Propen-1,2,3-tricarbonsure
1-Propene-1,2,3-tricarboxylic acid · aconiticaci · ACONITIC ACID · citridinic acid · achilleaic acid · 3-carboxyglutaconic acid · Aconitic Acid, 10 mM in DMSO · 3-carboxy-2-pentenedioic acid
Identifikatoren & physikalische Daten
| CAS No. | 499-12-7 |
|---|---|
| Summenformel | C6H6O6 |
| Durchschnittliche Molmasse | 174,11 g/mol |
| Monoisotopische Masse | 174,01643791 g/mol |
| SMILES | O=C(O)C=C(CC(=O)O)C(=O)O |
| InChIKey | GTZCVFVGUGFEME-UHFFFAOYSA-N |
| PubChem CID | 309 |
| ChEMBL | CHEMBL153658 |
| ChEBI | CHEBI:22211 |
| EC No. | 207-877-0 |
| DTXSID | DTXSID9060102 |
| Lokaler Name | Propen-1,2,3-tricarbonsure |
Chemische & physikalische Eigenschaften
| XLogP | -1 |
|---|---|
| Polarare Oberfläche (TPSA) | 112 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 251 |
| Schmelzpunkt | 192°C (rough estimate) |
| Siedepunkt | 225.05°C (rough estimate) |
| Dichte | 1.4285 (rough estimate) |
| Brechungsindex | 1.5860 (estimate) |
| FEMA | 2010 | ACONITIC ACID |
| Löslichkeit | Soluble 16 % in water at 13 ℃, 33% in water at 25 ℃. Decomposes when heated to 200° C. Soluble in alcohol and most perfume and flavor materials, poorly soluble in hydrocarbons (Terpenes, etc.). |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 2.39±0.36(Predicted) |
| Farbe | Colorless (white) crystal leaves or plates |
| Geruch | Vegetative, musty and nutty with a dry, toasted nuance |
| JECFA Number | 627 |
| LogP (Verteilungskoeffizient) | 0.63 |
| EPA chemische Informationen | 1-Propene-1,2,3-tricarboxylic acid (499-12-7) |
Sicherheit & Vorschriften
| TSCA-Inventar-Status | TSCA listed |
|---|---|
| Toxizität | LD50 intravenous in mouse: 180mg/kg |
| Gefahrstoffdaten | 499-12-7(Hazardous Substances Data) |
Anwendungen & Verwendung
Occurrence
Reported found in beet root, sugarcane, the leaves and tubers of Aconitum napellus, and other natural products (Pelargonium species).
Verwenden
Aconitic Acid is a flavoring substance which occurs in the leaves and tubers of aconitum napellus l. And other ranunculaceae. Transaconitic acid can be isolated during sugar cane processing, by precipitation as the calcium salt from cane sugar or molasses. It may be synthesized by sulfuric acid dehydration of citric acid but not by the methanesulfonic acid method. It is used in a maximum level, as served, of 0.003% for baked goods, 0.002% for alcoholic beverages, 0.0015% for frozen dairy products, 0.0035% for soft candy, and 0.0005% or less for all other food categories.
Herstellung & Synthese
synthetische
By dehydration of citric acid with concentrated H2SO4: Aconitic acid prepared by this or other methods has the transconfiguration; the cis-isomer is little known. Trans-aconitic acid can be isolated during sugarcane processing by precipitation as the calcium salt from cane sugar or molasses.