97-54-1 Usage
Description
Different sources of media describe the Description of 97-54-1 differently. You can refer to the following data:
1. Isoeugenol is a phenylpropene, a propenyl-substituted guaiacol
existing 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.
2. Isoeugenol has a floral odor reminiscent of carnation. May be
prepared by the alkaline isomerization of eugenol obtained from
essential oils high in eugenol.
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.
Chemical Properties
Different sources of media describe the Chemical Properties of 97-54-1 differently. You can refer to the following data:
1. Isoeugenol has a floral odor reminiscent of carnation.
2. light yellow-green viscous liquid
3. Isoeugenol occurs in many essential oils, mostly with eugenol,
but not as the main component. Commercial isoeugenol is a mixture of (E)- and
(Z)-isomers, in which the (E)-isomer dominates because it is thermodynamically
more stable. Isoeugenol is a yellowish, viscous liquid with a fine clove odor, with
that of the crystalline trans-isomer being the more delicate.Isoeugenol can be hydrogenated catalytically to form dihydroeugenol. Vanillin
was formerly prepared by oxidation of isoeugenol. Additional fragrance materials
are prepared by esterification or etherification of the hydroxy group.Isoeugenol can be hydrogenated catalytically to form dihydroeugenol. Vanillin
was formerly prepared by oxidation of isoeugenol. Additional fragrance materials
are prepared by esterification or etherification of the hydroxy group.
Occurrence
The commercial product is a mixture of cis- and trans-isomers; reported found in the essential oils of ylangylang and nutmeg; also in the oil from flowers of Michelia champaca and in the oil from seeds of Nectandra puchury. Reported found
in 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.
Uses
Different sources of media describe the Uses of 97-54-1 differently. You can refer to the following data:
1. Isoeugenol is used inmanufacture of vanillin; perfumes; flavoring; fragrance in perfumery, over-the-counter medicines, dental materials, foods; some
perfumery uses (soap gardenia; coffee; abronea; tuberose; jonquil); natural occurrence (nutmeg oil).
2. 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).
3. isoeugenol is a volatile oil fraction derived from eugenol. It is also found in ylang-ylang and nutmeg oils. It is used in cosmetics as a fragrance or to mask odor.
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.
Definition
ChEBI: A phenylpropanoid that is an isomer of eugenol in which the allyl substituent is replaced by a prop-1-enyl group.
Taste threshold values
Taste characteristics at 10 ppm: sweet spice and clove with woody and phenolic nuances.
General Description
Pale yellow oily liquid with a spice-clove odor. Freezes at 14°F. Density 1.08 g / cm3. Occurs in ylang-ylang oil and other essential oils.
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.
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.
Controlled lignosulfonate depolymerization: Via solvothermal fragmentation coupled with catalytic hydrogenolysis/hydrogenation in a continuous flow reactor
Al-Naji, Majd,Antonietti, Markus,Brandi, Francesco
supporting information, p. 9894 - 9905 (2021/12/24)
Sodium lignosulfonate (LS) was valorized to low molecular weight (Mw) fractions by combining solvothermal (SF) and catalytic hydrogenolysis/hydrogenation fragmentation (SHF) in a continuous flow system. This was achieved in either alcohol/H2O (EtOH/H2O or MeOH/H2O) or H2O as a solvent and Ni on nitrogen-doped carbon as a catalyst. The tunability according to the temperature of both SF and catalytic SHF of LS has been separately investigated at 150 °C, 200 °C, and 250 °C. In SF, the minimal Mw was 2994 g mol-1 at 250 °C with a dispersity (?) of 5.3 using MeOH/H2O. In catalytic SHF using MeOH/H2O, extremely low Mw was found (433 mg gLS-1) with a ? of 1.2 combined with 34 mg gLS-1. The monomer yield was improved to 42 mg gLS-1 using dual catalytic beds. These results provide direct evidence that lignin is an unstable polymer at elevated temperatures and could be efficiently deconstructed under hydrothermal conditions with and without a catalyst. This journal is
Alkali/alkaline earth ion-exchanged and palladium dispersed MCM-22 zeolite as a potential catalyst for eugenol isomerization and Heck coupling reactions
Augustin, A.,Haripriya, T. V.,Sahu, P.,Sakthivel, A.,Shanbhag, G. V.,Sreenavya, A.
, (2020/11/13)
Abstract: Alkali and alkaline earth metal ions (Na+, K+, Cs+, Mg2+) exchanged MCM-22 zeolites were prepared and subsequently palladium (2 wt.%; Pd) was dispersed on above exchanged MCM-22 zeolite materials. All the MCM-22 materials were systematically characterized by FTIR, powder X-ray diffraction, N2 sorption analysis and temperature-programmed desorption (TPD) of CO2. The XRD pattern and FTIR data confirmed the existence of the MCM-22 framework structure even after exchanging bulky metal ions and palladium loading. TPD studies using CO2 supports that the cesium and magnesium incorporated MCM-22 possess a strong and large number of basic sites. The alkali and alkaline-earth metal ions exchanged MCM-22 catalysts were explored for industrially important eugenol isomerisation, whereas the palladium containing MCM-22 materials were utilised for Heck coupling reaction of styrene with iodobenzene. The Cs-MCM-22 showed the best activity for the eugenol isomerization with the isoeugenol yield of 76%. The Cs/Pd-MCM-22 was shown as promising heterogeneous catalyst for Heck coupling reaction of styrene with iodobenzene and yield 99% stilbene. For both isomerization and Heck coupling reaction, the catalysts retain their activities even after several runs. Graphic Abstract: Among different alkali and alkaline earth ion-exchanged MCM-22 materials, cesium containing MCM-22 was shown as a promising catalyst for isomerization of lignin-derived biomass model compound viz., eugenol. Subsequently, the palladium dispersed CsMCM-22 was found to be the potential catalyst for Heck coupling under ambient conditions.[Figure not available: see fulltext.].
