5-Hydroxyindoleacetic Acid (HCID 1826)

Names & identifiers

Preferred name: 5-Hydroxyindoleacetic Acid
IUPAC: 2-(5-hydroxy-1H-indol-3-yl)acetic acid
English name: 5-HYDROXYINDOLE-3-ACETIC ACID
Molecular formula: C10H9NO3
Molecular weight: 191.18

Names & synonyms

5-Hydroxyindole-3-acetic acid54-16-02-(5-hydroxy-1H-indol-3-yl)acetic acid5-HIAA5-Hydroxyindoleacetic acidHydroxyindoleacetic acid5-Hydroxyindol-3-ylacetic acidYHC763JY1PCHEBI:27823NSC-90432NSC90432Acid, Hydroxyindoleacetic

Show more names

HIAA5-oxyindoleaceticacid5-HYDROXY-3-INDOLEACETIC ACID5&＃0395-HO-IAANSC 90432Nature ProductTIMTEC-BB SBB003639

5 Hydroxy 3 Indoleacetic Acid5 Hydroxyindolamine Acetic Acid5-Hydroxyindolamine Acetic AcidAcid, 5-Hydroxy-3-IndoleaceticAcetic Acid, 5-HydroxyindolamineAcid, 5-Hydroxyindolamine AceticRefChem:789490200-195-4

Database identifiers

CAS: 54-16-0
PubChem CID: 1826
DTXSID: DTXSID50861582
ChEMBL: CHEMBL395915
ChEBI: CHEBI:27823
UNII: YHC763JY1P
EC Number: 200-195-4
Nikkaji: J11.030B

Properties

Computed structural properties

XLogP: 1.1
Topological polar surface area: 73.3 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 14
Formal charge: 0
Complexity: 231

Experimental & physicochemical properties

Solubility · 2 items

24 mg/mL

>28.7 [ug/mL] (The mean of the results at pH 7.4)

Melting Point161 - 163 °C

Physical Description · 2 items

Light red crystalline solid; [Sigma-Aldrich MSDS]

Solid

Collision Cross Section · 3 items

148.4 Å² [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；137.1 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；140.9 Å² [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

140.9 Å² [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

141.1 Å² [M+H]+；148.6 Å² [M+Na]+；137.3 Å² [M-H]-

Physicochemical properties

Melting point: 161 · 161-164 °C (dec.) (lit.)
Boiling point: 326.92 °C · 326.92°C (rough estimate)
Density: 1.2722 · 1.2722 (rough estimate)
refractive index: 1.531 · 1.5310 (estimate)
storage temp.: -20 °C · -20°C
solubility: Soluble in ethanol (50 mg/ml).
form: crystalline
pka: 4.54 · 4.54±0.30(Predicted)
color: off-white to purple
Sensitive: Light Sensitive
BRN: 168797 · 168797
Stability: Air Sensitive, Light Sensitive
Major Application: clinical testing
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)
InChIKey: DUUGKQCEGZLZNO-UHFFFAOYSA-N
SMILES: OC(=O)Cc1c[nH]c2ccc(O)cc12
CAS DataBase Reference: 54 · 54-16-0
EWG's Food Scores: 1 · 1
NCI Dictionary of Cancer Terms: 5 · 5-hydroxyindoleacetic acid
FDA UNII: 763 JY1P · YHC763JY1P
UNSPSC Code: 41116107 · 41116107
NACRES: 77 · NA.77
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P271-P280
Safety Statements: 22 · 22-24/25
WGK Germany: 3 · 3
RTECS: 3650000 · NL3650000
F: 8 · 8-10-23
HS Code: 29339980 · 29339980
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]；H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 2 items

Chemical: 1H-Indole-3-acetic acid, 5-hydroxy-

5-Hydroxyindol-3-ylacetic acid: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia

Hazards SummaryCauses somnolence in intraperitoneal lethal-dose studies of mice (LD50 = 1,125 mg/kg); [RTECS] May cause irritation; [Sigma-Aldrich MSDS] See Indole-3-butyric acid.

Hazard Classes and CategoriesAcute Tox. 4 (100%)；Skin Irrit. 2 (100%)；Eye Irrit. 2A (100%)；STOT SE 3 (100%)

Regulatory information

Regulatory Information · 2 items

Chemical: 1H-Indole-3-acetic acid, 5-hydroxy-

5-Hydroxyindol-3-ylacetic acid: Does not have an individual approval but may be used under an appropriate group standard

Safety data

F: 8-10-23
wgk: 3
rtecs: NL3650000
hs_code: 29339980
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 22-24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
Precautionary statements: P261-P271-P280

Chemistry & industry

Pharmacology

Tissue LocationsBrain；Liver；Neuron；Platelet；Prostate；Spleen；Testis

Cellular LocationsCytoplasm；Mitochondria

Metabolite PathwaysTryptophan metabolism

Uses & manufacturing

UsesIndole-3-acetic acid is a naturally occurring plant-growth hormone; [EPA]

Applications · 4 items

Description5-hydroxy Indole-3-acetic acid (5-HIAA) is the primary metabolite of serotonin (5-HT; ). It is formed when 5-HT is metabolized by monamine oxidase and aldehyde dehydrogenase in the liver. 5-HIAA is excreted in urine and has been used as a biomarker for detection of neuroendocrine tumors and an internal standard for the quantification of serotonin metabolism in rat brain using mass spectrometry. 5-HIAA has also been associated with autism, insomnia, and chronic migraine.

Uses5-Hydroxyindole-3-acetic acid is a major serotonin metabolite.

Uses5-Hydroxyindole-3-acetic acid is an impurity of chlorpheniramine (C424300), an antihistaminic agent.

General Description5-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).