Cis-4-Hydroxy-D-Proline

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  • Identifiers

    CAS number
    2584-71-6

    Molecular formula
    C5H9NO3

    SMILES
    C1[C@H](CN[C@H]1C(=O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 83.86%
    Sweet 26.49%
    Caramellic 16.92%
    Savory 16.87%
    Bitter 15.27%
    Nutty 14.79%
    Fishy 14.42%
    Milky 14.24%
    Buttery 13.92%
    Popcorn 13.82%

     

    Flavor
    Odorless 55.06%
    Bitter 49.99%
    Very mild 24.72%
    Sweet-like 24.52%
    Bland 23.53%
    Mild 22.31%
    Yeast 20.97%
    Alkaline 19.89%
    Formyl 19.79%
    Urine 19.65%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -3.3

    pKa est.
    6.91 (neutral)

    Molecular weight
    131.13 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    333°C

    Flash point

    • 189.19 ˚C est.

  • Synonyms

    • cis-4-Hydroxy-D-proline
    • 2584-71-6
    • (2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid
    • (4R)-4-hydroxy-D-proline
    • D-PROLINE, 4-HYDROXY-, (4R)-
    • (R)-allo-Hydroxyproline
    • 4-Hydroxy-D-alloproline
    • EINECS 219-963-5
    • NSC 524341
    • CHEBI:16231
    • DTXSID20180494
    • ALLO-4-HYDROXY-D-PROLINE
    • RefChem:577351
    • DTXCID30102985
    • (2R,4R)-4-hydroxypyrrolidin-1-ium-2-carboxylate
    • 219-963-5
    • h-d-cis-hyp-oh
    • MFCD00005252
    • CHEMBL1229563
    • D-cis-Hydroxyproline
    • (2R,4R)-4-hydroxypyrrolidinium-2-carboxylate
    • D-allo-Hydroxyproline
    • cis4-hydroxy-D-proline
    • D-4-Allo-hydroxy-proline
    • cis-4-hydroxy-(D)-proline
    • (cis)-4-Hydroxy-D-proline
    • SCHEMBL85624
    • orb1302629
    • BDBM50357230
    • EBC-44264
    • MSK170598
    • s3367
    • AKOS000279991
    • AKOS005258604
    • CS-W008129
    • FH24331
    • HY-W008129
    • AS-12556
    • SY003831
    • cis-4-hydroxy-pyrrolidine-2-carboxylic acid
    • H1358
    • NS00074090
    • EN300-82445
    • C03440
    • 4-(R)-hydroxypyrrolidine-2-(R)-carboxylic acid
    • (2R,4R)-4-hydroxy pyrrolidine-2-carboxylic acid
    • (2r,4r)-4-hydroxy-pyrrolidine-2-carboxylic acid
    • 584H716
    • F040068
    • Q27101809
    • cis-4-Hydroxy-D-proline, Vetec(TM) reagent grade, 98%
    • (2R,4R)-(+)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
    • UYA
    • 2584-71-6

