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H8876

5-Hydroxyindole-3-acetic acid

Name: 5-Hydroxyindole-3-acetic acid
Brand: SIGMA

≥98% (HPLC), crystalline

Synonym(s):

5-HIAA

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₉NO₃

CAS Number:

54-16-0

Molecular Weight:

191.18

NACRES:

NA.77

PubChem Substance ID:

24278130

UNSPSC Code:

12352106

EC Number:

200-195-4

MDL number:

MFCD00005639

Beilstein/REAXYS Number:

168797

Assay:

≥98% (HPLC)

Form:

crystalline

Quality level:

200

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Properties

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)

Description

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.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Combining tissue transcriptomics and urine metabolomics for breast cancer biomarker identification

Nam H, et al.

Bioinformatics, 25(23), 3151-3157 (2009)

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)

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)

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