Lithocholic Acid

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  • Identifiers

    CAS number
    434-13-9

    Molecular formula
    C24H40O3

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

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Woody 72.48%
    Balsamic 51.51%
    Sandalwood 47.66%
    Amber 46.48%
    Sweet 41.52%
    Dry 39.39%
    Musk 35.67%
    Cedar 34.02%
    Animal 32.72%
    Powdery 29.95%

     

    Flavor
    Fruity 36.32%
    Sweet 34.93%
    Woody 32.1%
    Fruit 30.61%
    Herbal 27.91%
    Herb 25.45%
    Odorless 24.85%
    Fatty 24.68%
    Mild 23.1%
    Waxy 22.96%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    6.3

    pKa est.
    6.85 (neutral)

    Molecular weight
    376.6 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Boiling point est.
    335°C

    Melting point expt.

    • 363 to 367 °F (NTP, 1992)
    • 184-186 °C
    • 186 °C

    Flash point

    • 252.12 ˚C est.

    Solubility expt.

    • less than 1 mg/mL at 67.5 °F (NTP, 1992)
    • FREELY SOL IN HOT ALC; MORE SOL IN BENZENE THAN DESOXYCHOLIC ACID; INSOL IN PETROLEUM ETHER, GASOLINE, WATER; SLIGHTLY SOL IN GLACIAL ACETIC ACID (ABOUT 0.2 G IN 3 ML); MORE SOL IN ETHER THAN CHOLIC OR DESOXYCHOLIC ACID; SOL IN ABOUT 10 TIMES ITS WT OF ETHYL ACETATE
    • In water, 0.38 mg/l at 25 °C.
    • 0.000377 mg/mL

  • Synonyms

    • LITHOCHOLIC ACID
    • 434-13-9
    • 3alpha-Hydroxy-5beta-cholanic acid
    • 3alpha-Hydroxy-5beta-cholan-24-oic acid
    • 3alpha-Hydroxycholanic acid
    • 3-alpha-Hydroxycholanic acid
    • NCI-C03861
    • 3alpha-Hydroxy-5beta-cholanoic acid
    • 3alpha-Hydroxy-5beta-cholanate
    • 5-beta-Cholanic acid, 3-alpha-hydroxy-
    • 5beta-Cholan-24-oic acid, 3alpha-hydroxy-
    • DTXSID6020779
    • Cholan-24-oic acid, 3-hydroxy-, (3alpha,5beta)-
    • 17beta-(1-Methyl-3-carboxypropyl)etiocholan-3alpha-ol
    • 5QU0I8393U
    • 17-beta-(1-Methyl-3-carboxypropyl)ethiocholan-3-alpha-ol
    • 5-beta-Cholan-24-oic acid, 3-alpha-hydroxy-
    • (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-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
    • NSC-683770
    • DTXCID80779
    • CHEBI:16325
    • Cholan-24-oic acid, 3-hydroxy-, (3-alpha,5-beta)-
    • NSC-657956
    • Acid, Isolithocholic
    • Acid, Lithocholic
    • (4R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-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:153789
    • (4R)-4-((2S,5R,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo(8.7.0.02,7.011,15)heptadecan-14-yl)pentanoic acid
    • 207-099-1
    • Lithocolic acid
    • 3-Hydroxycholan-24-oic acid
    • MFCD00003682
    • 5beta-Cholanic acid-3alpha-ol
    • (3alpha,5beta)-3-hydroxycholan-24-oic acid
    • 3-alpha-Hydroxy-5-beta-cholanic acid
    • NSC683770
    • (3-alpha,5-beta)-3-Hydroxycholan-24-oic acid
    • CHEMBL1478
    • 3.alpha.-Hydroxycholanic acid
    • ST069335
    • (R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
    • Litocholic acid
    • LITHOCHOLICACID
    • (3beta,5beta,14beta,17alpha)-3-Hydroxycholan-24-Oic Acid
    • 3|A-Hydroxy-5|A-cholanic acid
    • (4S)-4-((1S,2S,11S,5R,7R,10R,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0. 0<2,7>.0<11,15>]heptadec-14-yl)pentanoic acid
    • CCRIS 363
    • HSDB 4113
    • SR-05000000450
    • EINECS 207-099-1
    • NSC 657956
    • BRN 3217757
    • Cholan-24-oic acid, 3-hydroxy-, (3.alpha.,5.beta.)-
    • 3alpha-Hydroxy-5beta-cholan-24-oic Acid (Lithocholic Acid)
    • UNII-5QU0I8393U
    • lithocholic-acid
    • NSC657956
    • Cholan-24-oic acid, 3-hydroxy-, (3a,5b)-
    • Prestwick_88
    • Ursodeoxycholic Acid EP Impurity C
    • 4OA
    • CAS-434-13-9
    • Lithocholic acid CRS
    • NSC 683770
    • 4q0a
    • (3|A,5|A)-3-Hydroxycholan-24-oic Acid
    • Prestwick0_000796
    • Prestwick1_000796
    • Prestwick2_000796
    • Prestwick3_000796
    • Spectrum5_002021
    • bmse000686
    • UPCMLD-DP153
    • 3-Hydroxy-5-cholanic acid
    • cid_9903
    • Lithocholic acid, >=95%
    • BIDD:PXR0054
    • SCHEMBL28449
    • BSPBio_000932
    • GTPL611
    • 4-10-00-00785 (Beilstein Handbook Reference)
    • MLS002154006
    • 3a-Hydroxy-5ss-cholanic acid
    • LITHOCHOLIC ACID [MI]
    • SPBio_002871
    • BPBio1_001026
    • orb1306119
    • 3a-hydroxy-5b-cholan-24-oate
    • LITHOCHOLIC ACID [HSDB]
    • UPCMLD-DP153:001
    • 5ss--Cholan-24-oic acid-3a-ol
    • HMS1570O14
    • HMS2097O14
    • HMS2269C14
    • HMS3714O14
    • 3a-hydroxy-5b-cholan-24-oic acid
    • HY-B0172
    • MSK10393
    • Tox21_201868
    • Tox21_302791
    • 3a-Hydroxy-5ss-cholan-24-oic acid
    • 5.beta.-Cholanic acid-3.alpha.-ol
    • BDBM50236238
    • EBC-07670
    • LMST04010003
    • s4003
    • SBB012598
    • (3a,5b)-3-hydroxy-cholan-24-oate
    • 5beta-Cholan-24-oic acid-3alpha-ol
    • AKOS016010251
    • LITHOCHOLIC ACID [EP IMPURITY]
    • CCG-220796
    • CS-2049
    • DS-3878
    • FL24913
    • ST 24:1;O3
    • (3a,5b)-3-Hydroxycholan-24-Oic acid
    • 3.alpha.-Hydroxy-5.beta.-cholanic acid
    • NCGC00091272-01
    • NCGC00091272-04
    • NCGC00091272-06
    • NCGC00091272-07
    • NCGC00091272-08
    • NCGC00256451-01
    • NCGC00259417-01
    • (3a,5b)-3-hydroxy-cholan-24-oic acid
    • (4R)-4-[(1R,3aS,3bR,5aR,7R,9aS,9bS,11aR)-7-hydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid
    • 434-13-9

