Zimtsure

Bezeichnung:Zimtsure

CAS-Nr621-82-9

Englisch Name:Cinnamic acid

CBNumberCB0345387

SummenformelC9H8O2

Molgewicht148.16

MOL-Datei621-82-9.mol

Synonyma

Zimtsure

Zimtsure physikalisch-chemischer Eigenschaften

Schmelzpunkt	133 °C(lit.)
Siedepunkt	300 °C(lit.)
Dichte	1.2475
Brechungsindex	1.5049 (estimate)
FEMA	2288 \| CINNAMIC ACID
Flammpunkt	>230 °F
storage temp.	Sealed in dry,Room Temperature
Löslichkeit	Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand	Solid
pka	pK (25°) 4.46
Farbe	White to Off-White
PH	3.76(1 mM solution);3.23(10 mM solution);2.72(100 mM solution)
Geruch (Odor)	at 100.00 %. balsam sweet storax
Geruchsart	balsamic
Wasserlöslichkeit	511.2mg/L(25 ºC)
JECFA Number	657
Stabilität	Stable. Combustible. Incompatible with strong oxidizing agents.
LogP	2.13
CAS Datenbank	621-82-9(CAS DataBase Reference)
NIST chemische Informationen	2-Propenoic acid, 3-phenyl-(621-82-9)
EPA chemische Informationen	Cinnamic acid (621-82-9)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
WGK Germany	1
RTECS-Nr.	GD7850000
Toxizität	LD50 (g/kg): 3.57 orally in rats; >5.0 dermally in rabbits (Letizia)

Gefahreninformationscode (GHS)

Cinnamic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Aussehen Eigenschaften
C9H8O2; 3-Phenylacrylsäure, trans-3-Phenylpropensäure. Feinkristallines, farbloses Pulver mit aromatischem Geruch.
Gefahren für Mensch und Umwelt
Reizt die Augen, Atmungsorgane und die Haut.
Heftige Reaktion mit starken Basen möglich.
LD₅₀ (oral, Ratte): 2500 mg/kg.
Schutzmaßnahmen und Verhaltensregeln
Schutzhandschuhe als kurzzeitiger Staubschutz.
Verhalten im Gefahrfall
Trocken aufnehmen. Der Entsorgung zuführen. Nachreinigen.
Kohlendioxid, Wasser, Pulver, Schaum.
Brennbar.
Erste Hilfe
Nach Hautkontakt: Mit reichlich Wasser abwaschen.
Nach Augenkontakt: Mit reichlich Wasser bei geöffnetem Lidspalt mindestens 15 Minuten ausspülen. Sofort Augenarzt hinzuziehen.
Nach Einatmen: Frischluft.
Nach Verschlucken: Reichlich Wasser trinken. Erbrechen auslösen. Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminierte Kleidung entfernen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Als feste Laborchemikalienabfälle.
Beschreibung
Cinnamic acid is a white crystalline organic acid, which is slightly soluble in water.
It is obtained from oil of cinnamon, or from balsams such as storax. It is also found in shea butter and is the best indication of its environmental history and post-extraction conditions. It can also be made synthetically.
Cinnamic acid is used in flavors, synthetic indigo, and certain pharmaceuticals, though its primary use is in the manufacturing of the methyl, ethyl, and benzyl esters for the perfume industry. Cinnamic acid has a honey- like odor; it and its more volatile ethyl ester (ethyl cinnamate) are flavor components in the essential oil of cinnamon, in which related cinnamaldehyde is the major constituent. Cinnamic acid is also part of the biosynthetic shikimate and phenyl propanoid pathways. Its biosynthesis is performed by action of the enzyme phenylalanine ammonia - lyase (PAL) on phenylalanine.
Cinnamic acid is freely soluble in benzene, diethyl ether, acetone, and it is insoluble in hexane.
Cinnamic acid is also a kind of self-inhibitor produced by fungal spore to prevent germination.
Chemische Eigenschaften
Cinnamic acid is almost odorless with a burning taste, and then turning sweet and reminiscent of apricot.
Occurrence
The trans- form has been found among the constituents of the essential oils of basil, Chinese cinnamon, Melaleuca bracteata, Alpinia galanga. It is reported found in Peru balsam, Asian and American storax and cocoa leaves. Also reported found in strawberry fruit, beer, cognac, starfruit (Averrhoa carambola L) and loquat. The cis- form is present in the oil of Alpinia malacensis.
Verwenden
cinnamic acid has sunscreen capabilities. Some manufacturers use it to replace PABA because of its lower allergic and phototoxic reaction incidence. Cinnamic acid is found in cinnamon leaves and cocoa leaves, and is an essential oil of certain mushrooms. It may cause allergic skin rashes.
Verwenden
fragrance & flavoring agent, antidiabetic
Verwenden
Cinnamic Acid is a flavoring agent that consists of crystalline scales, white in color, with an odor resembling honey and flowers. it is slightly soluble in water, soluble in alcohol, chloroform, acetic acid, acetone, benzene, and most oils, and alkali salts soluble in water. it is obtained by chemical synthesis. it is also termed 3-phenylpro- penoic acid.
synthetische
Two isomers, trans- and cis- exist; the trans-isomer is of interest for use in flavoring; in addition to the extraction from natural sources (storax), it can be prepared as follows: (1) from benzaldehyde, anhydrous sodium acetate and acetic anhydride in the presence of pyridine (Perkin reaction); (2) from benzaldehyde and ethyl acetate (Claisen condensation); (3) from benzaldehyde and acetylene chloride; (4) by oxidation of benzylidene acetone with sodium hypochlorite.
Definition
ChEBI: A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.
Synthesis Reference(s)
Journal of the American Chemical Society, 75, p. 1068, 1953 DOI: 10.1021/ja01101a016
The Journal of Organic Chemistry, 59, p. 710, 1994 DOI: 10.1021/jo00083a006
Sicherheitsprofil
Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. A skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and fumes.
Synthese
Rainer Ludwig Claisen (1851–1930), German chemist, described for the first time in 1890 the synthesis of cinnamates by reacting aromatic aldehydes with esters. The reaction is known as the Claisen condensation.
läuterung methode
Crystallise the acid from *benzene, CCl4, hot water, water/EtOH (3:1), or 20% aqueous EtOH. Dry it at 60o in vacuo. It is steam volatile. [Beilstein 9 IV 2002.]

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