Hordenine

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  • Identifiers

    CAS number
    539-15-1

    Molecular formula
    C10H15NO

    SMILES
    CN(C)CCC1=CC=C(C=C1)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Fishy 39.04%
    Animal 37.26%
    Cheesy 35.77%
    Sweet 35.45%
    Phenolic 33.1%
    Ripe 30.85%
    Smoky 26.69%
    Meaty 24.4%
    Spicy 23.78%
    Burnt 22.72%

     

    Flavor
    Mild 37.38%
    Phenolic 33.34%
    Herbal 29.98%
    Medicinal 27.65%
    Meaty 26.54%
    Spicy 25.78%
    Creosote 22.85%
    Woody 22.82%
    Fruity 21.62%
    Spice 21.49%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.1

    pKa est.
    10.03 (weak base)

    Molecular weight
    165.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    276°C

    Melting point expt.

    • 117.5 °C

    Flash point

    • 118.55 ˚C est.

    Solubility expt.

    • 7 mg/mL

  • Synonyms

    • Hordenine
    • 539-15-1
    • 4-[2-(Dimethylamino)ethyl]phenol
    • 4-(2-(Dimethylamino)ethyl)phenol
    • Anhaline
    • N,N-Dimethyltyramine
    • 4-(2-Dimethylaminoethyl)phenol
    • Peyocactine
    • Anhalin
    • Cactine
    • Eremursine
    • Ordenina
    • p-(2-Dimethylaminoethyl)phenol
    • DTXSID2046096
    • K3489CA082
    • CHEBI:5764
    • DTXCID0026096
    • N,N-Dimethyl-4-hydroxy-beta-phenethylamine
    • RefChem:38568
    • 208-710-4
    • Hordenin
    • Phenol, 4-[2-(dimethylamino)ethyl]-
    • Ordenine
    • p-Hydroxy-N,N-dimethylphenethylamine
    • MFCD00051462
    • Ordenina;Peyocactine
    • Hordenine (sulfate)
    • N,N-Dimethyl-p-hydroxyphenethylamine
    • p-[2-(Dimethylamino)ethyl]phenol
    • N,N-dimethyl-4-hydroxyphenylethylamine
    • Phenol, p-[2-(dimethylamino)ethyl]-
    • NCGC00160162-02
    • Ordenina (sulfate); Peyocactine (sulfate)
    • 2-(4-Hydroxyphenyl)-N,N-dimethylethylamine
    • N,N-Dimethyl-2-(4-hydroxyphenyl)ethylamine
    • N,N-Dimethyl-4-hydroxy-.beta.-phenethylamine
    • CAS-539-15-1
    • P-(2-(DIMETHYLAMINO)ETHYL)PHENOL
    • PHENOL, P-(2-(DIMETHYLAMINO)ETHYL)-
    • Eremursin
    • Hordetin
    • Desvenlafaxine Phenol Impurity
    • UNII-K3489CA082
    • EINECS 208-710-4
    • N-dimethyl-4-hydroxyphenylethylamine
    • Hordenine (Standard)
    • HORDENINE [MI]
    • HORDENINE [WHO-DD]
    • SCHEMBL36798
    • Hordenine, analytical standard
    • CHEMBL505789
    • orb1304883
    • SCHEMBL10491917
    • 4-(2-dimethylaminoethyl)-phenol
    • HY-N0113R
    • HMS3656M13
    • Hordenine, >=97.0% (HPLC)
    • HY-N0113
    • MSK40054
    • phenol, 4-(2-dimethylamino)ethyl-
    • Tox21_111748
    • 4-Hydroxy-N,N-dimethylphenethylamine
    • EBC-13340
    • s2385
    • STL565154
    • 4-[2-(Dimethylamino)ethyl]phenol #
    • AKOS000277358
    • Tox21_111748_1
    • CCG-266321
    • FH09413
    • GS-0924
    • NCGC00160162-01
    • NCGC00160162-03
    • NCGC00160162-04
    • AC-11302
    • AC-34131
    • SY053066
    • 2-(4-Hydroxyphenyl)-N,N-dimethylethanamine
    • DB-052423
    • CS-0007797
    • H1351
    • NS00006025
    • ST45026104
    • SW219673-1
    • benzene, 1-(2-dimethylamino)ethyl-4-hydroxy-
    • C06199
    • EN300-7358623
    • 595H059
    • F239138
    • Q119915
    • SR-05000002241
    • SR-05000002241-2
    • BRD-K93631643-001-02-4
    • BRD-K93631643-001-03-2
    • BRD-K93631643-065-01-1
    • 539-15-1

