Glucosyringic acid

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  • Identifiers

    CAS number
    33228-65-8

    Molecular formula
    C15H20O10

    SMILES
    COC1=CC(=CC(=C1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)OC)C(=O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 70.33%
    Vanilla 43.37%
    Sweet 32.28%
    Milky 31.1%
    Creamy 26.38%
    Balsamic 22.81%
    Caramellic 21.69%
    Dairy 20.86%
    Phenolic 19.33%
    Savory 18.75%

     

    Flavor
    Bitter 59.04%
    Odorless 42.88%
    Bland 34.86%
    Sweet-like 28.6%
    Very mild 26.71%
    Sweet 22.08%
    Eugenol 21.25%
    Mild 21.12%
    Parsley 20.74%
    Very slight 20.29%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.0

    pKa est.
    5.86 (weak acid)

    Molecular weight
    360.31 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1653°C

    Flash point

    • 242.63 ˚C est.

  • Synonyms

    • Glucosyringic acid
    • 33228-65-8
    • Gluco-syringic acid
    • DTXSID20186870
    • 3,5-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoic acid
    • 3,5-dimethoxy-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxybenzoic acid
    • RefChem:143655
    • DTXCID60109361
    • 4-(beta-d-glucopyranosyloxy)-3,5-dimethoxybenzoic acid
    • Benzoic acid, 4-(beta-D-glucopyranosyloxy)-3,5-dimethoxy-
    • 3,5-dimethoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid
    • orb1297356
    • CHEMBL5082798
    • SCHEMBL19806792
    • syringate 4-O-beta-glucopyranoside
    • EX-A4054
    • HY-N3953
    • Syringic acid-4--D-glucopyranoside
    • AKOS030573575
    • EBC-615751
    • FS-9763
    • DA-73777
    • syringic acid-4-O-beta-D-glucopyranoside
    • 4-glucopyranosyloxy-3,5-dimethoxy benzoic acid
    • G89291
    • 3,5-dimethoxybenzoic acid-4-O-beta-D-glucopyranoside
    • 4-O-beta-D-glucopyranosyloxy-3,5-dimethoxy-benzoic acid
    • Syringic acid 4--glucopyranoside; Syringic acid glucoside
    • 3,5-dimethoxy benzene carbonic acid-4-O-beta-D-pyranglucose
    • 33228-65-8

