3,4-Dihydroxyzimtsure
3,4-DIHYDROXYCINNAMIC ACID · (E)-3-(3,4-Dihydroxyphenyl)acrylic acid · Caffeic · CAFFIC ACID · 31-39-5 · 3-(3,4-DIHYDROXYPHENYL)ACRYLIC ACID · Caffeic acid 0 · 4-(2’-carboxyvinyl)-1,2-dihydroxybenzene
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=Cc1ccc(O)c(O)c1 |
| InChIKey | QAIPRVGONGVQAS-UHFFFAOYSA-N |
| PubChem CID | 2518 |
| ChEMBL | CHEMBL3181904 |
| DTXSID | DTXSID5020231 |
| Lokaler Name | 3,4-Dihydroxyzimtsure |
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 | Stimulant |
| Schmelzpunkt | 211-213 °C (dec.) (lit.) |
| Siedepunkt | 272.96°C (rough estimate) |
| Dichte | 1.2933 (rough estimate) |
| Brechungsindex | 1.4500 (estimate) |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | ethanol: 50 mg/mLsoluble in hot water |
| Aggregatzustand | powder |
| pKa (Säurekonstante) | 4.58±0.10(Predicted) |
| Farbe | yellow to tan |
| Merck | 14,1635 |
| BRN | 2210883 |
| Henry-Konstante | 7.0×1010 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents, strong bases. |
| Kosmetik-Inhaltsstoffe Funktionen | FRAGRANCEANTIOXIDANT |
| 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) | 1.150 |
| CAS Datenbank | 331-39-5(CAS DataBase Reference) |
| NIST chemische Informationen | Cinnamic acid, 3,4-dihydroxy-(331-39-5) |
| EPA chemische Informationen | 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)- (331-39-5) |
Sicherheit & Vorschriften
| Wassergefährdungsklasse (WGK) | 3 |
|---|---|
| Zollcode | 29182990 |
| RTECS-Nr. | GD8950000 |
| R-Sätze (R) | 36/37/38-40-63-68 |
| Gefahrensymbole | Xn,Xi |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 26-36/37/39-36 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 331-39-5(Hazardous Substances Data) |
| Gefahrenklasse | Carc. 2 |
Anwendungen & Verwendung
Beschreibung
Caffeic acid is abundant in the whole plant of Solidago decurrens Lour. (Yi Zhi Huang Hua), fruit of Crataegus pinnatifida Bge. var. major N.E.Br. (Shan Li Hong), Salix myrtillacea Anderss. (Po Liu), rhizome of Cimicifuga foetida L., rhizome of Polypodiaceae Polypodium vulgare L. (Ou Ya Shui Long Gu), peel of Rutaceae Citrus limonum (Ning Meng), the whole plant of Polygonaceae Polygonum aviculare L. (Pian Xu), root of Valeriana officinalis L. (Xie Cao), the whole plant of Thymus mongolicus Ronn (She Xiang), leaves of Eucommia ulmoides (Du Zhong), and other herbal plants. It is a kind of polyhydroxy styrene acid, with the general chemical properties of phenolic acid. It is easily oxidized for the reason of the unsaturated double bonds, particularly unstable in alkaline solutionCaffeic acid has both cis and trans isomers, and the two isomers of caffeic acid have a mutual transformation in plants, which may regulate some important physiological process. Caffeic acid exists in plants in the main form of complexes; free state accounts for a few proportion.
Verwenden
Caffeic Acid is a constituent of plants, probably occurs in plants only in conjugated forms. Caffeic acid is found in all plants because it is a key intermediate in the biosynthesis of lignin, one of the principal sources of biomass. Caffeic acid is one of the main natural phenols in argan oi.