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133760

Sigma-Aldrich

trans-Cinnamic acid

97%

Synonym(s):

trans-3-Phenylacrylic acid, Cinnamic acid

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About This Item

Linear Formula:
C6H5CH=CHCOOH
CAS Number:
140-10-3
Molecular Weight:
148.16
Beilstein/REAXYS Number:
1905952
EC Number:
205-398-1
MDL number:
MFCD00004369
UNSPSC Code:
12352100
eCl@ss:
39023931
PubChem Substance ID:
24848120
NACRES:
NA.22

Quality Level

200

assay

97%

form

solid

bp

300 °C (lit.)

mp

132-135 °C (lit.)

functional group

carboxylic acid
phenyl

SMILES string

OC(=O)\C=C\c1ccccc1

InChI

1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+

InChI key

WBYWAXJHAXSJNI-VOTSOKGWSA-N

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Application

trans-Cinnamic acid was used to establish library of phenolic compounds by liquid chromatography/ultraviolet and mass spectrometry/mass spectrometry.

Biochem/physiol Actions

trans-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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 1

flash_point_f

320.0 °F - closed cup

flash_point_c

160 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT2411
0000207856
MKCQ9252
MKCP8118
MKCN6727

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Jingquan Yu et al.
Journal of chemical ecology, 35(12), 1471-1477 (2010-01-12)
To obtain insight into interspecies interactions mediated by allelochemicals, the response of cucumber (Cucumis sativus L. cv Jinyan No.4) and figleaf gourd (Cucurbita ficifolia Bouché) seedlings to trans-cinnamic acid (CA) (1) was investigated. While trans-CA is an autotoxin in cucumber
Chiung-Man Tsai et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 48(3), 494-501 (2012-12-12)
Dietary polyphenols have been reported as an effective phytochemical for health protection and cinnamic acid (CA) is one of the polyphenols that has been demonstrated having chemopreventive potential. It was known that the early and distal metastasis might lead to
Jianping Sun et al.
Molecules (Basel, Switzerland), 12(3), 679-693 (2007-09-14)
Liquid chromatography/ultraviolet (LC/UV) and mass spectrometry/mass spectrometry (MS/MS) libraries containing 39 phenolic compounds were established by coupling a LC and an ion trap MS with an electrospray ionization (ESI) source, operated in negative ion mode. As a result, the deprotonated
Barbara Speranza et al.
Microorganisms, 8(6) (2020-06-25)
Twelve fungal strains were assayed to investigate their resistance to cinnamic and vanillic acids and their ability to remove these compounds from a liquid medium. In a first step, the effect of the two aromatic acids (1 g/L) on the
Bianca C Pérez et al.
Journal of medicinal chemistry, 56(2), 556-567 (2013-01-01)
The control of malaria is challenged by drug resistance, and new antimalarial drugs are needed. New drug discovery efforts include consideration of hybrid compounds as potential multitarget antimalarials. Previous work from our group has demonstrated that hybrid structures resulting from
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