  • Applications

    Lithocholic Acid (CAS 434-13-9) is primarily used in pharmaceutical research and biochemical studies as a bile-acid scaffold and as a starting point for synthesizing lithocholate derivatives; it also serves as a tool compound to investigate bile-acid receptor pathways such as FXR and TGR5 in receptor biology. In analytical settings, it is employed as a reference material for bile-acid analysis by LC-MS and chromatography. In chemical manufacturing, it is used as an intermediate or building block for the preparation of steroidal/bile-acid derivatives for medicinal chemistry. Depending on formulation goals, lithocholic acid and its derivatives may be evaluated for niche surfactant or solubilization applications in specialty cosmetics or coatings, under appropriate regulatory controls. Applications are typically confined to research, development, and formulation studies, and are subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 53.2
    methanol 31.78
    isopropanol 38.86
    water 0.25
    ethyl acetate 41.94
    n-propanol 54.43
    acetone 64.56
    n-butanol 44.71
    acetonitrile 14.44
    DMF 65.49
    toluene 35.19
    isobutanol 27.56
    1,4-dioxane 102.08
    methyl acetate 23.8
    THF 331.83
    2-butanone 42.54
    n-pentanol 16.5
    sec-butanol 12.93
    n-hexane 0.77
    ethylene glycol 3.81
    NMP 32.77
    cyclohexane 2.15
    DMSO 53.34
    n-butyl acetate 34.52
    n-octanol 9.89
    chloroform 79.83
    n-propyl acetate 21.67
    acetic acid 21.74
    dichloromethane 49.89
    cyclohexanone 66.3
    propylene glycol 6.52
    isopropyl acetate 44.83
    DMAc 62.77
    2-ethoxyethanol 46.21
    isopentanol 32.74
    n-heptane 0.88
    ethyl formate 15.74
    1,2-dichloroethane 33.97
    n-hexanol 26.92
    2-methoxyethanol 85.53
    isobutyl acetate 20.31
    tetrachloromethane 12.39
    n-pentyl acetate 31.23
    transcutol 153.1
    n-heptanol 18.39
    ethylbenzene 10.05
    MIBK 39.73
    2-propoxyethanol 102.73
    tert-butanol 30.47
    MTBE 29.18
    2-butoxyethanol 57.91
    propionic acid 16.75
    o-xylene 15.53
    formic acid 8.94
    diethyl ether 45.92
    m-xylene 23.87
    p-xylene 11.16
    chlorobenzene 26.57
    dimethyl carbonate 22.4
    n-octane 0.43
    formamide 16.5
    cyclopentanone 94.72
    2-pentanone 52.38
    anisole 27.87
    cyclopentyl methyl ether 56.96
    gamma-butyrolactone 75.22
    1-methoxy-2-propanol 87.89
    pyridine 63.03
    3-pentanone 30.55
    furfural 55.39
    n-dodecane 0.27
    diethylene glycol 53.0
    diisopropyl ether 11.4
    tert-amyl alcohol 11.77
    acetylacetone 67.93
    n-hexadecane 0.34
    acetophenone 26.23
    methyl propionate 35.36
    isopentyl acetate 39.51
    trichloroethylene 70.96
    n-nonanol 11.16
    cyclohexanol 21.49
    benzyl alcohol 25.17
    2-ethylhexanol 12.38
    isooctanol 14.73
    dipropyl ether 18.27
    1,2-dichlorobenzene 21.46
    ethyl lactate 16.42
    propylene carbonate 34.28
    n-methylformamide 29.28
