5353-15-1

Usage

Uses

Used in Flavoring and Fragrance Industry:
Eugenol is used as a flavoring agent in the food and beverage industry due to its aromatic and spicy flavor profile. It imparts a warm, sweet, and slightly clove-like taste to various food products, enhancing their overall flavor experience.
Used in the Production of Fragrances and Essential Oils:
Eugenol is also utilized in the creation of fragrances and essential oils, where its unique scent contributes to the development of various olfactory compositions. Its aromatic properties make it a valuable ingredient in perfumes, colognes, and other scented products.
Used in Medicinal Applications:
Eugenol has been studied for its potential medicinal properties, such as its anti-inflammatory and analgesic effects. It is being explored for its ability to alleviate pain and reduce inflammation, making it a promising candidate for use in pharmaceutical formulations.
Used in Dental Applications:
In the dental industry, eugenol is used in dental cement formulations, particularly in endodontic treatments. Its antiseptic and analgesic properties make it suitable for use in dental procedures, helping to manage pain and prevent infection.
Used in Antimicrobial Applications:
Eugenol exhibits antimicrobial properties, making it useful in various applications where the inhibition of microbial growth is required. It can be found in some mouthwashes and oral hygiene products to help maintain oral health by reducing the growth of harmful bacteria.

InChI:InChI=1/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5,7-8H,1,6H2,2-4H3

Synthetic route

1,2,4-trimethoxy-benzene (135-77-3) + (η3-allyl)Fe(CO)4BF4 → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1)

Conditions	Yield
With carbon monoxide In nitromethane at 25℃; under 760 Torr; for 20h;	87%

methylallylether (627-40-7) + C9H11F3O5SSi → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1)

Conditions	Yield
With cesium fluoride In tetrahydrofuran at 50℃; for 28h; Claisen Rearrangement; Inert atmosphere;	60%

2,4,5-trimethoxycinnamyltosylhydrazone (437761-99-4) → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1)

Conditions	Yield
With sodium tetrahydroborate In acetic acid at 90 - 120℃; for 12h;	43%

(1R*,2R*,3S*)-1,3-bis(2',4',5'-trimethoxyphenyl)-2-methylpent-4-en-1-ol → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1) + (+/-)-(2R,3R,4S,5S)-2-(bromomethyl)-4-methyl-1,3-bis(2',4',5'-trimethoxyphenyl)-tetrahydrofuran

Conditions	Yield
With Bromotrichloromethane; cyclohexa-1,4-diene; {4-[3,5-bis(trifluoromethyl)phenyl]-4-oxybut-3-en-2-one}-cobalt(II) In toluene at 60℃; for 11h; optical yield given as %de; diastereoselective reaction;	A 36% B 22%

methanol (67-56-1) + 1,2-dimethoxy-4-(2-propenyl)benzene (93-15-2) → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1)

Conditions	Yield
With toluene-4-sulfonic acid; sodium hydroxide; sodium perchlorate 1) electrolysis, 4.5h, 15 deg C 2) MeOH, 10 min, room temperature; Yield given. Multistep reaction;
With hydrogenchloride; sodium hydroxide; sodium perchlorate 1.) electrolyzed at room temp.; Yield given. Multistep reaction;

3,4-dimethoxyphenol (2033-89-8) + allyl bromide (106-95-6) + dimethyl sulfate (77-78-1) → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1) + 2-allyl-1,3,4-trimethoxybenzene (5353-16-2)

Conditions	Yield
Multistep reaction;

1-(allyloxy)-3,5-dimethoxybenzene (6906-64-5) + methyl iodide (74-88-4) → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1)

Conditions	Yield
(i) (heating), (ii) KOH, EtOH, (iii) /BRN= 969135/; Multistep reaction;

C12H16O3 (5273-86-9) → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 62 percent / DDQ; silica gel / dioxane / 20 °C 2: 79 percent / methanol / 20 °C 3: 43 percent / NaBH4 / acetic acid; acetic acid / 12 h / 90 - 120 °C View Scheme

trans 2,4,5-trimethoxy cinnamaldehyde (99217-07-9, 106128-88-5, 99217-06-8) → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 79 percent / methanol / 20 °C 2: 43 percent / NaBH4 / acetic acid; acetic acid / 12 h / 90 - 120 °C View Scheme

asaronic acid (490-64-2) + allyl bromide (106-95-6) → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1)

Conditions	Yield
With copper(I) oxide; palladium diacetate; dimethyl sulfoxide; silver carbonate In toluene at 110℃; for 2h; chemoselective reaction;	89 %Chromat.

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) → asaraldehyde (4460-86-0)

Conditions	Yield
With sodium dichromate In acetic acid; benzene for 6h; Heating;

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) → 1-(2'-Bromopropyl)-2,4,5-trimethoxybenzene (105591-38-6)

Conditions	Yield
With hydrogen bromide In chloroform at 0℃; for 2h; Yield given;

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) → C12H16O3 (5273-86-9) + α-asarone (2883-98-9)

Conditions	Yield
With potassium hydroxide In ethanol

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) → α-asarone (2883-98-9)

Conditions	Yield
With potassium hydroxide In ethanol

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) → asarone (494-40-6, 2883-98-9, 5273-86-9)

Conditions	Yield
With potassium hydroxide In ethanol Heating;

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) → asaronic acid (490-64-2)

Conditions	Yield
With potassium permanganate In acetone Heating;

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) → 1-propyl-2,4,5-trimethoxybenzene (6906-65-6)

