Citramalic acid, (+)-

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  • Identifiers

    CAS number
    6236-09-5

    Molecular formula
    C5H8O5

    SMILES
    C[C@](CC(=O)O)(C(=O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 55.86%
    Sour 45.76%
    Caramellic 34.32%
    Buttery 34.11%
    Sweet 29.89%
    Creamy 29.03%
    Milky 28.77%
    Sharp 25.65%
    Fatty 23.58%
    Dairy 23.41%

     

    Flavor
    Odorless 69.75%
    Sour 43.39%
    Very mild 34.63%
    Acidic 30.04%
    Mild 30.01%
    Caramellic 25.48%
    Bland 24.43%
    Yeast 22.61%
    Sharp 22.46%
    Musty 22.03%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.9

    pKa est.
    5.37 (weak acid)

    Molecular weight
    148.11 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    335°C

    Flash point

    • 175.28 ˚C est.

  • Synonyms

    • (S)-2-Hydroxy-2-methylsuccinic acid
    • 6236-09-5
    • (S)-(+)-Citramalic acid
    • L-citramalic acid
    • (+)-citramalic acid
    • (S)-Citramalic acid
    • (2S)-2-hydroxy-2-methylbutanedioic acid
    • Citramalic acid, (+)-
    • B3FC6PA80I
    • (2S)-2-hydroxy-2-methylsuccinic acid
    • (+)-METHYLMALIC ACID
    • CHEBI:29003
    • Butanedioic acid, 2-hydroxy-2-methyl-, (2S)-
    • DTXSID901017263
    • EINECS 228-350-1
    • RefChem:577450
    • DTXCID601475458
    • 228-350-1
    • S-citramalic acid
    • (S)-2-methylmalic acid
    • L-alpha-hydroxypyrotartaric acid
    • (S)-citramalate
    • (3S)-citramalic acid
    • S-alpha-hydroxypyrotartaric acid
    • Malic acid, 2-methyl-
    • (3S)-alpha-hydroxypyrotartaric acid
    • MFCD00066436
    • L-(+)-Citramalic acid
    • UNII-B3FC6PA80I
    • A1H6S
    • SCHEMBL1357615
    • (S)-alpha-Hydroxypyrotartaric acid
    • 2-Hydroxy-2-methylsuccinic acid #
    • (S)-2-Hydroxy-2-methylsuccinicacid
    • CITRAMALIC ACID D-FORM [MI]
    • SB37977
    • (2S)-2-hydroxy-2-methyl-butanedioic acid
    • CS-0435033
    • NS00080633
    • Butanedioic acid, 2-hydroxy-2-methyl-, (S)-
    • C02614
    • Q27104026
    • EF5DE549-7AF1-4D1B-A53A-1E4256301878
    • 6236-09-5

