3-Hydroxymugineic acid

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  • Identifiers

    CAS number
    74235-23-7

    Molecular formula
    C12H20N2O9

    SMILES
    C1[C@H]([C@H](N1C[C@@H]([C@@H](C(=O)O)NCC[C@@H](C(=O)O)O)O)C(=O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 74.07%
    Sweet 42.79%
    Savory 29.14%
    Cooling 18.21%
    Alcoholic 18.08%
    Milky 18.03%
    Fishy 16.6%
    Buttery 15.84%
    Bitter 15.64%
    Clean 15.11%

     

    Flavor
    Odorless 68.46%
    Bitter 49.71%
    Bland 34.85%
    Mild 29.74%
    Very mild 29.3%
    Sweet-like 27.01%
    Yeast 22.33%
    Nitrile 19.19%
    Faint 19.13%
    Oriental 18.74%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -7.1

    pKa est.
    4.99 (weak acid)

    Molecular weight
    336.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    895°C

    Flash point

    • 315.05 ˚C est.

  • Synonyms

    • 3-Hydroxymugineic acid
    • 3-HMA
    • 74235-23-7
    • CHEBI:38158
    • 4-[(2S,3R)-2-carboxy-3-hydroxyazetidin-1-yl]-N-[(3S)-3-carboxy-3-hydroxypropyl]-L-allothreonine
    • 1-Azetidinebutanoic acid, 2-carboxy-alpha-((3-carboxy-3-hydroxypropyl)amino)-beta,3-dihydroxy-, (2S-(1(alphar*(R*),betar*),2alpha,3alpha))-
    • 4-((2S,3R)-2-carboxy-3-hydroxyazetidin-1-yl)-N-((3S)-3-carboxy-3-hydroxypropyl)-L-allothreonine
    • RefChem:94355
    • (2S,3R)-1-[(2S,3S)-3-carboxy-3-[[(3S)-3-carboxy-3-hydroxypropyl]amino]-2-hydroxypropyl]-3-hydroxyazetidine-2-carboxylic acid
    • Epi-hydroxymugineic acid
    • SCHEMBL1057620
    • DTXSID90995714
    • Q27117400
    • 4-(2-Carboxy-3-hydroxyazetidin-1-yl)-N-(3-carboxy-3-hydroxypropyl)threonine
    • 74235-23-7

