(+-)-5-Hydroxytryptophan

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  • Identifiers

    CAS number
    56-69-9

    Molecular formula
    C11H12N2O3

    SMILES
    C1=CC2=C(C=C1O)C(=CN2)CC(C(=O)O)N

    Safety labels

    Flammable
    Flammable

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 80.42%
    Savory 31.27%
    Bitter 23.55%
    Meaty 21.88%
    Cooked 21.78%
    Milky 21.7%
    Burnt 17.72%
    Cooling 16.28%
    Animal 15.35%
    Dairy 15.23%

     

    Flavor
    Bitter 82.49%
    Odorless 60.26%
    Bland 32.86%
    Mild 30.46%
    Sweet-like 23.06%
    Very mild 20.94%
    Nitrile 20.47%
    Yeast 19.83%
    Cedarleaf 19.38%
    Very strong 19.01%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.2

    pKa est.
    7.05 (neutral)

    Molecular weight
    220.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    535°C

    Melting point expt.

    • 298-300 °C (decomposes)
    • MP: 273 °C (decomposes); specific optical rotation: +16.0 deg at 22 °C (c=1 in 4M HCl); -32 deg at 22 °C (c=1 in H2O) /(S)-5-Hydroxytryptophan/

    Flash point

    • 281.68 ˚C est.

    Solubility expt.

    • Solubilities: 2.5 g/100 mL in 50% boiling alcohol; 5.5 g/100 mL in water at 100 °C
    • In water, 1X10+4 mg/L at 5 °C

  • Synonyms

    • 5-hydroxytryptophan
    • 56-69-9
    • 114-03-4
    • 5-HTP
    • DL-5-HTP
    • (+-)-5-Hydroxytryptophan
    • 9181P3OI6N
    • CHEBI:28171
    • DTXSID50859863
    • 5 Hydroxytryptophan
    • Tryptophan, 5 Hydroxy
    • 5-hydroxytryptophan DL-
    • RefChem:905501
    • DTXCID90208816
    • 200-284-8
    • 2-azaniumyl-3-(5-hydroxy-1H-indol-3-yl)propanoate
    • Oxytryptophan
    • Tryptophan, 5-Hydroxy-
    • 5-Hydroxy-DL-tryptophan
    • DL-5-Hydroxytryptophan
    • 2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
    • DL-Hydroxytryptophan
    • 5-Hydroxytryptophan DL-form
    • H-DL-Trp(5-OH)-OH
    • MFCD00005651
    • D,L-5-hydroxytryptophan
    • 5-hydroxy tryptophan
    • NSC-92523
    • 5-HTP/5-Hydroxytryptophan
    • (+/-)-5-Hydroxytryptophan
    • 5-hydroxytryptophan (5-HTP)
    • 5-hydroxyltryptophan
    • DL-Pretonine
    • 72572-98-6
    • Dl-oxitriptan
    • USAF CB-96
    • H-L-Trp(5-OH)-OH
    • 5-hydroxytryptophan, dl-
    • 5-Hydroxytryptophan L form
    • HSDB 4295
    • NCI-C56644
    • Tryptophan, 5-hydroxy-, dl
    • 5-22-14-00278 (Beilstein Handbook Reference)
    • EINECS 200-284-8
    • Tryptophan, 5-hydroxy-, L-
    • NSC 92523
    • BRN 0088199
    • DL-Tryptophan, 5-hydroxy-
    • UNII-9181P3OI6N
    • (+/-)-5-Hydroxytryptophan; 5-HTP; 5-Hydroxy-DL-tryptophan; DL-Hydroxytryptophan; NSC 92523;
    • 5-Hydroxytryptophan #
    • 5-Hydroxytryptophan/5-HTP
    • SCHEMBL43242
    • MLS006011926
    • 2-Amino-3-(5-hydroxy-1H-indol-3-yl)propanoicacid
    • (.+-.)-5-Hydroxytryptophan
    • CHEMBL162789
    • orb1304632
    • 5-Hydroxytryptophan, AldrichCPR
    • SCHEMBL19871232
    • 5-HYDROXYTRYPTOPHAN [MI]
    • HMS3372G05
    • HMS3656M11
    • HMS3884H15
    • HMS5080H18
    • HMS5083H06
    • WLN: T56 BMJ D1YZVQ GQ
    • 5-HYDROXYTRYPTOPHAN [HSDB]
    • HY-N0122
    • MSK14864
    • NSC92523
    • BBL012270
    • EBC-03613
    • s2374
    • SBB003354
    • STK803137
    • AKOS003382640
    • AKOS016050369
    • CCG-235444
    • FH05792
    • 5-Hydroxy-L-tryptophan from fermentation
    • NCGC00015526-02
    • NCGC00015526-04
    • AC-13632
    • AC-23979
    • SMR000326745
    • SY048412
    • VS-03256
    • DB-051092
    • CS-0007832
    • NS00093559
    • SW219417-1
    • 56H699
    • C01017
    • DL-2-Amino-3-(5-hydroxyindolyl)propionic acid
    • EN300-244707
    • H-8300
    • N88462
    • 2-amino-3-(5-hydroxyindol-3-yl)propanoic acid
    • ( inverted exclamation markA)-5-Hydroxytryptophan
    • F306984
    • SR-01000003309
    • propanoic acid, 2-amino-3-(5-hydroxyindol-3-yl)-
    • SR-01000003309-1
    • BRD-A73930134-001-02-2
    • BRD-A73930134-001-03-0
    • Q27103541
    • 56-69-9

