Oleoylethanolamide

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  • Identifiers

    CAS number
    111-58-0

    Molecular formula
    C20H39NO2

    SMILES
    CCCCCCCC/C=C\CCCCCCCC(=O)NCCO

    Safety labels

    Corrosive
    Corrosive

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Waxy 44.14%
    Fatty 43.12%
    Meaty 36.05%
    Oily 33.61%
    Savory 32.54%
    Fishy 28.3%
    Odorless 28.06%
    Citrus 26.68%
    Fresh 24.43%
    Herbal 22.95%

     

    Flavor
    Fatty 35.08%
    Faint 30.67%
    Waxy 29.61%
    Bland 28.99%
    Mild 28.92%
    Odorless 26.19%
    Slightly waxy 23.01%
    Fat 22.2%
    Delicate 21.51%
    Bay oil 21.37%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    6.3

    pKa est.
    7.43 (neutral)

    Molecular weight
    325.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    405°C

    Flash point

    • 211.25 ˚C est.

  • Synonyms

    • oleoylethanolamide
    • 111-58-0
    • N-(2-Hydroxyethyl)oleamide
    • Oleoyl Ethanolamide
    • (Z)-N-(2-hydroxyethyl)octadec-9-enamide
    • Oleoyl monoethanolamide
    • OLEIC MONOETHANOLAMIDE
    • N-(9Z-octadecenoyl)-ethanolamine
    • N-(cis-9-octadecenoyl) ethanolamine
    • 1HI5J9N8E6
    • 9-Octadecenamide, N-(2-hydroxyethyl)-
    • DTXSID1044516
    • 9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-
    • CHEBI:71466
    • RefChem:856533
    • DTXCID9024516
    • 203-884-8
    • Oleoylethanolamine
    • n-oleoylethanolamine
    • Oleylethanolamide
    • Oleamide MEA
    • N-oleoyl ethanolamine
    • N-oleoylethanolamide
    • (9Z)-N-(2-hydroxyethyl)octadec-9-enamide
    • N-oleoyl ethanolamide
    • MFCD00045972
    • N-(2-Hydroxyethyl)-9-octadecenamide
    • Oleic acid ethanolamide
    • (9Z)-N-(2-Hydroxyethyl)-9-octadecenamide
    • N-(Hydroxyethyl)oleamide
    • N-(hydroxyethyl) oleamide
    • OEA
    • CHEMBL280065
    • N-?Oleoylethanolamide
    • SR-01000076041
    • EINECS 203-884-8
    • UNII-1HI5J9N8E6
    • Monoethanolamine oleic acid amide
    • 9-Octadecenamide, N-(2-hydroxyethyl)-, (Z)-
    • 5YM
    • Olemsartan Medoximil
    • C18:1 Anandamide
    • oleoyl 1-ethanolamide
    • Tocris-1484
    • N-Oleoyl-2-aminoethanol
    • Oleoylethanolamide (OEA)
    • Spectrum5_002037
    • Lopac-O-0383
    • Oleic acid monoethanolamide
    • Lopac0_000942
    • MLS002153155
    • SCHEMBL177713
    • GTPL2661
    • orb1309303
    • orb3025241
    • BDBM29080
    • N-(9Z-octadecenoyl) ethanolamine
    • GLXC-22224
    • HMS2233E21
    • HMS3262N06
    • HMS3412D21
    • HMS3649J05
    • HMS3676D21
    • OLEYLETHANOLAMIDE [WHO-DD]
    • NAE 18:1
    • Tox21_500942
    • LMFA08040015
    • MSK159624
    • N-Oleoylethanolamine, ~98% (TLC)
    • NAE(18:1)
    • AKOS015839895
    • N-(2-Hydroxyethyl)-9Z-octadecenamide
    • CCG-205023
    • EBC-615639
    • LP00942
    • MSK159624-100M
    • SDCCGSBI-0050916.P002
    • MSK159624-1000M
    • NCGC00015761-01
    • NCGC00015761-02
    • NCGC00015761-03
    • NCGC00015761-04
    • NCGC00015761-05
    • NCGC00015761-06
    • NCGC00015761-07
    • NCGC00015761-12
    • NCGC00025182-01
    • NCGC00025182-02
    • NCGC00025182-04
    • NCGC00025182-05
    • NCGC00025182-06
    • NCGC00261627-01
    • AS-15152
    • BP-43134
    • FO180525
    • SMR001230650
    • SY102076
    • Oleic Acid Ethanolamide; Oleoylethanolamide
    • HY-107542
    • CS-0028847
    • EU-0100942
    • NS00013916
    • O0345
    • C20792
    • D82195
    • O 0383
    • 111O580
    • 9-OCTADECENAMIDE, N-(2-HYDROXYETHYL)-, Z
    • A802386
    • Q7086404
    • SR-01000076041-1
    • SR-01000076041-3
    • SR-01000076041-8
    • BRD-K66956375-001-11-3
    • C18:1 anandamide, 9Z-octadecenoylethanolamide, powder
    • N-Oleoylethanolamine Solution in Methanol, 1000ug/mL
    • N-Oleoylethanolamine Solution in Methanol, 100ug/mL
    • (Z)-N-(2-hydroxyethyl)octadec-9-enamide;Oleoylethanolamide
    • N-Oleoylethanolamide; Oleamide MEA; Oleic acid monoethanolamide
    • N-oleoyl ethanolamine, Oleoyl monoethanolamide, Oleoylethanolamide
    • 111-58-0