  • Applications

    3-Hydroxymugineic acid (CAS 74235-23-7) is a natural siderophore in the mugineic acid family with strong iron-chelating properties and a key role in plant iron acquisition. In agriculture and plant-nutrition research, it is used to study iron uptake mechanisms and iron-use efficiency in crops, and may serve as an ingredient in chelated-iron formulations or biostimulant solutions aimed at improving iron availability. It is also employed as a chemical intermediate or reference standard for the synthesis of mugineic acid derivatives and for analytical methods quantifying this compound in plant samples. In industrial and analytical contexts, 3-Hydroxymugineic acid is often explored as a metal-chelating agent and reference material for developing chelated-metal products and related analytical approaches.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.5
    methanol 1.98
    isopropanol 0.28
    water 154.84
    ethyl acetate 0.31
    n-propanol 0.41
    acetone 0.44
    n-butanol 0.33
    acetonitrile 0.21
    DMF 24.35
    toluene 0.25
    isobutanol 0.25
    1,4-dioxane 0.61
    methyl acetate 0.18
    THF 0.96
    2-butanone 0.36
    n-pentanol 0.21
    sec-butanol 0.3
    n-hexane 0.1
    ethylene glycol 13.68
    NMP 48.52
    cyclohexane 0.17
    DMSO 68.29
    n-butyl acetate 0.18
    n-octanol 0.13
    chloroform 0.05
    n-propyl acetate 0.14
    acetic acid 2.8
    dichloromethane 0.09
    cyclohexanone 1.22
    propylene glycol 6.32
    isopropyl acetate 0.21
    DMAc 22.53
    2-ethoxyethanol 2.63
    isopentanol 0.26
    n-heptane 0.21
    ethyl formate 0.34
    1,2-dichloroethane 0.15
    n-hexanol 0.39
    2-methoxyethanol 9.75
    isobutyl acetate 0.06
    tetrachloromethane 0.05
    n-pentyl acetate 0.12
    transcutol 2.17
    n-heptanol 0.3
    ethylbenzene 0.14
    MIBK 0.33
    2-propoxyethanol 3.4
    tert-butanol 0.38
    MTBE 0.11
    2-butoxyethanol 1.29
    propionic acid 1.08
    o-xylene 0.43
    formic acid 53.73
    diethyl ether 0.19
    m-xylene 0.31
    p-xylene 0.15
    chlorobenzene 0.05
    dimethyl carbonate 1.19
    n-octane 0.07
    formamide 34.9
    cyclopentanone 1.49
    2-pentanone 0.59
    anisole 0.16
    cyclopentyl methyl ether 0.86
    gamma-butyrolactone 2.32
    1-methoxy-2-propanol 6.36
    pyridine 0.57
    3-pentanone 0.65
    furfural 3.25
    n-dodecane 0.02
    diethylene glycol 11.36
    diisopropyl ether 0.11
    tert-amyl alcohol 0.42
    acetylacetone 1.15
    n-hexadecane 0.03
    acetophenone 0.4
    methyl propionate 0.88
    isopentyl acetate 0.13
    trichloroethylene 0.18
    n-nonanol 0.14
    cyclohexanol 0.79
    benzyl alcohol 0.4
    2-ethylhexanol 0.24
    isooctanol 0.18
    dipropyl ether 0.42
    1,2-dichlorobenzene 0.06
    ethyl lactate 0.94
    propylene carbonate 0.69
    n-methylformamide 7.63
    2-pentanol 0.32
    n-pentane 0.1
    1-propoxy-2-propanol 1.8
    1-methoxy-2-propyl acetate 0.8
    2-(2-methoxypropoxy) propanol 1.05
    mesitylene 0.24
    ε-caprolactone 1.08
    p-cymene 0.17
    epichlorohydrin 0.73
    1,1,1-trichloroethane 0.04
    2-aminoethanol 7.22
    morpholine-4-carbaldehyde 15.42
    sulfolane 18.33
    2,2,4-trimethylpentane 0.04
    2-methyltetrahydrofuran 0.42
    n-hexyl acetate 0.12
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 1.44
    sec-butyl acetate 0.09
    tert-butyl acetate 0.25
    decalin 0.06
    glycerin 49.94
    diglyme 2.23
    acrylic acid 2.53
    isopropyl myristate 0.06
    n-butyric acid 0.81
    acetyl acetate 0.22
    di(2-ethylhexyl) phthalate 0.11
    ethyl propionate 0.26
    nitromethane 3.17
    1,2-diethoxyethane 0.25
    benzonitrile 0.14
    trioctyl phosphate 0.13
    1-bromopropane 0.08
    gamma-valerolactone 5.15
    n-decanol 0.12
    triethyl phosphate 0.29
    4-methyl-2-pentanol 0.19
    propionitrile 0.19
    vinylene carbonate 0.7
    1,1,2-trichlorotrifluoroethane 5.28
    DMS 0.28
    cumene 0.11
    2-octanol 0.15
    2-hexanone 0.18
    octyl acetate 0.09
    limonene 0.25
    1,2-dimethoxyethane 1.41
    ethyl orthosilicate 0.25
    tributyl phosphate 0.12
    diacetone alcohol 1.7
    N,N-dimethylaniline 0.38
    acrylonitrile 0.46
    aniline 0.46
    1,3-propanediol 3.49
    bromobenzene 0.04
    dibromomethane 0.07
    1,1,2,2-tetrachloroethane 0.24
    2-methyl-cyclohexyl acetate 0.19
    tetrabutyl urea 0.34
    diisobutyl methanol 0.19
    2-phenylethanol 0.37
    styrene 0.09
    dioctyl adipate 0.1
    dimethyl sulfate 5.69
    ethyl butyrate 0.24
    methyl lactate 5.15
    butyl lactate 0.44
    diethyl carbonate 0.13
    propanediol butyl ether 1.31
    triethyl orthoformate 0.29
    p-tert-butyltoluene 0.15
    methyl 4-tert-butylbenzoate 0.59
    morpholine 1.32
    tert-butylamine 0.19
    n-dodecanol 0.1
    dimethoxymethane 4.13
    ethylene carbonate 0.48
    cyrene 4.4
    2-ethoxyethyl acetate 0.22
    2-ethylhexyl acetate 0.11
    1,2,4-trichlorobenzene 0.08
    4-methylpyridine 0.41
    dibutyl ether 0.09
    2,6-dimethyl-4-heptanol 0.19
    DEF 2.82
    dimethyl isosorbide 2.14
    tetrachloroethylene 0.27
    eugenol 0.78
    triacetin 0.29
    span 80 0.95
    1,4-butanediol 1.34
    1,1-dichloroethane 0.05
    2-methyl-1-pentanol 0.17
    methyl formate 3.2
    2-methyl-1-butanol 0.3
    n-decane 0.05
    butyronitrile 0.14
    3,7-dimethyl-1-octanol 0.09
    1-chlorooctane 0.06
    1-chlorotetradecane 0.03
    n-nonane 0.05
    undecane 0.03
    tert-butylcyclohexane 0.03
    cyclooctane 0.14
    cyclopentanol 0.8
    tetrahydropyran 0.33
    tert-amyl methyl ether 0.26
    2,5,8-trioxanonane 2.07
    1-hexene 0.11
    2-isopropoxyethanol 0.91
    2,2,2-trifluoroethanol 3.9
    methyl butyrate 0.33

    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