Glycocholic Acid

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  • Identifiers

    CAS number
    475-31-0

    Molecular formula
    C26H43NO6

    SMILES
    C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 59.96%
    Cooling 48.51%
    Mint 38.59%
    Woody 26.59%
    Savory 21.78%
    Spicy 21.22%
    Balsamic 21.09%
    Herbal 18.51%
    Warm 17.78%
    Animal 17.75%

     

    Flavor
    Bitter 51.51%
    Odorless 40.03%
    Bland 26.21%
    Sweet-like 24.29%
    Cedarleaf 22.41%
    Mild 21.06%
    Mentholic 20.43%
    Sandalwood 20.29%
    Green tea 20.14%
    Leaves 19.98%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    2.9

    pKa est.
    5.78 (weak acid)

    Molecular weight
    465.6 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    189°C

    Melting point expt.

    • 166.5 °C
    • 170 °C

    Flash point

    • 313.79 ˚C est.

    Solubility expt.

    • 3.3 mg/L (at 20 °C)
    • 0.0033 mg/mL

  • Synonyms

    • Glycocholic acid
    • 475-31-0
    • N-Choloylglycine
    • Cholylglycine
    • G59NX3I3RT
    • DTXSID2047436
    • 2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid
    • DTXCID0027436
    • CHEBI:17687
    • N-(3Alpha,7Alpha,12Alpha-trihydroxy-5Beta-cholan-24-oyl)-glycine
    • N-((3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxy-24-oxocholan-24-yl)glycine
    • Glycine, N-((3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl)-
    • N-[(3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl]glycine
    • 2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid
    • 2-(((4R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta(a)phenanthren-17-yl)pentanoyl)amino)acetic acid
    • 2-((4R)-4-((1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo(8.7.0.0^(2,7).0^(11,15))heptadecan-14-yl)pentanamido)acetic acid
    • RefChem:389020
    • Glycine, N-[(3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl]-
    • 207-494-9
    • glycocholate
    • Glycine, N-choloyl-
    • MFCD00065902
    • N-CHOLYLGLYCINE
    • CHEMBL411070
    • ((R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoyl)glycine
    • C26H43NO6
    • 3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-oylglycine
    • Glycine, N-[(3a,5b,7a,12a)-3,7,12-trihydroxy-24-oxocholan-24-yl]-
    • N-(3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-oyl)glycine
    • GCH
    • 2-((R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamido)acetic acid
    • UNII-G59NX3I3RT
    • Glycylcholate
    • N-choloyl-Glycine
    • CAS-475-31-0
    • Prestwick_768
    • EINECS 207-494-9
    • Prestwick0_000521
    • Prestwick1_000521
    • Prestwick2_000521
    • Prestwick3_000521
    • Spectrum5_002011
    • bmse000651
    • Glycocholic acid (Standard)
    • BIDD:PXR0160
    • Glycoreductodehydrocholic acid
    • SCHEMBL29022
    • BSPBio_000501
    • MLS002153857
    • GLYCOCHOLIC ACID [MI]
    • SPBio_002422
    • BPBio1_000553
    • GTPL4544
    • orb1304965
    • HY-N1423R
    • 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholan-24-oic acid N-(carboxymethyl)amide
    • GLYCOCHOLIC ACID [WHO-DD]
    • HMS1569J03
    • HMS2096J03
    • HMS2231A05
    • N-(3-alpha,7-alpha,12-alpha-Trihydroxycholan-24-oyl)glycine
    • 2-[(R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanamido]acetic Acid
    • HY-N1423
    • MSK10389
    • N-(Carboxymethyl)-3alpha,7alpha,12alpha-trihydroxyglycine cholate
    • Tox21_302549
    • BDBM50375589
    • LMST05030001
    • s4958
    • STL565148
    • AKOS015965042
    • N-(3alpha,7alpha,12alpha-Trihydroxy-24-oxo-5beta-cholan-24-yl)glycine
    • CCG-269413
    • CS-W020037
    • DS-0968
    • EBC-616015
    • FG16282
    • NCGC00163115-02
    • NCGC00256646-01
    • 2-[(4R)-4-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11S,11aR)-4,7,11-trihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanamido]acetic acid
    • AC-30905
    • SMR001233215
    • SY111643
    • NS00014841
    • ST51037266
    • 3a,7a,12a-Trihydroxy-5b-cholan-24-oylglycine
    • C01921
    • 475G310
    • 3a,7a,12a-Trihydroxy-5b-cholanic acid-24-glycine
    • Q2701638
    • BRD-K54771420-001-03-2
    • [(3,7,12-Trihydroxy-24-oxocholan-24-yl)amino]acetic acid #
    • 3a,7a,12a-Trihydroxy-N-(carboxymethyl)-5b-cholan-24-amide
    • N-(carboxymethyl)-3a,7a,12a-trihydroxy-5b-Cholan-24-amide
    • 3?,7?,12?-Trihydroxy-5?-cholan-24-oic acid n-[carboxymethyl]amide
    • 5beta-Cholanic acid-3alpha,7alpha,12alpha-triol N-(carboxymethyl)-amide
    • N-[(3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl]-glycine
    • N-[(3alpha,5beta,7alpha,8xi,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl]glycine
    • N-[(3beta,5beta,7beta,9beta,12beta)-3,7,12-trihydroxy-24-oxocholan-24-yl]glycine
    • 2-[(4R)-4-((1S,2S,7S,11S,16S,5R,9R,10R,14R,15R)-5,9,16-trihydroxy-2,15-dimethy ltetracyclo[8.7.0.0<2,7>.0<11,15>]heptadec-14-yl)pentanoylamino]acetic acid
    • 2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]pentanamido]acetic acid
    • 475-31-0

