(+)Clausenamide

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  • Identifiers

    CAS number
    109905-95-5

    Molecular formula
    C18H19NO3

    SMILES
    CN1[C@@H]([C@@H]([C@H](C1=O)O)C2=CC=CC=C2)[C@@H](C3=CC=CC=C3)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 48.53%
    Sweet 41.66%
    Bitter 32.77%
    Vanilla 26.72%
    Spicy 26.27%
    Balsamic 25.49%
    Fruity 22.75%
    Almond 22.57%
    Phenolic 18.98%
    Powdery 18.92%

     

    Flavor
    Bitter 81.02%
    Odorless 25.51%
    Sweet-like 21.54%
    Cedarleaf 19.83%
    Nitrile 19.66%
    Orange flower 19.05%
    Butyric 18.97%
    Orange blossom 18.79%
    Rosy 18.53%
    Pastry 18.52%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.5

    pKa est.
    6.26 (neutral)

    Molecular weight
    297.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    669°C

    Flash point

    • 204.96 ˚C est.

  • Synonyms

    • (+)-Clausenamide
    • 109905-95-5
    • (3R,4S,5S)-3-hydroxy-5-[(R)-hydroxy(phenyl)methyl]-1-methyl-4-phenylpyrrolidin-2-one
    • (+)Clausenamide
    • (3R,4S,5S)-3-hydroxy-5-((R)-hydroxy(phenyl)methyl)-1-methyl-4-phenylpyrrolidin-2-one
    • RefChem:1049017
    • Clausenamide
    • 103541-15-7
    • (3R,4S,5S)-3-HYDROXY-5-[(R)-HYDROXY-PHENYL-METHYL]-1-METHYL-4-PHENYL-P YRROLIDIN-2-ONE
    • 3-hydroxy-5-[hydroxy(phenyl)methyl]-1-methyl-4-phenylpyrrolidin-2-one
    • Zetaclausenamide
    • CHEMBL508970
    • SCHEMBL6369855
    • (+)-CLA
    • DTXSID10908462
    • CHEBI:229080
    • GLXC-22946
    • (3R,4S,5S)-3-Hydroxy-5-((R)-hydroxyphenylmethyl)-1-methyl-4-phenylpyrrolidin-2-one
    • 541C157
    • 2-Pyrrolidinone,3-hydroxy-5-((R)-hydroxyphenylmethyl)-1-methyl-4-phenyl-, (3R,4S,5S)-rel
    • DL-Xylonic acid, 3,4-dideoxy-4-(methylamino)-3-phenyl-5-C-phenyl-, gamma-lactam, (S*)-
    • 103541-15-7

