • WMBWREPUVVBILR-NQIIRXRSSA-N
    • (2R,3S)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate
    • HY-N0522
    • MSK40201
    • BDBM50236531
    • s9058
    • (-)-Gallocatechin gallate (Standard)
    • AKOS015901852
    • AC-6044
    • CCG-269313
    • CS-7698
    • EBC-474046
    • FG40482
    • NCGC00390250-01
    • BS-50638
    • DA-59404
    • (-)-Gallocatechin gallate, analytical standard
    • A11681
    • (-)-Gallocatechin gallate, 98%, from green tea
    • 233G969
    • BRD-K19216856-001-01-9
    • Q27166763
    • (-)-Gallocatechin gallate, from green tea, >=98% (HPLC)
    • (2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl3,4,5-trihydroxybenzoate
    • [(2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl] 3,4,5-trihydroxybenzoate
    • BENZOIC ACID, 3,4,5-TRIHYDROXY-, (2S,3R)-3,4-DIHYDRO-5,7-DIHYDROXY-2-(3,4,5-TRIHYDROXYPHENYL)-2H-1-BENZOPYRAN-3-YL ESTER
    • 4233-96-9

  • Applications

    (-)-Gallocatechin gallate (CAS 4233-96-9) is used primarily as a natural antioxidant with stabilizing potential in cosmetic and personal care formulations to protect product integrity and shelf life. It is also evaluated for food processing and beverage applications as a natural antioxidant that may help extend product stability. In the polymer and coatings sector, it is studied as an antioxidant/stabilizer additive to inhibit oxidative degradation in resins, coatings, and inks, potentially benefiting material durability and color stability. The compound is also investigated as a polyphenol-rich ingredient in nutraceutical or pharmaceutical research, and as a chiral building block or intermediate in organic synthesis. All uses are subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2.03
    methanol 1.37
    isopropanol 0.72
    water 0.12
    ethyl acetate 1.87
    n-propanol 1.62
    acetone 1.09
    n-butanol 0.75
    acetonitrile 0.54
    DMF 61.28
    toluene 0.06
    isobutanol 0.38
    1,4-dioxane 9.5
    methyl acetate 2.23
    THF 13.26
    2-butanone 2.23
    n-pentanol 0.2
    sec-butanol 0.96
    n-hexane 0.0
    ethylene glycol 13.83
    NMP 32.7
    cyclohexane 0.0
    DMSO 78.07
    n-butyl acetate 0.33
    n-octanol 0.78
    chloroform 0.03
    n-propyl acetate 0.47
    acetic acid 12.38
    dichloromethane 0.04
    cyclohexanone 1.27
    propylene glycol 17.64
    isopropyl acetate 0.79
    DMAc 72.4
    2-ethoxyethanol 76.77
    isopentanol 0.37
    n-heptane 0.01
    ethyl formate 1.56
    1,2-dichloroethane 0.07
    n-hexanol 0.13
    2-methoxyethanol 227.43
    isobutyl acetate 0.09
    tetrachloromethane 0.01
    n-pentyl acetate 0.69
    transcutol 36.61
    n-heptanol 0.62
    ethylbenzene 0.02
    MIBK 0.34
    2-propoxyethanol 24.04
    tert-butanol 0.75
    MTBE 0.48
    2-butoxyethanol 10.91
    propionic acid 4.21
    o-xylene 0.06
    formic acid 27.07
    diethyl ether 0.69
    m-xylene 0.05
    p-xylene 0.02
    chlorobenzene 0.01
    dimethyl carbonate 5.28
    n-octane 0.01
    formamide 44.83
    cyclopentanone 4.08
    2-pentanone 1.0
    anisole 0.47
    cyclopentyl methyl ether 1.24
    gamma-butyrolactone 11.1
    1-methoxy-2-propanol 91.91
    pyridine 2.14
    3-pentanone 0.78
    furfural 10.27
    n-dodecane 0.01
    diethylene glycol 34.01
    diisopropyl ether 0.08
    tert-amyl alcohol 0.96
