2-hydroxy-N-(2-hydroxyethyl)propanamide

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  • Identifiers

    CAS number
    5422-34-4

    Molecular formula
    C5H11NO3

    SMILES
    CC(C(=O)NCCO)O

  • Odor profile

    Fragrance
    Odorless 47.59%
    Sweet 46.85%
    Fishy 31.53%
    Savory 29.64%
    Buttery 23.93%
    Meaty 19.6%
    Milky 19.52%
    Alcoholic 18.26%
    Caramellic 17.45%
    Creamy 15.69%

     

    Flavor
    Odorless 68.73%
    Very mild 28.04%
    Sweet-like 27.56%
    Sweet 24.19%
    Mild 22.56%
    Bland 22.2%
    Very slight 21.22%
    Yeast 21.02%
    Sour 20.31%
    Acidic 19.83%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.4

    pKa est.
    7.14 (neutral)

    Molecular weight
    133.15 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point

    • 380.00 °C. @ 760.00 mm Hg

    Flash point

    • 175.42 ˚C est.

    Solubility expt.

    • Very soluble in water; insoluble in pentane and diethyl ether
    • Slightly soluble (in ethanol)

  • Synonyms

    • N-(2-Hydroxyethyl)lactamide
    • 5422-34-4
    • 2-Hydroxy-N-(2-hydroxyethyl)propanamide
    • Lactamide MEA
    • n-lactoyl ethanolamine
    • Propanamide, 2-hydroxy-N-(2-hydroxyethyl)-
    • Lactic acid monoethanolamide
    • Lactamide, N-(2-hydroxyethyl)-
    • N-2-Hydroxyethyllactamide
    • N-Hydroxyaethyllactamid
    • Lipamide LMEA
    • Incromectant LMEA
    • 2-Lactamidoethanol
    • N-beta-Hydroxyethyllactamide
    • NSC 11062
    • N-(beta-Hydroxyethyl)lactamide
    • CCRIS 3086
    • N-Hydroxyaethyllactamid [German]
    • Monoethanolamine lactic acid amide
    • N-(beta-Hydroxyethyl)-2-hydroxypropionamide
    • EINECS 226-546-1
    • n-lactoylethanolamine
    • BRN 1702912
    • AI3-03133
    • 900T44YNC7
    • N-(.beta.-Hydroxyethyl)-2-hydroxypropionamide
    • NSC-11062
    • LACTOYL MONOETHANOLAMIDE
    • FEMA NO. 4256
    • DTXSID20863533
    • N-(.beta.-Hydroxyethyl)lactamide
    • N-LACTOYL ETHANOLAMINE [FHFI]
    • 2-HYDROXY-N-(2-HYDROXYETHYL)-, (+/-)-
    • UNII-900T44YNC7
    • Mackamide LME
    • MFCD00037805
    • 2-hydroxy-N-(2-hydroxy-ethyl)-propionamide
    • Parapel LAM-100
    • Schercomid LME-100
    • N-(2-Hydroxyethyl)-2-hydroxypropionamide
    • SCHEMBL49978
    • LACTAMIDE MEA [INCI]
    • N-(2-Hydroxyethyl)-lactamide
    • DTXCID30812133
    • CHEBI:173359
    • NSC11062
    • AKOS006229794
    • N-(2-hydroxyethyl)-lactic acid amide
    • AS-64098
    • FH133348
    • CS-0153945
    • H0378
    • NS00013806
    • 1-hydroxyethane-1-(2'-hydroxyethyl)carbonamide
    • D90852
    • (+-)-Propanamide, 2-hydroxy-N-(2-hydroxyethyl)
    • SR-01000944886
    • SR-01000944886-1
    • 2-Hydroxy-N-(2-hydroxyethyl)propanamide, AldrichCPR
    • Q27271269

