Geniposidic Acid

Overview IFRA Request a quote

  • Identifiers

    CAS number
    27741-01-1

    Molecular formula
    C16H22O10

    SMILES
    C1C=C([C@@H]2[C@H]1C(=CO[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)O)CO

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 73.87%
    Sweet 27.46%
    Savory 19.51%
    Milky 18.33%
    Cooling 17.74%
    Caramellic 17.68%
    Vanilla 16.9%
    Bitter 16.03%
    Spicy 14.99%
    Mint 13.82%

     

    Flavor
    Bitter 71.06%
    Odorless 37.58%
    Sweet-like 27.58%
    Bland 25.87%
    Very mild 24.68%
    Fatty 23.13%
    Cauliflower 20.25%
    Alkaline 19.94%
    Cedarleaf 19.93%
    Fenugreek 19.7%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -2.7

    pKa est.
    4.43 (weak acid)

    Molecular weight
    374.34 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2491°C

    Flash point

    • 272.53 ˚C est.

  • Synonyms

    • Geniposidic acid
    • 27741-01-1
    • DTXSID40182091
    • (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-carboxylic acid
    • (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-carboxylic acid
    • RefChem:142879
    • DTXCID50104582
    • MFCD00210294
    • CHEBI:5301
    • (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-carboxylic acid
    • Cyclopenta[c]pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, (1S,4aS,7aS)-
    • (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-carboxylic acid
    • (1S,4aS,7aS)-1-(beta-D-Glucopyranosyloxy)-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
    • CHEMBL460031
    • Geniposidinsaure
    • genioisidic acid
    • geniposidic-acid
    • Osidic acid
    • Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, (1S,4aS,7aS)-
    • SCHEMBL227010
    • orb1306388
    • GLXC-06684
    • HY-N0010
    • Geniposidic acid, >=98% (HPLC)
    • BDBM50478834
    • MSK158027
    • AKOS015896744
    • AC-8846
    • CCG-268347
    • EBC-616272
    • FG40477
    • NCGC00346663-03
    • AS-75051
    • DA-53546
    • NS00097611
    • S2413
    • AB01559137_03
    • 741G011
    • Q5533206
    • BRD-K73771095-001-02-5
    • BRD-K73771095-001-03-3
    • (1S,4aS,7aS)-1-(|_-D-Glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)cyclopenta[c]pyran-4-carboxylic acid
    • Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, (1S-(1alpha,4aalpha,7aalpha))-
    • Cyclopenta[c]pyran-4-carboxylic acid, 1-(|A-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, (1S,4aS,7aS)-
    • 27741-01-1

