Ergothioneine

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  • Identifiers

    CAS number
    497-30-3

    Molecular formula
    C9H15N3O2S

    SMILES
    C[N+](C)(C)[C@@H](CC1=CNC(=S)N1)C(=O)[O-]

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 48.36%
    Fruity 25.52%
    Savory 24.33%
    Roasted 23.54%
    Cooling 22.23%
    Meaty 20.76%
    Cooked 20.38%
    Mint 18.58%
    Grape 17.77%
    Bitter 17.76%

     

    Flavor
    Bitter 66.44%
    Odorless 37.78%
    Bland 30.95%
    Mild 20.35%
    Cedarleaf 18.91%
    Sweet-like 18.7%
    Nitrile 18.58%
    Green pepper 18.12%
    Heather 18.08%
    Broom 17.9%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    0.3

    pKa est.
    4.61 (weak acid)

    Molecular weight
    229.3 g/mol

    Flash point

    • -88.11 ˚C est.

  • Synonyms

    • ERGOTHIONEINE
    • 497-30-3
    • L-Ergothioneine
    • Sympectothion
    • Ergothionine
    • Thioneine
    • l-Thioneine
    • Thiasine
    • L(+)-Ergothioneine
    • Thiolhistidine-betaine
    • BDZ3DQM98W
    • DTXSID901020082
    • (2S)-3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-(trimethylazaniumyl)propanoate
    • CHEBI:4828
    • (2S)-3-(2-sulfanylidene-2,3-dihydro-1H-imidazol-4-yl)-2-(trimethylazaniumyl)propanoate
    • 1H-Imidazole-4-ethanaminium, alpha-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-, inner salt, (S)-
    • 2 Thiol L histidine betaine
    • (alphaS)-alpha-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt
    • NSC-7175
    • 2-Thiol-L-histidine-betaine
    • RefChem:591076
    • DTXCID901477922
    • 5-((2S)-2-carboxy-2-(trimethylazaniumyl)ethyl)-1H-imidazole-2-thiolate
    • 207-843-5
    • L-(+)-Ergothioneine
    • (S)-3-(2-Thioxo-2,3-dihydro-1H-imidazol-4-yl)-2-(trimethylammonio)propanoate
    • NSC 7175
    • MFCD00167474
    • ergothioneine (thione form)
    • Thioeine
    • (S)-(1-Carboxy-2-(2-mercaptoimidazol-4-yl)ethyl)trimethylammonium hydroxide
    • NSC7175
    • 2-Mercaptohistidine Betaine
    • UNII-BDZ3DQM98W
    • erythrothioneine
    • thiolhistidinebetaine
    • EINECS 207-843-5
    • ERGOLD
    • Ergothioneine L-(+)
    • ergothioneine thione form
    • AI3-23492
    • ERGOTHIONEINE [MI]
    • SCHEMBL188140
    • SCHEMBL188141
    • orb1299136
    • orb3012990
    • SCHEMBL9985141
    • CHEMBL5209630
    • CHEBI:82707
    • HMS2089D04
    • 2-mercaptohistidine trimethylbetaine
    • HY-N1914
    • MSK169210
    • AKOS027325505
    • CCG-207908
    • EBC-616355
    • FE22785
    • 1H-Imidazole-4-ethanaminium, .alpha.-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-, inner salt, (.alpha.S)-
    • 1H-Imidazole-4-ethanaminium, alpha-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-, inner salt, (alphaS)-
    • DA-64818
    • SY382275
    • CS-0018211
    • D83035
    • AB01275464-01
    • Ergothionine;L-(+)-Ergothioneine;Erythrothioneine
    • Q614788
    • (2S)-3-(2-mercapto-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate
    • (2S)-3-(2-mercapto-1H-imidazol-5-yl)-2-(trimethylazaniumyl)propanoate
    • (2S)-3-(2-sulfanyl-1H-imidazol-4-yl)-2-(trimethylazaniumyl)propanoate
    • 3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoate
    • Nalpha,Nalpha,Nalpha-trimethyl-2-sulfanylidene-2,3-dihydro-L-histidine
    • (2S)-3-(2-Thioxo-2,3-dihydro-1H-imidazol-4-yl)-2-(trimethylammonio)propanoate
    • (2S)-3-(2-thioxo-2,3-dihydro-1H-imidazol-4-yl)-2-(trimethylazaniumyl)propanoate
    • (.ALPHA.S)-.ALPHA.-CARBOXY-2,3-DIHYDRO-N,N,N-TRIMETHYL-2-THIOXO-1H-IMIDAZOLE-4-ETHANAMINIUM INNER SALT
    • (a-S)-a-Carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt
    • [(1S)-2-hydroxy-2-oxo-1-[(2-thioxo-1,3-dihydroimidazol-4-yl)methyl]ethyl]-trimethyl-ammonium
    • 1H-Imidazole-4-ethanaminium, alpha-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-, hydroxide, inner salt, (S)-
    • 1H-Imidazole-4-ethaniminium, alpha-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-, hydroxide, inner salt, (S)-
    • Ammonium, (1-carboxy-2-(2-mercaptoimidazol-4-yl)ethyl)trimethyl-, hydroxide, inner salt, L-(+)-
    • 497-30-3

