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93-28-7

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93-28-7 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 93-28-7 differently. You can refer to the following data:
1. liquid
2. Eugenol Acetate occurs in clove oil, together with eugenol. It is a crystalline solid (mp 29°C) or yellowish liquid with a slightly fruity, clove odor. Eugenol acetate is prepared by acetylation of eugenol with acetic anhydride and is used in floral compositions to accentuate floral, spicy characters.
3. Eugenyl acetate has a characteristic odor reminiscent of clove oil, with a burning, aromatic favor.

Occurrence

Reported found in the essential oils of Laurus nobilis, clove buds and leaves, cassia leaf and cinnamon leaf, root and bark

Uses

Eugenol Acetate is a constituent of Clove oil, an essential oil from the clove plant, Syzygium aromaticum. Clove oil is a natural analgaesic and antiseptic used primarily in dentistry for its main ingredient Eugenol. Clove oil can also be purchased in pharmacies over the counter, as a home remedy for dental pain relief, mainly toothache; it is also often found in the aromatherapy section of health food stores.

Preparation

By direct acetylation of eugenol using acetic anhydride.

Flammability and Explosibility

Notclassified

Safety Profile

Moderately toxic by ingestion. A skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also EUGENOL, ALLYL COMPOUNDS, and ESTERS.

Check Digit Verification of cas no

The CAS Registry Mumber 93-28-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 3 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 93-28:
(4*9)+(3*3)+(2*2)+(1*8)=57
57 % 10 = 7
So 93-28-7 is a valid CAS Registry Number.
InChI:InChI=1/C12H14O3/c1-4-5-10-6-7-11(15-9(2)13)12(8-10)14-3/h4,6-8H,1,5H2,2-3H3

93-28-7 Well-known Company Product Price

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  • (Code)Product description
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  • TCI America

  • (E0210)  Eugenol Acetate  >98.0%(GC)

  • 93-28-7

  • 25g

  • 245.00CNY

  • Detail
  • Sigma-Aldrich

  • (04733)  Acetyleugenol  analytical standard

  • 93-28-7

  • 04733-100MG

  • 710.19CNY

  • Detail

93-28-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Eugenol Acetate

1.2 Other means of identification

Product number -
Other names (2-methoxy-4-prop-2-enylphenyl) acetate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:93-28-7 SDS

93-28-7Relevant articles and documents

Continuous ion-exchange resin catalysed esterification of eugenol for the optimized production of eugenyl acetate using a packed bed microreactor

Lerin,Catani,Oliveira,Massi,Bortolini,Cavazzini,Giovannini

, p. 76898 - 76903 (2015)

A green scalable flow-synthesis process for the production of eugenyl acetate, an eugenol derivative with potential applications in food and medicinal chemistry, was developed. Through batch experiments, the anion-exchange resin Amberlyst A-21 was recognized as a suitable catalyst for the esterification of eugenol with acetic anhydride. Next, the process was switched from batch- to flow-mode by using a packed-bed microreactor integrated in an instrumental platform that permitted at the same time continuous control of the main process parameters (flow rate, feed mixture composition, temperature) and the on-line HPLC analysis of the reactor effluent. Thanks to this apparatus, a number of experiments with different reaction conditions have been easily performed to evaluate the effects of temperature and reagent molar ratios on eugenyl acetate production. The results have been used to carry out a central composite rotatable experimental design (CCRD) whose derived response surface model (RSM) suggested an optimal temperature and acetic anhydride to eugenol molar ratio of 95 °C and 3:1, respectively. The goodness of these theoretically deduced parameters has been experimentally confirmed obtaining, with a flow rate of 40 μL min-1, a 95% conversion. The Amberlyst A-21 packed-bed microreactor also demonstrated good long-term stability ensuring, under the above optimized conditions, a high and stable conversion (over 93%) for prolonged reaction times.

