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2,4,5-Trimethoxybenzaldehyd
Asarylaldehyde · ASARALDEHYDE · Gazarin · ASARONALDEHYDE · Benzaldehyde, 2,4,5-trimethoxy- · 3,4,6-trimethoxybenzaldehyde · NCI-C61632 · Azarylaldehyde
Identifikatoren & physikalische Daten
| CAS No. | 4460-86-0 |
|---|---|
| Summenformel | C10H12O4 |
| Durchschnittliche Molmasse | 196,2 g/mol |
| Monoisotopische Masse | 196,07355886 g/mol |
| SMILES | COc1cc(OC)c(OC)cc1C=O |
| InChIKey | IAJBQAYHSQIQRE-UHFFFAOYSA-N |
| PubChem CID | 20525 |
| ChEMBL | CHEMBL1164301 |
| ChEBI | CHEBI:113543 |
| EC No. | 224-713-3 |
| DTXSID | DTXSID1022217 |
| Lokaler Name | 2,4,5-Trimethoxybenzaldehyd |
Chemische & physikalische Eigenschaften
| XLogP | 1,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 44,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 183 |
| Stoffklassen | Other Classes -> Benzaldehydes |
| Löslichkeit | less than 1 mg/mL at 72 °F (NTP, 1992)Soluble in water, ethyl ether, chloroform, ligroinChloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)<0.1 g/100 mL at 22 ºC |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Siedepunkt | 284 °F at 4 mmHg (Sublimes) (NTP, 1992)140°C 4mm |
| Schmelzpunkt | 234 to 237 °F (NTP, 1992)114 °C112-114 °C (lit.) |
| Dampfdruck | 0.00113 [mmHg] |
| Physical Description | 2,4,5-trimethoxybenzaldehyde is a beige powder. (NTP, 1992)Beige solid[CAMEO] White to pale brown solid[MSDSonline] |
| Collision Cross Section | 137.08 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]138.3 Ų [M+H]+ [CCS Type: TW |
| Dichte | 1.2166 (rough estimate) |
| Brechungsindex | 1.5550 (estimate) |
| Flammpunkt | 140°C/4mm subl. |
| Lagerbedingungen | Keep in dark place,Sealed in dry,Room Temperature |
| Aggregatzustand | Fine Crystalline Powder |
| Farbe | White to light beige |
| BRN | 1951403 |
| InChI | 1S/C10H12O4/c1-12-8-5-10(14-3)9(13-2)4-7(8)6-11/h4-6H,1-3H3 |
| InChIKey | IAJBQAYHSQIQRE-UHFFFAOYSA-N |
| SMILES | [H]C(=O)c1cc(OC)c(OC)cc1OC |
| LogP (Verteilungskoeffizient) | 1.634 (est) |
| CAS Datenbank | 4460-86-0(CAS DataBase Reference) |
| NIST chemische Informationen | Benzaldehyde, 2,4,5-trimethoxy-(4460-86-0) |
| EPA chemische Informationen | 2,4,5-Trimethoxybenzaldehyde (4460-86-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, 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 4 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Brandgefahren | Flash point data for this chemical are not available, but it is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to related compounds are skin and gastrointestinal tract irritation, sensitization, blistering, nausea, vomiting, diarrhea, urinary tract irritation, initial excitement, convulsions and central nervous system depression. (NTP, 1992) |
| Gefahrenübersicht | Similar compounds cause gastrointestinal tract irritation and convulsions[CAMEO] May cause irritation[MSDSonline] |
| Reaktive Gruppe | Aldehydes |
| Reactivity Profile | 2,4,5-TRIMETHOXYBENZALDEHYDE is light sensitive. (NTP, 1992). |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Brandbekämpfung | Fires involving this material can be controlled with 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: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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. |
| Entsorgungsverfahren | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Personal Protective Equipment (PPE) | MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. |
