20675-95-0

Usage

Uses

Used in Food Industry:
Eugenol is used as a flavoring agent in the food industry due to its distinctive, spicy taste that enhances the flavor profile of various food products.
Used in Fragrance Industry:
In the fragrance industry, eugenol is utilized as a component in perfumes and soaps, where its pleasant aroma contributes to the overall scent profile.
Used in Oral Health Products:
Eugenol is employed as an active ingredient in oral health products, such as dental cements and temporary filling materials, due to its antiseptic, analgesic, and anti-inflammatory properties, which help in reducing pain and inflammation in the oral cavity.
Used in Traditional Medicine:
In traditional medicine, eugenol is used for its therapeutic benefits, including its antiseptic, analgesic, and anti-inflammatory actions, making it a popular remedy for various ailments.
Used in Pharmaceutical Industry:
Eugenol has potential applications in the pharmaceutical industry due to its antimicrobial properties, which can be harnessed for the development of new antibiotics or as an adjunct to existing treatments.
Used in Agricultural Industry:
In agriculture, eugenol's insecticidal properties make it a candidate for the development of eco-friendly pest control solutions, reducing the reliance on chemical pesticides.
The provided materials do not include specific application reasons for each industry, so the uses listed are based on the general properties and known applications of eugenol.

InChI:InChI=1/C11H14O3/c1-4-5-8-6-9(13-2)11(12)10(7-8)14-3/h4-7,12H,1-3H3/b5-4+

Upstream product

• 6627-88-9 4-allyl-2,6-dimethoxyphenol 
• 58623-87-3 2,6-dimethoxy-4-(2-propenylidene)-2,5-cyclohexadien-1-one 
• 94930-90-2 sinapyl acetate 
• 71051-98-4 Isobutyric acid 2,6-dimethoxy-4-((E)-propenyl)-phenyl ester 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 5438-54-0 1,3-dimethoxy-2-[(prop-2-en-1-yl)oxy]benzene 
• 20675-96-1 Syringenin 
• 1530-32-1 ethyltriphenylphosphonium bromide 
• 134-96-3 syringic aldehyde 
• 6635-22-9 2,6-dimethoxy-4-(prop-1-en-1-yl)-phenol 

Downstream Products

• 89706-47-8 1-(4-hydroxy-3,5-dimethoxyphenyl)-2-<2,6-dimethoxy-4-(1-propenyl)phenoxy>propane 
• 89706-37-6 4-{2-[2,6-Dimethoxy-4-((E)-propenyl)-phenoxy]-propylidene}-2,6-dimethoxy-cyclohexa-2,5-dienone 
• 50544-08-6 5,5'-(2,3-dimethylbutane-1,4-diyl)bis(1,2,3-trimethoxybenzene) 
• 50513-74-1 trans-6,7,8-trimethoxy-2,3-dimethyl-1-(3,4,5-timethoxyphenyl)-1,2-dihydronaphthalene 
• 657393-29-8 (2S)-(2,6-dimethoxy-4-propenyl-phenoxy)-1-(3,4,5-trimethoxy-phenyl)-propan-1-one 
• 487-12-7 isoelemicin 
• 835922-48-0 (S)-1-(3,4,5-trimethoxyphenyl)-2-propanol 
• 835922-46-8 (R)-1-(3,4,5-trimethoxyphenyl)-2-propanol 
• 32883-50-4 1-(3,4,5-trimethoxyphenyl)propan-2-ol 

Relevant academic research and scientific papers

Total synthesis of (±)-Eusiderin K and (±)-Eusiderin J

(±)-Eusiderin K and (±)-Eusiderin J were first synthesized from pyrogallol, in which the Claisen Rearrangement was used to afford two important C6-C3 units.

Total synthesis of six natural products of benzodioxane neolignans

(±)-Eusiderin E, (±)-Eusiderin F, (±)-Eusiderin K, (±)-Eusiderin J, (±)-Eusiderin M and (±)-Eusiderin G were first synthesized from pyrogallol, in which the Claisen Rearrangement was used to afford two important C6-C3 units.

Photoacid-Enabled Synthesis of Indanes via Formal [3 + 2] Cycloaddition of Benzyl Alcohols with Olefins

An environmentally friendly and highly diastereoselective method for synthesizing indanes has been developed via a metastable-state photoacid system containing catalytic protonated merocyanine (MEH). Under visible-light irradiation, MEH yields a metastable spiro structure and liberated protons, which facilitates the formation of carbocations from benzyl alcohols, thus delivering diverse molecules in the presence of various nucleophiles. Mainly, a variety of indanes could be easily obtained from benzyl alcohols and olefins, and water is the only byproduct.

Synthesis, antiepileptic effects, and structure-activity relationships of α-asarone derivatives: In vitro and in vivo neuroprotective effect of selected derivatives

In the present study, we compared the antiepileptic effects of α-asarone derivatives to explore their structure-activity relationships using the PTZ-induced seizure model. Our research revealed that electron-donating methoxy groups in the 3,4,5-position on phenyl ring increased antiepileptic potency but the placement of other groups at different positions decreased activity. Besides, in allyl moiety, the optimal activity was reached with either an allyl or a 1-butenyl group in conjugation with the benzene ring. The compounds 5 and 19 exerted better neuroprotective effects against epilepsy in vitro (cell) and in vivo (mouse) models. This study provides valuable data for further exploration and application of these compounds as potential anti-seizure medicines.