  • Applications

    (+)Clausenamide is used primarily as an intermediate and chiral building block in pharmaceutical synthesis, supporting the construction of heterocyclic and other active compounds. It is commonly evaluated as a reagent or scaffold in asymmetric synthesis and can serve as a chiral auxiliary in enantioselective transformations. In analytical and process contexts, (+)Clausenamide can be used as a reference standard or research chemical for method development, quality control, and medicinal chemistry studies. The compound is also encountered in academic and industrial research as a potential basis for developing new pharmaceutical candidates, subject to applicable regulations for handling and use.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 8.36
    methanol 23.84
    isopropanol 3.45
    water 1.21
    ethyl acetate 6.95
    n-propanol 4.53
    acetone 10.8
    n-butanol 3.92
    acetonitrile 6.14
    DMF 72.33
    toluene 3.92
    isobutanol 2.52
    1,4-dioxane 21.53
    methyl acetate 7.21
    THF 39.82
    2-butanone 7.49
    n-pentanol 3.04
    sec-butanol 1.98
    n-hexane 0.06
    ethylene glycol 11.75
    NMP 21.33
    cyclohexane 0.2
    DMSO 62.65
    n-butyl acetate 5.79
    n-octanol 3.81
    chloroform 18.33
    n-propyl acetate 4.84
    acetic acid 31.91
    dichloromethane 17.33
    cyclohexanone 19.79
    propylene glycol 5.62
    isopropyl acetate 7.27
    DMAc 86.48
    2-ethoxyethanol 21.85
    isopentanol 5.06
    n-heptane 0.21
    ethyl formate 8.96
    1,2-dichloroethane 14.15
    n-hexanol 5.44
    2-methoxyethanol 39.82
    isobutyl acetate 3.73
    tetrachloromethane 1.43
    n-pentyl acetate 6.63
    transcutol 48.73
    n-heptanol 7.01
    ethylbenzene 3.16
    MIBK 8.44
    2-propoxyethanol 23.79
    tert-butanol 5.65
    MTBE 2.37
    2-butoxyethanol 21.63
    propionic acid 8.24
    o-xylene 4.01
    formic acid 41.43
    diethyl ether 2.69
    m-xylene 3.77
    p-xylene 3.46
    chlorobenzene 6.68
    dimethyl carbonate 18.84
    n-octane 0.2
    formamide 81.14
    cyclopentanone 28.65
    2-pentanone 6.91
    anisole 9.09
    cyclopentyl methyl ether 7.18
    gamma-butyrolactone 34.09
    1-methoxy-2-propanol 23.91
    pyridine 24.76
    3-pentanone 5.61
    furfural 45.02
    n-dodecane 0.21
    diethylene glycol 33.95
    diisopropyl ether 1.18
    tert-amyl alcohol 3.65
    acetylacetone 23.15
    n-hexadecane 0.25
    acetophenone 15.19
    methyl propionate 9.17
    isopentyl acetate 7.21
    trichloroethylene 39.48
    n-nonanol 4.71
    cyclohexanol 3.72
    benzyl alcohol 12.19
    2-ethylhexanol 3.69
    isooctanol 6.04
    dipropyl ether 3.39
    1,2-dichlorobenzene 9.11
    ethyl lactate 9.0
    propylene carbonate 16.84
    n-methylformamide 26.63
    2-pentanol 2.15
    n-pentane 0.06
    1-propoxy-2-propanol 13.18
    1-methoxy-2-propyl acetate 14.85
    2-(2-methoxypropoxy) propanol 16.77
    mesitylene 2.55
    ε-caprolactone 15.27
    p-cymene 3.16
    epichlorohydrin 41.82
    1,1,1-trichloroethane 5.51
    2-aminoethanol 12.59
    morpholine-4-carbaldehyde 42.73
    sulfolane 45.38
    2,2,4-trimethylpentane 0.14
    2-methyltetrahydrofuran 7.44
    n-hexyl acetate 7.17
    isooctane 0.12
    2-(2-butoxyethoxy)ethanol 22.71
    sec-butyl acetate 3.88
    tert-butyl acetate 9.16
    decalin 0.31
    glycerin 23.62
    diglyme 47.37
    acrylic acid 16.14
    isopropyl myristate 3.89
    n-butyric acid 11.8
    acetyl acetate 10.28
    di(2-ethylhexyl) phthalate 6.59
    ethyl propionate 5.53
    nitromethane 56.25
    1,2-diethoxyethane 10.11
    benzonitrile 10.92
    trioctyl phosphate 4.31
    1-bromopropane 1.98
    gamma-valerolactone 47.07
    n-decanol 3.38
    triethyl phosphate 6.17
    4-methyl-2-pentanol 3.25
    propionitrile 5.31
    vinylene carbonate 22.34
    1,1,2-trichlorotrifluoroethane 49.66
    DMS 11.26
    cumene 2.47
    2-octanol 3.26
    2-hexanone 4.79
    octyl acetate 4.81
    limonene 3.19
    1,2-dimethoxyethane 31.74
    ethyl orthosilicate 5.82
    tributyl phosphate 4.35
    diacetone alcohol 17.17
    N,N-dimethylaniline 8.02
    acrylonitrile 13.95
    aniline 8.88
    1,3-propanediol 18.16
    bromobenzene 5.38
    dibromomethane 6.89
    1,1,2,2-tetrachloroethane 27.55
    2-methyl-cyclohexyl acetate 7.85
    tetrabutyl urea 7.67
    diisobutyl methanol 3.17
    2-phenylethanol 14.39
    styrene 3.31
    dioctyl adipate 6.87
    dimethyl sulfate 30.81
    ethyl butyrate 5.68
    methyl lactate 16.9
    butyl lactate 9.78
    diethyl carbonate 5.69
    propanediol butyl ether 12.99
    triethyl orthoformate 6.39
    p-tert-butyltoluene 2.81
    methyl 4-tert-butylbenzoate 17.57
    morpholine 19.58
    tert-butylamine 2.17
    n-dodecanol 2.49
    dimethoxymethane 38.24
    ethylene carbonate 15.85
    cyrene 24.35
    2-ethoxyethyl acetate 13.15
    2-ethylhexyl acetate 5.0
    1,2,4-trichlorobenzene 11.57
    4-methylpyridine 11.81
    dibutyl ether 3.02
    2,6-dimethyl-4-heptanol 3.17
    DEF 12.93
    dimethyl isosorbide 31.88
    tetrachloroethylene 19.48
    eugenol 20.66
    triacetin 12.99
    span 80 12.67
    1,4-butanediol 6.37
    1,1-dichloroethane 4.69
    2-methyl-1-pentanol 3.86
    methyl formate 27.38
    2-methyl-1-butanol 3.3
    n-decane 0.36
    butyronitrile 4.31
    3,7-dimethyl-1-octanol 4.05
    1-chlorooctane 1.69
    1-chlorotetradecane 0.79
    n-nonane 0.26
    undecane 0.27
    tert-butylcyclohexane 0.24
    cyclooctane 0.13
    cyclopentanol 4.24
    tetrahydropyran 7.66
    tert-amyl methyl ether 2.73
    2,5,8-trioxanonane 33.88
    1-hexene 0.43
    2-isopropoxyethanol 12.4
    2,2,2-trifluoroethanol 20.38
    methyl butyrate 7.36

    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