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H9772

Sigma-Aldrich

5-Hydroxy-L-tryptophan

≥98% (TLC), suitable for HPLC

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Synonym(s):
L-2-Amino-3-(5-hydroxyindolyl)propionic acid, L-5-HTP
Empirical Formula (Hill Notation):
C11H12N2O3
CAS Number:
4350-09-8
Molecular Weight:
220.22
EC Number:
224-411-1
MDL number:
MFCD00064341
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24278131
NACRES:
NA.77

Assay

≥98% (TLC)

Quality Level

200

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

Gene Information

human ... HTR1A(3350) , HTR1B(3351) , HTR1D(3352) , HTR1E(3354) , HTR1F(3355) , HTR2A(3356) , HTR2B(3357) , HTR2C(3358) , HTR3A(3359) , HTR3B(9177) , HTR3C(170572) , HTR3D(200909) , HTR3E(285242) , HTR4(3360) , HTR5A(3361) , HTR5B(645694) , HTR6(3362) , HTR7(3363)

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General description

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

Application

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

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.
Immediate precursor of serotonin; L-aromatic amino acid decarboxylase substrate.

Caution

Light sensitive

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Erin J Golden et al.
eLife, 10 (2021-05-20)
Embryonic taste bud primordia are specified as taste placodes on the tongue surface and differentiate into the first taste receptor cells (TRCs) at birth. Throughout adult life, TRCs are continually regenerated from epithelial progenitors. Sonic hedgehog (SHH) signaling regulates TRC
Endocrine taste cells
Kokrashvili Z, et al.
The British Journal of Nutrition, 111(S1), S23-S29 (2014)
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