97-54-1 Usage
Description
Isoeugenol is a phenylpropene, a propenyl-substituted guaiacol, that occurs naturally in some essential oils of plants. It is produced by plants as defense compounds against animals and microorganisms and as floral attractants of pollinators. It can also be used as inhibitors of lipid peroxidation and as free radicals scavenger. Because of its antimicrobial properties as well as pleasing aromas and flavors, humans, since antiquity, have used plant material containing phenylpropenes to preserve and flavor their food. Isoeugenol has a floral odor reminiscent of carnation and is a pale yellow oily liquid with a spice-clove odor.
Uses
Used in Flavor and Fragrance Industry:
Isoeugenol is used as a flavoring agent for its sweet spice and clove taste with woody and phenolic nuances, and as a fragrance component in perfumery due to its floral odor reminiscent of carnation.
Used in Manufacturing Industry:
Isoeugenol is used in the manufacture of vanillin, a key component in the production of various flavorings and fragrances.
Used in Analytical Chemistry:
Isoeugenol may be used as an analytical reference standard for the determination of the analyte in bioconversion broth using reversed-phase high-performance liquid chromatography with ultraviolet detection (RP-HPLC-UV).
Used in Cosmetics Industry:
Isoeugenol is used in cosmetics as a fragrance or to mask odor, taking advantage of its pleasant aroma.
Used in Perfumery:
Isoeugenol is used in various perfumery applications, such as soap gardenia, coffee, abronea, tuberose, and jonquil, to provide specific scents and enhance the overall fragrance.
Used in Food and Beverage Industry:
Isoeugenol is found in various food items and beverages, such as bilberry, guava, blackberry, tomato, cinnamon, clove bud and stem, nutmeg, mace, thymus, tea, coffee, fatty fish, beer, rum, plum, mushroom, dill, malt wort, elder flower, cuttlefish, Chinese quince, pimento leaf, and maté, contributing to their unique flavors and aromas.
Used in Dental Materials:
Isoeugenol is used in dental materials, such as cement, due to its antimicrobial properties and pleasant aroma.
Used in Over-the-Counter Medicines:
Isoeugenol is used in over-the-counter medicines, likely for its antimicrobial properties and potential applications in pain relief or other medicinal purposes.
Natural Occurrence:
Isoeugenol is found in essential oils of ylang-ylang, nutmeg, and other plants, such as Michelia champaca and Nectandra puchury. It is also present in a variety of food items and beverages, as mentioned above.
References
Koeduka, Takao, et al. "Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of a coniferyl alcohol ester." Proceedings of the National Academy of Sciences 103.26 (2006): 10128-10133.
Rajakumar, D. V., and M. N. A. Rao. "Dehydrozingerone and isoeugenol as inhibitors of lipid peroxidation and as free radical scavengers." Biochemical pharmacology 46.11 (1993): 2067-2072.
Preparation
The starting material for the synthesis of isoeugenol is eugenol.The
sodium or potassium salt of eugenol is isomerized to isoeugenol by heating. Isomerization
can also be achieved catalytically in the presence of ruthenium [346]
or rhodium compounds.
Fire Hazard
ISOEUGENOL is combustible.
Contact allergens
Isoeugenol is a mixture of two cis and trans isomers.
It occurs in ylang-ylang and other essential oils. It is a
common allergen of perfumes and cosmetics such as
deodorants and is contained in fragrance mix. Its presence
in cosmetics is indicated in the INGREDIENTS
series. Substitution by esters such as isoeugenyl acetate
(not indicated on the package) does not always
resolve the allergenic problem, because of the in vivo
hydrolysis of the substitute into isoeugenol.
Synthesis
By the alkaline isomerization of eugenol obtained from essential oils high in eugenol.
Check Digit Verification of cas no
The CAS Registry Mumber 97-54-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 7 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 97-54:
(4*9)+(3*7)+(2*5)+(1*4)=71
71 % 10 = 1
So 97-54-1 is a valid CAS Registry Number.