  • Applications

    Glycocholic Acid (CAS 475-31-0) is used primarily as a scaffold for bile acid-based drug conjugates and as an intermediate in pharmaceutical research and development; in cosmetics and personal care it is evaluated as a mild biosurfactant and bile acid-based emulsifier; in household cleaners and detergents it can act as a wetting agent and emulsification aid; in industrial manufacturing it is used as a building block for functionalized bile acid derivatives and as a reference substrate for analytical and enzymatic studies related to bile acid metabolism.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 7.21
    methanol 30.6
    isopropanol 1.61
    water 0.42
    ethyl acetate 1.82
    n-propanol 2.35
    acetone 7.31
    n-butanol 1.3
    acetonitrile 1.18
    DMF 23.85
    toluene 0.44
    isobutanol 0.85
    1,4-dioxane 12.37
    methyl acetate 1.54
    THF 42.73
    2-butanone 2.44
    n-pentanol 1.14
    sec-butanol 0.57
    n-hexane 0.04
    ethylene glycol 5.56
    NMP 18.74
    cyclohexane 0.06
    DMSO 68.49
    n-butyl acetate 1.41
    n-octanol 1.03
    chloroform 1.71
    n-propyl acetate 1.31
    acetic acid 20.02
    dichloromethane 1.44
    cyclohexanone 5.77
    propylene glycol 3.33
    isopropyl acetate 1.62
    DMAc 22.67
    2-ethoxyethanol 16.29
    isopentanol 0.97
    n-heptane 0.05
    ethyl formate 2.3
    1,2-dichloroethane 1.12
    n-hexanol 1.33
    2-methoxyethanol 30.26
    isobutyl acetate 0.9
    tetrachloromethane 0.55
    n-pentyl acetate 2.11
    transcutol 16.92
    n-heptanol 1.62
    ethylbenzene 0.31
    MIBK 1.9
    2-propoxyethanol 19.06
    tert-butanol 1.24
    MTBE 0.56
    2-butoxyethanol 10.87
    propionic acid 2.16
    o-xylene 0.36
    formic acid 24.21
    diethyl ether 1.22
    m-xylene 0.44
    p-xylene 0.41
    chlorobenzene 0.52
    dimethyl carbonate 3.02
    n-octane 0.04
    formamide 22.88
    cyclopentanone 12.93
    2-pentanone 2.52
    anisole 1.32
    cyclopentyl methyl ether 2.7
    gamma-butyrolactone 14.28
    1-methoxy-2-propanol 13.61
    pyridine 4.37
    3-pentanone 1.53
    furfural 12.02
    n-dodecane 0.02
    diethylene glycol 25.0
    diisopropyl ether 0.3
    tert-amyl alcohol 0.57
    acetylacetone 7.86
    n-hexadecane 0.03
    acetophenone 2.21
    methyl propionate 2.16
    isopentyl acetate 1.53
    trichloroethylene 2.57
    n-nonanol 1.12
    cyclohexanol 0.8
    benzyl alcohol 2.29
    2-ethylhexanol 0.55
    isooctanol 1.07
    dipropyl ether 0.96
    1,2-dichlorobenzene 0.57
    ethyl lactate 2.3
    propylene carbonate 4.0
    n-methylformamide 12.6
    2-pentanol 0.5
    n-pentane 0.04
    1-propoxy-2-propanol 7.3
    1-methoxy-2-propyl acetate 5.18
    2-(2-methoxypropoxy) propanol 5.98
    mesitylene 0.29
