5-Hydroxyindole-2-carboxylic acid

Name: 5-Hydroxyindole-2-carboxylic acid
Brand: ALDRICH
Price: 86.25 USD
Availability: InStock

≥96.5%

Synonym(s):

NSC 117338

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About This Item

Empirical Formula (Hill Notation):

C₉H₇NO₃

CAS Number:

21598-06-1

Molecular Weight:

177.16

Beilstein/REAXYS Number:

153214

EC Number:

244-468-6

MDL number:

MFCD00005615

UNSPSC Code:

12352100

PubChem Substance ID:

24848591

NACRES:

NA.22

Key Documents

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Quality Level

200

assay

≥96.5%

form

powder

mp

249 °C (dec.) (lit.)

solubility

chloroform/ethanol (1:1): soluble 50 mg/mL, clear to slightly hazy, yellow to brown

functional group

carboxylic acid

SMILES string

Oc1ccc2[nH]c(cc2c1)C(O)=O

InChI

1S/C9H7NO3/c11-6-1-2-7-5(3-6)4-8(10-7)9(12)13/h1-4,10-11H,(H,12,13)

InChI key

BIMHWDJKNOMNLD-UHFFFAOYSA-N

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1 of 4

This Item	H31859	126268	343412
Sigma-Aldrich 143510 5-Hydroxyindole-2-carboxylic acid	Sigma-Aldrich H31859 5-Hydroxyindole	Sigma-Aldrich 126268 2,4-Dihydroxypyrimidine-5-carboxylic acid	Sigma-Aldrich 343412 Cyclopropane-1,1-dicarboxylic acid
assay ≥96.5%	assay 97%	assay 95%	assay 97%
solubility chloroform/ethanol (1:1): soluble 50 mg/mL, clear to slightly hazy, yellow to brown	solubility -	solubility -	solubility methanol: soluble 1 g/10 mL, clear, colorless
Quality Level 200	Quality Level 100	Quality Level 100	Quality Level 200
form powder	form -	form powder	form -
mp 249 °C (dec.) (lit.)	mp 106-108 °C (lit.)	mp 283 °C (dec.) (lit.)	mp 134-136 °C (lit.)
functional group carboxylic acid	functional group -	functional group carboxylic acid	functional group carboxylic acid

General description

5-Hydroxyindole-2-carboxylic acid on oxidation with KMnO₄ yields pyrrole-2,3,5-tricarboxylic acid[1].

Application

5-Hydroxyindole-2-carboxylic acid was used in HPLC-amperometric detection of serotonin in plasma, platelets and urine[2].

Reactant for preparation of indole C5-O-substituted seco-cyclopropylindole analogs as potential anticancer agents
Reactant for microwave combinatorial synthesis of indolic arylpiperazine derivatives as ligands for 5-HT1A, 5-HT2A, and 5-HT2C receptors
Reactant for preparation of melanins as novel nature-inspired radioprotectors
Reactant for preparation of 5-Hydroxyindole-2-carboxylic acid amides as histamine-3 receptor inverse agonists for the treatment of obesity
Reactant for preparation of conformationally constrained peptidomimetic inhibitors of signal transducer and activator of transcription 3 (Stat3)
Reactant for preparation of oxadiazole analogs as nonpeptidic SH2 inhibitors of tyrosine kinase ZAP-70

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Isolation of oligomers of 5,6-dihydroxyindole-2-carboxylic acid from the eye of the catfish.

S Ito et al.

The Biochemical journal, 143(1), 207-217 (1974-10-01)

The reflecting material of the tapetum lucidum of the sea catfish (Arius felis) was chromatographed on Sephadex LH-20 in methanol-dimethyl sulphoxide-formic acid. Two components were present: one, showing an absorption maximum at 330nm, was tapetal pigment; the other, at 257nm

Validation of HPLC-amperometric detection to measure serotonin in plasma, platelets, whole blood, and urine.

E Pussard et al.

Clinical chemistry, 42(7), 1086-1091 (1996-07-01)

We describe an isocratic liquid-chromatographic method with amperometric detection for determination of serotonin by rapid sample preparation. Platelet-poor plasma and platelets were injected after a single deproteinization step with perchloric acid. Addition of sodium borohydride to whole blood avoids oxidation

Simultaneous determination of N-ethylpentylone, dopamine, 5-hydroxytryptamine and their metabolites in rat brain microdialysis by liquid chromatography tandem mass spectrometry.

Zebin Lin et al.

Biomedical chromatography : BMC, 33(10), e4626-e4626 (2019-06-22)

N-Ethylpentylone (NEP) is a popular synthetic cathinone abused worldwide. To obtain more information about its pharmacokinetics and pharmacodynamics, a rapid, simple and sensitive liquid chromatography-tandem mass spectrometry method was developed for the determination of NEP, two important neurotransmitters, dopamine and

Targeted metabolomics for the quantitative measurement of 9 gut microbiota-host co-metabolites in rat serum, urine and feces by liquid chromatography-tandem mass spectrometry.

Yifeng Zeng et al.

Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 1110-1111, 133-143 (2019-02-27)

Gut microbiota-host co-metabolites play an essential role in maintaining homeostasis, and their concentration changes are closely related to a variety of diseases. Developing a targeted metabolomics analytical platform for these co-metabolites will help to elucidate the relationship between intestinal flora

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5-Hydroxyindole-2-carboxylic acid