Benzeneacetic acid, alpha-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester, (alphaS)-

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  • Identifiers

    CAS number
    101-31-5

    Molecular formula
    C17H23NO3

    SMILES
    CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)[C@H](CO)C3=CC=CC=C3

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Odorless 39.98%
    Sweet 35.88%
    Floral 29.98%
    Fruity 27.89%
    Cooling 26.38%
    Balsamic 25.05%
    Grape 24.46%
    Mint 21.92%
    Fresh 21.77%
    Herbal 21.64%

     

    Flavor
    Bitter 68.78%
    Odorless 33.48%
    Bland 23.4%
    Sweet-like 22.78%
    Mild 21.65%
    Cedarleaf 20.56%
    Heather 19.99%
    Broom 19.73%
    Nitrile 19.55%
    Genet 19.37%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.8

    pKa est.
    8.43 (weak base)

    Molecular weight
    289.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    440°C

    Melting point expt.

    • 108.5 °C

    Flash point

    • 191.15 ˚C est.

    Solubility expt.

    • 3560 mg/L (at 20 °C)

  • Synonyms

    • Benzeneacetic acid, alpha-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (alphaS)-
    • Benzeneacetic acid, .alpha.-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (.alpha.S)-
    • BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-, (3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, (.ALPHA.S)-
    • Benzeneacetic acid, alpha-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester, (alphaS)-
    • RefChem:562898
    • Benzeneacetic acid, .alpha.-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo3.2.1oct-3-yl ester, (.alpha.S)-
    • Benzeneacetic acid, alpha-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo3.2.1oct-3-yl ester, (alphaS)-
    • L-Hyoscyamine
    • hyoscyamine
    • 101-31-5
    • Daturine
    • (-)-Hyoscyamine
    • Duboisine
    • (-)-Atropine
    • L-Tropine tropate
    • (S)-(-)-Hyoscyamine
    • Cystospaz
    • l-Atropine
    • (S)-Atropine
    • Hyoscyamine (L)
    • Levsin
    • Bellafoline
    • Hyoscyaminum
    • Atropine, (s)-
    • ENDO-ATROPINE
    • Tropine, (-)-tropate
    • [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2S)-3-hydroxy-2-phenylpropanoate
    • PX44XO846X
    • Levsinex SR
    • (1R,5S)-8-METHYL-8-AZABICYCLO[3.2.1]OCT-3-YL (2R)-3-HYDROXY-2-PHENYLPROPANOATE
    • [3(S)-endo]-alpha-(hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester
    • NSC-757064
    • A1EBT
    • (1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2S)-3-hydroxy-2-phenylpropanoate
    • (2S)-3-hydroxy-2-phenylpropanoic acid [(5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] ester
    • l-Hyopscyamine
    • tropan-3alpha-yl (2S)-3-hydroxy-2-phenylpropanoate
    • L-Hyoscamine
    • Hyospaz
    • Hyosyne
    • Levbid
    • (-)-Hycosamine
    • Symax Duotab
    • Hyoscyamine, l-
    • Levsin SL
    • (1R,3r,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2S)-3-hydroxy-2-phenylpropanoate
    • (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl (2S)-3-hydroxy-2-phenylpropanoate
    • Symax SL
    • Symax SR
    • Tropic acid, (-)-, ester with tropine
    • Benzeneacetic acid, a-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (aS)-
    • OIN
    • SMR000718747
    • Hyoscyamine [USP:BAN]
    • UNII-PX44XO846X
    • Hyocyamine
    • Daturin
    • Tropine, (-)-tropate (ester)
    • (leo)-atropine
    • (S)atropine
    • HSDB 3552
    • 2arm
    • Tropine-L-tropate
    • (leo)-hyoscyamine
    • (-)-Hyoscyamin
    • HYO
    • Prestwick_273
    • EINECS 202-933-0
    • Hyoscyamine (USP)
    • (3beta)-Hyoscyamine
    • (S)-(leo)-hyoscyamine
    • HYOSCYAMINE [MI]
    • Prestwick3_000233
    • L-Hyoscyamine (Standard)
    • HYOSCYAMINE [HSDB]
    • HYOSCYAMINE [VANDF]
    • HYOSCYAMINUM [HPUS]
    • HYOSCYAMINE [MART.]
    • SCHEMBL41316
    • BSPBio_000305
    • HYOSCYAMINE [WHO-DD]
    • MLS001304011
    • MLS002154242
    • MLS002222193
    • SCHEMBL249586
    • BPBio1_000337
    • orb1310126
    • SCHEMBL1649244
    • 1alphaH,5alphaH-Tropan-3alpha-ol (-)-tropate (ester)
    • CHEMBL1234973
    • CHEMBL1331216
    • CHEMBL2449003
    • CHEBI:17486
    • CHEBI:92712
    • HY-N0471R
    • DTXSID20941522
    • DTXSID80889335
    • HMS2095P07
    • HMS2231N11
    • HMS3712P07
    • HYOSCYAMINE [USP MONOGRAPH]
    • MSK10190
    • BDBM50497835
    • MFCD00067306
    • AKOS015896332
    • AKOS016843532
    • Hyoscyamine dried down 100 microg/mL
    • CCG-220233
    • DB00424
    • EBC-616653
    • FH36337
    • NSC 757064
    • L-TROPIC ACID ESTER WITH TROPINE
    • NCGC00179608-01
    • AC-34425
    • AS-75498
    • 4247B
    • NS00066992
    • 5934-50-9
    • C02046
    • D00147
    • F14785
    • AH-034/21167047
    • Q413762
    • SR-01000799139
    • SR-01000799139-2
    • BRD-K40530731-001-02-5
    • 101-31-5