| Ökotoxizitätswerte | LC50 Pimephales promelas (Fathead minnow) at 80 mg/L for 24 hr /conditions of bioassay not specified/LC50 Pimephales promelas (Fathead minnow, age 34 days) 49.5 mg/L for 96 hr (95% confidence limits: 45.5-53.8 mg/L)flow through, 24.5 °C, dissolved oxygen 7.0 mg/L, hardness 44.5 mg/L CaCO3, alkalinity 43.0 mg/L CaCO3, pH 7.70 /98% pure/ |
| Natural Pollution Sources | 14: 101 (1981)] NINETEEN COMPOUNDS WERE FOUND IN SHIN-I DRUG OILASARYLALDEHYDE WAS ISOLATED & IDENTIFIED.[KIKUCHI T ET ALSTUDIES ON THE CONSTITUENTS OF CRUDE DRUG "SHIN-I" (DRIED BUDS OF MAGNOLIA SALICIFOLIA MAXIM)WAKANYAKU SHINPOJUMU, |
| Non-Human Toxicity Excerpts | /GENOTOXICITY/ 2,4,5-Trimethoxy benzaldehyde (TMB) was tested for mutagenicity in the Salmonella/microsome preincubation assay using a protocol approved by the National Toxicology Program. TMB was tested at doses of 0, 100, 333, 1000, 3333, and 10,000 ug/plate in four Salmonella typhimurium strains (TA98, TA100, TA1535, and TA1537) in the presence and absence of Aroclor-induced rat and/or hamster liver S9. TMB was negative in these tests and the highest ineffective dose level tested (not causing formation of a precipitate) in any Salmonella tester strain was 3333 ug/plate.[Zeiger E et alEnviron Mutagen 9:1-110 (1987)]/GENOTOXICITY/ 2,4,5-Trimethoxybenzaldehyde tested postive in the NTP's in vitro cytogenetics tests for chromosome aberrations and sister chromatid exchanges. It also tested positive in the mouse lymphoma assay, but was negative in the Ames Salmonella mutagenicity tests. /From table/[DHHS/NTPGenotoxicity Studies of 2,4,5-TRIMETHOXYBENZALDEHYDE. Available from, as of February 22, 2007: http://ntp.niehs.nih.gov/index.cfm?objectid=6DE337DB-F1F6-975E-7701E15B968E0682]/GENOTOXICITY/ Several aldehydes and peroxides were tested for mutagenicity using Salmonella typhimurium tester strains TA97a, TA100, TA102 and TA104, in the presence and absence of Aroclor-induced liver S9 mix from F344 rats and B6C3F1 mice, in either preincubation or vapour phase protocols. ... 2,4,5-Trimethoxybenzaldehyde was mutagenic only in strain TA1538 with rat liver S9. ...[Dillon D et alMutagenesis 13 (1): 19-26 (1998)] |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29124990 |
| RTECS-Nr. | CU8460000 |
| R-Sätze (R) | 36/37/38-34 |
| Gefahrensymbole | C |
| Sicherheitshinweise (S) | 22-24/25-45-36/37/39-27-26 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 4460-86-0(Hazardous Substances Data) |
| Gefahrenklasse | Acute Tox. 4 Oral |
Anwendungen & Verwendung
Beschreibung
2,4,5-Trimethoxybenzaldehyde (2,4,5-TMBA) is a natural cyclooxygenase-2 (COX-2) activity inhibitor that is present in carrot seeds (Daucus carota L.) and can be synthesised using Indonesia Sweet Flag (Acorus calamus) as a raw material. 2,4,5-TMBA may serve as a synthetic intermediate component for various pharmaceuticals. In addition, 2,4,5-TMBA is also considered a candidate drug for oral non-steroidal anti-inflammatory drugs (NSAIDs)[1].[1] LERRICK R I. Synthesis of Nonsteroidal Anti-Inflammatory Drug (NSAID) 2,4,5-Trimethoxybenzaldehyde from Indonesian Calamus oil and Its In Silico Pharmacokinetic Study[J]. Canadian Journal of Chemistry, 2022, 20 1. DOI:10.1139/cjc-2022-0121.
Verwenden
2,4,5-Trimethoxybenzaldehyde is used in the synthesis of stilbene and hydrostibene derivatives as potential anticancer agents, inhibiting tubulin. Also used in the synthesis of HIV-RT inhibitors.