Synthesis of eugenyl acetate by enzymatic reactions in supercritical carbon dioxide

dos Santos, Philipe,Zabot, Giovani L.,Meireles, M. Angela A.,Mazutti, Marcio A.,Martínez, Julian

, p. 1 - 9 (2016)

Supercritical carbon dioxide (SC-CO2) as reaction medium has gained attention in the production of terpenic esters catalyzed by lipases. Therefore, this work investigated the production of eugenyl acetate by esterification of eugenol and acetic anhydride in SC-CO2 using two commercial lipases (Lipozyme 435 and Novozym 435) as catalysts. The influence of enzyme concentration (1–10% weight/weight), substrates’ molar ratio (1:1 to 5:1), temperature (40–60?°C) and pressure of SC-CO2 (10–30?MPa) on the esterification rate (X; %) and specific productivity (SP; kg of product/kg of catalyst x hour) were evaluated. A home-made high-pressure stirred-batch reactor (100?ml) was used in the experiments. The use of Novozym 435 achieved higher conversion and specific productivity of eugenyl acetate than Lipozyme 435. An excess of acetic anhydride (5:1?M/M) and high enzyme concentration (10%) achieved higher esterification rates than the lowest conditions (1% and 1:1?M/M). The optimal temperatures and pressure for the synthesis of eugenyl acetate in SC-CO2 were 50 and 60?°C at 10?MPa, respectively. The phase behavior of the reaction system and the synthesis in organic medium were also studied. Kinetic experiments performed at 40, 50 and 60?°C indicated that the reaction follows the simple Ping-Pong Bi-Bi mechanism and the affinity of acetic anhydride to enzyme was larger than that of eugenol.

Biotechnological Potential of Eugenol and Thymol Derivatives Against Staphylococcus aureus from Bovine Mastitis

Nunes, Daiana O. S.,Vinturelle, Rafaelle,Martins, Francislene J.,dos Santos, Thiago F.,Valverde, Alessandra Leda,Ribeiro, Carlos Magno R.,Castro, Helena C.,Folly, Evelize

, p. 1846 - 1855 (2021/04/29)

Bovine mastitis is an infectious disease that affects the mammary gland of dairy cattle with considerable economic losses. Staphylococcus aureus is the main microorganism involved in this highly contagious process, and the treatment is only using antibiotics. Currently, the search for new treatment and/or compounds is still in need due to microbial resistance. In this work, we evaluated the potential of eugenol and thymol derivatives against S. aureus strains from bovine mastitis. On that purpose, nine derivatives were synthesized from eugenol and thymol (1–9), and tested against 15 strains of S. aureus from subclinical bovine mastitis. Initially, the strains were evaluated for the biofilm production profile, and those with strong adherence were selected to the antimicrobial sensitivity determination in the Minimum Inhibitory Concentration (MIC) assays. Herein the compounds toxicity was also evaluated by in silico analysis using Osiris DataWarrior software. The results showed that 60% of the strains were considered strongly adherent and three strains (S. aureus 4271, 4745 and 4746) were selected for the MIC tests. Among the nine eugenol and thymol derivatives tested, four were active against the evaluated strains (MIC = 32?μg?mL?1) within CLSI standard values. In silico analysis showed that all derivatives had cLopP ??4 and TPSA 140 ?2, and similar theoretical toxicity parameters to some antibiotics currently on the market. These molecules also showed negative drug-likeness values, pointing to the originality of these structures and theoretical feasibility on escaping of resistance mechanism and act against resistant strains. Thus, these eugenol derivatives may be considered as promising for the development of new treatments against bovine mastitis and future exploring on this purpose.

Scalable green approach toward fragrant acetates

Puchl'Ová, Eva,Szolcsányi, Peter

, (2020/08/07)

The advantageous properties of ethylene glycol diacetate (EGDA) qualify it as a useful substitute for glycerol triacetate (GTA) for various green applications. We scrutinised the lipase-mediated acetylation of structurally diverse alcohols in neat EGDA furnishing the range of naturally occurring fragrant acetates. We found that such enzymatic system exhibits high reactivity and selectivity towards activated (homo) allylic and non-activated primary/secondary alcohols. This feature was utilised in the scalable multigram synthesis of fragrant (Z)-hex-3-en-1-yl acetate in 70percent yield. In addition, the Lipozyme 435/EGDA system was also found to be applicable for the chemo-selective acetylation of (hydroxyalkyl) phenols as well as for the kinetic resolution of chiral secondary alcohols. Lastly, its discrimination power was demonstrated in competitive experiments of equimolar mixtures of two isomeric alcohols. This enabled the practical synthesis of 1-pentyl acetate isolated as a single product in 68percent yield from the equimolar mixture of 1-pentanol and 3-pentanol.

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