65287-96-9

Basic information

• Product Name: 4-(2-HYDROXYETHYL)-5-METHYL-1,2-DIHYDRO-3H-PYRAZOL-3-ONE
• Synonyms: 4-(2-HYDROXYETHYL)-5-METHYL-1,2-DIHYDRO-3H-PYRAZOL-3-ONE;1,2-Dihydro-4-(2-hydroxyethyl)-5-methyl-3H-pyrazol-3-one;2,3-Dihydro-4-(2-hydroxyethyl)-5-methyl-3-oxo-1H-pyrazole;4-(2-hydroxyethyl)-5-methyl-1,2-dihydropyrazol-3-one;4-(2-hydroxyethyl)-5-methyl-2,4-dihydro-3H-pyrazol-3-one;4-(2-Hydroxy-ethyl)-5-methyl-2H-pyrazol-3-ol
• CAS NO: 65287-96-9
• Molecular Formula: C6H10N2O2
• Molecular Weight: 142.16
• Mol File: 65287-96-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 185-188
• Appearance: /
• Density: 1.168 g/cm³
• Refractive Index: 1.5
• CAS DataBase Reference: 4-(2-HYDROXYETHYL)-5-METHYL-1,2-DIHYDRO-3H-PYRAZOL-3-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-HYDROXYETHYL)-5-METHYL-1,2-DIHYDRO-3H-PYRAZOL-3-ONE(65287-96-9)
• EPA Substance Registry System: 4-(2-HYDROXYETHYL)-5-METHYL-1,2-DIHYDRO-3H-PYRAZOL-3-ONE(65287-96-9)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 65287-96-9(Hazardous Substances Data)

Usage

General Description

4-(2-Hydroxyethyl)-5-methyl-1,2-dihydro-3H-pyrazol-3-one, also known as ethylmaltol, is a synthetic organic compound with a molecular formula C7H10N2O2. It is a white crystalline powder with a sweet, caramel-like odor, and it is commonly used as a flavor enhancer in food and beverages. Ethylmaltol is known for its ability to enhance the sweetness and aroma of various products, particularly in the food industry. It is also used in the production of tobacco products and is added to e-liquids for electronic cigarettes to create a sweeter flavor. Additionally, ethylmaltol has been studied for its potential antioxidant and anti-inflammatory properties, making it a compound of interest in the pharmaceutical and cosmetic industries.

InChI:InChI=1/C6H10N2O2/c1-4-5(2-3-9)6(10)8-7-4/h9H,2-3H2,1H3,(H2,7,8,10)

Upstream product

• 517-23-7 3-acetyl-2-oxo-4,5-dihydrofuran 

Downstream Products

• 7721-57-5 7-methyl-5,6-diazaspiro[2.4]hept-6-en-4-one 

Relevant articles and documents

3-pyrazolone analogues of the 3-isoxazolol metabotropic excitatory amino acid receptor agonist homo-AMPA. Synthesis and pharmacological testing

We have previously shown that the higher homologue of (S)-glutamic acid [(S)-Glu], (S)-α-aminoadipic acid [(S)-α-AA] is selectively recognized by the mGlu2 and mGlu6 subtypes of the family of metabotropic glutamic acid (mGlu) receptors. Furthermore, a number of analogues of (S)-α-AA, in which the terminal carboxyl group has been replaced by various bioisosteric groups, such as phosphonic acid or 3-isoxazolol groups, have been shown to interact selectively with different subtypes of mGlu receptors. In this paper we report the synthesis of the 3-pyrazolone bioisosteres of α-AA, compounds (RS)-2-amino-4-(1,2-dihydro-5-methyl-3-oxo-3H-pyrazol-4-yl)butyric acid (1) and (RS)-2-amino-4-(1,2-dihydro-1,5-dimethyl-3-oxo-3H-pyrazol-4-yl)butyric acid (2). At a number of steps in the reaction sequences used, the reactions took unexpected courses and provided products which could not be transformed into the target compounds, and attempts to synthesize the 2,5-dimethyl isomer of 2, compound 3, failed. An X-ray crystallographic analysis of the intermediate 1,2-dihydro-4-(2-hydroxyethyl)-2,5-dimethyl-3H-pyrazol-3-one (5b) confirmed the expected regioselectivity of the reaction between methylhydrazine and α-acetylbutyrolactone (4). Neither 1 nor 2 showed significant effects at the different types of ionotropic glutamic acid receptors or at mGlu(1a) (group I), mGlu2 (group II), and mGlu(4a) and mGlu6 (group III) receptors, representing the three indicated groups of mGlu receptors.