Fagomine

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  • Identifiers

    CAS number
    53185-12-9

    Molecular formula
    C6H13NO3

    SMILES
    C1CN[C@@H]([C@H]([C@@H]1O)O)CO

    Safety labels

  • Odor profile

    Fragrance
    Odorless 66.7%
    Sweet 45.91%
    Fishy 29.93%
    Alcoholic 21.53%
    Caramellic 18.4%
    Cooling 16.18%
    Bitter 16.09%
    Woody 15.77%
    Animal 15.02%
    Vanilla 14.66%

     

    Flavor
    Sweet 65.7%
    Odorless 52.77%
    Bitter 45.78%
    Sweet-like 30.04%
    Cauliflower 23.14%
    Alkaline 22.03%
    Very slight 21.98%
    Mentholic 20.7%
    Soup 20.5%
    Fenugreek 19.89%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.4

    pKa est.
    6.8 (neutral)

    Molecular weight
    147.17 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    366°C

    Melting point expt.

    • 186 - 188 °C

    Flash point

    • 172.72 ˚C est.

  • Synonyms

    • Fagomine
    • 53185-12-9
    • D-Fagomine
    • (2r,3r,4r)-2-(hydroxymethyl)piperidine-3,4-diol
    • 1,2,5-Trideoxy-1,5-imino-D-arabino-hexitol
    • 1M10C1P4SM
    • DTXSID10201243
    • D-arabino-Hexitol, 1,2,5-trideoxy-1,5-imino-
    • RefChem:139877
    • GlyTouCan:G77337UC
    • DTXCID10123734
    • G77337UC
    • 3,4-Piperidinediol, 2-(hydroxymethyl)-, (2R,3R,4R)-
    • CHEMBL108084
    • (2R,3R,4R)-2-(Hydroxymethyl)-3,4-piperidinediol
    • FAG
    • UNII-1M10C1P4SM
    • (D)-fagomine
    • SureCN142574
    • FAGOMINE, (D)-
    • FAGOMINE, (+)-
    • SCHEMBL142574
    • CHEBI:4969
    • orb1678996
    • BDBM50240725
    • AKOS006345435
    • CS-0365
    • EBC-618377
    • MF03611
    • AC-26456
    • HY-13005
    • MS-22836
    • 1,5-imino-1,2,5-trideoxy-D-arabino-hexitol
    • F83787
    • (2r,3r,4r)-2-hydroxymethylpiperidine-3,4-diol
    • (2R,3R,4R)-2-Hydroxymethyl-piperidine-3,4-diol
    • 2-(Hydroxymethyl)-(2R,3R,4R)-3,4-Piperidinediol
    • BRD-K61536264-001-01-3
    • Q27106598
    • 53185-12-9