  • Applications

    (+-)-5-Hydroxytryptophan (CAS 56-69-9) is used primarily as a dietary supplement ingredient (nutraceutical) and as a pharmaceutical synthesis intermediate for serotonin-related compounds. In research and development, it functions as a biochemical reagent in neurochemistry studies and enzyme assays, and it can be used as an analytical standard for chromatographic quantification of tryptophan derivatives.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.05
    methanol 0.12
    isopropanol 0.06
    water 1.54
    ethyl acetate 0.25
    n-propanol 0.03
    acetone 0.15
    n-butanol 0.05
    acetonitrile 0.06
    DMF 3.51
    toluene 0.03
    isobutanol 0.04
    1,4-dioxane 0.18
    methyl acetate 0.17
    THF 0.91
    2-butanone 0.2
    n-pentanol 0.08
    sec-butanol 0.08
    n-hexane 0.01
    ethylene glycol 1.52
    NMP 12.93
    cyclohexane 0.01
    DMSO 1.54
    n-butyl acetate 0.26
    n-octanol 0.04
    chloroform 0.01
    n-propyl acetate 0.22
    acetic acid 1.54
    dichloromethane 0.01
    cyclohexanone 0.4
    propylene glycol 0.87
    isopropyl acetate 0.23
    DMAc 13.48
    2-ethoxyethanol 2.83
    isopentanol 0.12
    n-heptane 0.03
    ethyl formate 0.2
    1,2-dichloroethane 0.01
    n-hexanol 0.17
    2-methoxyethanol 3.66
    isobutyl acetate 0.11
    tetrachloromethane 0.02
    n-pentyl acetate 0.14
    transcutol 2.19
    n-heptanol 0.13
    ethylbenzene 0.05
    MIBK 0.26
    2-propoxyethanol 2.68
    tert-butanol 0.23
    MTBE 0.09
    2-butoxyethanol 1.28
    propionic acid 0.28
    o-xylene 0.06
    formic acid 12.17
    diethyl ether 0.05
    m-xylene 0.05
    p-xylene 0.09
    chlorobenzene 0.01
    dimethyl carbonate 0.67
    n-octane 0.01
    formamide 8.04
    cyclopentanone 1.01
    2-pentanone 0.24
    anisole 0.16
    cyclopentyl methyl ether 0.33
    gamma-butyrolactone 2.03
    1-methoxy-2-propanol 2.67
    pyridine 0.14
    3-pentanone 0.21
    furfural 2.84
    n-dodecane 0.01
    diethylene glycol 8.82
    diisopropyl ether 0.06
    tert-amyl alcohol 0.29
    acetylacetone 0.92
    n-hexadecane 0.01
    acetophenone 0.47
    methyl propionate 0.41
    isopentyl acetate 0.33
    trichloroethylene 0.03
    n-nonanol 0.05
    cyclohexanol 0.15
    benzyl alcohol 0.29
    2-ethylhexanol 0.18
    isooctanol 0.14
    dipropyl ether 0.24
    1,2-dichlorobenzene 0.03
    ethyl lactate 1.16
    propylene carbonate 1.16
    n-methylformamide 0.9
    2-pentanol 0.09
    n-pentane 0.0
    1-propoxy-2-propanol 1.38
    1-methoxy-2-propyl acetate 1.19
    2-(2-methoxypropoxy) propanol 2.12
    mesitylene 0.06
    ε-caprolactone 0.79
    p-cymene 0.09
    epichlorohydrin 0.34
