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3-Indolepropionic acid structure
3-Indolepropionic acid structure

3-Indolepropionic acid

Iupac Name:3-(1H-indol-3-yl)propanoic acid
CAS No.: 830-96-6
Molecular Weight:189.21054
Modify Date.: 2022-11-29 04:25

3-Indolepropionic acid is shown to be a powerful antioxidant and has potential in the treatment for Alzheimer’s disease.


3-(1H-indol-3-yl)propanoic acid is an indol-3-yl carboxylic acid that is propionic acid substituted by a 1H-indol-3-yl group at position 3. It has a role as an auxin, a human metabolite and a plant metabolite. It derives from a propionic acid. It is a conjugate acid of a 3-(1H-indol-3-yl)propanoate.

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1. Names and Identifiers
1.1 Name
3-Indolepropionic acid
1.2 Synonyms

1H-Indole-3-propanoic acid 2-HYDROXYPROPANE 2-PPROPANOL 3-(1H-INDOL-3-YL)PROPANOIC ACID 3-(1H-Indol-3-yl)propionic acid 3-(1H-INDOL-3-YL)-PROPIONIC ACID 3-(3-INDOLYL)PROPANOIC ACID 3-(3-INDOLYL)-PROPIONIC ACID AKOS BBS-00004245 AKOS BBS-00006584 b-(3-Indolyl)propionic acid EINECS 212-600-1 Indole-3-propionic acid IPA MFCD00005660

1.3 CAS No.
1.4 CID
1.6 Molecular Formula
C11H11NO2 (isomer)
1.7 Inchi
1.8 InChkey
1.9 Canonical Smiles
1.10 Isomers Smiles
2. Properties
2.1 Density
0.960 g/mL at 20 °C
2.1 Melting point
2.1 Boiling point
82 °C(lit.)
2.1 Refractive index
n20/D 1.377(lit.)
2.1 Flash Point
53 °F
2.2 Precise Quality
2.2 PSA
2.2 logP
2.2 Solubility
ethanol: soluble50mg/mL, clear, yellow to orange
2.3 VaporDensity
2.1 (vs air)
2.4 Appearance
2.5 Storage
Ambient temperatures.
2.6 Chemical Properties
pale yellow to yellow crystalline powder
2.7 Color/Form
light yellow
2.8 pKa
2.9 Water Solubility
slightly soluble
2.10 Stability
Stable under normal temperatures and pressures.
2.11 StorageTemp
Sealed in dry,Room Temperature
3. Use and Manufacturing
3.1 Definition
ChEBI: An indol-3-yl carboxylic acid that is propionic acid substituted by a 1H-indol-3-yl group at position 3.
3.2 Purification Methods
Recrystallise it from EtOH/water [James & Ware J Phys Chem 89 5450 1985]. The picrate has m 143-144o, and the methyl ester crystallises from *C6H6 or MeOH with m 81-83o. [Beilstein 22 III/IV 1113, 22/3 V 114.] 3-Indolepropionic acid Preparation Products And Raw materials Raw materials
3.3 Usage


4. Safety and Handling
4.1 Hazard Codes
4.1 Risk Statements
4.1 Safety Statements
4.1 Hazard Declaration
UN 1987 3/PG 3
4.1 Caution Statement
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
4.1 WGK Germany
4.1 Specification

The 3-Indolepropionic acid, with the?CAS registry number830-96-6, has the IUPAC name of 3-(1H-indol-3-yl)propanoic acid. For being a kind of pale yellow to yellow crystalline powder, it is slightly soluble in water, ethanol, diethyl ether, acetone, benzene, chloroform and soluble in hot water while insoluble in cold water. It has a variety of product categories which include blocks; Carboxes; IndolesOxindoles; indole derivative; Indoles and derivatives; IndoleDerivative; Auxins; Biochemistry; Plant Growth Regulators; Simple Indoles. As to its usage, it is usually applied as the plants grow stimulin.

The physical properties of this chemical are as follows: (1)ACD/LogP: 1.76; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1; (4)ACD/LogD (pH 7.4): -0.79; (5)ACD/BCF (pH 5.5): 2.22; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 37.32; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 31.23; (13)Index of Refraction: 1.666; (14)Molar Refractivity: 54.27 cm3; (15)Molar Volume: 145.8 cm3; (16)Polarizability: 21.51×10-24 cm3; (17)Surface Tension: 61.8 dyne/cm; (18)Density: 1.297 g/cm3; (19)Flash Point: 206.4 °C; (20)Enthalpy of Vaporization: 70.75 kJ/mol; (21)Boiling Point: 417.6 °C at 760 mmHg; (22)Vapour Pressure: 1.01E-07 mmHg at 25°C; (23)Exact Mass: 189.078979; (24)MonoIsotopic Mass: 189.078979; (25)Topological Polar Surface Area: 53.1; (26)Heavy Atom Count: 14; (27)Complexity: 217.

