ISOEUGENOL CAS 97-54-1
Introduction：Basic information about ISOEUGENOL CAS 97-54-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
ISOEUGENOL Basic informationDescription 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;2-METHOXY-4-PROPENYLPHENOL;FEMA 2468;ISOEUGENOL |
| CAS: | 97-54-1 |
| MF: | C10H12O2 |
| MW: | 164.2 |
| EINECS: | 202-590-7 |
| Product Categories: | |
| Mol File: | 97-54-1.mol |
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) |
| refractive index | n |
| FEMA | 2468 | ISOEUGENOL |
| Fp | >230 °F |
| storage temp. | -20°C |
| solubility | Benzene (Slightly), Chloroform, Methanol (Sparingly) |
| pka | 10.10±0.31(Predicted) |
| form | Viscous Liquid |
| color | Clear yellow |
| Odor | at 100.00 %. sweet spicy clove woody allspice carnation floral |
| Odor Type | spicy |
| biological source | synthetic |
| Merck | 14,5171 |
| JECFA Number | 1260 |
| BRN | 1909602 |
| Stability: | Stable. Incompatible with strong oxidizing agents. |
| Major Application | cleaning products cosmetics environmental flavors and fragrances food and beverages personal care |
| Cosmetics Ingredients Functions | FLAVOURING PERFUMING |
| InChI | 1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+ |
| InChIKey | BJIOGJUNALELMI-ONEGZZNKSA-N |
| SMILES | OC1=CC=C(/C=C/C)C=C1OC |
| LogP | 2.48 |
| CAS DataBase Reference | 97-54-1(CAS DataBase Reference) |
| EPA Substance Registry System | Isoeugenol (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 | TSCA listed |
| HS Code | 29095000 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Dermal Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 Skin Sens. 1A STOT SE 3 |
| Hazardous Substances Data | 97-54-1(Hazardous Substances Data) |
| Toxicity | LD50 orally in rats: 1560 mg/kg (Jenner) |
| Description | 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. |
| 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. |
| Description | Isoeugenol has a floral odor reminiscent of carnation. May beprepared by the alkaline isomerization of eugenol obtained from essential oils high in eugenol. |
| Chemical Properties | Isoeugenol has a floral odor reminiscent of carnation. |
| Chemical Properties | light yellow-green viscous liquid |
| Chemical Properties | 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 thermodynamicallymore stable. Isoeugenol is a yellowish, viscous liquid with a fine clove odor, withthat of the crystalline trans-isomer being the more delicate. Isoeugenol can be hydrogenated catalytically to form dihydroeugenol. Vanillinwas formerly prepared by oxidation of isoeugenol. Additional fragrance materialsare prepared by esterification or etherification of the hydroxy group. Isoeugenol can be hydrogenated catalytically to form dihydroeugenol. Vanillinwas formerly prepared by oxidation of isoeugenol. Additional fragrance materialsare 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 foundin 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 | Isoeugenol is used inmanufacture of vanillin; perfumes; flavoring; fragrance in perfumery, over-the-counter medicines, dental materials, foods; someperfumery uses (soap gardenia; coffee; abronea; tuberose; jonquil); natural occurrence (nutmeg oil). |
| Uses | 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). |
| Uses | 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.Thesodium or potassium salt of eugenol is isomerized to isoeugenol by heating. Isomerizationcan 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. |
| Aroma threshold values | Detection: 100 ppb |
| 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. |
| Air & Water Reactions | Slightly water soluble . |
| 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 acommon allergen of perfumes and cosmetics such asdeodorants and is contained in fragrance mix. Its presencein cosmetics is indicated in the INGREDIENTSseries. Substitution by esters such as isoeugenyl acetate(not indicated on the package) does not alwaysresolve the allergenic problem, because of the in vivohydrolysis of the substitute into isoeugenol. |
| Synthesis | By the alkaline isomerization of eugenol obtained from essential oils high in eugenol. |
ISOEUGENOL Preparation Products And Raw materials
| Raw materials | Potassium hydroxide solution-->Eugenol-->Alkali Metals, plasma standard solution, Specpure, Ba,Be,Ca,Cs,K,Li,Mg,Na,Rb,Sr, 100μg/ml-->Safrole-->ISOAMYL ALCOHOL-->ISOSAFROLE-->Ylang Ylang Oil-->Mace oil-->Phenol, 4-[4-(dibutylamino)butyl]-2-methoxy--->Dibutylamine-->2-methoxy-4-prop-1-enylphenetole-->PROPENYL GUAETHOL |
| Preparation Products | Ethyl vanillin-->1-Benzyloxy-2-methoxy-4-propenylbenzene-->1-ACETOXY-2-METHOXY-4-(1-PROPENYL)BENZENE-->Methyl isoeugenol-->2,6-Dimethoxyphenol-->DIHYDROEUGENOL-->4-Propylphenol-->4-HYDROXY-3-METHOXYPHENYLACETONE-->Vanillic acid |