  • Applications

    Ergothioneine (CAS 497-30-3) is commonly evaluated for use in cosmetics/personal care as a natural antioxidant and skin-conditioning ingredient; it is also studied as a functional ingredient in foods and dietary supplements due to its radical-scavenging properties; in industrial manufacturing, it has been investigated as an antioxidant stabilizer for formulations and packaging to extend the shelf life of polymers and coatings; in research settings, its cytoprotective properties are being explored to inform pharmaceutical development, all subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 6.0
    methanol 42.82
    isopropanol 1.27
    water 288.19
    ethyl acetate 0.6
    n-propanol 2.83
    acetone 0.85
    n-butanol 1.15
    acetonitrile 0.67
    DMF 44.61
    toluene 0.13
    isobutanol 1.13
    1,4-dioxane 1.13
    methyl acetate 1.48
    THF 1.89
    2-butanone 0.85
    n-pentanol 0.51
    sec-butanol 0.95
    n-hexane 0.02
    ethylene glycol 71.55
    NMP 84.87
    cyclohexane 0.04
    DMSO 24.96
    n-butyl acetate 0.84
    n-octanol 0.45
    chloroform 2.69
    n-propyl acetate 0.48
    acetic acid 53.77
    dichloromethane 2.11
    cyclohexanone 2.49
    propylene glycol 36.4
    isopropyl acetate 0.33
    DMAc 50.12
    2-ethoxyethanol 7.68
    isopentanol 0.6
    n-heptane 0.04
    ethyl formate 3.71
    1,2-dichloroethane 0.99
    n-hexanol 1.14
    2-methoxyethanol 38.25
    isobutyl acetate 0.32
    tetrachloromethane 0.74
    n-pentyl acetate 0.63
    transcutol 7.81
    n-heptanol 1.0
    ethylbenzene 0.13
    MIBK 0.37
    2-propoxyethanol 9.37
    tert-butanol 1.01
    MTBE 0.13
    2-butoxyethanol 5.56
    propionic acid 14.0
    o-xylene 0.29
    formic acid 486.92
    diethyl ether 0.13
    m-xylene 0.23
    p-xylene 0.24
    chlorobenzene 0.35
    dimethyl carbonate 3.2
    n-octane 0.02
    formamide 247.37
    cyclopentanone 4.18
    2-pentanone 0.42
    anisole 0.37
    cyclopentyl methyl ether 0.59
    gamma-butyrolactone 14.58
    1-methoxy-2-propanol 11.09
    pyridine 1.69
    3-pentanone 0.56
    furfural 24.17
    n-dodecane 0.02
    diethylene glycol 32.29
    diisopropyl ether 0.05
    tert-amyl alcohol 0.93
    acetylacetone 1.16
    n-hexadecane 0.02
    acetophenone 1.51
    methyl propionate 1.87
    isopentyl acetate 0.77
    trichloroethylene 3.74
    n-nonanol 0.46
    cyclohexanol 1.0
    benzyl alcohol 1.87
    2-ethylhexanol 0.53
    isooctanol 0.68
    dipropyl ether 0.24
    1,2-dichlorobenzene 0.73
    ethyl lactate 3.97
    propylene carbonate 8.2
    n-methylformamide 49.3
    2-pentanol 0.38
    n-pentane 0.03
    1-propoxy-2-propanol 4.18
    1-methoxy-2-propyl acetate 2.32
    2-(2-methoxypropoxy) propanol 5.33
    mesitylene 0.17