  • Applications

    N-Lactoyl ethanolamine (CAS 5422-34-4) is the monoethanolamide of lactic acid and, by incorporating hydroxyl, amide and amine functions in one molecule, finds numerous uses: it serves as an intermediate for manufacturing non-ionic surfactants, metal corrosion inhibitors and lubricant additives where it forms protective boundary films; in cosmetics and personal-care formulations it acts as an emulsifier, humectant and skin-conditioning agent, stabilising oil-in-water emulsions, reducing irritation and providing softness in hair and skin products owing to its high hydrophilicity and biocompatibility; in agrochemicals and coatings it is employed as a solubiliser, dispersant and binder that enhances the persistence of pesticides and the adhesion of paints; in pharmaceuticals and biomedical research N-Lactoyl ethanolamine is studied as an endocannabinoid-like signalling molecule with potential anti-inflammatory, analgesic and lipid-metabolism-modulating activities, and is also used as an analytical standard for mapping the biosynthetic pathway of N-acylethanolamines; its environmental friendliness and ready biodegradability make it an attractive component for “green” formulations and sustainable chemical processes.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 98.45
    methanol 337.22
    isopropanol 40.67
    water 1253.75
    ethyl acetate 5.31
    n-propanol 51.27
    acetone 17.97
    n-butanol 37.93
    acetonitrile 16.47
    DMF 539.33
    toluene 1.16
    isobutanol 29.54
    1,4-dioxane 57.51
    methyl acetate 6.66
    THF 36.68
    2-butanone 9.33
    n-pentanol 20.29
    sec-butanol 27.1
    n-hexane 0.93
    ethylene glycol 291.97
    NMP 291.94
    cyclohexane 2.97
    DMSO 645.1
    n-butyl acetate 4.23
    n-octanol 8.44
    chloroform 5.28
    n-propyl acetate 4.21
    acetic acid 187.83
    dichloromethane 12.77
    cyclohexanone 31.93
    propylene glycol 146.22
    isopropyl acetate 3.45
    DMAc 244.05
    2-ethoxyethanol 92.6
    isopentanol 23.23
    n-heptane 1.79
    ethyl formate 26.43
    1,2-dichloroethane 10.69
    n-hexanol 13.06
    2-methoxyethanol 235.12
    isobutyl acetate 2.52
    tetrachloromethane 1.83
    n-pentyl acetate 4.48
    transcutol 78.49
    n-heptanol 10.0
    ethylbenzene 1.57
    MIBK 4.64
    2-propoxyethanol 45.37
    tert-butanol 35.48
    MTBE 8.27
    2-butoxyethanol 33.39
    propionic acid 49.33
    o-xylene 3.2
    formic acid 695.04
    diethyl ether 5.76
    m-xylene 1.9
    p-xylene 2.42
    chlorobenzene 2.46
    dimethyl carbonate 8.06
    n-octane 0.89
    formamide 430.51
    cyclopentanone 35.34
    2-pentanone 6.77
    anisole 5.99
    cyclopentyl methyl ether 11.27
    gamma-butyrolactone 56.41
    1-methoxy-2-propanol 87.94
    pyridine 16.09
    3-pentanone 5.78
    furfural 91.54
    n-dodecane 0.65
    diethylene glycol 99.64
    diisopropyl ether 1.89
    tert-amyl alcohol 27.95
    acetylacetone 10.62
    n-hexadecane 0.69
    acetophenone 9.37
    methyl propionate 8.93
    isopentyl acetate 4.32
    trichloroethylene 10.78
    n-nonanol 7.39
    cyclohexanol 28.95
    benzyl alcohol 17.32
