1835-14-9 Usage
Description
4'-Hydroxy-3'-methoxypropiophenone, also known as 1-(4-Hydroxy-3-methoxyphenyl)-1-propanone, is a chemical compound derived from Guaiacol. It is characterized by the presence of a hydroxyl and methoxy group attached to a propiophenone structure, which contributes to its unique chemical properties and potential applications.
Uses
Used in Flavor and Fragrance Industry:
4'-Hydroxy-3'-methoxypropiophenone is used as a precursor for the synthesis of various flavorants and fragrances, such as eugenol and vanillin. Its unique chemical structure allows it to be a versatile building block in the creation of a wide range of aromatic compounds, enhancing the sensory experience in food, beverages, and perfumery products.
As a derivative of Guaiacol, 4'-Hydroxy-3'-methoxypropiophenone plays a crucial role in the development of new and innovative flavor profiles, contributing to the ever-evolving landscape of the flavor and fragrance industry. Its ability to be transformed into other aromatic compounds makes it a valuable asset in the synthesis of complex and desirable scents and tastes.
Preparation
Preparation by Fries rearrangement of 2-methoxyphenyl propionate, (b.p.20 140–143°)with aluminium chloride in nitrobenzene, first at 60–80° for 1 h, then at r.t. overnight, at 60° for 1 h or at 50° for 5 h (44%) ;with aluminium chloride (2 mol) in nitromethane at r.t. for 24 h (65%)with aluminium chloride in carbon disulfidewith titanium tetrachloride (2 mol) in nitromethane at r.t. for 24 h (62%)with stannic chloride (2 mol) in nitromethane at r.t. for 24 h (69%)with antimony pentachloride (2 mol) in nitromethane at r.t. for 24 h (28%) with formation of important tars.
Synthesis Reference(s)
The Journal of Organic Chemistry, 15, p. 227, 1950 DOI: 10.1021/jo01148a001
Check Digit Verification of cas no
The CAS Registry Mumber 1835-14-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,3 and 5 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1835-14:
(6*1)+(5*8)+(4*3)+(3*5)+(2*1)+(1*4)=79
79 % 10 = 9
So 1835-14-9 is a valid CAS Registry Number.
InChI:InChI=1/C10H12O3/c1-3-8(11)7-4-5-9(12)10(6-7)13-2/h4-6,12H,3H2,1-2H3
1835-14-9Relevant articles and documents
Pew,Connors
, p. 585,588 (1969)
Non-plasmonic Ni nanoparticles catalyzed visible light selective hydrogenolysis of aryl ethers in lignin under mild conditions
Baeyens, Jan,Li, Peifeng,Ouyang, Yixuan,Sarina, Sarina,Su, Haijia,Xiao, Gang,Zhao, Yilin,Zhu, Huai-Yong
supporting information, p. 7780 - 7789 (2021/10/12)
Light-driven catalysis on catalytically versatile group VIII metals, which has been widely used in thermal catalysis, holds great potential in solar-to-chemical conversion. We report a novel photocatalysis process for the selective hydrogenolysis of aryl ethers in lignin on a heterogeneous catalyst of non-precious Ni nanoparticles supported on ZrO2. Three aryl ether bonds in lignin were successfully cleaved under mild conditions with excellent conversion and good to excellent selectivity under visible light irradiation. We also used solar irradiation to demonstrate a significant reduction in the total energy consumption. The light irradiation excited interband transitions in Ni nanoparticles and the resultant energetic electrons enhanced the activity of reductive cleavage of the aryl ethers. Its application potential was illustrated by the depolymerization of dealkaline lignin to give a total monomer yield of 9.84 wt% with vanillin, guaiacol, and apocynin as the three major products.
A convenient synthetic approach to dioncoquinone B and related compounds
Khmelevskaya, Ekaterina A.,Pelageev, Dmitry N.
supporting information, p. 1022 - 1024 (2019/03/13)
A total synthesis of dioncoquinone B and related compounds, including ancistroquinones B, C and malvon A, is presented. The strategy is based on available reagents and can be used as a preparative synthesis of a number of natural and synthetic biologically active (3-alkyl)-2,7,8-di(tri)methoxy(hydroxy)-1,4-naphthoquinones.