    2-pentanol 16.81
    n-pentane 1.27
    1-propoxy-2-propanol 63.04
    1-methoxy-2-propyl acetate 78.82
    2-(2-methoxypropoxy) propanol 38.72
    mesitylene 11.78
    ε-caprolactone 50.95
    p-cymene 7.98
    epichlorohydrin 98.52
    1,1,1-trichloroethane 30.27
    2-aminoethanol 15.83
    morpholine-4-carbaldehyde 67.67
    sulfolane 67.65
    2,2,4-trimethylpentane 0.71
    2-methyltetrahydrofuran 71.44
    n-hexyl acetate 28.6
    isooctane 0.93
    2-(2-butoxyethoxy)ethanol 61.63
    sec-butyl acetate 18.69
    tert-butyl acetate 47.0
    decalin 1.08
    glycerin 14.85
    diglyme 111.76
    acrylic acid 13.9
    isopropyl myristate 9.54
    n-butyric acid 42.21
    acetyl acetate 29.99
    di(2-ethylhexyl) phthalate 13.93
    ethyl propionate 21.79
    nitromethane 38.49
    1,2-diethoxyethane 42.22
    benzonitrile 21.69
    trioctyl phosphate 10.15
    1-bromopropane 17.13
    gamma-valerolactone 136.98
    n-decanol 6.78
    triethyl phosphate 13.63
    4-methyl-2-pentanol 14.57
    propionitrile 20.14
    vinylene carbonate 34.63
    1,1,2-trichlorotrifluoroethane 50.6
    DMS 25.28
    cumene 6.81
    2-octanol 8.1
    2-hexanone 20.48
    octyl acetate 12.37
    limonene 8.24
    1,2-dimethoxyethane 72.51
    ethyl orthosilicate 14.3
    tributyl phosphate 9.89
    diacetone alcohol 47.49
    N,N-dimethylaniline 17.15
    acrylonitrile 21.44
    aniline 37.23
    1,3-propanediol 41.84
    bromobenzene 24.64
    dibromomethane 32.15
    1,1,2,2-tetrachloroethane 54.42
    2-methyl-cyclohexyl acetate 21.93
    tetrabutyl urea 12.89
    diisobutyl methanol 8.78
    2-phenylethanol 36.5
    styrene 10.81
    dioctyl adipate 15.08
    dimethyl sulfate 31.86
    ethyl butyrate 24.78
    methyl lactate 24.65
    butyl lactate 30.28
    diethyl carbonate 15.53
    propanediol butyl ether 34.25
    triethyl orthoformate 22.58
    p-tert-butyltoluene 7.77
    methyl 4-tert-butylbenzoate 36.79
    morpholine 119.96
    tert-butylamine 13.66
    n-dodecanol 3.97
    dimethoxymethane 130.46
    ethylene carbonate 33.72
    cyrene 33.36
    2-ethoxyethyl acetate 55.76
    2-ethylhexyl acetate 26.31
    1,2,4-trichlorobenzene 27.95
    4-methylpyridine 51.83
    dibutyl ether 8.86
    2,6-dimethyl-4-heptanol 8.78
    DEF 33.58
    dimethyl isosorbide 67.93
    tetrachloroethylene 39.65
    eugenol 38.54
    triacetin 35.35
    span 80 30.21
    1,4-butanediol 9.94
    1,1-dichloroethane 33.59
    2-methyl-1-pentanol 12.66
    methyl formate 18.53
    2-methyl-1-butanol 20.28
    n-decane 0.67
    butyronitrile 25.21
    3,7-dimethyl-1-octanol 10.23
    1-chlorooctane 3.87
    1-chlorotetradecane 1.06
    n-nonane 0.55
    undecane 0.4
    tert-butylcyclohexane 0.93
    cyclooctane 0.88
    cyclopentanol 24.23
    tetrahydropyran 94.94
    tert-amyl methyl ether 15.04
    2,5,8-trioxanonane 61.28
    1-hexene 3.36
    2-isopropoxyethanol 33.49
    2,2,2-trifluoroethanol 13.12
    methyl butyrate 23.39

    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