1,2-Dimethoxy-4-(2-propenyl)benzol
EUGENOL METHYL ETHER · 4-ALLYL-1,2-DIMETHOXYBENZENE · jiaji · FEMA 2475 · EUGENYL METHYL ETHER · 1,2-DIMETHOXY-4-(2-PROPENYL)BENZENE · O-Methyleugenol · 3-METHYLEUGENOL
Identifikatoren & physikalische Daten
| CAS No. | 93-15-2 |
|---|---|
| Summenformel | C11H14O2 |
| Durchschnittliche Molmasse | 178,23 g/mol |
| Monoisotopische Masse | 178,09937969 g/mol |
| SMILES | C=CCc1ccc(OC)c(OC)c1 |
| InChIKey | ZYEMGPIYFIJGTP-UHFFFAOYSA-N |
| PubChem CID | 7127 |
| ChEMBL | CHEMBL108861 |
| ChEBI | CHEBI:4918 |
| EC No. | 202-223-0 |
| DTXSID | DTXSID5025607 |
| Lokaler Name | 1,2-Dimethoxy-4-(2-propenyl)benzol |
Chemische & physikalische Eigenschaften
| XLogP | 2,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 18,5 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 156 |
| Stoffklassen | Other Classes -> Ethers, OtherCarcinogens |
| Kosmetika | Cosmetics ingredient -> FlavorFragranceOther (Specify)SolventMasking |
| SpringerMaterials Properties | Optical coefficient |
| Duftstoffe | Fragrance substance (Methyl eugenol) -> IFRA amendment 51Fragrance Ingredient (Eugenyl methyl ether) -> IFRA transparency List |
| LogP (Verteilungskoeffizient) | 3.45 |
| Geruch | Mild-spicy, slightly herbal odorClove, carnation odor |
| Geschmack | BITTER, BURNING TASTE |
| Lebensmittelzusatzstoffe | Use unspecified -> FDA Substance added to food |
| Dichte | 1.0396 at 68 °F (NTP, 1992) - Denser than waterwill sink1.032-1.036 at 25 °C1.036 g/mL at 25 °C (lit.) |
| Color/Form | Crystals from hexaneColorless to pale yellow liquid |
| Löslichkeit | less than 1 mg/mL at 66 °F (NTP, 1992)Soluble in most organic solventsSoluble in ethanol, ethyl etherSoluble in fixed oilsinsoluble in glycerin and propylene glycolIn water, 500 mg/L at 25 °C0.5 mg/mL at 25 °C0.5g/l |
| Flammpunkt | 210 °F (NTP, 1992)99 °C99 °C (210 °F) (closed cup)>230 °F |
| Schmelzpunkt | -4 °C (lit.) |
| Siedepunkt | 254-255 °C (lit.) |
| Dampfdruck | 0.463-1.983Pa at 25℃ |
| Brechungsindex | n20/D 1.534(lit.) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Oil |
| Farbe | Colourless to Pale Yellow |
| Geruch | at 1.00 % in dipropylene glycol. sweet fresh warm spicy clove carnation cinnamon |
| Geruchsart | spicy |
| Biologische Quelle | synthetic |
| Merck | 14,6073 |
| BRN | 1910871 |
| Henry-Konstante | 1.8×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents. |
| Hauptanwendungen | flavors and fragrances |
| Kosmetik-Inhaltsstoffe Funktionen | FRAGRANCEPERFUMING |
| InChI | 1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4,6-8H,1,5H2,2-3H3 |
| InChIKey | ZYEMGPIYFIJGTP-UHFFFAOYSA-N |
| SMILES | COc1ccc(CC=C)cc1OC |
| LogP (Verteilungskoeffizient) | 2.74-3.03 |
| CAS Datenbank | 93-15-2(CAS DataBase Reference) |
| NIST chemische Informationen | Benzene, 1,2-dimethoxy-4-(2-propenyl)-(93-15-2) |
| EPA chemische Informationen | Methyleugenol (93-15-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 6.1% (110 of 1814) of reports.WarningH302 (93.9%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P261, P264, P270, P272, P280, P301+P317, P302+P352, P318, P321, P330, P333+P317, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1814 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Danger |
|---|---|
| Regulatorische Informationen | Chemical: Benzene, 1,2-dimethoxy-4-(2-propenyl)-Hazard Traits - CarcinogenicityRegulation (EC) No 1831/2003 (amended)Benzene, 1,2-dimethoxy-4-(2-propen-1-yl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1,2-dimethoxy-4-(2-propen-1-yl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 10-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/23881Methyl eugenol: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Benzene, 1,2-dimethoxy-4-(2-propenyl)-: Human health tier II assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | This chemical is combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound include nausea, vomiting, diarrhea, circulatory collapse, dizziness, rapid and shallow breathing, unconsciousness, convulsions, abdominal burning, dysuria, hematuria, tachycardia, bronchial irritation, anuria, pulmonary edema, bronchial pneumonia and renal damage. |
| Gefahrenübersicht | A skin and eye irritant[CAMEO] Causes sleep in mice after 200 mg/kg intraperitoneal injectionCauses evidence of liver injury in mice after high-dose feeding studies[HSDB] An irritant |
Anwendungen & Verwendung
Occurrence
Reported in the essential oils of Myrtaceae and Luraceae; it was identifed originally in the essential oil from roots of Asarum europaeum L and Asarum canadense L Subsequently, it was identifed as the main constituent of the oil from wood of Dacrydium franklinii Hook (97 5%), in Melaleuca bracteata F v M (leaves, 90 to 95%), in Cinnamomum oliveri Bail (leaves, 90 to 95%), and as a minor constituent in the oils of betel, citronella, Japanese calamus, pimenta, hyacinth, rose, basil, bay, cajeput and others Reported found in heated blackberry, pepper, lovage seed, chervil, lemon balm, alpinia species, clove buds, nutmeg, pepper, mace, tarragon, Ocimum sanctum, laurel, myrtle leaf and berry, rosemary, pimento berry and mastic gum leaf oil
Verwenden
Methyl eugenol may be used as an analytical reference standard for the quantification of the analyte in the following: Essential oil of Pimenta pseudocaryophyllus using high-performance liquid chromatography (HPLC). The purity of the extracted compound is then determined by gas chromatography coupled to flame ionization detector (GC/FID). Stem bark of Cinnamomum zeylanicum Blume using reversed-phase high-performance liquid chromatography (RP-HPLC) with UV-visible detection. Rosa hybrida using gas-chromatography coupled to mass spectrometry (GC-MS) technique.
Herstellung & Synthese
synthetische
Usually prepared by methylation of eugenol.