  • Applications

    Glucosyringic acid (CAS 33228-65-8) is a phenolic glycoside found in natural sources and can serve as a building block for more complex phenolic derivatives. In industrial practice, it is evaluated as an intermediate in organic synthesis for various products and bulk formulations; it is also studied as a natural antioxidant and potential stabilizer for cosmetic and personal care formulations. It may act as a precursor or stabilizing component in polymer systems, coatings, and inks. Additionally, due to its plant-derived origin, glucosyringic acid is considered in fragrance research and the analysis of natural extracts. Subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 16.31
    methanol 32.85
    isopropanol 8.75
    water 28.01
    ethyl acetate 3.25
    n-propanol 9.31
    acetone 11.06
    n-butanol 6.27
    acetonitrile 4.57
    DMF 118.85
    toluene 1.13
    isobutanol 3.02
    1,4-dioxane 15.01
    methyl acetate 4.2
    THF 22.58
    2-butanone 4.61
    n-pentanol 3.04
    sec-butanol 4.89
    n-hexane 0.2
    ethylene glycol 94.71
    NMP 112.62
    cyclohexane 1.18
    DMSO 458.36
    n-butyl acetate 1.01
    n-octanol 2.08
    chloroform 0.66
    n-propyl acetate 1.32
    acetic acid 73.24
    dichloromethane 1.09
    cyclohexanone 8.78
    propylene glycol 52.66
    isopropyl acetate 1.77
    DMAc 120.48
    2-ethoxyethanol 44.25
    isopentanol 3.08
    n-heptane 0.71
    ethyl formate 4.13
    1,2-dichloroethane 1.88
    n-hexanol 2.24
    2-methoxyethanol 118.81
    isobutyl acetate 0.49
    tetrachloromethane 0.31
    n-pentyl acetate 1.11
    transcutol 33.71
    n-heptanol 2.61
    ethylbenzene 0.59
    MIBK 1.71
    2-propoxyethanol 17.38
    tert-butanol 7.58
    MTBE 1.59
    2-butoxyethanol 10.69
    propionic acid 12.82
    o-xylene 1.35
    formic acid 278.98
    diethyl ether 2.93
    m-xylene 0.89
    p-xylene 0.7
    chlorobenzene 0.41
    dimethyl carbonate 10.65
    n-octane 0.41
    formamide 274.19
    cyclopentanone 14.96
    2-pentanone 3.85
    anisole 1.67
    cyclopentyl methyl ether 7.24
    gamma-butyrolactone 21.49
    1-methoxy-2-propanol 49.42
    pyridine 6.67
    3-pentanone 3.66
    furfural 18.45
    n-dodecane 0.22
    diethylene glycol 52.31
    diisopropyl ether 0.75
    tert-amyl alcohol 4.65
    acetylacetone 9.1
    n-hexadecane 0.24
    acetophenone 3.12
    methyl propionate 6.58
    isopentyl acetate 0.81
    trichloroethylene 2.11
    n-nonanol 2.1
    cyclohexanol 8.03
    benzyl alcohol 4.41
    2-ethylhexanol 1.14
    isooctanol 1.63
    dipropyl ether 2.78
    1,2-dichlorobenzene 0.5
    ethyl lactate 5.66
    propylene carbonate 6.0
    n-methylformamide 54.3
    2-pentanol 3.37
    n-pentane 0.34
    1-propoxy-2-propanol 8.76
    1-methoxy-2-propyl acetate 3.94
    2-(2-methoxypropoxy) propanol 10.28
    mesitylene 0.62
    ε-caprolactone 8.88
    p-cymene 0.61
    epichlorohydrin 10.65
    1,1,1-trichloroethane 0.48
    2-aminoethanol 65.13
    morpholine-4-carbaldehyde 76.45
    sulfolane 77.6
    2,2,4-trimethylpentane 0.13
    2-methyltetrahydrofuran 7.32
    n-hexyl acetate 1.48
    isooctane 0.06
    2-(2-butoxyethoxy)ethanol 15.41
    sec-butyl acetate 0.78
    tert-butyl acetate 2.02
    decalin 0.23
    glycerin 160.23
    diglyme 27.63
    acrylic acid 22.39
    isopropyl myristate 0.79
    n-butyric acid 9.26
    acetyl acetate 3.01
    di(2-ethylhexyl) phthalate 1.32
    ethyl propionate 1.78
    nitromethane 69.77
    1,2-diethoxyethane 3.83
    benzonitrile 1.31
    trioctyl phosphate 1.27
    1-bromopropane 0.77
    gamma-valerolactone 34.71
    n-decanol 1.69
    triethyl phosphate 1.83
    4-methyl-2-pentanol 1.22
    propionitrile 2.11
    vinylene carbonate 5.6
    1,1,2-trichlorotrifluoroethane 34.43
    DMS 2.86
    cumene 0.41
    2-octanol 1.47
    2-hexanone 1.45
    octyl acetate 1.29
    limonene 1.01
    1,2-dimethoxyethane 22.56
    ethyl orthosilicate 1.7
    tributyl phosphate 1.1
    diacetone alcohol 10.34
    N,N-dimethylaniline 2.34
    acrylonitrile 4.37
    aniline 3.67
    1,3-propanediol 59.21
    bromobenzene 0.31
    dibromomethane 0.66
    1,1,2,2-tetrachloroethane 2.53
    2-methyl-cyclohexyl acetate 1.45
    tetrabutyl urea 2.96
    diisobutyl methanol 0.91
    2-phenylethanol 2.73
    styrene 0.56
    dioctyl adipate 1.7
    dimethyl sulfate 29.89
    ethyl butyrate 1.5
    methyl lactate 23.76
    butyl lactate 2.84
    diethyl carbonate 1.28
    propanediol butyl ether 11.47
    triethyl orthoformate 2.05
    p-tert-butyltoluene 0.61
    methyl 4-tert-butylbenzoate 4.69
    morpholine 27.03
    tert-butylamine 2.19
    n-dodecanol 1.33
    dimethoxymethane 36.77
    ethylene carbonate 4.51
    cyrene 19.56
    2-ethoxyethyl acetate 2.73
    2-ethylhexyl acetate 0.65
    1,2,4-trichlorobenzene 0.85
    4-methylpyridine 3.67
    dibutyl ether 1.4
    2,6-dimethyl-4-heptanol 0.91
    DEF 15.09
    dimethyl isosorbide 13.28
    tetrachloroethylene 2.17
    eugenol 5.53
    triacetin 4.17
    span 80 7.99
    1,4-butanediol 20.57
    1,1-dichloroethane 0.62
    2-methyl-1-pentanol 1.67
    methyl formate 30.19
    2-methyl-1-butanol 2.94
    n-decane 0.39
    butyronitrile 1.77
    3,7-dimethyl-1-octanol 1.06
    1-chlorooctane 0.63
    1-chlorotetradecane 0.32
    n-nonane 0.38
    undecane 0.28
    tert-butylcyclohexane 0.11
    cyclooctane 0.59
    cyclopentanol 11.36
    tetrahydropyran 6.87
    tert-amyl methyl ether 2.23
    2,5,8-trioxanonane 22.8
    1-hexene 0.42
    2-isopropoxyethanol 13.38
    2,2,2-trifluoroethanol 41.29
    methyl butyrate 2.25

    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