ISOEUGENOL

ISOEUGENOL Basic information
Description References
Product Name:ISOEUGENOL
Synonyms:4-HYDROXY-3-METHOXY-1-PROPENYLBENZENE;4-PROPENYL-2-METHOXYPHENOL;4-PROPENYLGUAIACOL;3-METHOXY-4-HYDROXYPROPENYLBENZENE;2-METHOXY-4-((E)-PROPENYL)-PHENOL;FEMA 2468;ISOEUGENOL;ISOEUGENOL 6504
CAS:97-54-1
MF:C10H12O2
MW:164.2
EINECS:202-590-7
Product Categories:
Mol File:97-54-1.mol
ISOEUGENOL Structure
ISOEUGENOL Chemical Properties
Melting point -10 °C
Boiling point 266 °C
density 1.082 g/mL at 25 °C
vapor density >1 (vs air)
vapor pressure <0.01 mm Hg ( 20 °C)
FEMA 2468 | ISOEUGENOL
refractive index n20/D 1.575(lit.)
Fp >230 °F
storage temp. -20°C
solubility Benzene (Slightly), Chloroform, Methanol (Sparingly)
form Viscous Liquid
pka10.10±0.31(Predicted)
color Clear yellow
Odorat 100.00 %. sweet spicy clove woody allspice carnation floral
Odor Typespicy
Merck 14,5171
JECFA Number1260
BRN 1909602
Stability:Stable. Incompatible with strong oxidizing agents.
LogP2.48
CAS DataBase Reference97-54-1(CAS DataBase Reference)
EPA Substance Registry SystemIsoeugenol (97-54-1)
Safety Information
Hazard Codes Xn
Risk Statements 22-36/37/38-43
Safety Statements 26-36-36/37-24/25
RIDADR UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany 2
RTECS SL7875000
TSCA Yes
HS Code 29095000
Hazardous Substances Data97-54-1(Hazardous Substances Data)
ToxicityLD50 orally in rats: 1560 mg/kg (Jenner)
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
ISOEUGENOL Usage And Synthesis
DescriptionIsoeugenol 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.
ReferencesKoeduka, 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.
DescriptionIsoeugenol has a floral odor reminiscent of carnation. May be prepared by the alkaline isomerization of eugenol obtained from essential oils high in eugenol.
Chemical PropertiesIsoeugenol 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.

Chemical Propertieslight yellow-green viscous liquid
Chemical PropertiesIsoeugenol has a floral odor reminiscent of carnation.
OccurrenceThe 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.
UsesIsoeugenol 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).
UsesIsoeugenol 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).
Usesisoeugenol 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.
PreparationThe 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.
DefinitionChEBI: A phenylpropanoid that is an isomer of eugenol in which the allyl substituent is replaced by a prop-1-enyl group.
Aroma threshold valuesDetection: 100 ppb
Taste threshold valuesTaste characteristics at 10 ppm: sweet spice and clove with woody and phenolic nuances.
General DescriptionPale 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.
Air & Water ReactionsSlightly water soluble .
Fire HazardISOEUGENOL is combustible.
Contact allergensIsoeugenol 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.
SynthesisBy the alkaline isomerization of eugenol obtained from essential oils high in eugenol.
trans-2,4,5-Trimethoxycinnamic acid ISOEUGENOL BENZYL ETHER,BENZYL ISOEUGENOL ETHER,BENZYL ISOEUGENOL 3,4-(Methylenedioxy)cinnamic acid 3,4-Dimethoxycinnamonitrile 3,4-dihydro-5,6,7-trimethoxy-2-naphthoic acid AMYL OXY ISOEUGENOL REPLACER cis-Isoeugenol methyl ether cis-isoeugenol o-Methoxy-p-propenylphenol alkyl(C=15) ether TRANS-ISOEUGENOL trans-Isoeugenol methyl ether,(E)-Isoeugenol methyl ether 3,4-DIMETHOXYCINNAMIC ACID trans-2,3,4-Trimethoxycinnamic acid Benzyl alcohol, ether with isoeugenol,BENZYL ISOEUGENOL FORTE,BENZYL ISOEUGENOL,ISOEUGENOL BENZYL ETHER,BENZYL ISOEUGENOL ETHER ACETYL ISOEUGENOL O-METHYL ISOEUGENOL chavicine (E)-isoeugenol,trans-isoeugenol,(e)-isoeugenol,trans-2-methoxy-4-propenylphenol

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