Cholic Acid

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  • Identifiers

    CAS number
    81-25-4

    Molecular formula
    C24H40O5

    SMILES
    C[C@H](CCC(=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
    Woody 47.14%
    Mint 44.33%
    Odorless 42.41%
    Cooling 41.54%
    Balsamic 41.05%
    Sweet 33.66%
    Herbal 32.94%
    Spicy 31.53%
    Camphoreous 28.56%
    Pine 26.43%

     

    Flavor
    Bitter 32.26%
    Odorless 31.18%
    Minty 30.19%
    Herbal 28.67%
    Fatty 26.75%
    Sweet 25.77%
    Fruity 25.41%
    Fruit 23.84%
    Cedarleaf 23.12%
    Sweet-like 23.11%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.6

    pKa est.
    5.79 (weak acid)

    Molecular weight
    408.6 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    194°C

    Melting point expt.

    • 198 °C
    • 198 °C (anhydrous)
    • Crystals from alcohol + water. MP: 155-156 °C /Cholic acid methyl ester/
    • Crystals from ethyl acetate + petroleum ether. MP: 162-163 °C /Cholic acid ethyl ester/
    • 197 - 201 °C

    Flash point

    • 279.44 ˚C est.

    Solubility expt.

    • 175 mg/L (at 20 °C)
    • In water, 175 mg/L at 20 °C
    • In water, 0.28 g/L at 15 °C
    • In alcohol 30.56 g/L; ether 1.22 g/L; chloroform 5.08 g/L; benzene 0.36 g/L; acetone 28.24 g/L; glacial acetic acid 152.12 g/L (all at 15 °C). Soluble in solutions of alkali hydroxides or carbonates
    • Soluble in ethanol, acetone, alkalies; very soluble in ethyl ether, chloroform
    • Soluble in glacial acetic acid; practically insoluble in benzene
    • 0.175 mg/mL

  • Synonyms

    • cholic acid
    • 81-25-4
    • Cholalic acid
    • Colalin
    • Cholalin
    • Cholbam
    • Cholsaeure
    • cholicacid
    • NSC-6135
    • kolbam
    • orphacol
    • 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholan-24-oic acid
    • 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid
    • Cholic acid, 5beta-
    • 3,7,12-Trihydroxycholanic acid
    • (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]pentanoic acid
    • G1JO7801AE
    • DTXSID6040660
    • CHEBI:16359
    • 3-alpha,7-alpha,12-alpha-Trihydroxycholansaeure
    • 17-beta-(1-Methyl-3-carboxypropyl)etiocholane-3alpha,7alpha,12alpha-triol
    • 3,7,12-Trihydroxy-cholan-24-oic acid (3-alpha,5-beta,7-alpha,12-alpha)
    • Cholan-24-oic acid, 3,7,12-trihydroxy-, (3alpha,5beta,7alpha,12alpha)-
    • Cholan-24-oic acid, 3,7,12-trihydroxy-, (3-alpha,5-beta,7-alpha,12-alpha)-
    • (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)pentanoic acid
    • RefChem:54816
    • DTXCID4020660
    • Cholan-24-oic acid, 3,7,12-trihydroxy-, (3-alpha, 5-beta, 7-alpha, 12-alpha)-
    • (4R)-4-((1S,2S,5R,7S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo(8.7.0.02,7.011,15)heptadecan-14-yl)pentanoic acid
    • (4R)-4-((1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo(8.7.0.02,7.011,15)heptadecan-14-yl)pentanoic acid
    • 201-337-8
    • MFCD00003672
    • Cholic acid [USAN]
    • (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)pentanoic acid
