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Caffeic Acid
trans-Caffeic acid · (E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid · C01197 · AKOS B004050 · trans-Caffeate · rans-Caffeicaci · （E)-CAFFEIC ACID · RARECHEM BK HC T335
Identifikatoren & physikalische Daten
| CAS No. | 331-39-5 |
|---|---|
| Summenformel | C9H8O4 |
| Durchschnittliche Molmasse | 180,16 g/mol |
| Monoisotopische Masse | 180,04225874 g/mol |
| SMILES | O=C(O)/C=C/c1ccc(O)c(O)c1 |
| InChIKey | QAIPRVGONGVQAS-DUXPYHPUSA-N |
| PubChem CID | 689043 |
| ChEMBL | CHEMBL145 |
| ChEBI | CHEBI:36281 |
| EC No. | 206-361-2 |
| DTXSID | DTXSID901316055 |
Chemische & physikalische Eigenschaften
| XLogP | 1,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 77,8 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 212 |
| Stoffklassen | Other Classes -> Organic Acids |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Kosmetika | Cosmetics ingredient -> Conditioning/Emollient |
| LogP (Verteilungskoeffizient) | log Kow = 1.151.29 |
| Color/Form | Yellow crystals from concentrated aqueous solutions. Alkaline solns turn from yellow to orange. |
| Löslichkeit | less than 1 mg/mL at 72 °F (NTP, 1992)Sparingly soluble in cold water. Freely soluble in hot water, cold alcohol.ethanol: 50 mg/mL |
| Decomposition | When heated to decomposition it emits acrid smoke and fumes. |
| Schmelzpunkt | 433 to 437 °F (decomposes) (NTP, 1992)Decomposes at 223-225 °C (Softens at 194 °C).211-213 °C (dec.)(lit.) |
| Dampfdruck | 0.00000025 [mmHg] |
| Physical Description | 3,4-dihydroxycinnamic acid appears as yellow prisms or plates (from chloroform or ligroin) or pale yellow granules. Alkaline solutions turn from yellow to orange. (NTP, 1992)Yellow solidSlightly soluble in cold water, soluble in hot water[Merck Index] Light yellow powder[MSDSonline] |
| Dissociation Constants | 4.62 (at 25 °C)pKa = 4.62 at 25 °C |
| Collision Cross Section | 129.9 Ų [M+H-H2O]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]128.84 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]133.2 Ų [M-H]- |
| Siedepunkt | 416.8±35.0 °C(Predicted) |
| Dichte | 1.478±0.06 g/cm3(Predicted) |
| Lagerbedingungen | Storage temp. 2-8°C |
| Aggregatzustand | powder |
| pKa (Säurekonstante) | 4.58±0.10(Predicted) |
| Farbe | yellow to tan |
| BRN | 1954563 |
| Hauptanwendungen | food and beverages |
| InChI | 1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+ |
| InChIKey | QAIPRVGONGVQAS-DUXPYHPUSA-N |
| SMILES | OC(=O)\C=C\c1ccc(O)c(O)c1 |
| LogP (Verteilungskoeffizient) | 1.420 (est) |
| CAS Datenbank | 501-16-6(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (62.7%): Causes skin irritation [Warning Skin corrosion/irritation]P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 83 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H319 (97.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] |
|---|---|
| Regulatorische Informationen | Hazard Traits - Carcinogenicity3,4-Dihydroxycinnamic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits acrid smoke and fumes. (NTP, 1992) |
| Gefahrenübersicht | Causes epithelial hyperplasia in forestomach of rats given 20 g/kg of diet for 4 weeks[HSDB] An irritantTargets G.I. tract and kidneys[MSDSonline] |
| Reaktive Gruppe | Acids, Carboxylic |
| Reactivity Profile | 3,4-DIHYDROXYCINNAMIC ACID is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions |
Anwendungen & Verwendung
Verwenden
trans-Caffeic Acid is a useful synthetic intermediate. It was used as a reactant to synthesize N-caffeoylphenalkylamide derivatives as bacterial efflux pump inhibitors. It is also used to prepare caffeic acid phenethyl ester analogs with antitumor structures.