501-19-9

Usage

Uses

Used in Food and Beverage Industry:
Eugenol is used as a flavoring agent in the food and beverage industry, imparting a unique taste and aroma to various products. Its natural origin and pleasant scent make it a popular choice for enhancing the flavor profile of food items and beverages.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, eugenol is employed for its antimicrobial, anti-inflammatory, and analgesic properties. It is a key ingredient in toothpaste, mouthwash, and topical pain relief products, helping to combat oral bacteria, reduce inflammation, and alleviate pain.
Used in Cosmetic Industry:
Eugenol is utilized in the cosmetic industry as a fragrance component in perfumes and personal care products. Its natural and pleasant aroma adds a desirable scent to these products, enhancing their appeal to consumers.
Used in Antimicrobial Applications:
Eugenol is used as an antimicrobial agent, effectively inhibiting the growth of various microorganisms. This property makes it suitable for use in products that require preservation and protection against microbial contamination.
Used in Anti-inflammatory and Analgesic Applications:
Due to its anti-inflammatory and analgesic properties, eugenol is used in formulations for treating inflammation and pain. It can be found in topical creams, gels, and ointments, providing relief from muscle aches, joint pain, and other inflammatory conditions.
However, it is important to note that eugenol can also act as a potential irritant and sensitizer, especially when used in high concentrations. Therefore, it should be used with caution and in appropriate amounts to ensure safety and effectiveness.

InChI:InChI=1/C10H12O2/c1-3-4-8-5-6-10(12-2)9(11)7-8/h3,5-7,11H,1,4H2,2H3

Synthetic route

5-allyl-2-methoxyphenyl acetate (1941-09-9) → chavibetol (501-19-9)

Conditions	Yield
With lithium hydroxide monohydrate; water In tetrahydrofuran; methanol for 3.5h;	84%

Estragole (140-67-0) → chavibetol (501-19-9)

Conditions	Yield
Stage #1: Estragole With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 2h; Stage #2: With Trimethyl borate In tetrahydrofuran; cyclohexane at 0℃; for 1h; Stage #3: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; cyclohexane; water at 20℃; for 2h;	72%

2-acetoxy-4-chloro-1-methoxybenzene (66037-03-4) + allyl-trimethyl-silane (762-72-1) → chavibetol (501-19-9)

Conditions	Yield
With caesium carbonate In 2,2,2-trifluoroethanol for 18h; Irradiation;	57%

mucobromic acid (766-38-1) + chavibetol (501-19-9) → C14H13BrO4

Conditions	Yield
Stage #1: mucobromic acid; chavibetol With sodium hydroxide In water at 20℃; for 1h; Sonication; Stage #2: With sodium tetrahydroborate In water at 0℃; for 1h;	86%

2,3-epoxy-3-methylcyclohexanone (21889-89-4) + chavibetol (501-19-9) → 2-(5-allyl-2-methoxyphenoxy)-3-methylcyclohex-2-en-1-one

Conditions	Yield
With potassium carbonate In acetonitrile at 82℃; for 14h; Inert atmosphere;	77%

chavibetol (501-19-9) + dimethyl sulfoxide (67-68-5) → 5-(2-hydroxy-3-(methylthio)propyl)-2-methoxyphenol

Conditions	Yield
With ammonium iodide; water at 130℃; for 24h; Schlenk technique;	65%

Upstream product

• 917-64-6 methyl magnesium iodide 
• 93-15-2 1,2-dimethoxy-4-(2-propenyl)benzene 
• 74-96-4 ethyl bromide 
• 94-59-7 1-allyl-3,4-methylenedioxybenzene 
• 4125-43-3 O-allyl guaiacol 
• 56-23-5 tetrachloromethane 
• 60-29-7 diethyl ether 
• 108-88-3 toluene 
• 66037-03-4 2-acetoxy-4-chloro-1-methoxybenzene 
• 762-72-1 allyl-trimethyl-silane 
• 269410-23-3 2-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol 
• 1746-13-0 allyl phenyl ether 
• 140-67-0 Estragole 
• 120-80-9 benzene-1,2-diol 

Downstream Products

• 155583-46-3 2-ethoxy-4-allyl-1-methoxy-benzene 
• 1941-09-9 5-allyl-2-methoxyphenyl acetate 
• 92-42-2 4-methoxy-3-ethoxy-1-trans-propenyl-benzene 
• 105253-83-6 (5-allyl-2-methoxy-phenoxy)-acetic acid 
• 19754-21-3 1-allyl-2,3-dimethoxy-benzene 
• 645-08-9 Isovanillic acid 
• 60444-56-6 3-acetoxy-4-methoxybenzoic acid 
• 195140-75-1 3-(3-benzyloxy-4-methoxy-phenyl)-propane-1,2-diol 
• 19784-98-6 Isochavibetol 
• 58539-27-8 2-methoxy-4-propylphenol 

Relevant academic research and scientific papers

A Cascade Strategy Enables a Total Synthesis of (±)-Morphine

Morphine has been a target for synthetic chemists since Robinson proposed its correct structure in 1925, resulting in a large number of total syntheses of morphine alkaloids. Here we report a total synthesis of (±)-morphine that employs two key strategic cyclizations: 1) a diastereoselective light-mediated cyclization of an O-arylated butyrolactone to form a tricyclic cis-fused benzofuran and 2) a cascade ene–yne–ene ring closing metathesis to forge the tetracyclic morphine core. This approach enables a short and stereoselective synthesis of morphine in an overall yield of 6.6 %.

