Indole-3-pyruvic acid (HCID 803)

Overview

3-(indol-3-yl)pyruvic acid is a 2-oxo monocarboxylic acid that is pyruvic acid substituted by a 1H-indol-3-yl group at position 3. It has been found in Lycopersicon esculentum. It has a role as a Saccharomyces cerevisiae metabolite and a plant metabolite. It is an indol-3-yl carboxylic acid and a 2-oxo monocarboxylic acid. It is functionally related to a pyruvic acid. It is a conjugate acid of a 3-(indol-3-yl)pyruvate.

Names & identifiers

Preferred name: Indole-3-pyruvic acid
IUPAC: 3-(1H-indol-3-yl)-2-oxopropanoic acid
English name: 3-(3-Indolyl)-2-oxopropanoic acid
Molecular formula: C11H9NO3
Molecular weight: 203.19

Names & synonyms

Indole-3-pyruvic acid392-12-1indolepyruvateindol-3-yl pyruvic acidDTXSID30420531H-Indole-3-propanoic acid, alpha-oxo-alpha-Oxo-1H-indole-3-propanoic acid4QM0LT13A8NSC-88874DTXCID10220533-(1H-indol-3-yl)-2-oxidanylidene-propanoic acidRefChem:790954

Show more names

indole-3-pyruvicIndole-3-pyrubateTIMTEC-BB SBB003515INDOLE PYRUVIC ACID3-INDOLEPYRUVIC ACIDb-Indolepyruvic acid

206-874-13-(1H-Indol-3-yl)-2-oxopropanoic acidIndole-3-pyruvate3-Indolylpyruvic acidIndolepyruvic acid3-(indol-3-yl)pyruvic acidIndolyl-3-pyruvate3-(3-Indolyl)-2-oxopropanoic acid

Database identifiers

CAS: 392-12-1
PubChem CID: 803
DTXSID: DTXSID3042053
ChEMBL: CHEMBL485012
ChEBI: CHEBI:29750
UNII: 4QM0LT13A8
EC Number: 206-874-1
Nikkaji: J39.033J

Properties

Computed structural properties

XLogP: 1.3
Topological polar surface area: 70.2 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 3
Heavy atoms: 15
Formal charge: 0
Complexity: 277

Experimental & physicochemical properties

Collision Cross Section · 4 items

141.6 Å² [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID3042053]

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

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

137.8 Å² [M-H]-

Physicochemical properties

Melting point: 215 °C · 215 °C (dec.)(lit.)
Boiling point: 341.49 °C · 341.49°C (rough estimate)
Density: 1.2621 · 1.2621 (rough estimate)
refractive index: 1.495 · 1.4950 (estimate)
storage temp.: -20 °C · -20°C
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
pka: 2.61 · 2.61±0.54(Predicted)
color: light yellow
BRN: 172966 · 172966
InChI: 1S/C11H9NO3/c13-10(11(14)15)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H,14,15)
InChIKey: RSTKLPZEZYGQPY-UHFFFAOYSA-N
SMILES: OC(=O)C(=O)Cc1c[nH]c2ccccc12
CAS DataBase Reference: 392 · 392-12-1(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 4 QM0LT13A8 · 4QM0LT13A8
NIST Chemistry Reference: -3 · Indole-3-pyruvic acid(392-12-1)
EPA Substance Registry System: -3 · Indole-3-pyruvic acid (392-12-1)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs: Respiratory system
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36-24/25
WGK Germany: 3 · 3
RTECS: 1880000 · NM1880000
F: 8 · 8-10-23
HS Code: 2933998090 · 2933998090
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

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

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

F: 8-10-23
PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
rtecs: NM1880000
hs_code: 2933998090
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36-24/25
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 3 items

Drugs used to prevent SEIZURES or reduce their severity.

Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here.

Substances that eliminate free radicals. Among other effects, they protect PANCREATIC ISLETS against damage by CYTOKINES and prevent myocardial and pulmonary REPERFUSION INJURY.

Applications · 2 items

Description3-(3-Indolyl)-2-oxopropanoic acid is an important organic compound and an important precursor for the preparation of tryptophan. Tryptophan and D-tryptophan, and DL-tryptophan can also be synthesized by amination hydrogenation. In addition, 3-(3-Indolyl)-2-oxopropanoic acid is an intermediate in the conversion of tryptophan to indoleacetic acid in plants. Indoleacetic acid is an important growth hormone in plants and also plays an important role in regulating plant growth.

UsesIndole-3-pyruvic acid can be used:As a precursor for the synthesis of chromopyrrolic acid by a heme-containing enzyme.As a reactant in the Biginelli-like scaffold syntheses.

Upstream & downstream products

Downstream products

Pyruvic acid

Suppliers50 total

上海康恩博医药科技有限公司17510465506 · [email protected]

上海策嵘生物科技有限公司[email protected]

艾吉析科技（上海）有限公司17717235263 · [email protected]

南京修合医药科技有限公司19848384152 · [email protected]

上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]

Additional notes

DefinitionChEBI: A 2-oxo monocarboxylic acid that is pyruvic acid substituted by a 1H-indol-3-yl group at position 3. It has been found in Lycopersicon esculentum