  • Applications

    Benzeneacetic acid, alpha-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester, (alphaS)- (CAS 101-31-5) is a chiral tropane-like ester that is primarily utilized as an intermediate/building block in pharmaceutical research. It serves as a scaffold for the synthesis of tropane-derivative drug candidates and is used in medicinal chemistry investigations for SAR exploration; it is employed in asymmetric synthesis as a chiral building block or precursor for catalysts and enantioenriched intermediates; it is supplied for contract synthesis and custom manufacturing to CROs/CMOs; and it is used in academic and industrial research as a platform for library generation and receptor-ligand interaction studies.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 57.27
    methanol 130.54
    isopropanol 39.51
    water 6.92
    ethyl acetate 64.18
    n-propanol 56.11
    acetone 108.11
    n-butanol 49.73
    acetonitrile 51.08
    DMF 232.9
    toluene 19.57
    isobutanol 40.23
    1,4-dioxane 160.54
    methyl acetate 57.58
    THF 175.78
    2-butanone 73.25
    n-pentanol 28.51
    sec-butanol 25.43
    n-hexane 0.42
    ethylene glycol 58.83
    NMP 117.12
    cyclohexane 1.92
    DMSO 368.31
    n-butyl acetate 41.76
    n-octanol 10.26
    chloroform 513.21
    n-propyl acetate 35.65
    acetic acid 199.97
    dichloromethane 415.49
    cyclohexanone 127.72
    propylene glycol 54.72
    isopropyl acetate 38.24
    DMAc 235.86
    2-ethoxyethanol 119.2
    isopentanol 45.8
    n-heptane 0.64
    ethyl formate 62.7
    1,2-dichloroethane 199.54
    n-hexanol 26.23
    2-methoxyethanol 246.24
    isobutyl acetate 28.39
    tetrachloromethane 25.53
    n-pentyl acetate 22.01
    transcutol 438.6
    n-heptanol 14.51
    ethylbenzene 8.49
    MIBK 39.31
    2-propoxyethanol 115.57
    tert-butanol 36.8
    MTBE 12.41
    2-butoxyethanol 58.36
    propionic acid 78.43
    o-xylene 14.97
    formic acid 181.39
    diethyl ether 19.76
    m-xylene 18.74
    p-xylene 13.86
    chlorobenzene 47.1
    dimethyl carbonate 46.7
    n-octane 0.37
    formamide 244.94
    cyclopentanone 155.47
    2-pentanone 58.29
    anisole 24.28
    cyclopentyl methyl ether 42.47
    gamma-butyrolactone 196.92
    1-methoxy-2-propanol 139.43
    pyridine 97.37
    3-pentanone 43.39
    furfural 185.46
    n-dodecane 0.5
    diethylene glycol 159.42
    diisopropyl ether 5.43
    tert-amyl alcohol 22.23
    acetylacetone 102.08
    n-hexadecane 0.58
    acetophenone 43.77
    methyl propionate 58.08
    isopentyl acetate 39.07
    trichloroethylene 447.25
    n-nonanol 11.43
    cyclohexanol 43.24
    benzyl alcohol 45.93
    2-ethylhexanol 13.95
    isooctanol 12.95
    dipropyl ether 10.82
    1,2-dichlorobenzene 52.45
    ethyl lactate 37.86
    propylene carbonate 102.01
    n-methylformamide 151.88
    2-pentanol 19.48
    n-pentane 0.58
    1-propoxy-2-propanol 63.36
    1-methoxy-2-propyl acetate 72.57