    • Cholan-24-oic acid, 3,7,12-trihydroxy-, (3a,5b,7a,12a)-
    • C24H40O5
    • HSDB 982
    • Ursodeoxycholic Acid EP Impurity B
    • TERPENES AND TERPENOIDS
    • CHEMBL205596
    • NSC6135
    • 129874-08-4
    • CHD
    • 3a,7a,12a-Trihydroxy-5b-cholanic acid
    • 3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta-cholan-24-oic acid
    • 5beta-Cholan-24-oic acid, 3alpha,7alpha,12alpha-trihydroxy-
    • 3,7,12-Trihydroxycholan-24-oic acid, (3alpha,5beta,7alpha,12alpha)-
    • Cholic acid (sodium)
    • (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]pentanoic acid
    • 4-[(3R,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]pentanoic acid
    • (3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxycholan-24-oic acid
    • 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholan-24-oic Acid (Cholic Acid)
    • 4-((1S,2S,7S,11S,16S,5R,9R,10R,14R,15R)-5,9,16-trihydroxy-2,15-dimethyltetracy clo[8.7.0.0<2,7>.0<11,15>]heptadec-14-yl)pentanoic acid
    • SMR000112165
    • Colalin (VAN)
    • Cholsaeure [German]
    • 5beta-Cholanic acid-3alpha,7alpha,12alpha-triol
    • Cholan-24-oic acid, 3,7,12-trihydroxy-, (3.alpha.,5.beta.,7.alpha.,12.alpha.)-
    • UNII-G1JO7801AE
    • Cholalate
    • OrphacolReg
    • cholic-acid
    • CCRIS 1626
    • (3alpha,5beta,7alpha,8xi,12alpha)-3,7,12-trihydroxycholan-24-oic acid
    • 5b-Cholate
    • 5b-Cholic acid
    • Cholic acid CRS
    • CholsA currencyure
    • Cholbam (TN)
    • EINECS 201-337-8
    • Cholic acid (8CI)
    • 5.beta.-Cholic acid
    • BRN 2822009
    • Spectrum5_002005
    • CHOLIC ACID [MI]
    • 3alpha,7alpha,12alpha-Trihydroxycholanic acid
    • bmse000650
    • CHOLIC ACID [FCC]
    • CHOLIC ACID [JAN]
    • Cholic acid (JAN/USAN)
    • EC 201-337-8
    • CHOLIC ACID [HSDB]
    • BIDD:PXR0196
    • SCHEMBL27461
    • GTPL609
    • 3.alpha.,7.alpha.,12.alpha.-Trihydroxy-5.beta.-cholanic acid
    • 4-10-00-02072 (Beilstein Handbook Reference)
    • MLS001066422
    • MLS002207051
    • CHOLIC ACID [USP-RS]
    • CHOLIC ACID [WHO-DD]
    • 3a,7a,12a-Trihydroxycholanate
    • 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanoic acid
    • orb1304796
    • CHOLIC ACID [EMA EPAR]
    • BDBM21675
    • BDBM21680
    • 3-alpha,7-alpha,12-alpha-Trihydroxycholansaeure [German]
    • MSK2328
    • CHOLIC ACID [EP IMPURITY]
    • CHOLIC ACID [ORANGE BOOK]
    • HMS2268L18
    • 3a,7a,12a-Trihydroxy-b-cholanate
    • 3a,7a,12a-Trihydroxycholanic acid
    • BB_NC-02012
    • HY-N0324
    • 3a,7a,12a-Trihydroxy-5b-cholanate
    • 5b-Cholanic acid-3a,7a,12a-triol
    • BBL029799
    • EBC-08822
    • LMST04010001
    • s3742
    • STK801993
    • US11208418, Example Obeticholic
    • 3a,7a,12a-Trihydroxy-5b-cholanoate
    • 3a,7a,12a-Trihydroxy-beta-cholanate
    • AKOS005622502
    • 3a,7a,12a-Trihydroxy-b-cholanic acid
    • CCG-268746
    • CS-6608
    • DB02659
    • FC09616
    • US10208081, E6-ECDCA
    • US10266560, Example 6-ECDCA
    • 3,7,12-Trihydroxy-cholan-24-oic acid
    • 3a,7a,12a-Trihydroxy-5A-cholanic acid
    • NCGC00142384-03
    • 81-25-4