    ε-caprolactone 4.98
    p-cymene 0.28
    epichlorohydrin 12.59
    1,1,1-trichloroethane 0.63
    2-aminoethanol 8.41
    morpholine-4-carbaldehyde 29.72
    sulfolane 25.39
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 3.42
    n-hexyl acetate 2.16
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 10.75
    sec-butyl acetate 0.79
    tert-butyl acetate 1.87
    decalin 0.04
    glycerin 13.22
    diglyme 18.76
    acrylic acid 3.83
    isopropyl myristate 0.55
    n-butyric acid 3.08
    acetyl acetate 2.41
    di(2-ethylhexyl) phthalate 1.34
    ethyl propionate 1.15
    nitromethane 21.63
    1,2-diethoxyethane 3.18
    benzonitrile 1.28
    trioctyl phosphate 0.94
    1-bromopropane 0.33
    gamma-valerolactone 34.97
    n-decanol 0.63
    triethyl phosphate 0.93
    4-methyl-2-pentanol 0.5
    propionitrile 0.74
    vinylene carbonate 4.38
    1,1,2-trichlorotrifluoroethane 15.43
    DMS 2.06
    cumene 0.26
    2-octanol 0.68
    2-hexanone 1.74
    octyl acetate 0.99
    limonene 0.3
    1,2-dimethoxyethane 15.36
    ethyl orthosilicate 0.87
    tributyl phosphate 0.75
    diacetone alcohol 5.07
    N,N-dimethylaniline 1.1
    acrylonitrile 1.5
    aniline 1.16
    1,3-propanediol 9.67
    bromobenzene 0.4
    dibromomethane 0.75
    1,1,2,2-tetrachloroethane 2.18
    2-methyl-cyclohexyl acetate 1.38
    tetrabutyl urea 1.4
    diisobutyl methanol 0.36
    2-phenylethanol 2.9
    styrene 0.29
    dioctyl adipate 1.27
    dimethyl sulfate 7.11
    ethyl butyrate 1.16
    methyl lactate 4.83
    butyl lactate 3.11
    diethyl carbonate 0.77
    propanediol butyl ether 8.94
    triethyl orthoformate 1.31
    p-tert-butyltoluene 0.26
    methyl 4-tert-butylbenzoate 4.04
    morpholine 13.6
    tert-butylamine 0.31
    n-dodecanol 0.35
    dimethoxymethane 20.01
    ethylene carbonate 3.25
    cyrene 10.31
    2-ethoxyethyl acetate 5.21
    2-ethylhexyl acetate 1.01
    1,2,4-trichlorobenzene 0.86
    4-methylpyridine 2.33
    dibutyl ether 0.58
    2,6-dimethyl-4-heptanol 0.36
    DEF 3.45
    dimethyl isosorbide 11.0
    tetrachloroethylene 2.28
    eugenol 5.1
    triacetin 3.58
    span 80 4.96
    1,4-butanediol 3.84
    1,1-dichloroethane 0.57
    2-methyl-1-pentanol 0.69
    methyl formate 10.7
    2-methyl-1-butanol 0.62
    n-decane 0.06
    butyronitrile 0.79
    3,7-dimethyl-1-octanol 0.63
    1-chlorooctane 0.25
    1-chlorotetradecane 0.07
    n-nonane 0.05
    undecane 0.04
    tert-butylcyclohexane 0.03
    cyclooctane 0.04
    cyclopentanol 1.64
    tetrahydropyran 3.04
    tert-amyl methyl ether 0.48
    2,5,8-trioxanonane 11.67
    1-hexene 0.16
    2-isopropoxyethanol 6.36
    2,2,2-trifluoroethanol 6.83
    methyl butyrate 1.63

    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