5-Hydroxyectoine

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  • Identifiers

    CAS number
    165542-15-4

    Molecular formula
    C6H10N2O3

    SMILES
    CC1=NC[C@@H]([C@H](N1)C(=O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 72.17%
    Nutty 31.8%
    Roasted 29.61%
    Popcorn 27.03%
    Sweet 25.36%
    Meaty 22.36%
    Savory 22.01%
    Caramellic 20.01%
    Burnt 19.68%
    Cooked 17.26%

     

    Flavor
    Bitter 50.87%
    Odorless 44.92%
    Very mild 21.98%
    Mild 20.99%
    Bland 20.71%
    Sweet-like 20.64%
    Roasted 20.49%
    Taco 19.9%
    Nutty 19.68%
    Bread crust 19.68%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.2

    pKa est.
    7.96 (neutral)

    Molecular weight
    158.16 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    404°C

    Flash point

    • 177.71 ˚C est.

  • Synonyms

    • 5-Hydroxyectoine
    • (4S,5S)-5-Hydroxy-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid
    • (5S,6S)-5-hydroxy-2-methyl-1,4,5,6-tetrahydropyrimidine-6-carboxylic acid
    • CHEBI:49432
    • RefChem:789461
    • (4S,5S)-5-hydroxy-2-methyl-1,4,5,6-tetrahydropyrimidin-3-ium-4-carboxylate
    • (5S,6S)-5-hydroxy-2-methyl-1,4,5,6-tetrahydropyrimidin-1-ium-6-carboxylate
    • Hydroxyectoine
    • Hydroxyectoin
    • 165542-15-4
    • beta-hydroxyectoine
    • 4-pyrimidinecarboxylic acid, 1,4,5,6-tetrahydro-5-hydroxy-2-methyl-, (4S,5S)-
    • Ronacare hydroxyectoin
    • Thp(A)
    • CIJ7YN252E
    • (S,S)-1,4,5,6-Tetrahydro-5-hydroxy-2-methyl-4-pyrimidinecarboxylic acid
    • 4-Pyrimidinecarboxylic acid, 1,4,5,6-tetrahydro-5-hydroxy-2-methyl-, (S-(R*,R*))-
    • (4S,5S)-2-methyl-4-carboxy-5-hydroxy-3,4,5,6-tetrahydropyrimidine
    • (S,S)-2-methyl-5-hydroxy-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid
    • UNII-CIJ7YN252E
    • (S,S)-beta-Hydroxyectoine
    • Hydroxyectoine, primary pharmaceutical reference standard
    • Hydroxy ectoine
    • Hydroxy ection
    • 6CS
    • .BETA.-HYDROXYECTOINE
    • SCHEMBL748472
    • orb2695528
    • orb2695533
    • CHEMBL1230488
    • SCHEMBL15281462
    • DTXSID80167963
    • KIIBBJKLKFTNQO-WHFBIAKZSA-N
    • Hydroxyectoine, >=95% (HPLC)
    • (S,S)-.BETA.-HYDROXYECTOINE
    • MFCD01863080
    • MSK160509
    • AKOS015911339
    • FH44799
    • CS-0027199
    • ST51037613
    • G78482
    • Q27121627
    • (4S,5S)-5-Hydroxy-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylicacid
    • (4S,5S)-5-hydroxy-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid
    • (S,S)--Hydroxyectoine; 5-Hydroxyectoine; Pyrostatin A; Pyrostatine A; -Hydroxyectoine
    • 4-Pyrimidinecarboxylicacid,1,4,5,6-tetrahydro-5-hydroxy-2-methyl-,(4S,5S)-
    • 165542-15-4