  • Applications

    Fagomine (CAS 53185-12-9) is a naturally occurring, polyhydroxylated piperidine alkaloid that acts as a potent glycosidase inhibitor in biochemical assays. In practice, its primary applications are as a research reagent and lead scaffold for carbohydrate mimetics in pharmaceutical development, enabling exploration of alpha-glucosidase-targeted therapies and studies of postprandial glucose management. It is also used as a synthetic building block or intermediate for the preparation of polyhydroxylated piperidine libraries and related glycomimetic compounds. Additionally, fagomine is sometimes evaluated in nutraceutical or functional-ingredient research to investigate modulation of carbohydrate digestion, with application boundaries governed by regulation and formulation considerations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.19
    methanol 6.63
    isopropanol 0.52
    water 648.02
    ethyl acetate 1.26
    n-propanol 0.82
    acetone 0.67
    n-butanol 0.68
    acetonitrile 0.47
    DMF 17.75
    toluene 0.18
    isobutanol 0.65
    1,4-dioxane 2.42
    methyl acetate 0.42
    THF 3.76
    2-butanone 0.47
    n-pentanol 0.46
    sec-butanol 0.6
    n-hexane 0.05
    ethylene glycol 42.6
    NMP 56.98
    cyclohexane 0.16
    DMSO 117.23
    n-butyl acetate 0.89
    n-octanol 0.96
    chloroform 0.53
    n-propyl acetate 0.53
    acetic acid 37.38
    dichloromethane 0.52
    cyclohexanone 3.71
    propylene glycol 12.05
    isopropyl acetate 0.95
    DMAc 21.05
    2-ethoxyethanol 8.67
    isopentanol 0.85
    n-heptane 0.25
    ethyl formate 1.52
    1,2-dichloroethane 0.47
    n-hexanol 1.62
    2-methoxyethanol 20.3
    isobutyl acetate 0.33
    tetrachloromethane 0.68
    n-pentyl acetate 0.89
    transcutol 14.82
    n-heptanol 1.78
    ethylbenzene 0.15
    MIBK 1.03
    2-propoxyethanol 10.5
    tert-butanol 1.24
    MTBE 0.29
    2-butoxyethanol 6.84
    propionic acid 6.01
    o-xylene 0.49
    formic acid 441.36
    diethyl ether 0.22
    m-xylene 0.53
    p-xylene 0.18
    chlorobenzene 0.26
    dimethyl carbonate 1.76
    n-octane 0.13
    formamide 134.66
    cyclopentanone 5.38
    2-pentanone 0.88
    anisole 0.4
    cyclopentyl methyl ether 2.13
    gamma-butyrolactone 11.59
    1-methoxy-2-propanol 11.05
    pyridine 0.99
    3-pentanone 0.72
    furfural 19.11
    n-dodecane 0.08
    diethylene glycol 36.94
    diisopropyl ether 0.25
    tert-amyl alcohol 1.43
    acetylacetone 3.43
    n-hexadecane 0.09
    acetophenone 1.22
    methyl propionate 1.58
    isopentyl acetate 0.92
    trichloroethylene 1.13
    n-nonanol 0.93
    cyclohexanol 2.02
    benzyl alcohol 1.39
    2-ethylhexanol 1.21
    isooctanol 1.51
    dipropyl ether 0.75
    1,2-dichlorobenzene 0.54
    ethyl lactate 3.01
    propylene carbonate 5.45
    n-methylformamide 12.59
    2-pentanol 0.59
    n-pentane 0.06
    1-propoxy-2-propanol 6.15
    1-methoxy-2-propyl acetate 3.3
    2-(2-methoxypropoxy) propanol 6.64
    mesitylene 0.62
    ε-caprolactone 5.43
    p-cymene 0.69
    epichlorohydrin 3.49
    1,1,1-trichloroethane 0.39
    2-aminoethanol 21.39
    morpholine-4-carbaldehyde 36.54
    sulfolane 63.09
    2,2,4-trimethylpentane 0.09
    2-methyltetrahydrofuran 1.62
    n-hexyl acetate 1.06
    isooctane 0.08
    2-(2-butoxyethoxy)ethanol 9.02
    sec-butyl acetate 0.44
    tert-butyl acetate 1.36
    decalin 0.11
    glycerin 92.92
    diglyme 13.96
    acrylic acid 12.79
    isopropyl myristate 0.5
    n-butyric acid 6.24
    acetyl acetate 1.65
    di(2-ethylhexyl) phthalate 1.47
    ethyl propionate 0.68
    nitromethane 17.3
    1,2-diethoxyethane 0.86
    benzonitrile 0.84
    trioctyl phosphate 1.34
    1-bromopropane 0.13
    gamma-valerolactone 17.07
    n-decanol 0.71
    triethyl phosphate 1.44
    4-methyl-2-pentanol 0.82
    propionitrile 0.34
    vinylene carbonate 4.43
    1,1,2-trichlorotrifluoroethane 32.0
    DMS 1.32
    cumene 0.23
    2-octanol 0.87
    2-hexanone 0.38
    octyl acetate 0.73
    limonene 0.9
    1,2-dimethoxyethane 3.46
    ethyl orthosilicate 1.26
    tributyl phosphate 1.16
    diacetone alcohol 6.44
    N,N-dimethylaniline 0.76
    acrylonitrile 0.88
    aniline 0.9
    1,3-propanediol 16.63
    bromobenzene 0.2
    dibromomethane 0.3
    1,1,2,2-tetrachloroethane 1.33
    2-methyl-cyclohexyl acetate 1.29
    tetrabutyl urea 1.9
    diisobutyl methanol 1.16
    2-phenylethanol 2.1
    styrene 0.11
    dioctyl adipate 0.93
    dimethyl sulfate 10.13
    ethyl butyrate 1.05
    methyl lactate 9.94
    butyl lactate 3.03
    diethyl carbonate 0.65
    propanediol butyl ether 8.23
    triethyl orthoformate 1.32
    p-tert-butyltoluene 0.75
    methyl 4-tert-butylbenzoate 4.38
    morpholine 3.39
    tert-butylamine 0.4
    n-dodecanol 0.55
    dimethoxymethane 4.24
    ethylene carbonate 3.02
    cyrene 15.91
    2-ethoxyethyl acetate 1.51
    2-ethylhexyl acetate 0.74
    1,2,4-trichlorobenzene 0.76
    4-methylpyridine 0.78
    dibutyl ether 0.35
    2,6-dimethyl-4-heptanol 1.16
    DEF 4.86
    dimethyl isosorbide 12.31
    tetrachloroethylene 2.35
    eugenol 5.37
    triacetin 2.56
    span 80 7.27
    1,4-butanediol 6.12
    1,1-dichloroethane 0.19
    2-methyl-1-pentanol 0.61
    methyl formate 7.24
    2-methyl-1-butanol 0.87
    n-decane 0.13
    butyronitrile 0.38
    3,7-dimethyl-1-octanol 1.01
    1-chlorooctane 0.29
    1-chlorotetradecane 0.15
    n-nonane 0.12
    undecane 0.1
    tert-butylcyclohexane 0.09
    cyclooctane 0.16
    cyclopentanol 3.18
    tetrahydropyran 0.74
    tert-amyl methyl ether 0.54
    2,5,8-trioxanonane 13.18
    1-hexene 0.06
    2-isopropoxyethanol 3.74
    2,2,2-trifluoroethanol 48.26
    methyl butyrate 0.97

    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