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H9772

Sigma-Aldrich

5-Hydroxy-L-tryptophan

≥98% (TLC), suitable for HPLC

Synonym(s):

L-2-Amino-3-(5-hydroxyindolyl)propionic acid, L-5-HTP

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About This Item

Empirical Formula (Hill Notation):
C11H12N2O3
CAS Number:
Molecular Weight:
220.22
EC Number:
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.77

Pricing and availability is not currently available.

product name

5-Hydroxy-L-tryptophan, powder

Assay

≥98% (TLC)

Quality Level

form

powder

technique(s)

HPLC: suitable

color

white to faint beige

storage temp.

2-8°C

SMILES string

N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(O)=O

InChI

1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)/t9-/m0/s1

InChI key

LDCYZAJDBXYCGN-VIFPVBQESA-N

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General description

5-Hydroxy-L-tryptophan (5-HTP) is naturally found in Griffonia simplicifolia.[1]

Application

5-Hydroxy-L-tryptophan has been used:
  • to inject experimental mice for serotonin detection[2]
  • as a precursor of 5-hydroxytryptamine and injected in pregnant mice and neonatal rats for vital neutral red staining of lung slices[3]
  • as a standard in citrate-acetate buffer for its use in high performance liquid chromatography (HPLC) analysis[4]

Biochem/physiol Actions

Hydroxylation of L-tryptophan occurs in the brain during serotonin synthesis. This is a step that controls the production of serotonin and also yields 5-hydroxy-l-tryptophan (5-HTP) as a metabolite. Thus, consumption 5-HTP, increases the serotonin level, which might result in depression, lack of sleep and severe headache.[1]
Immediate precursor of serotonin; L-aromatic amino acid decarboxylase substrate.

Caution

Light sensitive

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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    Andrew N Bubak et al.
    PloS one, 14(1), e0203980-e0203980 (2019-01-30)
    Despite the conserved function of aggression across taxa in obtaining critical resources such as food and mates, serotonin's (5-HT) modulatory role on aggressive behavior appears to be largely inhibitory for vertebrates but stimulatory for invertebrates. However, critical gaps exist in
    Enhanced synthesis of 5-hydroxy-l-tryptophan through tetrahydropterin regeneration
    Hara R and Kino K
    AMB Express, 3(1), 70-70 (2013)
    M G Marrero et al.
    Scientific reports, 10(1), 9712-9712 (2020-06-18)
    Dairy calves are born with a naïve immune system, making the pre-weaning phase a critical window for immune development. In the U.S., 40-60% of dairy farms feed milk replacer to pre-weaned calves, which are devoid of bioactive factors with immunological
    Endocrine taste cells
    Kokrashvili Z, et al.
    The British Journal of Nutrition, 111(S1), S23-S29 (2014)
    Hai-Ling Yu et al.
    Neuroscience letters, 593, 24-28 (2015-03-18)
    Oleoylethanolamide (OEA) is an endocannabinoid analogy that belongs to a family of endogenous acylethanolamides. Increasing evidence suggests that OEA may act as an endogenous neuroprotective factor and participate in the control of mental disorder-related behaviors. In the present study, we

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