6-{[Amino(phenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

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  • Identifiers

    CAS number
    856649-99-5

    Molecular formula
    C16H19N3O4S

    SMILES
    CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C

  • Odor profile

    Fragrance
    Odorless 73.43%
    Savory 29.78%
    Meaty 27.17%
    Cooked 24.03%
    Cooling 22.31%
    Roasted 20.86%
    Bitter 19.85%
    Nutty 16.92%
    Popcorn 16.58%
    Milky 16.06%

     

    Flavor
    Bitter 85.67%
    Odorless 38.89%
    Bland 25.76%
    Sweet-like 20.03%
    Nitrile 19.52%
    Cedarleaf 19.22%
    Mild 18.54%
    Heather 18.11%
    Taco 18.0%
    Broom 17.97%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.1

    pKa est.
    4.33 (weak acid)

    Molecular weight
    349.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    622°C

    Flash point

    • 274.06 ˚C est.

  • Synonyms

    • Alpen
    • Guicitrine
    • Deripen
    • Wypicil
    • 6-{[amino(phenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
    • Ampen
    • AMPI
    • D-(-)-.alpha.-Aminobenzylpenicillin
    • Ampipenin, nt3
    • NCGC00018160-02
    • Pen A Oral
    • P 50
    • .alpha.-Aminobenzylpenicillin
    • SCHEMBL242460
    • CHEMBL1617921
    • D-(-)-.alpha.-Aminopenicillin
    • CHEBI:94334
    • DTXSID20859077
    • BCP25420
    • BHC17365
    • BBL016496
    • STK803647
    • AKOS000641681
    • AKOS022060556
    • 6-[(2-amino-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
    • LS-14499
    • NCI60_004295
    • SY076914
    • NS00000689
    • SR-01000318615
    • SR-01000318615-1
    • WLN: T45 ANV ESTJ CMVYZR& F1 F1 GVQ -D
    • 6-D(-)-.alpha.-Aminophenylacetamido-penicillanic acid
    • BRD-A16754160-001-01-5
    • BRD-A16754160-236-01-7
    • Q27166159
    • 6-(D-(-)-.alpha.-Aminophenylacetamido)penicillanic acid
    • Ampicillin acid;Aminobenzylpenicillin;Piperacillin EP Impurity A
    • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,3-dimethyl-7-oxo-, D-(-)-
    • D-(-)-4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,3-dimethyl-7-oxo-
    • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,3-dimethyl-7-oxo-, [2S-[2.alpha.,5.alpha.,6.beta.(S )]]-
    • 6-[(2-amino-1-oxo-2-phenylethyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
    • 7-(2-amino-2-phenyl-acetyl)amino-3,3-dimethyl-6-oxo-2-thia-5-azabicyclo[3.2.0]heptane-4carboxylic acid
    • 856649-99-5
    • D-(-)-6-(2-Amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

