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H8876

Sigma-Aldrich

5-Hydroxyindole-3-acetic acid

≥98% (HPLC), crystalline

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Synonym(s):
5-HIAA
Empirical Formula (Hill Notation):
C10H9NO3
CAS Number:
Molecular Weight:
191.18
Beilstein/REAXYS Number:
168797
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

crystalline

color

white to purple

mp

161-164 °C (dec.) (lit.)

storage temp.

−20°C

SMILES string

OC(=O)Cc1c[nH]c2ccc(O)cc12

InChI

1S/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14)

InChI key

DUUGKQCEGZLZNO-UHFFFAOYSA-N

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1 of 4

This Item
14351080961655697
vibrant-m

H8876

5-Hydroxyindole-3-acetic acid

vibrant-m

143510

5-Hydroxyindole-2-carboxylic acid

vibrant-m

55697

5-Hydroxyindole-3-acetic acid

form

crystalline

form

powder

form

powder

form

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

-

storage temp.

−20°C

storage temp.

-

storage temp.

−20°C

storage temp.

−20°C

color

white to purple

color

-

color

-

color

-

mp

161-164 °C (dec.) (lit.)

mp

249 °C (dec.) (lit.)

mp

-

mp

161-164 °C (dec.) (lit.)

General description

5-Hydroxyindole-3-acetic acid (5-HIAA) is the catabolic end product of serotonin pathway. 5-HIAA is present in body fluids like cerebrospinal fluid (CSF), blood and urine. The expression levels of 5-HIAA is different among the normal and cancer patients. Sepiapterin reductase deficiency results in low level of 5-HIAA in CSF. 5-HIAA level is low in CSF in patients with bipolar 1 disorder with childhood attention-deficit hyperactivity disorder (ADHD).

Application

5-Hydroxyindole-3-acetic acid has been used as standard for the measurement of 5-HIAA in the brain tissue of mice using high performance liquid chromatography (HPLC).

Biochem/physiol Actions

Major serotonin metabolite.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Articles

Serotonin (5-hydroxytryptamine) is principally found stored in three main cell types - i) serotonergic neurons in the CNS and in the intestinal myenteric plexus, ii) enterochromaffin cells in the mucosa of the gastrointestinal tract, and iii) in blood platelets. Metabolism of serotonin is carried out primarily by the outer mitochondrial membrane enzyme monoamine oxidase (MAO), which occurs as two molecular subtypes called MAO-A and MAO-B.

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