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4-Hydroxy-3,5-dimethoxybenzaldehyd
4-HYDROXY-3,5-DIMETHOXYBENZALDEHYDE · Benzaldehyde, 4-hydroxy-3,5-dimethoxy- · 3,5-DIMETHOXY-4-HYDROXYBENZALDEHYDE · Lilac aldehyde · SYRINGIC ALDEHYDE · FEMA 4049 · SYRINGA ALDEHYDE · Syring
Identifikatoren & physikalische Daten
| CAS No. | 134-96-3 |
|---|---|
| Summenformel | C9H10O4 |
| Durchschnittliche Molmasse | 182,17 g/mol |
| Monoisotopische Masse | 182,0579088 g/mol |
| SMILES | COc1cc(C=O)cc(OC)c1O |
| InChIKey | KCDXJAYRVLXPFO-UHFFFAOYSA-N |
| PubChem CID | 8655 |
| ChEMBL | CHEMBL225303 |
| ChEBI | CHEBI:67380 |
| EC No. | 205-167-5 |
| DTXSID | DTXSID2059643 |
| Lokaler Name | 4-Hydroxy-3,5-dimethoxybenzaldehyd |
Chemische & physikalische Eigenschaften
| XLogP | 0 |
|---|---|
| Polarare Oberfläche (TPSA) | 55,8 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 157 |
| Löslichkeit | Insoluble in waterSoluble (in ethanol)Chloroform, Methanol (Slightly)very sparingly soluble |
| Physical Description | Pale yellow solid[Merck Index]Very pale green needlesAlcoholic aroma |
| Kovats Retention Index | 1652165416171624.2289.61670.31662166916671643166416581662.81659.52934293029042907.3 |
| Schmelzpunkt | 110-113 °C(lit.) |
| Siedepunkt | 192-193 °C14 mm Hg(lit.) |
| Dichte | 1.013 |
| Brechungsindex | 1.4500 (estimate) |
| FEMA | 4049 | 4-HYDROXY-3,5,-DIMETHOXY BENZALDEHYDE |
| Flammpunkt | 192-193°C/14mm |
| Lagerbedingungen | Keep in dark place,Sealed in dry,Room Temperature |
| Aggregatzustand | Crystalline Powder |
| pKa (Säurekonstante) | 7.80±0.23(Predicted) |
| Farbe | Light yellow-green to brown |
| Geruch | at 100.00 %. mild plastic woody tonka sweet |
| Geruchsart | green |
| Biologische Quelle | synthetic |
| Merck | 14,9015 |
| JECFA Number | 1878 |
| BRN | 784514 |
| Henry-Konstante | 3.7×105 mol/(m3Pa) at 25℃, McFall et al. (2020) |
| Stabilität | Hygroscopic |
| Hauptanwendungen | cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care |
| InChI | 1S/C9H10O4/c1-12-7-3-6(5-10)4-8(13-2)9(7)11/h3-5,11H,1-2H3 |
| InChIKey | KCDXJAYRVLXPFO-UHFFFAOYSA-N |
| SMILES | COc1cc(C=O)cc(OC)c1O |
| LogP (Verteilungskoeffizient) | 1.30 |
| CAS Datenbank | 134-96-3(CAS DataBase Reference) |
| NIST chemische Informationen | Benzaldehyde, 4-hydroxy-3,5-dimethoxy-(134-96-3) |
| EPA chemische Informationen | Syringaldehyde (134-96-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (97.6%): Harmful if swallowed [Warning Acute toxicity, oral]H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (> 99.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1484 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: Benzaldehyde, 4-hydroxy-3,5-dimethoxy-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 22-01-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/23123Benzaldehyde, 4-hydroxy-3,5-dimethoxy-: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Causes altered sleep time (including change in righting reflex) in intraperitoneal lethal-dose studies of mice (LD50 = 1,000 mg/kg)[RTECS] Safe when used as a flavoring agent in food[JECFA] A skin and strong eye irritant[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Acute Tox. 4 (97.6%)Skin Irrit. 2 (100%)Eye Irrit. 2 (100%)STOT SE 3 (> 99.9%) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29124900 |
| RTECS-Nr. | CU5760000 |
| R-Sätze (R) | 22-36/37/38 |
| Gefahrensymbole | Xn,Xi |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 26-37/39-36 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Beschreibung
Syringaldehyde is an important constituent of many plant isolates and has widespread occurrence in wood products. It can be easily converted to trimethoxy-benzaldehyde which is an essential intermediate of the antibacterial drug trimethoprim. It is also used in the colorimetric determination of free chlorine in water.
Occurrence
Reported found in pineapple, beer, wine, grape brandy, rum, many different whisky products, sherry, roasted barley and hardwood smoke
Verwenden
Syringaldehyde is used in biological studies for the isolation and structural characterization of milled wood lignin, dioxane lignin, and cellulolytic lignin preparation from Brewer''s spent grain.
Herstellung & Synthese
synthetische
Vanillin is converted to 5-iodovanillin, which is treated with sodium methoxide to form 4-hydroxy-3,5- dimethyxybenzaldehyde.