    2-ethylhexanol 7.04
    isooctanol 7.83
    dipropyl ether 5.43
    1,2-dichlorobenzene 4.01
    ethyl lactate 13.6
    propylene carbonate 24.22
    n-methylformamide 222.37
    2-pentanol 12.59
    n-pentane 1.35
    1-propoxy-2-propanol 23.92
    1-methoxy-2-propyl acetate 8.64
    2-(2-methoxypropoxy) propanol 30.94
    mesitylene 2.16
    ε-caprolactone 32.75
    p-cymene 2.64
    epichlorohydrin 36.29
    1,1,1-trichloroethane 2.52
    2-aminoethanol 242.51
    morpholine-4-carbaldehyde 210.75
    sulfolane 170.49
    2,2,4-trimethylpentane 0.98
    2-methyltetrahydrofuran 19.26
    n-hexyl acetate 6.66
    isooctane 0.52
    2-(2-butoxyethoxy)ethanol 39.24
    sec-butyl acetate 2.54
    tert-butyl acetate 4.44
    decalin 1.08
    glycerin 296.91
    diglyme 70.75
    acrylic acid 80.56
    isopropyl myristate 2.99
    n-butyric acid 42.93
    acetyl acetate 4.44
    di(2-ethylhexyl) phthalate 8.95
    ethyl propionate 4.43
    nitromethane 123.11
    1,2-diethoxyethane 10.01
    benzonitrile 10.06
    trioctyl phosphate 6.66
    1-bromopropane 3.78
    gamma-valerolactone 96.98
    n-decanol 5.7
    triethyl phosphate 5.72
    4-methyl-2-pentanol 6.73
    propionitrile 10.56
    vinylene carbonate 28.96
    1,1,2-trichlorotrifluoroethane 83.18
    DMS 6.62
    cumene 1.99
    2-octanol 5.28
    2-hexanone 4.96
    octyl acetate 4.79
    limonene 4.15
    1,2-dimethoxyethane 82.47
    ethyl orthosilicate 5.55
    tributyl phosphate 6.35
    diacetone alcohol 18.54
    N,N-dimethylaniline 9.28
    acrylonitrile 22.26
    aniline 7.84
    1,3-propanediol 178.81
    bromobenzene 1.63
    dibromomethane 6.05
    1,1,2,2-tetrachloroethane 11.6
    2-methyl-cyclohexyl acetate 6.49
    tetrabutyl urea 12.03
    diisobutyl methanol 4.97
    2-phenylethanol 10.77
    styrene 1.65
    dioctyl adipate 7.4
    dimethyl sulfate 31.96
    ethyl butyrate 4.96
    methyl lactate 32.67
    butyl lactate 11.34
    diethyl carbonate 3.77
    propanediol butyl ether 40.75
    triethyl orthoformate 5.92
    p-tert-butyltoluene 2.46
    methyl 4-tert-butylbenzoate 15.34
    morpholine 78.92
    tert-butylamine 14.68
    n-dodecanol 4.61
    dimethoxymethane 58.08
    ethylene carbonate 21.53
    cyrene 54.22
    2-ethoxyethyl acetate 7.82
    2-ethylhexyl acetate 3.39
    1,2,4-trichlorobenzene 5.05
    4-methylpyridine 12.44
    dibutyl ether 3.9
    2,6-dimethyl-4-heptanol 4.97
    DEF 45.52
    dimethyl isosorbide 37.5
    tetrachloroethylene 10.0
    eugenol 23.22
    triacetin 10.87
    span 80 29.57
    1,4-butanediol 85.53
    1,1-dichloroethane 3.44
    2-methyl-1-pentanol 16.23
    methyl formate 110.94
    2-methyl-1-butanol 25.18
    n-decane 0.92
    butyronitrile 12.79
    3,7-dimethyl-1-octanol 6.9
    1-chlorooctane 2.24
    1-chlorotetradecane 1.23
    n-nonane 0.94
    undecane 0.74
    tert-butylcyclohexane 0.81
    cyclooctane 1.29
    cyclopentanol 42.18
    tetrahydropyran 17.35
    tert-amyl methyl ether 7.96
    2,5,8-trioxanonane 57.81
    1-hexene 1.87
    2-isopropoxyethanol 35.75
    2,2,2-trifluoroethanol 86.73
    methyl butyrate 9.35

    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