29417-89-8

Usage

Uses

Used in the Pharmaceutical Industry:
Eugenol is utilized as an active ingredient in the pharmaceutical sector, particularly for its anti-inflammatory and analgesic effects. It is often incorporated into medications aimed at alleviating pain and reducing inflammation, making it a valuable component in the development of various pharmaceutical products.
Used in the Food Industry:
In the food industry, eugenol serves as a flavoring agent and fragrance, adding a unique taste and aroma to a variety of products. Its natural and pleasant scent makes it a popular choice for enhancing the sensory experience of food items, contributing to its widespread use in this sector.
Used in Oral Hygiene Products:
Eugenol's antimicrobial properties make it a suitable ingredient for oral hygiene products, such as mouthwashes and toothpastes. It helps in maintaining oral health by combating bacteria and promoting a clean and fresh mouth environment.
Used in Natural Remedies:
Due to its antioxidant, anti-inflammatory, and antimicrobial characteristics, eugenol is also employed in the formulation of natural remedies. It is often used in traditional medicine and herbal formulations to address various health concerns, highlighting its versatility as a natural therapeutic agent.

Upstream product

• 1738-36-9 2-methoxyacetonitrile 
• 6921-34-2 benzylmagnesium chloride 
• 107940-09-0 (2-methoxy-1-trimethylsilyloxy-vinyloxy)-trimethyl-silane 
• 103-80-0 phenylacetyl chloride 
• 67-56-1 methanol 
• 4250-02-6 1-diazo-3-phenyl-2-propanone 
• 71-43-2 benzene 
• 69438-62-6 acide phenyl-1 dibromo-2,2 cyclopropane carboxylique 
• 22174-59-0 (3-methoxyprop-1-yn-1-yl)benzene 
• 140-29-4 phenylacetonitrile 
• 4455-77-0 (methoxymethyl)diphenylphosphine oxide 
• 300-57-2 allylbenzene 
• 95092-10-7 N-methoxy-N-methyl-2-phenylacetamide 
• 107-30-2 chloromethyl methyl ether 

Downstream Products

• 332135-43-0 2-benzyl-7-pyrazyl-3-methoxyquinoline 
• 332135-42-9 2-benzyl-7-bromo-3-methoxyquinoline 
• 160332-68-3 (R)-1-methoxy-3-phenyl-2-propanol 
• 586-38-9 3-Methoxybenzoic acid 

Relevant academic research and scientific papers

Highly efficient synthesis of functionalized α-oxyketones: Via Weinreb amides homologation with α-oxygenated organolithiums

An efficient, chemoselective homologation of Weinreb amides to the corresponding variously substituted α-oxyketones has been developed via the addition of lithiated α-oxygenated species. This one-step, experimentally easy, high yielding protocol is amenable not only for accessing simple α-oxyketones but also for more complex substituted ones ranging from primary and secondary alkyl-type to aromatic ones. Full delivery of the stereochemical information contained in the starting materials is observed through both the employment of enantioenriched Weinreb amides and optically active organolithium species.

Reaction of phosphonium ylides and aromatic nitriles under lewis acid conditions: An easy access to aryl-substituted α-methoxyacetophenones

In the presence of lithium chloride, as Lewis acid, the reaction of methoxymethyltriphenylphosphonium ylide 1 with aromatic nitriles 2 as phenacyl cation equivalents gives access to the corresponding α- methoxyacetophenones 3 in good yields.