    ε-caprolactone 4.31
    p-cymene 0.31
    epichlorohydrin 4.67
    1,1,1-trichloroethane 0.77
    2-aminoethanol 51.84
    morpholine-4-carbaldehyde 35.97
    sulfolane 32.84
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 0.76
    n-hexyl acetate 0.73
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 5.75
    sec-butyl acetate 0.25
    tert-butyl acetate 0.42
    decalin 0.03
    glycerin 124.63
    diglyme 7.03
    acrylic acid 31.16
    isopropyl myristate 0.24
    n-butyric acid 6.71
    acetyl acetate 0.77
    di(2-ethylhexyl) phthalate 1.75
    ethyl propionate 0.53
    nitromethane 31.92
    1,2-diethoxyethane 0.41
    benzonitrile 1.05
    trioctyl phosphate 1.06
    1-bromopropane 0.24
    gamma-valerolactone 16.66
    n-decanol 0.33
    triethyl phosphate 1.19
    4-methyl-2-pentanol 0.29
    propionitrile 0.72
    vinylene carbonate 9.95
    1,1,2-trichlorotrifluoroethane 41.7
    DMS 1.92
    cumene 0.16
    2-octanol 0.39
    2-hexanone 0.32
    octyl acetate 0.46
    limonene 0.34
    1,2-dimethoxyethane 3.08
    ethyl orthosilicate 0.89
    tributyl phosphate 1.09
    diacetone alcohol 2.84
    N,N-dimethylaniline 0.67
    acrylonitrile 2.43
    aniline 0.9
    1,3-propanediol 25.23
    bromobenzene 0.24
    dibromomethane 0.91
    1,1,2,2-tetrachloroethane 3.3
    2-methyl-cyclohexyl acetate 1.07
    tetrabutyl urea 1.87
    diisobutyl methanol 0.32
    2-phenylethanol 2.17
    styrene 0.12
    dioctyl adipate 0.75
    dimethyl sulfate 12.79
    ethyl butyrate 0.68
    methyl lactate 13.89
    butyl lactate 3.39
    diethyl carbonate 0.73
    propanediol butyl ether 8.09
    triethyl orthoformate 0.74
    p-tert-butyltoluene 0.3
    methyl 4-tert-butylbenzoate 3.25
    morpholine 2.63
    tert-butylamine 0.31
    n-dodecanol 0.23
    dimethoxymethane 5.06
    ethylene carbonate 4.89
    cyrene 17.18
    2-ethoxyethyl acetate 1.44
    2-ethylhexyl acetate 0.59
    1,2,4-trichlorobenzene 1.3
    4-methylpyridine 1.0
    dibutyl ether 0.11
    2,6-dimethyl-4-heptanol 0.32
    DEF 2.73
    dimethyl isosorbide 9.46
    tetrachloroethylene 3.56
    eugenol 5.8
    triacetin 2.58
    span 80 5.15
    1,4-butanediol 8.01
    1,1-dichloroethane 0.57
    2-methyl-1-pentanol 0.43
    methyl formate 32.02
    2-methyl-1-butanol 0.76
    n-decane 0.02
    butyronitrile 0.43
    3,7-dimethyl-1-octanol 0.4
    1-chlorooctane 0.1
    1-chlorotetradecane 0.05
    n-nonane 0.02
    undecane 0.02
    tert-butylcyclohexane 0.02
    cyclooctane 0.02
    cyclopentanol 2.15
    tetrahydropyran 0.34
    tert-amyl methyl ether 0.23
    2,5,8-trioxanonane 6.22
    1-hexene 0.06
    2-isopropoxyethanol 2.4
    2,2,2-trifluoroethanol 57.94
    methyl butyrate 0.98

    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