Structure–Activity Relationship of Anti-malarial Allylpyrocatechol Isolated from Piper betle

Malaria disease remains a serious worldwide health problem. In South-East Asia, one of the malaria infection “hot-spots,” medicinal plants such as Piper betle have traditionally been used for the treatment of malaria, and allylpyrocatechol (1), a constituent of P. betle, has been shown to exhibit anti-malarial activities. In this study, we verified that 1 showed in vivo anti-malarial activity through not only intraperitoneal (i.p.) but also peroral (p.o.) administration. Additionally, some analogs of 1 were synthesized and the structure–activity relationship was analyzed to disclose the crucial sub-structures for the potent activity.

Degradation of lignin with aqueous ammonium-based ionic liquid solutions under milder conditions

This study investigates the performance of two aqueous ionic liquids (ILs), dimethylbutylammonium acetate ([DMBA][Ac]) and dimethylbutylammonium butanoate ([DMBA][B]), solutions for depolymerizing alkali lignin into valuable phenolic compounds. The favorable operation conditions, including reaction temperature and reaction time, are explored. The extent of depolymerization of the lignin is evaluated by analysis with gel permeation chromatography (GPC). The results show that the average molecular weights of the depolymerized lignin samples can be reduced by as high as 93.8% and 86.8% after treating with the aqueous [DMBA][Ac] and [DMBA][B], respectively. Moreover, the aromatic chemical species in the depolymerized solutions are identified by using gas chromatography?mass spectrophotometry (GC-MS). The confirmation of the chemical species is further made by using a series of spectroscopic techniques, such as FT-IR, and 1H NMR and 13C NMR spectroscopy. Promising results have been achieved for the depolymerization of the lignin into valuable chemicals by using the proposed green media, aqueous solutions of ionic liquids [DMBA][Ac] and [DMBA][B], under milder conditions.

Structure–activity relationships and docking studies of hydroxychavicol and its analogs as xanthine oxidase inhibitors

Hydroxychavicol (HC), which is obtained from the leaves of Piper betle LINN. (Piperaceae), inhibits xanthine oxidase (XO) with an IC50 value of 16.7μM, making it more potent than the clinically used allopurinol (IC50=30.7μM). Herein, a structure–activity relationship analysis of the polar part analogs of HC was conducted and an inhibitor was discovered with a potency 13 times that of HC. Kinetic studies have revealed that HC and its active analog inhibit XO in an uncompetitive manner. The binding structure prediction of these inhibitor molecules to the XO complex with xanthine suggested that both compounds (HC and its analog) could simultaneously form hydrogen bonds with xanthine and XO.

A protocol to generate phthaloyl peroxide in flow for the hydroxylation of arenes

A flow protocol for the generation of phthaloyl peroxide has been developed. This process directly yields phthaloyl peroxide in high purity (>95%) and can be used to bypass the need to isolate and recrystallize phthaloyl peroxide, improving upon earlier batch procedures. The flow protocol for the formation of phthaloyl peroxide can be combined with arene hydroxylation reactions and provides a method for the consumption of peroxide as it is generated to minimize the accumulation of large quantities of peroxide.

Palladium-catalyzed allylic arylation of allylic ethers with arylboronic acids using hydrazone ligands

Unsymmetrical 1,3-diarylpropenes were synthesized in good to high yields by the palladium-catalyzed allylic arylation of allylic ethers, such as a cinnamyl phenyl ether, with a variety of arylboronic acids using a hydrazone 1a-Pd(OAc)2 system in DMAc/H2O. Using this catalyst, eugenol was also synthesized from allyl phenyl ether with (4-hydroxy-3- methoxyphenyl)boronic acid pinacol ester. A palladium-catalyzed allylic arylation of cinnamyl phenyl ether derivatives with a variety of arylboronic acids using 5 mol-% of a hydrazone 1a-Pd(OAc)2 system in DMAc/H 2O at 50 °C gave 1,3-diarylpropenes in good yields. We also succeeded with the synthesis of eugenol by a palladium-catalyzed allylic arylation. Copyright

Expeditious synthesis of bioactive allylphenol constituents of the genus Piper through a metal-free photoallylation procedure

Nine bioactive allylphenol (anisole) derivatives (e.g. eugenol, safrole and asaricin) present in several plants of the genus Piper have been synthesized in medium to high yield via aryl cation intermediates. This expeditious metal-free procedure involves the irradiation of the corresponding chlorophenols or chloroanisoles in a polar solvent (MeCN or, better, TFE or aqueous acetonitrile) in the presence of allyltrimethylsilane. Estragole has also been synthesized starting from the corresponding fluoroderivative and diazonium salt, though in a lower yield. The Royal Society of Chemistry 2005.

STRUCTURE-ACTIVITY RELATIONSHIPS OF PHENYLPROPANOIDS AS GROWTH INHIBITORS OF THE GREEN ALGA SELENASTRUM CAPRICORNUTUM

Twenty-seven commercial or synthetic phenylpropanoids have been tested in broth against the unicellular alga Selenastrum capricornutum.The antialgal activity seems to be linked to the number as well as to the position of the methoxyl group in the molecule.A slight effect of the side chain substitution was also observed. Key Word Index - Selenastrum capricornutum; allelochemicals; phenylpropanoids.