Conditions	Yield
With hydrogen; palladium on activated charcoal

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) → 2-(2,4,5-trimethoxyphenyl)acetaldehyde (22973-79-1)

Conditions	Yield
(i) O3, (ii) H2O; Multistep reaction;

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) + p-nitrobenzoyl peroxide (1712-84-1) → asaraldehyde (4460-86-0) + erythro-1-(2,4,5-trimethoxy)phenyl-1,2,3-tri(4-nitro)benzoyloxypropane + threo-1-(2,4,5-trimethoxy)phenyl-1,2,3-tri(4-nitro)benzoyloxypropane

Conditions	Yield
In acetonitrile at 25℃;

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) → trans 2,4,5-trimethoxy cinnamaldehyde (99217-07-9, 106128-88-5, 99217-06-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium dichromate / benzene; acetic acid / 6 h / Heating 2: alkaline medium / 1 h / Heating View Scheme

Upstream product

• 67-56-1 methanol 
• 93-15-2 1,2-dimethoxy-4-(2-propenyl)benzene 
• 2033-89-8 3,4-dimethoxyphenol 
• 106-95-6 allyl bromide 
• 77-78-1 dimethyl sulfate 
• 6906-64-5 4-(allyloxy)-1,2-dimethoxybenzene 
• 74-88-4 methyl iodide 
• 4460-86-0 asaraldehyde 
• 490-64-2 asaronic acid 
• 99217-07-9 trans 2,4,5-trimethoxy cinnamaldehyde 
• 5273-86-9 C₁₂H₁₆O₃ 
• 437761-99-4 2,4,5-trimethoxycinnamyltosylhydrazone 
• 135-77-3 1,2,4-trimethoxy-benzene 
• 627-40-7 methylallylether 

Downstream Products

• 4460-86-0 asaraldehyde 
• 5273-86-9 C₁₂H₁₆O₃ 
• 2883-98-9 α-asarone 
• 494-40-6 asarone 
• 490-64-2 asaronic acid 
• 6906-65-6 1-propyl-2,4,5-trimethoxybenzene 
• 22973-79-1 2-(2,4,5-trimethoxyphenyl)acetaldehyde 
• 99217-07-9 trans 2,4,5-trimethoxy cinnamaldehyde 

Relevant academic research and scientific papers

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.

Domino Processes of Arynes Reacting with Three Classes of Nucleophiles for Organic Syntheses

Synthetic application of arynes is broadened by their reactions with neutral N-, S-, and O-containing nucleophiles to produce three types of compounds. Accordingly, 1,2-dihydroquinolines are synthesized from Schiff bases, alkynes, and arynes through a Diels-Alder reaction. Epoxides are prepared from thioethers and arynes along with aldehydes or ketones through a Johnson-Corey-Chaykovsky reaction. Phenolic ethers are produced from allyl ethers and arynes through a Claisen-type rearrangement. These target molecules, including natural products γ-asarone, asaricin, and a cholesteryl phenolic ether, are formed through reactions initiated by arynes. These new reactions share a prevailing feature of domino processes, which are carried out in a single flask and afford the desired products in good to high yields.

Pd(ii)-catalyzed decarboxylative allylation and Heck-coupling of arene carboxylates with allylic halides and esters

This work demonstrates an alternative method to prepare allylated arenes and aryl-substituted allylic esters via catalytic decarboxylative C-C bond formation using aromatic carboxylic acids and allylic halides and esters.

Reductive and brominative termination of alkenol cyclization in aerobic cobalt-catalyzed reactions

(Chemical Equation Presented) Tetrahydrofur-2-ylmethyl radicals were stereoselectively generated from substituted pent-4-en-1-ols in aerobic cobalt(II)-catalyzed oxidations. Intermediates were trapped with cyclohexa -1,4-diene, γ-terpinene, BrCCl3, diethyl dibromomalonate, or electron-deficient olefins such as acrylonitrile or dimethyl fumarate to afford functionalized tetrahydrofurans in synthetically useful yields.

A mild and convenient procedure for the conversion of toxic β-asarone into rare phenylpropanoids: 2,4,5-Trimethoxycinnamaldehyde and γ-asarone

Oxidation of β-asarone (2) with DDQ gave trans-2,4,5- trimethoxycinnamaldehyde (3), which on treatment with p-toluenesulfonyl hydrazine provided corresponding α,β-unsaturated hydrazone derivative (4). Reduction of 4 with sodium borohydride in acetic acid afforded γ-asarone (1) in 43% yield.

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.

ANODIC 1,2- AND 1,4-ADDITION PRODUCTS FROM METHYL EUGENOL AS PREDICTED BY THE EECrCp MECHANISM

Anodic oxidation of 1,2-dimethoxy-4-allylbenzene (methyl eugenol) under a variety of constant current conditions in methanolic sodium hydroxide affords the 1,2- and 1,4-methanol addition products expected from the EECrCp mechanism.These results differ markedly from those recently reported.

ELECTROSYNTHESIS OF γ-ASARONE

γ-Asarone is synthesised in high yield, and conveniently, by anodic methoxylation of methyl eugenol, at constant current.The method is extremely simple and inexpensive.

IRON-MEDIATED AROMATIC ALLYLATION

Electron rich aromatic and heteroaromatic compounds react with (η3-allyl)Fe(CO)4BF4 to produce allylated aromatics in moderate to good yields.Unsymmetrically substituted allyl complexes afford the corresponding butenyl-, 1,1-dimethylallyl-, cinnamyl-, and geranyl-derivatives with moderate to excellent regioselectivity and complete stereoselectivity.