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H8876

Sigma-Aldrich

5-Hydroxyindole-3-acetic acid

≥98% (HPLC), crystalline

Synonym(s):

5-HIAA

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$37.10

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100 MG
$37.10
500 MG
$105.00
1 G
$183.00

About This Item

Empirical Formula (Hill Notation):
C10H9NO3
CAS Number:
54-16-0
Molecular Weight:
191.18
Beilstein/REAXYS Number:
168797
EC Number:
200-195-4
MDL number:
MFCD00005639
UNSPSC Code:
12352106
PubChem Substance ID:
24278130
NACRES:
NA.77

$37.10

Available to ship onMay 13, 2025Details

Request a Bulk Order

Product Name

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

Quality Level

200

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

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-Hydroxyindole-3-acetic acid (5-HIAA) is the catabolic end product of serotonin pathway.[1] 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.[2] Sepiapterin reductase deficiency results in low level of 5-HIAA in CSF.[1] 5-HIAA level is low in CSF in patients with bipolar 1 disorder with childhood attention-deficit hyperactivity disorder (ADHD).[3]

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).[4][5]

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCN0749
BCCL3424
BCCL9267
BCCJ4414
BCCH5209

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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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Articles

Serotonin Synthesis & Metabolism

Serotonin is stored in cells and metabolized by MAO, influencing CNS, GI, and platelet functions.

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