  • Applications

    Oleoylethanolamide (OEA) is an amide formed from oleic acid and ethanolamine and is primarily studied as a lipid signaling mediator, activating PPAR-α pathways and related to appetite regulation and metabolic processes. In industrial and research practice, it is regarded as a valuable reagent and reference compound for lipid biology and signaling research. Typical applications include: (1) pharmaceutical and metabolic research, (2) cosmetics and personal care formulation development where it is evaluated as a bioactive lipid ingredient for experimental formulations, (3) chemical synthesis and as a precursor for lipid amide derivatives in lipid chemistry, and (4) analytical chemistry and reference standards in laboratories for structural and property verification. Use depends on regulatory and formulation limits by region.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 32.79
    methanol 52.1
    isopropanol 28.66
    water 0.03
    ethyl acetate 60.95
    n-propanol 32.52
    acetone 59.09
    n-butanol 42.07
    acetonitrile 15.74
    DMF 103.85
    toluene 21.73
    isobutanol 29.83
    1,4-dioxane 87.42
    methyl acetate 39.63
    THF 259.93
    2-butanone 66.75
    n-pentanol 39.56
    sec-butanol 36.28
    n-hexane 6.12
    ethylene glycol 2.92
    NMP 204.82
    cyclohexane 23.14
    DMSO 257.16
    n-butyl acetate 87.23
    n-octanol 34.46
    chloroform 151.69
    n-propyl acetate 104.22
    acetic acid 44.63
    dichloromethane 156.48
    cyclohexanone 223.3
    propylene glycol 10.18
    isopropyl acetate 70.9
    DMAc 237.09
    2-ethoxyethanol 90.33
    isopentanol 56.82
    n-heptane 6.89
    ethyl formate 36.66
    1,2-dichloroethane 120.97
    n-hexanol 34.71
    2-methoxyethanol 86.67
    isobutyl acetate 72.69
    tetrachloromethane 35.36
    n-pentyl acetate 118.6
    transcutol 477.22
    n-heptanol 34.16
    ethylbenzene 22.16
    MIBK 89.08
    2-propoxyethanol 85.8
    tert-butanol 59.14
    MTBE 68.19
    2-butoxyethanol 97.71
    propionic acid 34.17
    o-xylene 26.7
    formic acid 12.46
    diethyl ether 43.69
    m-xylene 22.27
    p-xylene 30.3
    chlorobenzene 39.36
    dimethyl carbonate 19.08
    n-octane 3.88
    formamide 21.21
    cyclopentanone 194.5
    2-pentanone 84.0
    anisole 52.38
    cyclopentyl methyl ether 111.12
    gamma-butyrolactone 162.56
    1-methoxy-2-propanol 90.6
    pyridine 74.12
    3-pentanone 61.93
    furfural 135.07
    n-dodecane 2.71
    diethylene glycol 39.63
    diisopropyl ether 22.88
    tert-amyl alcohol 62.14
    acetylacetone 104.29
    n-hexadecane 3.19
    acetophenone 78.08
    methyl propionate 47.74
    isopentyl acetate 96.82
    trichloroethylene 189.71
    n-nonanol 34.61
    cyclohexanol 73.74
    benzyl alcohol 41.16
    2-ethylhexanol 35.27
    isooctanol 37.0
    dipropyl ether 56.65
    1,2-dichlorobenzene 53.73
    ethyl lactate 47.54
    propylene carbonate 99.61
    n-methylformamide 32.09
    2-pentanol 32.47
    n-pentane 4.13
