Nigericin Sodium

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  • Identifiers

    CAS number
    28643-80-3

    Molecular formula
    C40H67NaO11

    SMILES
    C[C@H]1CC[C@@H](O[C@H]1[C@@H](C)C(=O)[O-])C[C@@H]2C[C@H]([C@H]([C@@]3(O2)[C@@H](C[C@@](O3)(C)[C@H]4CC[C@@](O4)(C)[C@H]5[C@H](C[C@@H](O5)[C@@H]6[C@H](C[C@H]([C@@](O6)(CO)O)C)C)C)C)C)OC.[Na+]

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 41.61%
    Mint 27.48%
    Cooling 26.51%
    Woody 25.58%
    Floral 19.95%
    Milky 19.85%
    Sweet 19.72%
    Fresh 18.39%
    Creamy 18.04%
    Lactonic 17.75%

     

    Flavor
    Bitter 40.97%
    Fatty 28.97%
    Metallic 23.58%
    Minty 23.53%
    Sweet-like 22.51%
    Earthy 22.31%
    Cedarleaf 21.99%
    Fruity 21.27%
    Bouillon 20.98%
    Cauliflower 20.97%

     

    Odor impact est.
    Low

  • Properties

    pKa est.
    4.69 (weak acid)

    Molecular weight
    746.9 g/mol

    Flash point

    • 155.62 ˚C est.

  • Synonyms

    • Nigericin sodium
    • 28643-80-3
    • Sodium nigericin
    • NIGERICIN, MONOSODIUM SALT
    • UNII-DGN38HI976
    • DGN38HI976
    • NSC 292567
    • NSC-292567
    • Nigericin, sodium salt (1:1)
    • RefChem:165830
    • 608-231-4
    • Nigericin sodium salt
    • Antibiotic K178
    • sodium;(2R)-2-[(2R,3S,6R)-6-[[(2S,4R,5R,6R,7R,9R)-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-3-methyloxan-2-yl]propanoate
    • Nigericin (sodium salt)
    • sodium (R)-2-((2R,3S,6R)-6-(((2S,4R,5R,7R,9R,10R)-2-((2S,2'R,3'S,5R,5'R)-5'-((2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-2,3'-dimethyloctahydro-[2,2'-bifuran]-5-yl)-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]decan-7-yl)methyl)-3-methyltetrahydro-2H-pyran-2-yl)propanoate
    • SMR000875327
    • C40H67NaO11
    • MFCD27977549
    • Nigericin sodium salt?
    • MLS001336037
    • MLS001336038
    • orb1304550
    • CHEMBL2165715
    • SCHEMBL29739358
    • MSK7603
    • MOYOTUKECQMGHE-PDEFJWSRSA-M
    • GLXC-10876
    • NIGERICIN SODIUM SALT [MI]
    • MSK7603-100M
    • AKOS024418750
    • MSK7603-1000M
    • CCG-208241
    • CS-5717
    • EBC-616579
    • FN46958
    • Nigericin sodium salt, >=98% (TLC)
    • DA-66092
    • HY-100381
    • D82021
    • Nigericin sodium - from Streptomyces hygroscopicus
    • Nigericin sodium salt Solution in Methanol, 100ug/mL
    • Q27276393
    • Nigericin sodium salt Solution in Methanol, 1000ug/mL
    • sodium (2R)-2-[(2R,3S,6R)-6-{[(2S,4R,5R,7R,9R,10R)-2-[(2S,2'R,3'S,5R,5'R)-5'-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-2,3'-dimethyl-[2,2'-bioxolan]-5-yl]-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]decan-7-yl]methyl}-3-methyloxan-2-yl]propanoate
    • sodium(R)-2-((2R,3S,6R)-6-(((2S,4R,5R,7R,9R,10R)-2-((2S,2'R,3'S,5R,5'R)-5'-((2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-2,3'-dimethyloctahydro-[2,2'-bifuran]-5-yl)-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]decan-7-yl)methyl)-3-methyltetrahydro-2H-pyran-2-yl)propanoate
    • sodium;(2R)-2-[(2R,3S,6R)-6-[[(2S,4R,5R,6R,7R,9R)-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-tetrahydropyran-2-yl]-3-methyl-tetrahydrofuran-2-yl]-5-methyl-tetrahydrofuran-2-yl]-7-methoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-3-methyl-tetrahydropyran-2-yl]propanoate
    • Sodium;(2R)-2-[(3S,6R)-6-[[(2S,4R,5R,6R,7R,9R)-2-[(5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-3-methyloxan-2-yl]propanoate
    • 28643-80-3