  • Applications

    Chemical name: Hordenine; CAS number: 539-15-1 is a natural phenethylamine alkaloid primarily encountered as a plant metabolite (notably in barley). In practice its applications are mainly in chemical synthesis and research: it is used as a building block or intermediate for the preparation of other phenethylamine derivatives in pharmaceutical R&D, and it is sometimes employed as a reference standard or analytical material in method development (e.g., LC–MS). It is also marketed in some regions as a dietary supplement stimulant ingredient, commonly found in sports-nutrition formulations, but its use is subject to local regulations and formulation limits. In addition, it may be evaluated for fragrance or odorant applications in perfumery contexts, though this is not a major, widely standardized application. Overall, the main uses are as an intermediate for synthesis, as a component in analytical workflows, and as a regulatory-sensitive stimulant ingredient in supplements.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 420.0
    methanol 340.99
    isopropanol 234.52
    water 7.88
    ethyl acetate 112.96
    n-propanol 326.69
    acetone 78.56
    n-butanol 226.63
    acetonitrile 102.88
    DMF 203.79
    toluene 21.91
    isobutanol 188.58
    1,4-dioxane 207.37
    methyl acetate 145.55
    THF 151.77
    2-butanone 97.86
    n-pentanol 117.11
    sec-butanol 176.74
    n-hexane 3.92
    ethylene glycol 271.72
    NMP 98.07
    cyclohexane 5.75
    DMSO 232.3
    n-butyl acetate 65.3
    n-octanol 34.16
    chloroform 206.42
    n-propyl acetate 53.02
    acetic acid 357.96
    dichloromethane 121.18
    cyclohexanone 107.85
    propylene glycol 512.11
    isopropyl acetate 43.46
    DMAc 182.35
    2-ethoxyethanol 291.34
    isopentanol 129.18
    n-heptane 5.69
    ethyl formate 104.35
    1,2-dichloroethane 65.07
    n-hexanol 177.89
    2-methoxyethanol 547.94
    isobutyl acetate 35.95
    tetrachloromethane 36.04
    n-pentyl acetate 27.04
    transcutol 403.39
    n-heptanol 57.93
    ethylbenzene 15.27
    MIBK 33.2
    2-propoxyethanol 319.99
    tert-butanol 259.24
    MTBE 71.8
    2-butoxyethanol 120.62
    propionic acid 326.93
    o-xylene 23.12
    formic acid 248.48
    diethyl ether 40.05
    m-xylene 24.63
    p-xylene 20.37
    chlorobenzene 37.71
    dimethyl carbonate 39.85
    n-octane 2.44
    formamide 233.97
    cyclopentanone 126.37
    2-pentanone 53.24
    anisole 49.62
    cyclopentyl methyl ether 71.41
    gamma-butyrolactone 189.63
    1-methoxy-2-propanol 329.37
    pyridine 110.55
    3-pentanone 44.43
    furfural 188.63
    n-dodecane 2.04
    diethylene glycol 339.81
    diisopropyl ether 11.6
    tert-amyl alcohol 177.97
    acetylacetone 58.44
    n-hexadecane 2.14
    acetophenone 52.91
    methyl propionate 108.2
    isopentyl acetate 55.63
    trichloroethylene 181.91
    n-nonanol 31.45
    cyclohexanol 116.47
    benzyl alcohol 83.23
    2-ethylhexanol 65.95
    isooctanol 42.17
    dipropyl ether 37.73
    1,2-dichlorobenzene 41.13
    ethyl lactate 68.98
    propylene carbonate 109.86