  • Applications

    Citramalic acid (+) is used primarily as an intermediate in organic synthesis and as a scaffold for chiral building blocks in specialty chemical and pharmaceutical synthesis; it can act as a diacid monomer or co-monomer for biodegradable polymers and polyester-like materials; it also serves as a chelating agent capable of complexing metal ions in formulations, cleaning products, and coatings; in cosmetics and personal care, it may be used as a pH adjuster and stabilizer or as a chelating component; in industrial manufacturing it can participate as a crosslinking agent or pH modifier; it may be evaluated as a precursor for fragrance ester derivatives.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 421.95
    methanol 775.03
    isopropanol 299.75
    water 1052.74
    ethyl acetate 34.94
    n-propanol 292.29
    acetone 309.35
    n-butanol 231.61
    acetonitrile 63.68
    DMF 1480.07
    toluene 11.27
    isobutanol 154.8
    1,4-dioxane 255.6
    methyl acetate 43.48
    THF 686.44
    2-butanone 114.04
    n-pentanol 134.84
    sec-butanol 186.26
    n-hexane 11.3
    ethylene glycol 670.78
    NMP 342.51
    cyclohexane 5.82
    DMSO 1088.36
    n-butyl acetate 13.19
    n-octanol 34.42
    chloroform 12.9
    n-propyl acetate 25.26
    acetic acid 106.7
    dichloromethane 24.94
    cyclohexanone 78.29
    propylene glycol 339.53
    isopropyl acetate 27.85
    DMAc 520.84
    2-ethoxyethanol 530.1
    isopentanol 158.2
    n-heptane 8.39
    ethyl formate 98.69
    1,2-dichloroethane 35.69
    n-hexanol 76.02
    2-methoxyethanol 970.62
    isobutyl acetate 8.35
    tetrachloromethane 9.59
    n-pentyl acetate 11.26
    transcutol 98.95
    n-heptanol 44.59
    ethylbenzene 11.44
    MIBK 75.05
    2-propoxyethanol 241.87
    tert-butanol 395.4
    MTBE 85.48
    2-butoxyethanol 106.76
    propionic acid 65.72
    o-xylene 15.23
    formic acid 541.11
    diethyl ether 93.5
    m-xylene 15.64
    p-xylene 10.01
    chlorobenzene 4.3
    dimethyl carbonate 62.19
    n-octane 3.92
    formamide 590.48
    cyclopentanone 180.7
    2-pentanone 123.93
    anisole 46.76
    cyclopentyl methyl ether 121.3
    gamma-butyrolactone 156.59
    1-methoxy-2-propanol 520.71
    pyridine 38.54
    3-pentanone 61.62
    furfural 125.91
    n-dodecane 2.33
    diethylene glycol 368.53
    diisopropyl ether 24.68
    tert-amyl alcohol 223.04
    acetylacetone 93.93
    n-hexadecane 2.38
    acetophenone 33.9
    methyl propionate 63.76
    isopentyl acetate 10.97
    trichloroethylene 25.1
    n-nonanol 30.97
    cyclohexanol 84.89
    benzyl alcohol 60.65
    2-ethylhexanol 28.08
    isooctanol 29.53
    dipropyl ether 42.7
    1,2-dichlorobenzene 5.75
    ethyl lactate 45.77
    propylene carbonate 42.74
    n-methylformamide 636.86
    2-pentanol 130.25
    n-pentane 13.42
    1-propoxy-2-propanol 105.7
    1-methoxy-2-propyl acetate 30.79
    2-(2-methoxypropoxy) propanol 64.35
    mesitylene 13.1
    ε-caprolactone 56.12
    p-cymene 7.04
    epichlorohydrin 185.68
    1,1,1-trichloroethane 12.75
    2-aminoethanol 648.86
    morpholine-4-carbaldehyde 391.67
    sulfolane 249.83
    2,2,4-trimethylpentane 4.61
    2-methyltetrahydrofuran 176.54
    n-hexyl acetate 16.75
    isooctane 4.69
    2-(2-butoxyethoxy)ethanol 87.05
    sec-butyl acetate 14.51
    tert-butyl acetate 42.86
    decalin 3.53
    glycerin 593.35
    diglyme 170.61
    acrylic acid 63.33
    isopropyl myristate 9.54
    n-butyric acid 73.46
    acetyl acetate 13.49
    di(2-ethylhexyl) phthalate 10.9
    ethyl propionate 30.9
    nitromethane 190.35
    1,2-diethoxyethane 28.95
    benzonitrile 14.3
    trioctyl phosphate 12.13
    1-bromopropane 18.35
    gamma-valerolactone 249.13
    n-decanol 24.02
    triethyl phosphate 13.17
    4-methyl-2-pentanol 70.58
    propionitrile 46.85
    vinylene carbonate 32.08
    1,1,2-trichlorotrifluoroethane 134.85
    DMS 10.58
    cumene 9.98
    2-octanol 25.34
    2-hexanone 49.41
    octyl acetate 13.19
    limonene 10.33
    1,2-dimethoxyethane 555.38
    ethyl orthosilicate 13.56
    tributyl phosphate 8.99
    diacetone alcohol 150.54
    N,N-dimethylaniline 51.26
    acrylonitrile 58.72
    aniline 28.47
    1,3-propanediol 533.02
    bromobenzene 3.11
    dibromomethane 15.41
    1,1,2,2-tetrachloroethane 28.83
    2-methyl-cyclohexyl acetate 12.84
    tetrabutyl urea 21.68
    diisobutyl methanol 20.89
    2-phenylethanol 35.56
    styrene 9.4
    dioctyl adipate 12.64
    dimethyl sulfate 116.85
    ethyl butyrate 19.11
    methyl lactate 112.32
    butyl lactate 18.25
    diethyl carbonate 9.89
    propanediol butyl ether 75.92
    triethyl orthoformate 15.86
    p-tert-butyltoluene 8.01
    methyl 4-tert-butylbenzoate 37.0
    morpholine 360.48
    tert-butylamine 152.74
    n-dodecanol 18.35
    dimethoxymethane 641.58
    ethylene carbonate 30.43
    cyrene 111.16
    2-ethoxyethyl acetate 14.61
    2-ethylhexyl acetate 7.29
    1,2,4-trichlorobenzene 5.65
    4-methylpyridine 42.62
    dibutyl ether 15.92
    2,6-dimethyl-4-heptanol 20.89
    DEF 198.38
    dimethyl isosorbide 91.76
    tetrachloroethylene 26.25
    eugenol 51.02
    triacetin 14.1
    span 80 41.9
    1,4-butanediol 280.01
    1,1-dichloroethane 18.89
    2-methyl-1-pentanol 82.25
    methyl formate 422.45
    2-methyl-1-butanol 140.62
    n-decane 3.78
    butyronitrile 54.69
    3,7-dimethyl-1-octanol 23.89
    1-chlorooctane 8.87
    1-chlorotetradecane 4.19
    n-nonane 3.89
    undecane 2.87
    tert-butylcyclohexane 3.92
    cyclooctane 4.21
    cyclopentanol 167.54
    tetrahydropyran 120.91
    tert-amyl methyl ether 82.11
    2,5,8-trioxanonane 129.24
    1-hexene 22.64
    2-isopropoxyethanol 207.8
    2,2,2-trifluoroethanol 98.86
    methyl butyrate 50.04

    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