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Veratrumaldehyd
3,4-DIMETHOXYBENZALDEHYDE · 3,4-DIMETHOXYANILINE · Benzaldehyde, 3,4-dimethoxy- · VERATRYL ALDEHYDE · 204-373-2 · FEMA 3109 · METHYL VANILLIN · VERATRIC ALDEHYDE
Identifikatoren & physikalische Daten
| CAS No. | 120-14-9 |
|---|---|
| Summenformel | C9H10O3 |
| Durchschnittliche Molmasse | 166,17 g/mol |
| Monoisotopische Masse | 166,06299418 g/mol |
| SMILES | COc1ccc(C=O)cc1OC |
| InChIKey | WJUFSDZVCOTFON-UHFFFAOYSA-N |
| PubChem CID | 8419 |
| ChEMBL | CHEMBL1088937 |
| ChEBI | CHEBI:17098 |
| EC No. | 204-373-2 |
| DTXSID | DTXSID7026285 |
| Lokaler Name | Veratrumaldehyd |
Chemische & physikalische Eigenschaften
| XLogP | 1,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 35,5 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 147 |
| Duftstoffe | Fragrance Ingredient (Veratraldehyde) -> IFRA transparency List |
| LogP (Verteilungskoeffizient) | 1.22 |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Aromastoffe | EU Flavoring substances |
| Löslichkeit | less than 1 mg/mL at 72 °F (NTP, 1992)6.32 mg/mL at 25 °Cinsoluble in cold watersoluble in hot water oilssoluble (in ethanol)alcohol: freely soluble<0.1 g/100 mL at 22 ºC |
| Flammpunkt | greater than 230 °F (NTP, 1992)>230 °F |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Siedepunkt | 538 °F at 760 mmHg (NTP, 1992)281.00 °C. @ 760.00 mm Hg281 °C281 °C @760 [mm Hg]281 °C (lit.) |
| Schmelzpunkt | 108 to 109 °F (NTP, 1992)58 °C40-43 °C (lit.) |
| Physical Description | Veratraldehyde appears as needles or chunky light peach powder. Has an odor of vanilla beans. (NTP, 1992)Solidwhite crystalline solid |
| Dichte | 1.1708 (rough estimate) |
| Dampfdruck | 0.09Pa at 24℃ |
| Brechungsindex | 1.5260 (estimate) |
| FEMA | 3109 | VERATRALDEHYDE |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Lumps or Fused Solid |
| Farbe | White to yellow |
| Wichte | 1.15 (liquid) |
| Geruch | at 10.00 % in dipropylene glycol. sweet woody vanilla |
| Geruchsart | creamy |
| Biologische Quelle | synthetic |
| Merck | 14,9951 |
| JECFA Number | 877 |
| BRN | 473899 |
| Stabilität | Stable. Incompatible with strong bases, strong oxidizing agents. |
| Hauptanwendungen | flavors and fragrances |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMING |
| InChI | 1S/C9H10O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-6H,1-2H3 |
| InChIKey | WJUFSDZVCOTFON-UHFFFAOYSA-N |
| SMILES | [H]C(=O)c1ccc(OC)c(OC)c1 |
| LogP (Verteilungskoeffizient) | 0.8 at 25℃ |
| CAS Datenbank | 120-14-9(CAS DataBase Reference) |
| NIST chemische Informationen | Benzaldehyde, 3,4-dimethoxy-(120-14-9) |
| EPA chemische Informationen | Veratraldehyde (120-14-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1759 reports by companies from 13 notifications to the ECHA C&L Inventory.H302: Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Chemical: Benzaldehyde, 3,4-dimethoxy-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 15-04-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/203943,4-Dimethoxybenzaldehyde: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | This compound is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Exposure to this compound may cause skin, eye, mucous membrane or upper respiratory tract irritation. |
| Reaktive Gruppe | Aldehydes |
| Reactivity Profile | VERATRALDEHYDE is incompatible with strong oxidizing agents and strong bases. (NTP, 1992). VERATRALDEHYDE is an aldehyde. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Acute Tox. 4 (100%)Acute toxicity (Oral) - Category 4 |
| Brandbekämpfung | Fires involving this compound may be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| Protective Action Criteria (PAC) | 6.0 [mg/m3]66 [mg/m3]400 [mg/m3] |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992) |
| F | 9-23 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29124900 |
| RTECS-Nr. | YX5088000 |
| R-Sätze (R) | 22-38-36/37/38-36/38 |
| Toxizität | LD50 orally in Rabbit: 2000 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
| Gefahrensymbole | Xn,Xi |
| Sicherheitshinweise (S) | 26-22-24/25-36 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Acute Tox. 4 OralSkin Irrit. 2 |
Anwendungen & Verwendung
Occurrence
Reported among the constituents of the essential oils of Cymbopogon javanensis and Eryngium poterium. Also reported found in raspberry, ginger, peppermint oil, Bourbon vanilla and mastic gum oil.
Verwenden
Veratraldehyde was used in the preparation of 4-chloromethyl-2-(dimethoxyphenyl)-1,3-dioxolane. It was used in the synthesis of (+)-lithospermic acid, having anti-HIV activity. It forms 1:1 inclusion complexes with cyclodextrins. It reacts with 3-acetyl-2,5-dimethythiophene to yield chalcone dye, (2E)-3-(3,4-Dimethoxyphenyl)-1-(2,5-dimethylthiophen-3-yl)prop-2-en-1-one.
Herstellung & Synthese
synthetische
Prepared from vanillin by methylation of vanillin with dimethylsulfate under mildly alkaline conditions.