  • Applications

    6-{[Amino(phenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (CAS 856649-99-5) finds real-world use primarily in pharmaceutical contexts as a beta-lactam antibiotic core scaffold and as an intermediate in the synthesis of penicillin-type drugs, serves as a medicinal chemistry reagent for exploring structure-activity relationships (SAR) in beta-lactam chemistry, acts as an analytical reference standard or benchmark in quality control and method development for beta-lactam antibiotics, and is employed as a research building block in antibiotic discovery programs and enzyme-inhibition studies, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 7.16
    methanol 10.41
    isopropanol 2.66
    water 5.71
    ethyl acetate 2.32
    n-propanol 3.24
    acetone 2.25
    n-butanol 2.67
    acetonitrile 3.29
    DMF 22.6
    toluene 0.14
    isobutanol 1.4
    1,4-dioxane 2.86
    methyl acetate 1.94
    THF 8.64
    2-butanone 2.21
    n-pentanol 1.48
    sec-butanol 1.46
    n-hexane 0.02
    ethylene glycol 14.95
    NMP 16.46
    cyclohexane 0.03
    DMSO 26.9
    n-butyl acetate 1.5
    n-octanol 0.79
    chloroform 1.96
    n-propyl acetate 1.25
    acetic acid 23.02
    dichloromethane 1.88
    cyclohexanone 3.27
    propylene glycol 8.08
    isopropyl acetate 1.21
    DMAc 23.41
    2-ethoxyethanol 15.61
    isopentanol 1.72
    n-heptane 0.04
    ethyl formate 3.69
    1,2-dichloroethane 1.3
    n-hexanol 1.61
    2-methoxyethanol 42.53
    isobutyl acetate 0.6
    tetrachloromethane 0.34
    n-pentyl acetate 1.37
    transcutol 12.84
    n-heptanol 1.45
    ethylbenzene 0.12
    MIBK 1.67
    2-propoxyethanol 15.75
    tert-butanol 1.56
    MTBE 0.34
    2-butoxyethanol 9.03
    propionic acid 4.85
    o-xylene 0.13
    formic acid 87.28
    diethyl ether 0.83
    m-xylene 0.17
    p-xylene 0.17
    chlorobenzene 0.35
    dimethyl carbonate 3.3
    n-octane 0.03
    formamide 70.74
    cyclopentanone 6.19
    2-pentanone 2.43
    anisole 0.51
    cyclopentyl methyl ether 1.2
    gamma-butyrolactone 10.37
    1-methoxy-2-propanol 19.64
    pyridine 2.24
    3-pentanone 1.36
    furfural 13.25
    n-dodecane 0.02
    diethylene glycol 29.55
    diisopropyl ether 0.18
    tert-amyl alcohol 1.09
    acetylacetone 3.63
    n-hexadecane 0.03
    acetophenone 1.4
    methyl propionate 2.89
    isopentyl acetate 1.34
    trichloroethylene 3.19
    n-nonanol 0.82
    cyclohexanol 0.86
    benzyl alcohol 1.52
    2-ethylhexanol 0.71
    isooctanol 0.97
    dipropyl ether 0.63
    1,2-dichlorobenzene 0.51
    ethyl lactate 3.85
    propylene carbonate 4.76
    n-methylformamide 18.17
    2-pentanol 1.1
    n-pentane 0.03
    1-propoxy-2-propanol 6.99
    1-methoxy-2-propyl acetate 3.51
    2-(2-methoxypropoxy) propanol 5.09
    mesitylene 0.12
    ε-caprolactone 4.02
    p-cymene 0.21
    epichlorohydrin 9.13
    1,1,1-trichloroethane 0.63
    2-aminoethanol 14.37
    morpholine-4-carbaldehyde 18.15
    sulfolane 15.25
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 1.88
    n-hexyl acetate 1.24
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 7.74
    sec-butyl acetate 0.66
    tert-butyl acetate 1.07
    decalin 0.02
    glycerin 32.42
    diglyme 11.85
    acrylic acid 8.4
    isopropyl myristate 0.45
    n-butyric acid 5.87
    acetyl acetate 1.77
    di(2-ethylhexyl) phthalate 1.28
    ethyl propionate 1.29
    nitromethane 23.4
    1,2-diethoxyethane 1.59
    benzonitrile 1.32
    trioctyl phosphate 0.95
    1-bromopropane 0.41
    gamma-valerolactone 18.01
    n-decanol 0.58
    triethyl phosphate 1.15
    4-methyl-2-pentanol 0.75
    propionitrile 1.94
    vinylene carbonate 5.31
    1,1,2-trichlorotrifluoroethane 18.85
    DMS 1.55
    cumene 0.11
    2-octanol 0.68
    2-hexanone 1.17
    octyl acetate 0.75
    limonene 0.23
    1,2-dimethoxyethane 8.57
    ethyl orthosilicate 0.95
    tributyl phosphate 0.93
    diacetone alcohol 5.08
    N,N-dimethylaniline 0.49
    acrylonitrile 4.03
    aniline 0.69
    1,3-propanediol 19.23
    bromobenzene 0.23
    dibromomethane 0.87
    1,1,2,2-tetrachloroethane 2.38
    2-methyl-cyclohexyl acetate 1.09
    tetrabutyl urea 1.68
    diisobutyl methanol 0.47
    2-phenylethanol 2.16
    styrene 0.13
    dioctyl adipate 0.92
    dimethyl sulfate 7.29
    ethyl butyrate 1.3
    methyl lactate 9.17
    butyl lactate 3.3
    diethyl carbonate 1.05
    propanediol butyl ether 6.67
    triethyl orthoformate 1.2
    p-tert-butyltoluene 0.18
    methyl 4-tert-butylbenzoate 2.66
    morpholine 5.27
    tert-butylamine 0.42
    n-dodecanol 0.39
    dimethoxymethane 11.03
    ethylene carbonate 3.58
    cyrene 9.76
    2-ethoxyethyl acetate 2.82
    2-ethylhexyl acetate 0.86
    1,2,4-trichlorobenzene 0.75
    4-methylpyridine 1.37
    dibutyl ether 0.38
    2,6-dimethyl-4-heptanol 0.47
    DEF 3.86
    dimethyl isosorbide 9.21
    tetrachloroethylene 1.87
    eugenol 4.68
    triacetin 2.33
    span 80 4.05
    1,4-butanediol 6.2
    1,1-dichloroethane 0.69
    2-methyl-1-pentanol 1.01
    methyl formate 11.12
    2-methyl-1-butanol 1.37
    n-decane 0.04
    butyronitrile 1.85
    3,7-dimethyl-1-octanol 0.62
    1-chlorooctane 0.18
    1-chlorotetradecane 0.08
    n-nonane 0.03
    undecane 0.03
    tert-butylcyclohexane 0.02
    cyclooctane 0.02
    cyclopentanol 1.79
    tetrahydropyran 1.2
    tert-amyl methyl ether 0.42
    2,5,8-trioxanonane 8.4
    1-hexene 0.11
    2-isopropoxyethanol 5.66
    2,2,2-trifluoroethanol 14.93
    methyl butyrate 1.87

    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