  • Applications

    Nigericin Sodium (CAS 28643-80-3) is a polyether ionophore whose primary applications are in research and, historically, as an ionophore antibiotic in veterinary contexts. In the laboratory, it is used as an ion-transport tool to exchange K+ for H+, enabling controlled dissipation of proton gradients and clamping of membrane potential for studies of mitochondrial respiration and ATP synthesis; it is also used to permeabilize membranes to facilitate substrate and reagent access in enzymatic and biochemical assays; and it is employed to investigate ion-channel/transport protein function in cell biology and pharmacology. Its veterinary use, when present, is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 217.36
    methanol 308.41
    isopropanol 104.77
    water 1.06
    ethyl acetate 173.46
    n-propanol 233.05
    acetone 191.96
    n-butanol 142.94
    acetonitrile 88.13
    DMF 604.23
    toluene 46.64
    isobutanol 99.0
    1,4-dioxane 241.04
    methyl acetate 167.6
    THF 593.02
    2-butanone 210.58
    n-pentanol 79.43
    sec-butanol 92.17
    n-hexane 1.08
    ethylene glycol 65.95
    NMP 893.69
    cyclohexane 1.54
    DMSO 503.84
    n-butyl acetate 60.23
    n-octanol 26.65
    chloroform 411.0
    n-propyl acetate 74.42
    acetic acid 711.17
    dichloromethane 339.36
    cyclohexanone 284.78
    propylene glycol 115.97
    isopropyl acetate 94.2
    DMAc 646.32
    2-ethoxyethanol 296.06
    isopentanol 59.7
    n-heptane 0.92
    ethyl formate 153.47
    1,2-dichloroethane 163.74
    n-hexanol 44.66
    2-methoxyethanol 546.83
    isobutyl acetate 41.99
    tetrachloromethane 40.46
    n-pentyl acetate 77.28
    transcutol 270.14
    n-heptanol 35.78
    ethylbenzene 14.33
    MIBK 62.75
    2-propoxyethanol 259.76
    tert-butanol 47.53
    MTBE 38.59
    2-butoxyethanol 172.44
    propionic acid 264.76
    o-xylene 21.0
    formic acid 386.89
    diethyl ether 72.24
    m-xylene 21.92
    p-xylene 13.87
    chlorobenzene 79.45
    dimethyl carbonate 168.4
    n-octane 0.44
    formamide 367.78
    cyclopentanone 482.88
    2-pentanone 158.98
    anisole 55.63
    cyclopentyl methyl ether 146.99
    gamma-butyrolactone 690.72
    1-methoxy-2-propanol 370.59
    pyridine 279.08
    3-pentanone 118.57
    furfural 487.4
    n-dodecane 0.37
    diethylene glycol 187.49
    diisopropyl ether 9.84
    tert-amyl alcohol 51.68
    acetylacetone 192.72
    n-hexadecane 0.44
    acetophenone 89.65
    methyl propionate 213.85
    isopentyl acetate 49.82
    trichloroethylene 465.36
    n-nonanol 27.61
    cyclohexanol 71.82
    benzyl alcohol 96.59
    2-ethylhexanol 17.53
    isooctanol 22.73
    dipropyl ether 24.58
    1,2-dichlorobenzene 72.97
    ethyl lactate 80.81
    propylene carbonate 282.63
    n-methylformamide 454.67
    2-pentanol 50.88
    n-pentane 1.63
    1-propoxy-2-propanol 124.7
    1-methoxy-2-propyl acetate 131.24
