Citrulline, (+/-)-

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  • Identifiers

    CAS number
    627-77-0

    Molecular formula
    C6H13N3O3

    SMILES
    C(CC(C(=O)O)N)CNC(=O)N

  • Odor profile

    Fragrance
    Odorless 69.42%
    Savory 41.0%
    Fishy 35.39%
    Meaty 31.54%
    Cooling 24.31%
    Cheesy 20.13%
    Sweet 19.03%
    Cooked 18.92%
    Ripe 17.12%
    Pungent 16.24%

     

    Flavor
    Odorless 66.09%
    Mild 35.39%
    Bland 29.73%
    Bitter 28.54%
    Faint 24.86%
    Sweet-like 22.7%
    Yeast 22.65%
    Very mild 21.24%
    Sulfury 20.42%
    Nitrile 20.06%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    -4.3

    pKa est.
    6.5 (neutral)

    Molecular weight
    175.19 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    435°C

    Flash point

    • 212.38 ˚C est.

  • Synonyms

    • DL-Citrulline
    • 627-77-0
    • 2-Amino-5-ureidopentanoic acid
    • Citrullin
    • DL-2-Amino-5-ureidovaleric acid
    • 2-amino-5-(carbamoylamino)pentanoic acid
    • citrulina
    • Citrulline, (+/-)-
    • 1OYO2NV4NM
    • CITRULLINE, (DL)
    • DL-Ornithine, N5-(aminocarbonyl)-
    • Ornithine, N5-carbamoyl-, DL-
    • EINECS 211-012-2
    • MFCD00007955
    • NSC-46711
    • DL-Ornithine, N(5)-(aminocarbonyl)-
    • N(5)-carbamoyl-DL-ornithine
    • N(5)-(aminocarbonyl)ornithine
    • CHEBI:18211
    • NSC27425
    • NSC46711
    • N(5)-(aminocarbonyl)-DL-ornithine
    • NSC 46711
    • N~5~-carbamoylornithine
    • H-D-Orn(carbamoyl)-OH
    • NORVALINE, 5-((AMINOCARBONYL)AMINO)-
    • N(5)-carbamoylornithine
    • N~5~-carbamoyl-L-ornithine
    • 2-Amino-5-uredovaleric acid
    • cit
    • H-Orn(carbamoyl)-OH;L-Citrulline
    • MFCD00216469
    • Citrulline,(l)
    • citrulline (DL-form)
    • Spectrum_000037
    • .delta.-Ureidonorvaline
    • CITRULLINE, DL-
    • SpecPlus_000523
    • L(+)CITRULLINE
    • Spectrum2_001371
    • Spectrum3_001045
    • Spectrum4_001185
    • Spectrum5_001792
    • UNII-1OYO2NV4NM
    • N.delta.-Carbamylornithine
    • bmse000209
    • Epitope ID:141797
    • SCHEMBL20587
    • BSPBio_002570
    • KBioGR_001849
    • KBioSS_000397
    • N(.delta.)-Carbamylornithine
    • DivK1c_006619
    • SPBio_001322
    • SGCUT00061
    • SCHEMBL13282334
    • KBio1_001563
    • KBio2_000397
    • KBio2_002965
    • KBio2_005533
    • KBio3_001790
    • DTXSID40861910
    • to_000034
    • BBL027668
    • CCG-38847
    • NSC206276
    • s5124
    • STK802460
    • STL455121
    • AKOS005622468
    • L-(+)-2-Amino-5-ureidovaleric acid
    • L-CITRULLINE (1.12117)
    • N~5~-[hydroxy(imino)methyl]ornithine
    • CS-W017450
    • HY-W016734
    • PB48354
    • SDCCGMLS-0066976.P001
    • 2aAminoa5a(carbamoylamino)pentanoic acid
    • 2-azaniumyl-5-(carbamoylamino)pentanoate
    • NCGC00178596-01
    • .alpha.-Amino-.delta.-ureidovaleric acid
    • AS-60168
    • SY023288
    • SY032853
    • SY048344
    • DB-049088
    • DB-054282
    • NS00013538
    • D89239
    • EN300-1168657
    • L000975
    • SR-05000002410
    • SR-05000002410-1
    • BRD-A12237696-001-04-2
    • Q27102910

