Geniposide

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  • Identifiers

    CAS number
    24512-63-8

    Molecular formula
    C17H24O10

    SMILES
    COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC=C2CO)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Odorless 66.81%
    Sweet 29.63%
    Caramellic 19.39%
    Milky 19.15%
    Vanilla 18.78%
    Cooling 18.38%
    Mint 17.48%
    Savory 15.66%
    Spicy 15.39%
    Bitter 14.99%

     

    Flavor
    Bitter 77.99%
    Odorless 29.48%
    Sweet-like 27.53%
    Fatty 26.86%
    Bland 26.28%
    Very mild 21.8%
    Cedarleaf 20.7%
    Cauliflower 20.07%
    Alkaline 20.03%
    Fenugreek 19.6%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -2.3

    pKa est.
    4.58 (weak acid)

    Molecular weight
    388.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1922°C

    Flash point

    • 241.27 ˚C est.

  • Synonyms

    • Geniposide
    • 24512-63-8
    • 145295QLXY
    • DTXSID101318419
    • Cyclopenta[c]pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1S,4aS,7aS)-
    • methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
    • Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1S,4aS,7aS)-
    • methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-1,4a,5,7a-tetrahydrocyclopenta(c)pyran-4-carboxylate
    • methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
    • RefChem:37139
    • DTXCID701748230
    • methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)oxy-1,4a,5,7a-tetrahydrocyclopenta(c)pyran-4-carboxylate
    • Jasminoidin
    • 169799-41-1
    • MFCD16036219
    • CHEBI:5299
    • (1S,4aS,7aS)-Methyl 7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
    • methyl (1S,4aS,7aR)-7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
    • methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
    • UNII-145295QLXY
    • Geniposide CRS
    • Cyclopenta[c]pyran-4-carboxylic acid, 1-(ss-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1S,4aS,7aS)-; Cyclopenta[c]pyran-4-carboxylic acid, 1-(ss-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, [1S-(1a,4aa,7aa)]-; Geniposide (8CI)
    • Genipin 1-glucoside;
    • CHEMBL462894
    • orb1306089
    • orb1696869
    • Geniposide, >=98% (HPLC)
    • SCHEMBL28006822
    • GLXC-06546
    • HMS3884F17
    • (1S,4aS,7aS)-1-(beta-D-Glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-cyclopenta[c]pyran-4-carboxylic acid methyl ester
    • Methyl (1S)-1alpha-(beta-D-Glucopyranosyloxy)-7-(hydroxymethyl)-1,4aalpha,5,7aalpha-tetrahydrocyclopenta[c]pyran-4-carboxylate
    • MSK40032
    • BDBM50478840
    • s2411
    • AKOS025311228
    • CCG-268498
    • EBC-463044
    • MG09208
    • NCGC00346662-04
    • NCGC00346662-06
    • methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate
    • SY074418
    • NS00097664
    • C09781
    • AB01558902_03
    • F807856
    • BRD-K57275767-001-02-4
    • BRD-K57275767-001-03-2
    • Q27106709
    • (1S)-1alpha-(beta-D-Glucopyranosyloxy)-7-(hydroxymethyl)-1,4aalpha,5,7aalpha-tetrahydrocyclopenta[c]pyran-4-carboxylic Acid Methyl Ester
    • (1S,4aS,7aS)- 1-(ss-D-Glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)- cyclopenta[c]pyran-4-carboxylic acid methyl ester
    • CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)- 1,4A,5,7A-TETRAHYDRO-7-(HYDROXYMETHYL)-, METHYL ESTER, (1S,4AS,7AS)-
    • Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1S-(1alpha,4aalpha,7aalpha))-
    • Cyclopenta[c]pyran-4-carboxylic acid, 1-(|A-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1S,4aS,7aS)-
    • methyl (1S,4aS,7aS)-1-(beta-D-glucopyranosyloxy)-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
    • methyl(1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
    • 24512-63-8