The production method of this chemical: BAPNA have the diazotization reaction with sodium nitrite in the acidic condition, and then react with ethyl cyclopentanone-2-carboxylate to produce α-oxoethyldioic acid phenylhydrazone; Secondly, phenylhydrazone dissolve in the alcohol solution containing 20% sulfuric acid and have the reflux reaction for 4 hours to produce indole-2-carboxylic acid-3-propanoic acid; Thirdly heat it to 225-230℃ for half an hour till its reation finishs, and then dissolve the reactant into the boiling water and filter it after adding active carbon; Next concentrate the colatuie and crystallize and then go through the recrystallization with hot water to obtain this chemical.

When you are dealing with this chemical, you should be much more cautious. For being among the? irritant chemicals, it is irritating to eyes, respiratory system and skin and may cause inflammation to the skin or other mucous membranes. For anther thing, it is highly flammable and its vapours may cause drowsiness and dizziness.

Therefore, you should take the following instructions to protect yourself. Wear suitable protective clothing, gloves and eye/face protection and then avoid contacting with skin and eyes. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. When store it, keep the container tightly closed, away from sources of ignition - No smoking. Besides, do not breathe dust.
Additionally, you could obtain the molecular structure by converting the following datas:
(1)Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CCC(=O)O
(2)InChI: InChI=1S/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14)

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo intraperitoneal 100mg/kg (100mg/kg) LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA

Proceedings of the Society for Experimental Biology and Medicine. Vol. 34, Pg. 138, 1936.

4.2 Toxicity
LDLo intraperitoneal in mouse: 100mg/kg

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Signal word


Hazard statement(s)

H315 Causes skin irritation

H319 Causes serious eye irritation

H335 May cause respiratory irritation

Precautionary statement(s)








2.3 Other hazards which do not result in classification


9. Other Information
9.0 Usage
Indole-3-propionic acid is a reactant for preparation of fluorescent analogues of strigolactones, melanocortin receptors ligands, histamine H4 receptor agonists, and NR2B/NMDA receptor antagonists. It is also used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. It is also used to Study as an adjunct to improve perfusion after liver transplant.
9.1 Mesh Entry Terms
indole propionate
9.2 Manufacturing Info
1H-Indole-3-propanoic acid: INACTIVE
9.3 BRN
9.4 Description
Indole-3-propionic acid is a bacterial metabolite that has antioxidant and neuroprotective activities. It scavenges ABTS (Item No. 27317) radicals in a cell-free assay when used at concentrations ranging from 50 to 150 μM and decreases hydrogen peroxide-induced malondialdehyde (MDA) levels in rat striatal membranes (IC50 = 180 μM). Indole-3-propionic acid also decreases increases in MDA levels induced by amyloid β (1-42) (Item No. 20574) in PC12 cells. It decreases ischemia-induced increases in cell death of pyramidal neurons and levels of 4-hydroxy nonenal (HNE; Item No. 32100) and glial fibrillary acidic protein (GFAP) in the hippocampal CA1 region in gerbils when administered at a dose of 10 mg/kg per day.
9.5 Chemical Properties
pale yellow to yellow crystalline powder
9.6 Uses
3-Indolepropionic acid is a deamination product of Tryptophan (T947200) that protects the hippocampus (studied in gerbils) from ischemic damage and oxidative stress. It’s ability to protect the neurons in this way is attributed to its potent antioxidative effects. 3-Indolepropionic acid is also hypothesized to have protective effects on the thyroid gland.
9.7 Uses
Reactant for preparation of:
  • Fluorescent analogues of strigolactones
  • Anti-tumor agents
  • Melanocortin receptors ligands
  • Immunosuppressive agents
  • Iinhibitors of hepatitis C virus
  • Histamine H4 receptor agonists
  • NR2B/NMDA receptor antagonists
  • CB1 antagonist for the treatment of obesity
  • Antibacterial agents
  • Inhibitor of TGF-β receptor binding
Indole-3-propionic acid may be used in the synthesis of oxindole-3-propionic acid via reaction with N-bromosuccinimide in acetic acid followed by treatment with H2/Pd catalyst.
10. Computational chemical data
  • Molecular Weight: 189.21054g/mol
  • Molecular Formula: C11H11NO2
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 189.078978594
  • Monoisotopic Mass: 189.078978594
  • Complexity: 217
  • Rotatable Bond Count: 3
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 2
  • Topological Polar Surface Area: 53.1
  • Heavy Atom Count: 14
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
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