Silver ion-assisted solvolysis of 2,2-dibromo-1-phenylcyclopropanecarboxylic acid: Solvent-dependent competition between decarboxylation and ring closure

The solvolysis of the title compound has been studied in several alcohols (methanol, 2,2,2-trifluoroethanol, isopropyl alcohol, tert-butyl alcohol and ,1,1,3,3,3-hcxafluoro-2-propanol [HFP]) in the presence of an excess of silver trifluoroacetale. In all solvents the corresponding butenolide, 4-bromo-3-phenyl-2(5H)-furanone, was a major or the predominant product. Another product formed in all solvents but HFP was (Z)-4-alkoxy-3-bromo-2-phenyl-2-butenoic acid, which resulted from solvent attack on intermediate allylic cations. Furthermore, both 3-alkoxy-1-phenyl-1-propyne and 3-alkoxy-1-phenyl-1-propanone were formed except when reactions were performed in HFP; their formation involved decarboxylation and their total yield was 15-40%. Acta Chemica Scandinavica 1998.

Indium(III) chloride-promoted rearrangement of epoxides: A selective synthesis of substituted benzylic aldehydes and ketones

A simple and efficient procedure for the rearrangement of substituted epoxides catalyzed by InCl3 has been developed. Aryl-substituted epoxides isomerize with complete regioselectivity to form a single carbonyl compound via cleavage of the benzylic C-O bond. The reactions are simple, fast, and high yielding. This procedure is very mild compared to those catalyzed with BF3 and other Lewis acids and compatible with several acid-sensitive functionalities. This protocol provides a highly selective synthesis of substituted benzylic aldehydes and ketones. However, rearrangement of alkyl- substituted epoxides is not very selective.

Baker's yeast-mediated reduction of α-hydroxy ketones and derivatives: The steric course of the biotransformation

The results from the baker's yeast-mediated reduction of the acetates 3a- d and the methyl ethers 5a-d were compared with the same biotransformation which converts the α-hydroxy ketones 1a-d into the (R)-diols 2a-d (90- 98%ee); the acetates 3a-d afford the (S)-monoacetates 4a-d (72-94% ee) and the methyl ethers 5a-d are reduced to the (R)-monoethers 6a-d (64-76% ee).

Alkylation of Benzene with α-Diazoketones via Cycloheptatrienyl Intermediates

Benzyl ketones can be synthesised efficiently from benzene and α-diazoketones with sequential catalysis by rhodium(II) trifluoroacetate and trifluoroacetic acid; the process involves cycloheptatrienyl intermediates.

Metallic Nickel-Mediated Synthesis of Ketones by the Reaction of Benzylic, Allylic, Vinylic, and Pentafluorophenyl Halides with Acid Halides

Metallic nickel was investigated as a convenient coupling reagent for the synthesis of ketones by the reaction of benzylic, allylic, vinylic, and pentafluorophenyl halides with acid halides at 85 deg C in glyme.A variety of benzylic ketones with functional groups including halogen, cyano, methoxycarbonyl, and hydroxycarbonyl groups were prepared in good yields by this method.The reaction was demonstrated to proceed via organonickel halide intermediates formed by the smooth oxidative addition of benzylic and acyl halides to metallic nickel, which were trapped with electron-deficient olefins. (?-Allyl)nickel halides, prepared in situ at 85 deg C from allylic halides and the nickel, also worked for the preparation of ketones.Vinylic and pentafluorophenyl halides but not alkyl halides reacted with acid halides to give the corresponding ketones in moderate yields.

Mechanism of the Photochemical Wolff Rearrangement. The Role of Conformation in the Photolysis of α-Diazo Carbonyl Compounds.

Investigation of photochemical processes of several α-diazo carbonyl compounds reveals that the Wolff rearrangement to form ketene takes place directly from the singlet excited state of the s-Z conformer whereas the excited state of the s-E conformer dissociates nitrogen to generate singlet carbonyl carbene, which either undergoes characteristic carbenic reactions, e.g., insertion and 1,2-hydrogen shift, or gives rise to ketene.The migratory aptitude as well as the relative efficiency of other competing reactions from singlet carbene is shown to be an important factor in dete rmining which reaction pathway is favored.Substantial amounts of singlet carbene can be formed even under sensitized conditions, presumably via intersystem crossing from initially formed triplet carbene.