  • Applications

    Citrulline, (+/-)- (CAS 627-77-0) is used as a chemical building block and intermediate in the synthesis of pharmaceuticals and related amino acid derivatives; it is used as an ingredient in dietary supplements and is evaluated for inclusion in animal nutrition formulations; it serves as a substrate/reagent in biochemical and enzymatic research, including studies of the urea cycle; and it functions as an industrial intermediate in the production of specialty chemicals and other chemical products.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.02
    methanol 0.07
    isopropanol 0.02
    water 40.51
    ethyl acetate 0.14
    n-propanol 0.02
    acetone 0.06
    n-butanol 0.02
    acetonitrile 0.04
    DMF 1.85
    toluene 0.13
    isobutanol 0.02
    1,4-dioxane 0.13
    methyl acetate 0.06
    THF 0.24
    2-butanone 0.06
    n-pentanol 0.03
    sec-butanol 0.03
    n-hexane 0.06
    ethylene glycol 0.94
    NMP 14.6
    cyclohexane 0.05
    DMSO 5.86
    n-butyl acetate 0.11
    n-octanol 0.04
    chloroform 0.03
    n-propyl acetate 0.06
    acetic acid 1.38
    dichloromethane 0.04
    cyclohexanone 0.47
    propylene glycol 0.52
    isopropyl acetate 0.13
    DMAc 5.26
    2-ethoxyethanol 0.35
    isopentanol 0.05
    n-heptane 0.08
    ethyl formate 0.17
    1,2-dichloroethane 0.04
    n-hexanol 0.09
    2-methoxyethanol 0.66
    isobutyl acetate 0.04
    tetrachloromethane 0.05
    n-pentyl acetate 0.08
    transcutol 0.87
    n-heptanol 0.09
    ethylbenzene 0.09
    MIBK 0.13
    2-propoxyethanol 0.65
    tert-butanol 0.08
    MTBE 0.05
    2-butoxyethanol 0.4
    propionic acid 0.3
    o-xylene 0.3
    formic acid 14.37
    diethyl ether 0.03
    m-xylene 0.21
    p-xylene 0.14
    chlorobenzene 0.04
    dimethyl carbonate 0.31
    n-octane 0.03
    formamide 4.38
    cyclopentanone 0.57
    2-pentanone 0.1
    anisole 0.09
    cyclopentyl methyl ether 0.31
    gamma-butyrolactone 1.19
    1-methoxy-2-propanol 0.57
    pyridine 0.18
    3-pentanone 0.15
    furfural 3.12
    n-dodecane 0.01
    diethylene glycol 2.61
    diisopropyl ether 0.05
    tert-amyl alcohol 0.11
    acetylacetone 0.53
    n-hexadecane 0.01
    acetophenone 0.27
    methyl propionate 0.2
    isopentyl acetate 0.14
    trichloroethylene 0.08
    n-nonanol 0.05
    cyclohexanol 0.15
    benzyl alcohol 0.16
    2-ethylhexanol 0.11
    isooctanol 0.09
    dipropyl ether 0.13
    1,2-dichlorobenzene 0.09
    ethyl lactate 0.37
    propylene carbonate 0.93
    n-methylformamide 0.59
    2-pentanol 0.04
    n-pentane 0.02
    1-propoxy-2-propanol 0.45
    1-methoxy-2-propyl acetate 0.46
    2-(2-methoxypropoxy) propanol 0.89
    mesitylene 0.21
    ε-caprolactone 0.62
    p-cymene 0.15
    epichlorohydrin 0.19
    1,1,1-trichloroethane 0.04
    2-aminoethanol 0.4
    morpholine-4-carbaldehyde 4.67
    sulfolane 7.28
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 0.15
    n-hexyl acetate 0.08
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 0.71
    sec-butyl acetate 0.06
    tert-butyl acetate 0.22
    decalin 0.05
    glycerin 6.0
    diglyme 1.07
    acrylic acid 0.91
    isopropyl myristate 0.05
    n-butyric acid 0.35
    acetyl acetate 0.25
    di(2-ethylhexyl) phthalate 0.23
    ethyl propionate 0.13
    nitromethane 1.1
    1,2-diethoxyethane 0.1
    benzonitrile 0.12
    trioctyl phosphate 0.13
    1-bromopropane 0.02
    gamma-valerolactone 1.98
    n-decanol 0.04
    triethyl phosphate 0.25
    4-methyl-2-pentanol 0.06
    propionitrile 0.03
    vinylene carbonate 0.74
    1,1,2-trichlorotrifluoroethane 2.57
    DMS 0.24
    cumene 0.1
    2-octanol 0.06
    2-hexanone 0.06
    octyl acetate 0.07
    limonene 0.16
    1,2-dimethoxyethane 0.43
    ethyl orthosilicate 0.23
    tributyl phosphate 0.15
    diacetone alcohol 0.85
    N,N-dimethylaniline 0.26
    acrylonitrile 0.08
    aniline 0.2
    1,3-propanediol 0.27
    bromobenzene 0.04
    dibromomethane 0.03
    1,1,2,2-tetrachloroethane 0.11
    2-methyl-cyclohexyl acetate 0.2
    tetrabutyl urea 0.32
    diisobutyl methanol 0.13
    2-phenylethanol 0.22
    styrene 0.06
    dioctyl adipate 0.1
    dimethyl sulfate 1.94
    ethyl butyrate 0.16
    methyl lactate 1.24
    butyl lactate 0.33
    diethyl carbonate 0.11
    propanediol butyl ether 0.55
    triethyl orthoformate 0.21
    p-tert-butyltoluene 0.15
    methyl 4-tert-butylbenzoate 0.73
    morpholine 0.15
    tert-butylamine 0.04
    n-dodecanol 0.04
    dimethoxymethane 0.41
    ethylene carbonate 0.44
    cyrene 2.75
    2-ethoxyethyl acetate 0.16
    2-ethylhexyl acetate 0.12
    1,2,4-trichlorobenzene 0.11
    4-methylpyridine 0.21
    dibutyl ether 0.04
    2,6-dimethyl-4-heptanol 0.13
    DEF 0.58
    dimethyl isosorbide 2.11
    tetrachloroethylene 0.16
    eugenol 0.83
    triacetin 0.31
    span 80 0.74
    1,4-butanediol 0.18
    1,1-dichloroethane 0.02
    2-methyl-1-pentanol 0.05
    methyl formate 0.57
    2-methyl-1-butanol 0.04
    n-decane 0.02
    butyronitrile 0.03
    3,7-dimethyl-1-octanol 0.05
    1-chlorooctane 0.02
    1-chlorotetradecane 0.02
    n-nonane 0.02
    undecane 0.02
    tert-butylcyclohexane 0.03
    cyclooctane 0.05
    cyclopentanol 0.16
    tetrahydropyran 0.06
    tert-amyl methyl ether 0.1
    2,5,8-trioxanonane 1.42
    1-hexene 0.05
    2-isopropoxyethanol 0.21
    2,2,2-trifluoroethanol 2.32
    methyl butyrate 0.16

    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