    1,1,1-trichloroethane 0.01
    2-aminoethanol 0.71
    morpholine-4-carbaldehyde 6.98
    sulfolane 4.94
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 0.31
    n-hexyl acetate 0.09
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 1.94
    sec-butyl acetate 0.21
    tert-butyl acetate 0.44
    decalin 0.01
    glycerin 11.57
    diglyme 3.21
    acrylic acid 0.64
    isopropyl myristate 0.08
    n-butyric acid 0.46
    acetyl acetate 0.22
    di(2-ethylhexyl) phthalate 0.25
    ethyl propionate 0.36
    nitromethane 1.79
    1,2-diethoxyethane 0.21
    benzonitrile 0.11
    trioctyl phosphate 0.15
    1-bromopropane 0.01
    gamma-valerolactone 3.18
    n-decanol 0.05
    triethyl phosphate 0.57
    4-methyl-2-pentanol 0.13
    propionitrile 0.04
    vinylene carbonate 0.51
    1,1,2-trichlorotrifluoroethane 2.84
    DMS 0.34
    cumene 0.06
    2-octanol 0.08
    2-hexanone 0.23
    octyl acetate 0.1
    limonene 0.08
    1,2-dimethoxyethane 2.18
    ethyl orthosilicate 0.51
    tributyl phosphate 0.18
    diacetone alcohol 2.21
    N,N-dimethylaniline 0.29
    acrylonitrile 0.09
    aniline 0.1
    1,3-propanediol 0.92
    bromobenzene 0.01
    dibromomethane 0.0
    1,1,2,2-tetrachloroethane 0.04
    2-methyl-cyclohexyl acetate 0.39
    tetrabutyl urea 0.43
    diisobutyl methanol 0.19
    2-phenylethanol 0.34
    styrene 0.04
    dioctyl adipate 0.15
    dimethyl sulfate 1.99
    ethyl butyrate 0.42
    methyl lactate 2.37
    butyl lactate 0.54
    diethyl carbonate 0.3
    propanediol butyl ether 1.06
    triethyl orthoformate 0.53
    p-tert-butyltoluene 0.08
    methyl 4-tert-butylbenzoate 0.91
    morpholine 0.31
    tert-butylamine 0.06
    n-dodecanol 0.05
    dimethoxymethane 1.18
    ethylene carbonate 0.35
    cyrene 6.2
    2-ethoxyethyl acetate 0.36
    2-ethylhexyl acetate 0.25
    1,2,4-trichlorobenzene 0.05
    4-methylpyridine 0.15
    dibutyl ether 0.06
    2,6-dimethyl-4-heptanol 0.19
    DEF 0.98
    dimethyl isosorbide 4.34
    tetrachloroethylene 0.06
    eugenol 1.58
    triacetin 0.55
    span 80 1.03
    1,4-butanediol 0.71
    1,1-dichloroethane 0.01
    2-methyl-1-pentanol 0.17
    methyl formate 0.74
    2-methyl-1-butanol 0.11
    n-decane 0.01
    butyronitrile 0.05
    3,7-dimethyl-1-octanol 0.06
    1-chlorooctane 0.01
    1-chlorotetradecane 0.01
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.01
    cyclooctane 0.01
    cyclopentanol 0.23
    tetrahydropyran 0.07
    tert-amyl methyl ether 0.19
    2,5,8-trioxanonane 3.62
    1-hexene 0.03
    2-isopropoxyethanol 1.32
    2,2,2-trifluoroethanol 2.34
    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