  • Applications

    5-Hydroxyectoine (CAS 165542-15-4) is a compatible solute used as a stabilizer and protective additive in diverse formulations. In cosmetics and personal care, it acts as a humectant and protective agent, aiding moisture retention and formulation stability. In biopharmaceuticals and biotech, it serves as a stabilizer for proteins and enzymes in challenging formulations. In industrial cleaning and enzyme-based products, it helps stabilize enzymes and extend product shelf life. In bioprocessing and fermentation, it can function as an osmoprotectant to enhance cellular tolerance to stress during processing.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.31
    methanol 1.26
    isopropanol 0.22
    water 38.32
    ethyl acetate 0.3
    n-propanol 0.22
    acetone 0.41
    n-butanol 0.23
    acetonitrile 0.25
    DMF 20.22
    toluene 0.16
    isobutanol 0.24
    1,4-dioxane 0.53
    methyl acetate 0.19
    THF 2.7
    2-butanone 0.27
    n-pentanol 0.22
    sec-butanol 0.21
    n-hexane 0.05
    ethylene glycol 5.91
    NMP 30.29
    cyclohexane 0.04
    DMSO 80.06
    n-butyl acetate 0.49
    n-octanol 0.4
    chloroform 0.47
    n-propyl acetate 0.21
    acetic acid 2.18
    dichloromethane 0.69
    cyclohexanone 1.77
    propylene glycol 2.56
    isopropyl acetate 0.28
    DMAc 22.76
    2-ethoxyethanol 3.14
    isopentanol 0.43
    n-heptane 0.1
    ethyl formate 1.37
    1,2-dichloroethane 0.49
    n-hexanol 0.73
    2-methoxyethanol 8.04
    isobutyl acetate 0.14
    tetrachloromethane 0.41
    n-pentyl acetate 0.33
    transcutol 2.85
    n-heptanol 0.67
    ethylbenzene 0.19
    MIBK 0.56
    2-propoxyethanol 4.9
    tert-butanol 0.64
    MTBE 0.13
    2-butoxyethanol 2.75
    propionic acid 0.85
    o-xylene 0.37
    formic acid 35.12
    diethyl ether 0.09
    m-xylene 0.4
    p-xylene 0.29
    chlorobenzene 0.18
    dimethyl carbonate 0.74
    n-octane 0.05
    formamide 18.39
    cyclopentanone 3.17
    2-pentanone 0.44
    anisole 0.35
    cyclopentyl methyl ether 0.8
    gamma-butyrolactone 4.99
    1-methoxy-2-propanol 4.0
    pyridine 0.64
    3-pentanone 0.33
    furfural 11.93
    n-dodecane 0.03
    diethylene glycol 13.09
    diisopropyl ether 0.09
    tert-amyl alcohol 0.64
    acetylacetone 1.24
    n-hexadecane 0.04
    acetophenone 0.96
    methyl propionate 0.55
    isopentyl acetate 0.59
    trichloroethylene 0.92
    n-nonanol 0.44
    cyclohexanol 0.51
    benzyl alcohol 0.89
    2-ethylhexanol 0.57
    isooctanol 0.59
    dipropyl ether 0.38
    1,2-dichlorobenzene 0.42
    ethyl lactate 1.2
    propylene carbonate 2.38
    n-methylformamide 6.8
    2-pentanol 0.2
    n-pentane 0.03
    1-propoxy-2-propanol 2.71
    1-methoxy-2-propyl acetate 1.48
    2-(2-methoxypropoxy) propanol 3.5
    mesitylene 0.36
    ε-caprolactone 1.93
    p-cymene 0.4
    epichlorohydrin 2.77
    1,1,1-trichloroethane 0.34
    2-aminoethanol 3.8
    morpholine-4-carbaldehyde 16.68
    sulfolane 24.05
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 0.66
    n-hexyl acetate 0.45
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 3.44
    sec-butyl acetate 0.15
    tert-butyl acetate 0.5
    decalin 0.05
    glycerin 18.78
    diglyme 5.9
    acrylic acid 1.7
    isopropyl myristate 0.27
    n-butyric acid 1.16
    acetyl acetate 0.36
    di(2-ethylhexyl) phthalate 0.92
    ethyl propionate 0.31
    nitromethane 3.68
    1,2-diethoxyethane 0.35
    benzonitrile 0.78
    trioctyl phosphate 0.68
    1-bromopropane 0.16
    gamma-valerolactone 8.67
    n-decanol 0.35
    triethyl phosphate 0.93
    4-methyl-2-pentanol 0.32
    propionitrile 0.24
    vinylene carbonate 2.4
    1,1,2-trichlorotrifluoroethane 11.93
    DMS 0.55
    cumene 0.25
    2-octanol 0.34
    2-hexanone 0.28
    octyl acetate 0.38
    limonene 0.43
    1,2-dimethoxyethane 3.46
    ethyl orthosilicate 0.75
    tributyl phosphate 0.66
    diacetone alcohol 2.56
    N,N-dimethylaniline 0.79
    acrylonitrile 0.67
    aniline 0.44
    1,3-propanediol 3.12
    bromobenzene 0.17
    dibromomethane 0.38
    1,1,2,2-tetrachloroethane 1.06
    2-methyl-cyclohexyl acetate 0.79
    tetrabutyl urea 1.31
    diisobutyl methanol 0.47
    2-phenylethanol 1.22
    styrene 0.13
    dioctyl adipate 0.53
    dimethyl sulfate 5.09
    ethyl butyrate 0.54
    methyl lactate 3.38
    butyl lactate 1.28
    diethyl carbonate 0.42
    propanediol butyl ether 2.74
    triethyl orthoformate 0.65
    p-tert-butyltoluene 0.38
    methyl 4-tert-butylbenzoate 2.23
    morpholine 0.88
    tert-butylamine 0.22
    n-dodecanol 0.28
    dimethoxymethane 3.11
    ethylene carbonate 1.44
    cyrene 7.18
    2-ethoxyethyl acetate 0.49
    2-ethylhexyl acetate 0.43
    1,2,4-trichlorobenzene 0.49
    4-methylpyridine 0.82
    dibutyl ether 0.18
    2,6-dimethyl-4-heptanol 0.47
    DEF 2.35
    dimethyl isosorbide 6.67
    tetrachloroethylene 1.11
    eugenol 2.89
    triacetin 0.85
    span 80 2.41
    1,4-butanediol 1.72
    1,1-dichloroethane 0.2
    2-methyl-1-pentanol 0.38
    methyl formate 5.06
    2-methyl-1-butanol 0.36
    n-decane 0.05
    butyronitrile 0.3
    3,7-dimethyl-1-octanol 0.49
    1-chlorooctane 0.15
    1-chlorotetradecane 0.08
    n-nonane 0.05
    undecane 0.04
    tert-butylcyclohexane 0.05
    cyclooctane 0.04
    cyclopentanol 0.89
    tetrahydropyran 0.2
    tert-amyl methyl ether 0.25
    2,5,8-trioxanonane 5.89
    1-hexene 0.09
    2-isopropoxyethanol 1.38
    2,2,2-trifluoroethanol 4.79
    methyl butyrate 0.53

    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