  • Applications

    Cholic acid is primarily used as an amphiphilic building block and is commonly employed as an intermediate to synthesize bile acid derivatives that act as specialty surfactants and emulsifiers in cosmetics and personal care products; it is also used as a surfactant and emulsifying additive in household cleaners and detergents; in polymer and coating formulations it serves as a wetting agent and steroid-derived emulsifier; in pharmaceutical R&D it is used as a starting material to prepare bile acid–based derivatives for formulation development.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 26.16
    methanol 87.2
    isopropanol 7.95
    water 0.94
    ethyl acetate 8.42
    n-propanol 9.5
    acetone 26.34
    n-butanol 5.85
    acetonitrile 4.98
    DMF 50.54
    toluene 3.22
    isobutanol 4.18
    1,4-dioxane 43.11
    methyl acetate 5.43
    THF 200.34
    2-butanone 7.51
    n-pentanol 4.52
    sec-butanol 1.75
    n-hexane 0.2
    ethylene glycol 13.46
    NMP 27.19
    cyclohexane 0.33
    DMSO 153.4
    n-butyl acetate 7.45
    n-octanol 4.24
    chloroform 7.41
    n-propyl acetate 5.52
    acetic acid 30.68
    dichloromethane 5.5
    cyclohexanone 20.83
    propylene glycol 8.36
    isopropyl acetate 9.13
    DMAc 37.59
    2-ethoxyethanol 36.06
    isopentanol 5.07
    n-heptane 0.27
    ethyl formate 6.97
    1,2-dichloroethane 5.01
    n-hexanol 8.22
    2-methoxyethanol 76.98
    isobutyl acetate 4.66
    tetrachloromethane 2.49
    n-pentyl acetate 9.38
    transcutol 47.49
    n-heptanol 7.41
    ethylbenzene 1.95
    MIBK 10.43
    2-propoxyethanol 62.09
    tert-butanol 7.45
    MTBE 2.82
    2-butoxyethanol 32.99
    propionic acid 6.87
    o-xylene 2.3
    formic acid 35.89
    diethyl ether 6.66
    m-xylene 3.5
    p-xylene 2.31
    chlorobenzene 3.13
    dimethyl carbonate 10.48
    n-octane 0.2
    formamide 41.1
    cyclopentanone 45.86
    2-pentanone 11.17
    anisole 6.18
    cyclopentyl methyl ether 16.27
    gamma-butyrolactone 42.04
    1-methoxy-2-propanol 49.23
    pyridine 14.45
    3-pentanone 6.21
    furfural 27.4
    n-dodecane 0.12
    diethylene glycol 65.92
    diisopropyl ether 1.99
    tert-amyl alcohol 2.05
    acetylacetone 28.47
    n-hexadecane 0.14
    acetophenone 8.79
    methyl propionate 8.71
    isopentyl acetate 8.3
    trichloroethylene 10.16
    n-nonanol 4.59
    cyclohexanol 3.83
    benzyl alcohol 9.42
    2-ethylhexanol 3.26
    isooctanol 5.55
    dipropyl ether 4.83
    1,2-dichlorobenzene 3.17
    ethyl lactate 8.18
    propylene carbonate 13.22
    n-methylformamide 31.13
    2-pentanol 2.52
    n-pentane 0.21
    1-propoxy-2-propanol 28.67
    1-methoxy-2-propyl acetate 23.08
    2-(2-methoxypropoxy) propanol 17.71
    mesitylene 2.14
    ε-caprolactone 15.91
    p-cymene 1.91
    epichlorohydrin 44.32
    1,1,1-trichloroethane 3.47
    2-aminoethanol 24.53
    morpholine-4-carbaldehyde 53.22
    sulfolane 56.11
    2,2,4-trimethylpentane 0.11
    2-methyltetrahydrofuran 16.59
    n-hexyl acetate 8.9
    isooctane 0.16
    2-(2-butoxyethoxy)ethanol 30.77
    sec-butyl acetate 3.89
    tert-butyl acetate 10.87
    decalin 0.26
    glycerin 30.56
    diglyme 49.29
    acrylic acid 10.29
    isopropyl myristate 2.79
    n-butyric acid 11.6
    acetyl acetate 10.03
    di(2-ethylhexyl) phthalate 5.6
    ethyl propionate 5.18
    nitromethane 40.24
    1,2-diethoxyethane 11.53
    benzonitrile 5.9
    trioctyl phosphate 4.58
    1-bromopropane 1.66
    gamma-valerolactone 73.72
    n-decanol 2.79
    triethyl phosphate 4.11
    4-methyl-2-pentanol 3.09
    propionitrile 3.57
    vinylene carbonate 13.76
    1,1,2-trichlorotrifluoroethane 32.93
    DMS 8.33
    cumene 1.63
    2-octanol 3.25
    2-hexanone 6.19
    octyl acetate 4.38
    limonene 2.01
    1,2-dimethoxyethane 37.94
    ethyl orthosilicate 3.91
    tributyl phosphate 3.4
    diacetone alcohol 18.95
    N,N-dimethylaniline 4.93
    acrylonitrile 6.12
    aniline 5.81
    1,3-propanediol 30.0
    bromobenzene 2.53
    dibromomethane 3.34
    1,1,2,2-tetrachloroethane 8.55
    2-methyl-cyclohexyl acetate 6.23
    tetrabutyl urea 5.58
    diisobutyl methanol 2.42
    2-phenylethanol 13.6
    styrene 1.74
    dioctyl adipate 5.07
    dimethyl sulfate 21.55
    ethyl butyrate 5.55
    methyl lactate 15.5
    butyl lactate 12.13
    diethyl carbonate 3.63
    propanediol butyl ether 23.11
    triethyl orthoformate 5.7
    p-tert-butyltoluene 1.86
    methyl 4-tert-butylbenzoate 14.56
    morpholine 41.99
    tert-butylamine 2.01
    n-dodecanol 1.63
    dimethoxymethane 75.1
    ethylene carbonate 11.83
    cyrene 23.21
    2-ethoxyethyl acetate 18.33
    2-ethylhexyl acetate 5.43
    1,2,4-trichlorobenzene 4.18
    4-methylpyridine 9.4
    dibutyl ether 2.58
    2,6-dimethyl-4-heptanol 2.42
    DEF 9.99
    dimethyl isosorbide 32.6
    tetrachloroethylene 8.75
    eugenol 17.34
    triacetin 12.41
    span 80 15.89
    1,4-butanediol 10.5
    1,1-dichloroethane 3.05
    2-methyl-1-pentanol 2.97
    methyl formate 26.35
    2-methyl-1-butanol 2.77
    n-decane 0.27
    butyronitrile 4.05
    3,7-dimethyl-1-octanol 3.15
    1-chlorooctane 1.2
    1-chlorotetradecane 0.39
    n-nonane 0.23
    undecane 0.17
    tert-butylcyclohexane 0.22
    cyclooctane 0.21
    cyclopentanol 7.16
    tetrahydropyran 14.85
    tert-amyl methyl ether 2.04
    2,5,8-trioxanonane 31.63
    1-hexene 0.7
    2-isopropoxyethanol 18.09
    2,2,2-trifluoroethanol 15.09
    methyl butyrate 6.22

    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