    1-propoxy-2-propanol 86.5
    1-methoxy-2-propyl acetate 100.44
    2-(2-methoxypropoxy) propanol 88.84
    mesitylene 20.32
    ε-caprolactone 181.86
    p-cymene 21.44
    epichlorohydrin 179.37
    1,1,1-trichloroethane 108.44
    2-aminoethanol 13.65
    morpholine-4-carbaldehyde 156.42
    sulfolane 325.39
    2,2,4-trimethylpentane 6.95
    2-methyltetrahydrofuran 155.07
    n-hexyl acetate 113.83
    isooctane 3.78
    2-(2-butoxyethoxy)ethanol 131.47
    sec-butyl acetate 77.15
    tert-butyl acetate 107.18
    decalin 11.54
    glycerin 20.55
    diglyme 291.57
    acrylic acid 22.88
    isopropyl myristate 36.08
    n-butyric acid 90.87
    acetyl acetate 44.36
    di(2-ethylhexyl) phthalate 37.22
    ethyl propionate 73.28
    nitromethane 78.3
    1,2-diethoxyethane 129.55
    benzonitrile 44.66
    trioctyl phosphate 27.25
    1-bromopropane 62.11
    gamma-valerolactone 262.45
    n-decanol 21.91
    triethyl phosphate 51.42
    4-methyl-2-pentanol 30.06
    propionitrile 23.67
    vinylene carbonate 69.74
    1,1,2-trichlorotrifluoroethane 157.21
    DMS 50.76
    cumene 20.33
    2-octanol 27.65
    2-hexanone 97.07
    octyl acetate 44.11
    limonene 36.92
    1,2-dimethoxyethane 190.72
    ethyl orthosilicate 56.57
    tributyl phosphate 36.06
    diacetone alcohol 121.04
    N,N-dimethylaniline 47.36
    acrylonitrile 23.13
    aniline 30.74
    1,3-propanediol 32.04
    bromobenzene 43.45
    dibromomethane 100.09
    1,1,2,2-tetrachloroethane 207.51
    2-methyl-cyclohexyl acetate 83.96
    tetrabutyl urea 57.39
    diisobutyl methanol 28.61
    2-phenylethanol 40.94
    styrene 24.4
    dioctyl adipate 65.52
    dimethyl sulfate 53.74
    ethyl butyrate 85.58
    methyl lactate 34.28
    butyl lactate 89.64
    diethyl carbonate 46.58
    propanediol butyl ether 82.98
    triethyl orthoformate 77.51
    p-tert-butyltoluene 20.99
    methyl 4-tert-butylbenzoate 95.37
    morpholine 141.67
    tert-butylamine 35.12
    n-dodecanol 15.32
    dimethoxymethane 73.56
    ethylene carbonate 65.31
    cyrene 97.77
    2-ethoxyethyl acetate 136.96
    2-ethylhexyl acetate 76.71
    1,2,4-trichlorobenzene 67.6
    4-methylpyridine 72.42
    dibutyl ether 67.48
    2,6-dimethyl-4-heptanol 28.61
    DEF 120.45
    dimethyl isosorbide 173.15
    tetrachloroethylene 137.67
    eugenol 82.03
    triacetin 124.52
    span 80 83.43
    1,4-butanediol 14.62
    1,1-dichloroethane 82.83
    2-methyl-1-pentanol 50.25
    methyl formate 21.19
    2-methyl-1-butanol 48.73
    n-decane 5.96
    butyronitrile 36.91
    3,7-dimethyl-1-octanol 38.02
    1-chlorooctane 28.39
    1-chlorotetradecane 8.83
    n-nonane 5.55
    undecane 3.72
    tert-butylcyclohexane 8.89
    cyclooctane 5.94
    cyclopentanol 61.83
    tetrahydropyran 140.61
    tert-amyl methyl ether 64.42
    2,5,8-trioxanonane 166.82
    1-hexene 20.16
    2-isopropoxyethanol 75.94
    2,2,2-trifluoroethanol 19.46
    methyl butyrate 118.11

    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