    acetylacetone 3.64
    n-hexadecane 0.01
    acetophenone 0.48
    methyl propionate 4.05
    isopentyl acetate 0.24
    trichloroethylene 0.16
    n-nonanol 0.89
    cyclohexanol 0.38
    benzyl alcohol 0.56
    2-ethylhexanol 0.11
    isooctanol 0.38
    dipropyl ether 0.71
    1,2-dichlorobenzene 0.02
    ethyl lactate 3.16
    propylene carbonate 1.62
    n-methylformamide 19.49
    2-pentanol 0.36
    n-pentane 0.0
    1-propoxy-2-propanol 10.99
    1-methoxy-2-propyl acetate 4.28
    2-(2-methoxypropoxy) propanol 9.02
    mesitylene 0.03
    ε-caprolactone 3.18
    p-cymene 0.03
    epichlorohydrin 7.92
    1,1,1-trichloroethane 0.02
    2-aminoethanol 18.56
    morpholine-4-carbaldehyde 73.02
    sulfolane 23.36
    2,2,4-trimethylpentane 0.0
    2-methyltetrahydrofuran 2.15
    n-hexyl acetate 1.02
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 14.48
    sec-butyl acetate 0.25
    tert-butyl acetate 1.08
    decalin 0.0
    glycerin 97.12
    diglyme 32.31
    acrylic acid 6.84
    isopropyl myristate 0.37
    n-butyric acid 2.99
    acetyl acetate 0.92
    di(2-ethylhexyl) phthalate 0.5
    ethyl propionate 1.02
    nitromethane 30.16
    1,2-diethoxyethane 3.71
    benzonitrile 0.13
    trioctyl phosphate 0.45
    1-bromopropane 0.03
    gamma-valerolactone 47.64
    n-decanol 0.53
    triethyl phosphate 0.61
    4-methyl-2-pentanol 0.15
    propionitrile 0.39
    vinylene carbonate 1.44
    1,1,2-trichlorotrifluoroethane 19.64
    DMS 1.22
    cumene 0.01
    2-octanol 0.37
    2-hexanone 0.28
    octyl acetate 0.75
    limonene 0.05
    1,2-dimethoxyethane 37.58
    ethyl orthosilicate 0.57
    tributyl phosphate 0.37
    diacetone alcohol 6.5
    N,N-dimethylaniline 0.34
    acrylonitrile 1.1
    aniline 0.42
    1,3-propanediol 22.95
    bromobenzene 0.01
    dibromomethane 0.01
    1,1,2,2-tetrachloroethane 0.21
    2-methyl-cyclohexyl acetate 0.29
    tetrabutyl urea 1.04
    diisobutyl methanol 0.11
    2-phenylethanol 0.35
    styrene 0.02
    dioctyl adipate 0.96
    dimethyl sulfate 11.57
    ethyl butyrate 0.74
    methyl lactate 19.26
    butyl lactate 2.24
    diethyl carbonate 0.51
    propanediol butyl ether 10.94
    triethyl orthoformate 1.22
    p-tert-butyltoluene 0.04
    methyl 4-tert-butylbenzoate 2.42
    morpholine 24.12
    tert-butylamine 0.15
    n-dodecanol 0.32
    dimethoxymethane 38.23
    ethylene carbonate 1.07
    cyrene 8.54
    2-ethoxyethyl acetate 3.22
    2-ethylhexyl acetate 0.15
    1,2,4-trichlorobenzene 0.05
    4-methylpyridine 0.7
    dibutyl ether 0.54
    2,6-dimethyl-4-heptanol 0.11
    DEF 6.37
    dimethyl isosorbide 10.15
    tetrachloroethylene 0.11
    eugenol 2.98
    triacetin 2.97
    span 80 5.91
    1,4-butanediol 3.15
    1,1-dichloroethane 0.02
    2-methyl-1-pentanol 0.15
    methyl formate 10.68
    2-methyl-1-butanol 0.49
    n-decane 0.02
    butyronitrile 0.21
    3,7-dimethyl-1-octanol 0.35
    1-chlorooctane 0.08
    1-chlorotetradecane 0.03
    n-nonane 0.02
    undecane 0.01
    tert-butylcyclohexane 0.0
    cyclooctane 0.0
    cyclopentanol 0.83
    tetrahydropyran 1.14
    tert-amyl methyl ether 0.79
    2,5,8-trioxanonane 20.66
    1-hexene 0.01
    2-isopropoxyethanol 13.88
    2,2,2-trifluoroethanol 4.98
    methyl butyrate 1.12

    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