trans-Cinnamic acid

trans-Cinnamic acid Chemical Properties
Melting point 133 °C (lit.)
Boiling point 300 °C(lit.)
density 1.248
vapor pressure 1.3 hPa (128 °C)
refractive index 1.5049 (estimate)
Fp >230 °F
storage temp. 2-8°C
solubility 0.4g/l
form Crystalline Powder
pka4.44(at 25℃)
color White to almost white
Specific Gravity0.91
OdorFaint odour
PH3-4 (0.4g/l, H2O, 20℃)
PH Range3 - 4
Odor Typebalsamic
Water Solubility 0.4 g/L (20 ºC)
λmax273nm(MeOH)(lit.)
Merck 14,2299
BRN 1905952
Stability:Light Sensitive
InChIKeyWBYWAXJHAXSJNI-VOTSOKGWSA-N
LogP2.130
CAS DataBase Reference140-10-3(CAS DataBase Reference)
NIST Chemistry ReferenceCinnamic acid(140-10-3)
EPA Substance Registry System(E)-Cinnamic acid (140-10-3)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36-37/39
WGK Germany 1
RTECS GD7850000
TSCA Yes
HS Code 29163900
ToxicityLD50 orally in Rabbit: 2500 mg/kg LD50 dermal Rabbit > 5000 mg/kg
MSDS Information
ProviderLanguage
3-Phenyl-2-propenoic acid English
ACROS English
SigmaAldrich English
ALFA English
trans-Cinnamic acid Usage And Synthesis
Chemical PropertiesWhite to almost white crystalline powder. Insoluble in water, slightly soluble in hot water, easily soluble in benzene, acetone, ether, glacial acetic acid and other organic solvents.
Usestrans-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.
Usestrans-Cinnamic acid was used to establish library of phenolic compounds by liquid chromatography/ultraviolet and mass spectrometry/mass spectrometry.
DefinitionChEBI: Cinnamic acid is a monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia. It has a role as a plant metabolite. It is a member of styrenes and a member of cinnamic acids. It is a conjugate acid of a cinnamate.
General Descriptiontrans-Cinnamic acid is an α,β-unsaturated aromatic acid that can be used as a flavoring agent. It is mainly used to prepare ester derivatives that are used in perfume industry. trans-Cinnamic acid is the key volatile components of cinnamon essential oil.
Flammability and ExplosibilityNotclassified
Biochem/physiol Actionstrans-cinnamic acid has inhibitory effect on phorbol-12-myristate-13-acetate-induced invasion of human lung adenocarcinoma A549 cells. It is a potential agent which can prevent lung tumor cells from metastasizing. It induces intracellular release of Ca2+ from the vacuole to the cytoplasm which triggers phytotoxicity in cucumber.
Purification MethodsCrystallise 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.]
Cinnamic acid 3,4-dihydro-5,6,7-trimethoxy-2-naphthoic acid Methyl propiolate PHENYL RESIN ACRYLIC EMULSION Diphenyl ether Butyl acrylate PHENYL VALERATE 6-Benzylaminopurine Acrylic acid trans,trans-2,4-Undecadienal trans-Cinnamic acid 4-Methoxycinnamic acid 3-(Trifluoromethyl)cinnamic acid Methyl acrylate Poly(acrylic acid) Methyl methacrylate Phenyl salicylate

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