  • Applications

    Geniposide (CAS 24512-63-8) is primarily used as a biochemical precursor for the production of genipin, a natural crosslinking agent; as such, it is commonly employed in polymer and biomaterial applications where crosslinking of proteins, gels, and alginate/chitosan systems is desired. It can serve as an intermediate for the synthesis of derivatives used in coatings and inks, and related material formulations. In cosmetics and personal care, geniposide is explored as a starting material for fragrance or colorant chemistries derived from gardenia-type compounds, within formulation regulations. It is also encountered in industrial research as a specialty chemical for process development and as a reference material in natural product chemistry. All uses are subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 24.99
    methanol 79.03
    isopropanol 8.22
    water 9.94
    ethyl acetate 2.29
    n-propanol 10.68
    acetone 12.97
    n-butanol 9.2
    acetonitrile 4.22
    DMF 100.13
    toluene 0.67
    isobutanol 3.91
    1,4-dioxane 14.57
    methyl acetate 2.95
    THF 25.58
    2-butanone 5.39
    n-pentanol 3.41
    sec-butanol 4.51
    n-hexane 0.08
    ethylene glycol 58.19
    NMP 61.89
    cyclohexane 0.42
    DMSO 263.57
    n-butyl acetate 0.72
    n-octanol 3.03
    chloroform 1.6
    n-propyl acetate 0.88
    acetic acid 86.35
    dichloromethane 2.01
    cyclohexanone 11.69
    propylene glycol 34.79
    isopropyl acetate 1.28
    DMAc 70.88
    2-ethoxyethanol 37.75
    isopentanol 4.5
    n-heptane 0.21
    ethyl formate 5.59
    1,2-dichloroethane 2.15
    n-hexanol 2.41
    2-methoxyethanol 111.68
    isobutyl acetate 0.43
    tetrachloromethane 0.45
    n-pentyl acetate 1.79
    transcutol 46.91
    n-heptanol 3.45
    ethylbenzene 0.32
    MIBK 2.42
    2-propoxyethanol 18.36
    tert-butanol 4.56
    MTBE 0.9
    2-butoxyethanol 14.44
    propionic acid 11.04
    o-xylene 0.65
    formic acid 231.46
    diethyl ether 2.39
    m-xylene 0.53
    p-xylene 0.37
    chlorobenzene 0.48
    dimethyl carbonate 6.87
    n-octane 0.18
    formamide 185.44
    cyclopentanone 17.64
    2-pentanone 4.79
    anisole 1.13
    cyclopentyl methyl ether 4.14
    gamma-butyrolactone 20.34
    1-methoxy-2-propanol 48.41
    pyridine 7.1
    3-pentanone 3.12
    furfural 20.32
    n-dodecane 0.13
    diethylene glycol 47.91
    diisopropyl ether 0.45
    tert-amyl alcohol 3.09
    acetylacetone 8.25
    n-hexadecane 0.14
    acetophenone 2.25
    methyl propionate 4.51
    isopentyl acetate 0.82
    trichloroethylene 3.52
    n-nonanol 3.09
    cyclohexanol 5.84
    benzyl alcohol 3.77
    2-ethylhexanol 1.03
    isooctanol 2.27
    dipropyl ether 1.3
    1,2-dichlorobenzene 0.53
    ethyl lactate 4.59
    propylene carbonate 5.71
    n-methylformamide 52.13
    2-pentanol 3.24
    n-pentane 0.19
    1-propoxy-2-propanol 8.09
    1-methoxy-2-propyl acetate 3.48
    2-(2-methoxypropoxy) propanol 11.92
    mesitylene 0.39
    ε-caprolactone 9.5
    p-cymene 0.38
    epichlorohydrin 15.19
    1,1,1-trichloroethane 0.63
    2-aminoethanol 49.92
    morpholine-4-carbaldehyde 58.0
    sulfolane 50.16
    2,2,4-trimethylpentane 0.07
    2-methyltetrahydrofuran 5.72
    n-hexyl acetate 2.53
    isooctane 0.04
    2-(2-butoxyethoxy)ethanol 20.77
    sec-butyl acetate 0.52
    tert-butyl acetate 1.39
    decalin 0.1
    glycerin 104.63
    diglyme 30.11
    acrylic acid 20.23
    isopropyl myristate 1.04
    n-butyric acid 10.88
    acetyl acetate 2.1
    di(2-ethylhexyl) phthalate 2.26
    ethyl propionate 1.13
    nitromethane 57.89
    1,2-diethoxyethane 4.0
    benzonitrile 1.83
    trioctyl phosphate 2.06
    1-bromopropane 0.69
    gamma-valerolactone 45.43
    n-decanol 2.2
    triethyl phosphate 1.22
    4-methyl-2-pentanol 1.48
    propionitrile 2.53
    vinylene carbonate 6.73
    1,1,2-trichlorotrifluoroethane 34.4
    DMS 2.78
    cumene 0.24
    2-octanol 1.8
    2-hexanone 1.5
    octyl acetate 1.86
    limonene 0.68
    1,2-dimethoxyethane 20.4
    ethyl orthosilicate 1.1
    tributyl phosphate 1.58
    diacetone alcohol 8.84
    N,N-dimethylaniline 1.25
    acrylonitrile 5.12
    aniline 2.68
    1,3-propanediol 59.14
    bromobenzene 0.3
    dibromomethane 1.02
    1,1,2,2-tetrachloroethane 3.1
    2-methyl-cyclohexyl acetate 1.29
    tetrabutyl urea 3.45
    diisobutyl methanol 0.74
    2-phenylethanol 2.98
    styrene 0.32
    dioctyl adipate 2.32
    dimethyl sulfate 14.66
    ethyl butyrate 0.99
    methyl lactate 18.49
    butyl lactate 4.47
    diethyl carbonate 0.81
    propanediol butyl ether 17.78
    triethyl orthoformate 1.36
    p-tert-butyltoluene 0.37
    methyl 4-tert-butylbenzoate 4.92
    morpholine 24.73
    tert-butylamine 1.23
    n-dodecanol 1.52
    dimethoxymethane 36.14
    ethylene carbonate 5.12
    cyrene 18.46
    2-ethoxyethyl acetate 4.16
    2-ethylhexyl acetate 0.57
    1,2,4-trichlorobenzene 0.82
    4-methylpyridine 3.18
    dibutyl ether 1.22
    2,6-dimethyl-4-heptanol 0.74
    DEF 10.81
    dimethyl isosorbide 13.54
    tetrachloroethylene 3.02
    eugenol 7.15
    triacetin 4.85
    span 80 10.78
    1,4-butanediol 18.69
    1,1-dichloroethane 0.77
    2-methyl-1-pentanol 2.03
    methyl formate 31.84
    2-methyl-1-butanol 3.83
    n-decane 0.24
    butyronitrile 2.45
    3,7-dimethyl-1-octanol 1.65
    1-chlorooctane 0.69
    1-chlorotetradecane 0.3
    n-nonane 0.22
    undecane 0.17
    tert-butylcyclohexane 0.05
    cyclooctane 0.21
    cyclopentanol 8.18
    tetrahydropyran 6.19
    tert-amyl methyl ether 1.14
    2,5,8-trioxanonane 24.23
    1-hexene 0.23
    2-isopropoxyethanol 11.19
    2,2,2-trifluoroethanol 32.68
    methyl butyrate 1.85

    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