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Key Documents

H8876

Sigma-Aldrich

5-Hydroxyindole-3-acetic acid

≥98% (HPLC), crystalline

Synonym(s):

5-HIAA

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About This Item

Empirical Formula (Hill Notation):
C10H9NO3
CAS Number:
Molecular Weight:
191.18
Beilstein:
168797
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.77

product name

5-Hydroxyindole-3-acetic acid, ≥98% (HPLC), crystalline

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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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 Code

11 - Combustible Solids

WGK

WGK 3

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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Lower CSF HVA and 5-HIAA in bipolar disorder type 1 with a history of childhood ADHD
Ryden E, et al.
Journal of neural transmission (Vienna, Austria : 1996), 116(12), 1667-1674 (2009)
Combining tissue transcriptomics and urine metabolomics for breast cancer biomarker identification
Nam H, et al.
Bioinformatics, 25(23), 3151-3157 (2009)
Progression and recovery of Parkinsonism in a chronic progressive MPTP-induction model in the marmoset without persistent molecular and cellular damage
Franke SK, et al.
Neuroscience, 312, 247-259 (2016)
Chronic high dose of captopril induces depressive-like behaviors in mice: possible mechanism of regulatory T cell in depression
Park HS, et al.
Oncotarget, 8(42), 72528-72543 (2017)
Makoto Tsunoda et al.
Biomedical chromatography : BMC, 33(11), e4650-e4650 (2019-07-18)
Solid-phase extraction technologies are widely used for sample pretreatment in bioanalysis. Monolithic silica disk-packed spin columns modified with phenylboronate moieties have been developed for the selective extraction of cis-diol compounds such as catecholamines. However, in our preliminary studies, serotonin was

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