    2-(2-methoxypropoxy) propanol 69.21
    mesitylene 11.26
    ε-caprolactone 101.91
    p-cymene 8.71
    epichlorohydrin 269.7
    1,1,1-trichloroethane 98.88
    2-aminoethanol 82.31
    morpholine-4-carbaldehyde 163.93
    sulfolane 203.65
    2,2,4-trimethylpentane 0.64
    2-methyltetrahydrofuran 67.93
    n-hexyl acetate 26.22
    isooctane 0.54
    2-(2-butoxyethoxy)ethanol 99.44
    sec-butyl acetate 23.62
    tert-butyl acetate 36.98
    decalin 1.15
    glycerin 131.83
    diglyme 190.04
    acrylic acid 92.75
    isopropyl myristate 12.19
    n-butyric acid 114.22
    acetyl acetate 59.29
    di(2-ethylhexyl) phthalate 22.25
    ethyl propionate 29.34
    nitromethane 336.92
    1,2-diethoxyethane 54.86
    benzonitrile 49.17
    trioctyl phosphate 13.86
    1-bromopropane 38.56
    gamma-valerolactone 251.96
    n-decanol 8.84
    triethyl phosphate 22.19
    4-methyl-2-pentanol 15.54
    propionitrile 39.63
    vinylene carbonate 108.61
    1,1,2-trichlorotrifluoroethane 251.96
    DMS 45.36
    cumene 7.2
    2-octanol 7.57
    2-hexanone 30.91
    octyl acetate 16.69
    limonene 9.24
    1,2-dimethoxyethane 125.06
    ethyl orthosilicate 19.72
    tributyl phosphate 19.08
    diacetone alcohol 62.45
    N,N-dimethylaniline 19.17
    acrylonitrile 65.02
    aniline 43.94
    1,3-propanediol 132.01
    bromobenzene 46.78
    dibromomethane 174.45
    1,1,2,2-tetrachloroethane 345.63
    2-methyl-cyclohexyl acetate 31.19
    tetrabutyl urea 25.72
    diisobutyl methanol 9.26
    2-phenylethanol 42.54
    styrene 9.49
    dioctyl adipate 24.49
    dimethyl sulfate 87.98
    ethyl butyrate 28.67
    methyl lactate 64.17
    butyl lactate 37.04
    diethyl carbonate 25.44
    propanediol butyl ether 56.02
    triethyl orthoformate 25.62
    p-tert-butyltoluene 7.49
    methyl 4-tert-butylbenzoate 42.94
    morpholine 173.25
    tert-butylamine 10.94
    n-dodecanol 6.55
    dimethoxymethane 133.7
    ethylene carbonate 96.26
    cyrene 69.54
    2-ethoxyethyl acetate 55.35
    2-ethylhexyl acetate 28.29
    1,2,4-trichlorobenzene 67.99
    4-methylpyridine 64.23
    dibutyl ether 9.49
    2,6-dimethyl-4-heptanol 9.26
    DEF 62.71
    dimethyl isosorbide 107.76
    tetrachloroethylene 191.48
    eugenol 54.13
    triacetin 53.85
    span 80 45.72
    1,4-butanediol 48.25
    1,1-dichloroethane 130.6
    2-methyl-1-pentanol 27.03
    methyl formate 116.4
    2-methyl-1-butanol 34.55
    n-decane 0.7
    butyronitrile 38.67
    3,7-dimethyl-1-octanol 13.39
    1-chlorooctane 4.59
    1-chlorotetradecane 2.25
    n-nonane 0.52
    undecane 0.58
    tert-butylcyclohexane 0.83
    cyclooctane 0.73
    cyclopentanol 52.35
    tetrahydropyran 74.53
    tert-amyl methyl ether 11.4
    2,5,8-trioxanonane 137.72
    1-hexene 2.49
    2-isopropoxyethanol 60.87
    2,2,2-trifluoroethanol 118.61
    methyl butyrate 43.46

    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