  • Applications

    Geniposidic acid is an iridoid glycoside isolated from Gardenia species and is mainly used as a natural product intermediate. It is commonly evaluated as a starting material for the synthesis of genipin and other iridoids, enabling downstream crosslinking chemistries for biomaterials and polymer networks. It may be incorporated into cosmetic and personal-care formulations as a botanical ingredient or fragrance-related precursor, subject to formulation limits. In pharmaceutical and nutraceutical contexts, it serves as a reference compound and is studied for iridoid chemistry and related bioactivities. Analytical laboratories also use it as a standard for quality control of Gardenia-derived extracts.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 18.61
    methanol 69.97
    isopropanol 6.4
    water 20.29
    ethyl acetate 1.23
    n-propanol 7.99
    acetone 9.33
    n-butanol 6.56
    acetonitrile 2.4
    DMF 99.31
    toluene 0.45
    isobutanol 2.49
    1,4-dioxane 8.75
    methyl acetate 1.58
    THF 14.97
    2-butanone 3.51
    n-pentanol 2.13
    sec-butanol 3.19
    n-hexane 0.09
    ethylene glycol 75.28
    NMP 60.22
    cyclohexane 0.41
    DMSO 296.39
    n-butyl acetate 0.43
    n-octanol 1.75
    chloroform 0.42
    n-propyl acetate 0.47
    acetic acid 55.31
    dichloromethane 0.53
    cyclohexanone 7.26
    propylene glycol 40.16
    isopropyl acetate 0.75
    DMAc 67.3
    2-ethoxyethanol 31.04
    isopentanol 2.93
    n-heptane 0.24
    ethyl formate 2.7
    1,2-dichloroethane 0.82
    n-hexanol 1.77
    2-methoxyethanol 113.55
    isobutyl acetate 0.2
    tetrachloromethane 0.21
    n-pentyl acetate 0.93
    transcutol 33.26
    n-heptanol 2.26
    ethylbenzene 0.21
    MIBK 1.57
    2-propoxyethanol 15.16
    tert-butanol 3.41
    MTBE 0.6
    2-butoxyethanol 10.21
    propionic acid 7.35
    o-xylene 0.46
    formic acid 247.39
    diethyl ether 1.8
    m-xylene 0.37
    p-xylene 0.21
    chlorobenzene 0.17
    dimethyl carbonate 4.36
    n-octane 0.19
    formamide 190.89
    cyclopentanone 10.76
    2-pentanone 3.43
    anisole 0.6
    cyclopentyl methyl ether 2.94
    gamma-butyrolactone 11.08
    1-methoxy-2-propanol 47.13
    pyridine 4.21
    3-pentanone 2.24
    furfural 11.62
    n-dodecane 0.11
    diethylene glycol 46.07
    diisopropyl ether 0.36
    tert-amyl alcohol 2.21
    acetylacetone 5.29
    n-hexadecane 0.12
    acetophenone 1.19
    methyl propionate 2.92
    isopentyl acetate 0.43
    trichloroethylene 1.05
    n-nonanol 1.78
    cyclohexanol 4.34
    benzyl alcohol 2.0
    2-ethylhexanol 0.73
    isooctanol 1.35
    dipropyl ether 1.13
    1,2-dichlorobenzene 0.19
    ethyl lactate 2.88
    propylene carbonate 2.72
    n-methylformamide 47.26
    2-pentanol 2.48
    n-pentane 0.21
    1-propoxy-2-propanol 6.7
    1-methoxy-2-propyl acetate 2.24
    2-(2-methoxypropoxy) propanol 8.25
    mesitylene 0.28
    ε-caprolactone 5.35
    p-cymene 0.26
    epichlorohydrin 7.08
    1,1,1-trichloroethane 0.22
    2-aminoethanol 58.61
    morpholine-4-carbaldehyde 49.62
    sulfolane 36.89
    2,2,4-trimethylpentane 0.06
    2-methyltetrahydrofuran 3.4
    n-hexyl acetate 1.23
    isooctane 0.04
    2-(2-butoxyethoxy)ethanol 14.92
    sec-butyl acetate 0.28
    tert-butyl acetate 0.87
    decalin 0.07
    glycerin 129.67
    diglyme 21.41
    acrylic acid 14.08
    isopropyl myristate 0.54
    n-butyric acid 6.24
    acetyl acetate 0.97
    di(2-ethylhexyl) phthalate 1.09
    ethyl propionate 0.63
    nitromethane 38.23
    1,2-diethoxyethane 2.4
    benzonitrile 0.74
    trioctyl phosphate 1.12
    1-bromopropane 0.35
    gamma-valerolactone 31.62
    n-decanol 1.35
    triethyl phosphate 0.71
    4-methyl-2-pentanol 1.01
    propionitrile 1.32
    vinylene carbonate 2.96
    1,1,2-trichlorotrifluoroethane 22.13
    DMS 1.45
    cumene 0.15
    2-octanol 1.1
    2-hexanone 0.86
    octyl acetate 0.97
    limonene 0.47
    1,2-dimethoxyethane 13.16
    ethyl orthosilicate 0.66
    tributyl phosphate 0.82
    diacetone alcohol 6.59
    N,N-dimethylaniline 0.76
    acrylonitrile 2.84
    aniline 1.62
    1,3-propanediol 59.32
    bromobenzene 0.11
    dibromomethane 0.3
    1,1,2,2-tetrachloroethane 1.16
    2-methyl-cyclohexyl acetate 0.71
    tetrabutyl urea 2.02
    diisobutyl methanol 0.54
    2-phenylethanol 1.75
    styrene 0.18
    dioctyl adipate 1.08
    dimethyl sulfate 10.03
    ethyl butyrate 0.58
    methyl lactate 15.44
    butyl lactate 2.7
    diethyl carbonate 0.41
    propanediol butyl ether 13.55
    triethyl orthoformate 0.83
    p-tert-butyltoluene 0.26
    methyl 4-tert-butylbenzoate 2.83
    morpholine 17.34
    tert-butylamine 0.92
    n-dodecanol 0.95
    dimethoxymethane 29.18
    ethylene carbonate 2.23
    cyrene 13.67
    2-ethoxyethyl acetate 2.1
    2-ethylhexyl acetate 0.32
    1,2,4-trichlorobenzene 0.3
    4-methylpyridine 1.72
    dibutyl ether 0.75
    2,6-dimethyl-4-heptanol 0.54
    DEF 8.58
    dimethyl isosorbide 9.34
    tetrachloroethylene 1.25
    eugenol 4.45
    triacetin 2.48
    span 80 7.73
    1,4-butanediol 15.74
    1,1-dichloroethane 0.27
    2-methyl-1-pentanol 1.13
    methyl formate 23.13
    2-methyl-1-butanol 2.38
    n-decane 0.21
    butyronitrile 1.29
    3,7-dimethyl-1-octanol 0.92
    1-chlorooctane 0.42
    1-chlorotetradecane 0.18
    n-nonane 0.2
    undecane 0.14
    tert-butylcyclohexane 0.04
    cyclooctane 0.22
    cyclopentanol 5.78
    tetrahydropyran 4.01
    tert-amyl methyl ether 0.82
    2,5,8-trioxanonane 17.53
    1-hexene 0.2
    2-isopropoxyethanol 7.84
    2,2,2-trifluoroethanol 21.7
    methyl butyrate 1.01

    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