97-54-1Relevant articles and documents
Highly diastereoselective synthesis of new heterolignan-like 6,7-methylendioxy-tetrahydroquinolines using the clove bud essential oil as raw material
Merchan Arenas, Diego R.,Rojas Ruíz, Fernando A.,Kouznetsov, Vladimir V.
, p. 1388 - 1391 (2011)
The diastereoselective synthesis toward novel heterolignan-like 2-aryl-4-(4-hydroxy-3-methoxyphenyl)-6,7-methylendioxy-1,2,3, 4-tetrahydroquinolines using for the first time clove bud essential oil as a renewable material was carried out. The synthetic protocol consisted of the hydrodistillation of dried flower buds, the solid base-catalyzed isomerization of the obtained essential oil enriched with eugenol in order to give isoeugenol and its participation, as a chemical reagent (dienophile) in the BF 3·OEt2-catalyzed three component Povarov reaction, without previous purification. Final products were obtained as racemic mixtures of new trans-2,4-diaryl-r-3-Me-1,2,3,4-tetrahydroquinolines in moderate to good yields.
Discovery, Biocatalytic Exploration and Structural Analysis of a 4-Ethylphenol Oxidase from Gulosibacter chungangensis
Alvigini, Laura,Fraaije, Marco W.,Gran-Scheuch, Alejandro,Guo, Yiming,Mattevi, Andrea,Saifuddin, Mohammad,Trajkovic, Milos
, p. 3225 - 3233 (2021/10/04)
The vanillyl-alcohol oxidase (VAO) family is a rich source of biocatalysts for the oxidative bioconversion of phenolic compounds. Through genome mining and sequence comparisons, we found that several family members lack a generally conserved catalytic aspartate. This finding led us to study a VAO-homolog featuring a glutamate residue in place of the common aspartate. This 4-ethylphenol oxidase from Gulosibacter chungangensis (Gc4EO) shares 42 % sequence identity with VAO from Penicillium simplicissimum, contains the same 8α-N3-histidyl-bound FAD and uses oxygen as electron acceptor. However, Gc4EO features a distinct substrate scope and product specificity as it is primarily effective in the dehydrogenation of para-substituted phenols with little generation of hydroxylated products. The three-dimensional structure shows that the characteristic glutamate side chain creates a closely packed environment that may limit water accessibility and thereby protect from hydroxylation. With its high thermal stability, well defined structural properties and high expression yields, Gc4EO may become a catalyst of choice for the specific dehydrogenation of phenolic compounds bearing small substituents.
One-pot hydroformylation/O-acylation of propenylbenzenes for the synthesis of polyfunctionalized fragrances
Delolo, Fábio G.,Vieira, Gabriel M.,Villarreal, Jesus A.A.,dos Santos, Eduardo N.,Gusevskaya, Elena V.
, p. 272 - 279 (2020/06/17)
A process involving the hydroformylation/O-acylation of propenylbenzenes with a phenolic group is described for eugenol, isoeugenol, chavicol, propenyl guaethol, 2-allylphenol, and 2-allyl-6-methylphenol. The reactions occur in parallel, under the same reaction conditions in anisole, a solvent with an impressive sustainability rank comparable to those of ethanol and water. The products contain formyl and acetoxy moieties, both established olfactory groups in flavor and fragrance industry, and present potential as new fragrance components with less allergenic properties. To the best of our knowledge, this is the first time that a one-pot process involving hydroformylation combined with further functionalization in a remote site is described.
METHOD OF FORMING MONOMERS AND FURFURAL FROM LIGNOCELLULOSE
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Page/Page column 19; 21; 22, (2020/06/05)
The present disclosure relates to a method of producing monophenolicmonomers and furfural from lignocellulosic biomass beating the biomass in a solvent together with a zeolite based catalyst.