Cinnamic Acid
3-PHENYLACRYLIC ACID · CINNAMIC ACID, TRANS- · 3-PHENYL-2-PROPENOIC ACID · FEMA 2288 · (2E)-3-phenylprop-2-enoic acid · (E)-Cinnamic acid · (e)-2-propenoicaci · (E)-3-Phenylacrylic acid
Identifikatoren & physikalische Daten
| CAS No. | 140-10-3 |
|---|---|
| Summenformel | C9H8O2 |
| Durchschnittliche Molmasse | 148,16 g/mol |
| Monoisotopische Masse | 148,0524295 g/mol |
| SMILES | O=C(O)/C=C/c1ccccc1 |
| InChIKey | WBYWAXJHAXSJNI-VOTSOKGWSA-N |
| PubChem CID | 444539 |
| ChEMBL | CHEMBL27246 |
| ChEBI | CHEBI:27386 |
| EC No. | 205-398-1 |
| DTXSID | DTXSID5022489 |
| Lokaler Name | trans-zimtsure |
Chemische & physikalische Eigenschaften
| XLogP | 2,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 37,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 155 |
| Stoffklassen | Other Classes -> Organic Acids |
| SpringerMaterials Properties | Angular frequency |
| Duftstoffe | Fragrance Ingredient (Cinnamic acid) -> IFRA transparency ListFragrance Ingredient (trans-Cinnamic acid) -> IFRA transparency List |
| LogP (Verteilungskoeffizient) | 2.13 |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Aromastoffe | EU Flavoring substances |
| Löslichkeit | 0.546 mg/mLinsoluble in watersoluble in oilsslightly soluble (in ethanol)0.4g/l0.4 g/L (20 ºC) |
| Siedepunkt | 298.00 to 300.00 °C. @ 760.00 mm Hg300 °C300 °C(lit.) |
| Schmelzpunkt | 133 °C133 °C (lit.) |
| Physical Description | Solid with a honey floral odor[Merck Index] White crystalline solid[Alfa Aesar MSDS]White crystalline powder with a mild odorWhite crystalline scales, honey floral odour |
| Ionization Efficiency | Positive1.182.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Dissociation Constants | 4.45 |
| Dichte | 1.248 |
| Dampfdruck | 1.3 hPa (128 °C) |
| Brechungsindex | 1.5049 (estimate) |
| Flammpunkt | >230 °F |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | 4.44(at 25℃) |
| Aggregatzustand | Crystalline Powder |
| Farbe | White to almost white |
| Wichte | 0.91 |
| Geruch | Faint odour |
| pH | 3-4 (0.4g/l, H2O, 20℃) |
| Geruchsart | balsamic |
| Biologische Quelle | synthetic |
| Merck | 14,2299 |
| BRN | 1905952 |
| Henry-Konstante | 2.8×1011 mol/(m3Pa) at 25℃, Abraham and Jr. (2019) |
| Stabilität | Light Sensitive |
| Hauptanwendungen | flavors and fragrances |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMINGSKIN CONDITIONING |
| InChI | 1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+ |
| InChIKey | WBYWAXJHAXSJNI-VOTSOKGWSA-N |
| SMILES | OC(=O)\C=C\c1ccccc1 |
| LogP (Verteilungskoeffizient) | 2.130 |
| CAS Datenbank | 140-10-3(CAS DataBase Reference) |
| NIST chemische Informationen | Cinnamic acid(140-10-3) |
| EPA chemische Informationen | (E)-Cinnamic acid (140-10-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 97.8% (1644 of 1681) of all reports.Not ClassifiedAggregated GHS information provided per 1681 reports by companies from 7 notifications to the ECHA C&L Inventory.This chemical does not meet GHS hazard criteria for 76.1% (284 of 373) of all reports.WarningH315 (15.5%): Causes skin irritation [Warning Skin corrosion/irritation] |
|---|---|
| Regulatorische Informationen | Chemical: 2-Propenoic acid, 3-phenyl-, (E)-Chemical: 2-Propenoic acid, 3-phenyl-Regulation (EC) No 1831/2003 (amended)Status: Active Update: 06-02-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/238162-Propenoic acid, 3-phenyl-, (E)-: Does not have an individual approval but may be used under an appropriate group standardCinnamic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Cinnamic acid: Human health tier II assessment |
| Gefahrenübersicht | A mild skin irritantCauses gastrointestinal changes in acute oral studies of rats[RTECS] Safe when used as a flavoring agent in food[JECFA] An eye irritant[Alfa Aesar MSDS] See Hydrocinnamic acid.A mild skin and strong eye irritant |
| Hazard Classes and Categories | Skin Irrit. 2 (15.5%)Not Classified |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29163900 |
| RTECS-Nr. | GD7850000 |
| R-Sätze (R) | 36/37/38 |
| Toxizität | LD50 orally in Rabbit: 2500 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36-37/39 |
| Lagerklasse | 13 - Non Combustible Solids |
| Gefahrenklasse | Eye Irrit. 2 |
Anwendungen & Verwendung
Beschreibung
Die trans-3-Phenylacrylsäure bildet farblose, wenig wasserlösliche Blättchen. Die Säure kommt in frei und verestert in verschiedenen etherischen Ölen und Harzen vor. Technisch stellt man aus der Säure eine Vielzahl von Estern her, die in der Parfümindustrie ausgedehnte Verwendung finden.
Verwenden
trans-Cinnamic acid is used in flavors, synthetic indigo and pharmaceuticals. It is involved in the production of methyl, ethyl and benzyl esters, which is used in the perfume industry. It serves as a precursor to the sweetener aspartame through enzyme-catalyzed amination to phenylalanine. It is a self-inhibitor produced by fungal spores to prevent germination. In addition, it is used to establish phenolic compounds by liquid chromatography, ultraviolet and mass spectrometry. It is utilized as a potential agent, thereby preventing lung tumor cells from metastasizing. Further, it induces intracellular release of calcium ions from the vacuole to the cytoplasm in order to trigger phytotoxicity in cucumber.