  • Applications

    Cis-4-Hydroxy-D-Proline (CAS 2584-71-6) is an amino acid derivative used as a chiral building block in the synthesis of pharmaceutical intermediates and bioactive compounds; it is commonly employed as a precursor for peptidomimetics and hydroxyproline-containing peptides, and it is also utilized as a starting material for polymer and hydroxyproline-based material systems in materials research; it can serve as a scaffold in combinatorial libraries for biological screening.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.43
    methanol 0.83
    isopropanol 0.23
    water 364.58
    ethyl acetate 1.45
    n-propanol 0.27
    acetone 2.97
    n-butanol 0.23
    acetonitrile 0.32
    DMF 19.77
    toluene 0.2
    isobutanol 0.16
    1,4-dioxane 1.41
    methyl acetate 0.17
    THF 2.64
    2-butanone 0.29
    n-pentanol 0.21
    sec-butanol 0.16
    n-hexane 0.06
    ethylene glycol 26.19
    NMP 38.74
    cyclohexane 0.07
    DMSO 58.59
    n-butyl acetate 0.82
    n-octanol 0.69
    chloroform 0.69
    n-propyl acetate 0.42
    acetic acid 18.59
    dichloromethane 0.88
    cyclohexanone 2.26
    propylene glycol 6.25
    isopropyl acetate 1.17
    DMAc 16.17
    2-ethoxyethanol 5.95
    isopentanol 0.39
    n-heptane 0.19
    ethyl formate 1.88
    1,2-dichloroethane 0.57
    n-hexanol 1.01
    2-methoxyethanol 11.39
    isobutyl acetate 0.25
    tetrachloromethane 0.62
    n-pentyl acetate 0.62
    transcutol 10.62
    n-heptanol 1.17
    ethylbenzene 0.2
    MIBK 1.21
    2-propoxyethanol 9.05
    tert-butanol 0.94
    MTBE 0.19
    2-butoxyethanol 5.84
    propionic acid 1.7
    o-xylene 0.48
    formic acid 198.9
    diethyl ether 0.17
    m-xylene 0.6
    p-xylene 0.27
    chlorobenzene 0.23
    dimethyl carbonate 1.82
    n-octane 0.1
    formamide 57.42
    cyclopentanone 3.77
    2-pentanone 1.01
    anisole 0.57
    cyclopentyl methyl ether 1.2
    gamma-butyrolactone 7.58
    1-methoxy-2-propanol 7.4
    pyridine 0.72
    3-pentanone 0.47
    furfural 17.68
    n-dodecane 0.07
    diethylene glycol 33.72
    diisopropyl ether 0.24
    tert-amyl alcohol 0.66
    acetylacetone 6.23
    n-hexadecane 0.07
    acetophenone 1.61
    methyl propionate 1.07
    isopentyl acetate 0.89
    trichloroethylene 1.36
    n-nonanol 0.75
    cyclohexanol 0.62
    benzyl alcohol 1.33
    2-ethylhexanol 0.95
    isooctanol 1.04
    dipropyl ether 0.59
    1,2-dichlorobenzene 0.62
    ethyl lactate 2.81
    propylene carbonate 4.57
    n-methylformamide 7.54
    2-pentanol 0.24
    n-pentane 0.04
    1-propoxy-2-propanol 5.14
    1-methoxy-2-propyl acetate 3.14
    2-(2-methoxypropoxy) propanol 7.58
    mesitylene 0.64
    ε-caprolactone 2.92
    p-cymene 0.63
    epichlorohydrin 2.57
    1,1,1-trichloroethane 0.46
    2-aminoethanol 8.98
    morpholine-4-carbaldehyde 30.79
    sulfolane 31.67
    2,2,4-trimethylpentane 0.06
    2-methyltetrahydrofuran 0.71
    n-hexyl acetate 0.82
    isooctane 0.08
    2-(2-butoxyethoxy)ethanol 8.6
    sec-butyl acetate 0.36
    tert-butyl acetate 1.49
    decalin 0.09
    glycerin 58.05
    diglyme 13.8
    acrylic acid 4.98
    isopropyl myristate 0.52
    n-butyric acid 2.78
    acetyl acetate 2.01
    di(2-ethylhexyl) phthalate 1.58
    ethyl propionate 0.7
    nitromethane 13.23
    1,2-diethoxyethane 0.77
    benzonitrile 0.86
    trioctyl phosphate 1.29
    1-bromopropane 0.11
    gamma-valerolactone 13.2
    n-decanol 0.63
    triethyl phosphate 1.43
    4-methyl-2-pentanol 0.58
    propionitrile 0.16
    vinylene carbonate 4.29
    1,1,2-trichlorotrifluoroethane 22.75
    DMS 1.1
    cumene 0.32
    2-octanol 0.58
    2-hexanone 0.36
    octyl acetate 0.7
    limonene 0.65
    1,2-dimethoxyethane 4.63
    ethyl orthosilicate 1.21
    tributyl phosphate 1.1
    diacetone alcohol 6.8
    N,N-dimethylaniline 1.14
    acrylonitrile 0.53
    aniline 0.52
    1,3-propanediol 5.76
    bromobenzene 0.21
    dibromomethane 0.41
    1,1,2,2-tetrachloroethane 1.41
    2-methyl-cyclohexyl acetate 1.32
    tetrabutyl urea 2.12
    diisobutyl methanol 1.04
    2-phenylethanol 2.18
    styrene 0.16
    dioctyl adipate 0.96
    dimethyl sulfate 9.53
    ethyl butyrate 0.98
    methyl lactate 6.68
    butyl lactate 2.49
    diethyl carbonate 0.65
    propanediol butyl ether 7.04
    triethyl orthoformate 1.14
    p-tert-butyltoluene 0.65
    methyl 4-tert-butylbenzoate 4.43
    morpholine 1.42
    tert-butylamine 0.31
    n-dodecanol 0.52
    dimethoxymethane 5.88
    ethylene carbonate 2.54
    cyrene 15.43
    2-ethoxyethyl acetate 1.2
    2-ethylhexyl acetate 0.64
    1,2,4-trichlorobenzene 0.64
    4-methylpyridine 0.71
    dibutyl ether 0.3
    2,6-dimethyl-4-heptanol 1.04
    DEF 3.31
    dimethyl isosorbide 13.53
    tetrachloroethylene 2.01
    eugenol 6.78
    triacetin 2.19
    span 80 6.49
    1,4-butanediol 3.09
    1,1-dichloroethane 0.24
    2-methyl-1-pentanol 0.36
    methyl formate 7.85
    2-methyl-1-butanol 0.26
    n-decane 0.1
    butyronitrile 0.22
    3,7-dimethyl-1-octanol 0.88
    1-chlorooctane 0.22
    1-chlorotetradecane 0.14
    n-nonane 0.09
    undecane 0.08
    tert-butylcyclohexane 0.08
    cyclooctane 0.09
    cyclopentanol 0.97
    tetrahydropyran 0.29
    tert-amyl methyl ether 0.31
    2,5,8-trioxanonane 12.92
    1-hexene 0.08
    2-isopropoxyethanol 2.98
    2,2,2-trifluoroethanol 27.34
    methyl butyrate 0.95

    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