A Next-Generation Air-Stable Palladium(I) Dimer Enables Olefin Migration and Selective C?C Coupling in Air

We report a new air-stable PdI dimer, [Pd(μ-I)(PCy2tBu)]2, which triggers E-selective olefin migration to enamides and styrene derivatives in the presence of multiple functional groups and with complete tolerance of air. The same dimer also triggers extremely rapid C?C coupling (alkylation and arylation) at room temperature in a modular and triply selective fashion of aromatic C?Br, C?OTf/OFs, and C?Cl bonds in poly(pseudo)halogenated arenes, displaying superior activity over previous PdI dimer generations for substrates that bear substituents ortho to C?OTf.

Controllable synthesis of 2- And 3-aryl-benzomorpholines from 2-aminophenols and 4-vinylphenols

We present herein a method for the controllable synthesis of 3-aryl-benzomorpholine and 2-aryl-benzomorpholine cycloadducts via cross-coupling/annulation between electron-rich 2-aminophenols and 4-vinylphenols. Molecular oxygen was successfully used in the reaction as the terminal oxidant and the complete inversion of chemoselectivity was achieved by the adjustment of the solvents and bases at room temperature.

Hydrophilic (ν6-Arene)-Ruthenium(II) Complexes with P-OH ligands as catalysts for the isomerization of allylbenzenes and C-H bond arylation reactions in water

Half-sandwich ruthenium(II) complexes containing ν6-coordinated 3-phenylpropanol and phosphinous-acid-type ligands, namely, [RuCl2(ν6-C6H5CH2CH2CH2OH){P(OH)R2}] (R = Me (2a), Ph (2b), 4-C6H4CF3 (2c), 4-C6H4OMe (2d), OMe (2e), OEt (2f), and OPh (2g), have been synthesized in 44-88% yield by reacting [RuCl2{ν6:κ1(O)-C6H5CH2CH2CH2OH}] (1) with the appropriate pentavalent phosphorus oxide R2P(═O)H. The structure of [RuCl2(ν6-C6H5CH2CH2CH2OH){P(OH)Me2}] (2a) was unequivocally confirmed by X-ray diffraction methods. Compounds 2a-g proved to be catalytically active in the isomerization of allylbenzenes into the corresponding (1-propenyl)benzene derivatives employing water as the sole reaction solvent, with [RuCl2(ν6-C6H5CH2CH2CH2OH){P(OH)(OPh)2}] (2g) showing the best performance and a broad substrate scope (73-93% isolated yields with E/Z ratios around 90:10 employing 1 mol % of 2g and 3 mol % of K2CO3, and performing the catalytic reactions at 80 °C for 4-24 h). The results herein presented show for the first time the utility of phosphinous acids as auxiliary ligands for metal-catalyzed olefin isomerization processes, reactions in which a cooperative role for the P - OH unit is proposed. On the other hand, the utility of complexes 2a-g as catalysts for ortho-arylation reactions of 2-phenylpyridine in water is also briefly discussed.

Lignin Valorization by Cobalt-Catalyzed Fractionation of Lignocellulose to Yield Monophenolic Compounds

Herein, a catalytic reductive fractionation of lignocellulose is presented using a heterogeneous cobalt catalyst and formic acid or formate as a hydrogen donor. The catalytic reductive fractionation of untreated birch wood yields monophenolic compounds in up to 34 wt % yield of total lignin, which corresponds to 76 % of the theoretical maximum yield. Model compound studies revealed that the main role of the cobalt catalyst is to stabilize the reactive intermediates formed during the organosolv pulping by transfer hydrogenation and hydrogenolysis reactions. Additionally, the cobalt catalyst is responsible for depolymerization reactions of lignin fragments through transfer hydrogenolysis reactions, which target the β-O-4′ bond. The catalyst could be recycled three times with only negligible decrease in efficiency, showing the robustness of the system.

Concise access toward chiral hydroxy phenylpropanoids: formal synthesis of virolongin B; kigelin; kurasoin A; 4-hydroxysattabacin, and actinopolymorphol A

A simple, two step strategy consisting of Sharpless asymmetric dihydroxylation followed by regioselective breaking of [Formula presented] bond is utilized to target key chiral intermediates of natural products virolongin B, kigelin, kurasoin A, 4-hydroxy-sattabacin, and actinopolymorphol A. Derivatives of enantiopure hydroxy phenyl propanoids and α-hydroxy Weinreb amides are synthesized. The reductive cleavage of [Formula presented] bond in a regioselective manner is obtained using Pd/C in methanol.

Streamlined, asymmetric synthesis of 8,4′-oxyneolignans

Highly direct, modular syntheses of several natural 8,4′- oxyneolignans [(-)-1, (+)-1, (-)-2, and (-)-3] and some related variants [(-)-26, (+)-26, (+)-27, and (-)-28] are reported. Utilizing (S)- or (R)-methyl lactate as the chiral sources, two complementary syn- or anti-oriented routes were designed, encompassing nine and five steps, which were carried out to deliver the targets in an enantiomerically pure form. The embodiment of the two independent aryl and aryloxy moieties onto the lactate frame was performed according to a diversity-oriented protocol from the common precursors, aldehydes 6 and ent-6 for the syn-oriented routes and mesyl esters 19 and ent-19 for the anti-oriented routes. These syntheses set the stage for the generation of a wide and diverse repertoire of 8,4′-oxyneolignan compounds and the broad biological interrogation of its members.