    n-methylformamide 213.37
    2-pentanol 92.44
    n-pentane 3.62
    1-propoxy-2-propanol 180.77
    1-methoxy-2-propyl acetate 93.73
    2-(2-methoxypropoxy) propanol 93.54
    mesitylene 14.86
    ε-caprolactone 122.55
    p-cymene 17.09
    epichlorohydrin 178.24
    1,1,1-trichloroethane 72.34
    2-aminoethanol 502.64
    morpholine-4-carbaldehyde 197.29
    sulfolane 169.49
    2,2,4-trimethylpentane 4.48
    2-methyltetrahydrofuran 119.5
    n-hexyl acetate 38.33
    isooctane 3.45
    2-(2-butoxyethoxy)ethanol 140.09
    sec-butyl acetate 32.0
    tert-butyl acetate 51.25
    decalin 4.5
    glycerin 533.89
    diglyme 211.13
    acrylic acid 264.31
    isopropyl myristate 16.54
    n-butyric acid 305.0
    acetyl acetate 55.1
    di(2-ethylhexyl) phthalate 28.61
    ethyl propionate 49.35
    nitromethane 302.22
    1,2-diethoxyethane 63.3
    benzonitrile 59.03
    trioctyl phosphate 19.9
    1-bromopropane 29.09
    gamma-valerolactone 213.85
    n-decanol 24.79
    triethyl phosphate 32.67
    4-methyl-2-pentanol 47.84
    propionitrile 105.14
    vinylene carbonate 109.92
    1,1,2-trichlorotrifluoroethane 298.45
    DMS 44.35
    cumene 15.31
    2-octanol 24.83
    2-hexanone 41.17
    octyl acetate 24.11
    limonene 23.66
    1,2-dimethoxyethane 194.63
    ethyl orthosilicate 32.36
    tributyl phosphate 23.9
    diacetone alcohol 113.41
    N,N-dimethylaniline 37.73
    acrylonitrile 135.68
    aniline 87.0
    1,3-propanediol 438.35
    bromobenzene 29.48
    dibromomethane 72.07
    1,1,2,2-tetrachloroethane 167.73
    2-methyl-cyclohexyl acetate 48.4
    tetrabutyl urea 28.47
    diisobutyl methanol 29.38
    2-phenylethanol 86.96
    styrene 16.12
    dioctyl adipate 29.05
    dimethyl sulfate 63.77
    ethyl butyrate 49.25
    methyl lactate 121.04
    butyl lactate 45.84
    diethyl carbonate 38.22
    propanediol butyl ether 117.56
    triethyl orthoformate 40.49
    p-tert-butyltoluene 17.8
    methyl 4-tert-butylbenzoate 54.56
    morpholine 307.94
    tert-butylamine 117.34
    n-dodecanol 19.55
    dimethoxymethane 106.97
    ethylene carbonate 90.39
    cyrene 87.25
    2-ethoxyethyl acetate 52.51
    2-ethylhexyl acetate 38.87
    1,2,4-trichlorobenzene 57.83
    4-methylpyridine 86.03
    dibutyl ether 20.7
    2,6-dimethyl-4-heptanol 29.38
    DEF 80.97
    dimethyl isosorbide 119.71
    tetrachloroethylene 121.64
    eugenol 69.09
    triacetin 56.37
    span 80 84.78
    1,4-butanediol 164.56
    1,1-dichloroethane 72.21
    2-methyl-1-pentanol 78.46
    methyl formate 136.72
    2-methyl-1-butanol 131.41
    n-decane 3.05
    butyronitrile 87.65
    3,7-dimethyl-1-octanol 36.37
    1-chlorooctane 12.19
    1-chlorotetradecane 5.7
    n-nonane 2.86
    undecane 2.38
    tert-butylcyclohexane 5.16
    cyclooctane 2.68
    cyclopentanol 137.33
    tetrahydropyran 117.59
    tert-amyl methyl ether 53.46
    2,5,8-trioxanonane 146.83
    1-hexene 14.96
    2-isopropoxyethanol 159.51
    2,2,2-trifluoroethanol 130.7
    methyl butyrate 70.44

    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