    2-(2-methoxypropoxy) propanol 95.38
    mesitylene 8.21
    ε-caprolactone 371.09
    p-cymene 7.94
    epichlorohydrin 654.9
    1,1,1-trichloroethane 111.01
    2-aminoethanol 193.47
    morpholine-4-carbaldehyde 724.05
    sulfolane 673.69
    2,2,4-trimethylpentane 0.97
    2-methyltetrahydrofuran 226.28
    n-hexyl acetate 79.93
    isooctane 0.52
    2-(2-butoxyethoxy)ethanol 142.17
    sec-butyl acetate 48.28
    tert-butyl acetate 66.29
    decalin 1.18
    glycerin 209.62
    diglyme 258.13
    acrylic acid 302.4
    isopropyl myristate 16.95
    n-butyric acid 355.75
    acetyl acetate 141.17
    di(2-ethylhexyl) phthalate 35.83
    ethyl propionate 76.81
    nitromethane 755.92
    1,2-diethoxyethane 56.39
    benzonitrile 68.88
    trioctyl phosphate 23.69
    1-bromopropane 63.86
    gamma-valerolactone 1033.68
    n-decanol 14.69
    triethyl phosphate 31.48
    4-methyl-2-pentanol 19.44
    propionitrile 78.21
    vinylene carbonate 317.85
    1,1,2-trichlorotrifluoroethane 558.51
    DMS 79.74
    cumene 7.67
    2-octanol 15.64
    2-hexanone 69.78
    octyl acetate 34.47
    limonene 11.4
    1,2-dimethoxyethane 207.17
    ethyl orthosilicate 25.49
    tributyl phosphate 23.25
    diacetone alcohol 118.11
    N,N-dimethylaniline 33.36
    acrylonitrile 133.49
    aniline 99.25
    1,3-propanediol 252.41
    bromobenzene 70.48
    dibromomethane 176.66
    1,1,2,2-tetrachloroethane 293.61
    2-methyl-cyclohexyl acetate 41.83
    tetrabutyl urea 33.5
    diisobutyl methanol 6.74
    2-phenylethanol 68.56
    styrene 17.72
    dioctyl adipate 39.86
    dimethyl sulfate 290.4
    ethyl butyrate 50.55
    methyl lactate 222.18
    butyl lactate 81.02
    diethyl carbonate 33.88
    propanediol butyl ether 131.16
    triethyl orthoformate 40.13
    p-tert-butyltoluene 7.1
    methyl 4-tert-butylbenzoate 94.96
    morpholine 414.68
    tert-butylamine 14.01
    n-dodecanol 7.78
    dimethoxymethane 387.28
    ethylene carbonate 240.39
    cyrene 160.72
    2-ethoxyethyl acetate 145.29
    2-ethylhexyl acetate 38.07
    1,2,4-trichlorobenzene 106.63
    4-methylpyridine 205.49
    dibutyl ether 13.86
    2,6-dimethyl-4-heptanol 6.74
    DEF 239.41
    dimethyl isosorbide 149.81
    tetrachloroethylene 190.58
    eugenol 91.04
    triacetin 129.24
    span 80 90.01
    1,4-butanediol 91.35
    1,1-dichloroethane 133.61
    2-methyl-1-pentanol 43.65
    methyl formate 288.09
    2-methyl-1-butanol 80.07
    n-decane 0.91
    butyronitrile 68.18
    3,7-dimethyl-1-octanol 17.88
    1-chlorooctane 8.47
    1-chlorotetradecane 2.1
    n-nonane 0.71
    undecane 0.55
    tert-butylcyclohexane 0.86
    cyclooctane 0.67
    cyclopentanol 138.83
    tetrahydropyran 159.69
    tert-amyl methyl ether 40.1
    2,5,8-trioxanonane 139.1
    1-hexene 7.02
    2-isopropoxyethanol 135.23
    2,2,2-trifluoroethanol 304.67
    methyl butyrate 100.63

    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