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Cinnamic acid

Names

[ CAS No. ]:
621-82-9

[ Name ]:
Cinnamic acid

[Synonym ]:
(E)-3-Phenylprop-2-enoic acid
Propenoic acid, 3-phenyl-, (trans)-
Cinnamic acid
(2E)-3-Phenylacrylic acid
trans-Cinnamic Acid
EINECS 205-398-1
MFCD00004369
QV1U1R &&Trans or E Form
2-Propenoic acid, 3-phenyl-, (2E)-
4-09-00-02002 (Beilstein Handbook Reference)
trans-b-Carboxystyrene
2-Propenoicacid, 3-phenyl-

Biological Activity

[Description]:

Cinnamic acid has potential use in cancer intervention, with IC50s of 1-4.5 mM in glioblastoma, melanoma, prostate and lung carcinoma cells.

[Related Catalog]:

Natural Products >> Acids and Aldehydes
Research Areas >> Cancer

[Target]

Human Endogenous Metabolite


[In Vitro]

Treatment with Cinnamic acid (CINN) of various tumor cells of epithelial and neuroectodermal origin result in dose-dependent growth inhibition following a 3-day exposure. The inhibitory concentrations causing a 50% reduction in tumor-cell proliferation (IC50) are between 1.2 to 4.5 mM. It is also showed that 20 mM Cinnamic acid is needed to cause an IC50 in FS4 cells, i.e. 5 to 20 times more than for tumor cells. In addition to inhibiting tumor-cell proliferation, Cinnamic acid causes morphological changes consistent with melanocyte differentiation. Within 5 days of treatment with 5 mM Cinnamic acid, melanoma 1011 cells appear enlarged with a markedly increased cytoplasm-to-nuclear ratio and well organized cytoskeleton, developed long dendritic processes and became highly melanotic. The change in the capacity of Cinnamic acid -treated melanoma 1011, A375(M) and SKMEL28 cells to degrade and cross tissue barriers is assessed by an in vitro invasion assay using modified Boyden chambers with matrigel-coated filters. After 3 days of continuous treatment with Cinnamic acid, a dose-dependent loss of invasive capacity in 3 tested tumor lines is observed. Treatment with 5 mM Cinnamic acid results in 75-95% loss of invasiveness[1].

[Cell Assay]

The cell lines used, established from human malignant tumors, are A549 (lung cancer); PC3(M), Du145, and LNCaP (prostate cancer); A172, U251 (glioblastoma); and SKMEL28, A375(M), 1011 (melanoma). Growth rates are determined by cell counting. Briefly, 5 X104 cells are plated in each well of a 24-well plate, allowed to attach overnight, and treated with compounds (e.g., Cinnamic acid: 2.5, 5, 10, 20, 30 mM) the following day. Cells are grown for 3 days at 37°C in the presence or absence of the drug, then detached with trypsin/EDTA and counted in a Coulter counter. Viability is determined by Trypan-blue exclusion assay[1].

[References]

[1]. Liu L, et al. Cinnamic acid: a natural product with potential use in cancer intervention. Int J Cancer. 1995 Jul 28;62(3):345-50.


[Related Small Molecules]

3-Methyladenine | Hydrocortisone | Acetylcysteine(N-acetylcysteine) | Retinoic acid | Melatonine | Dinoprostone | Nicotinamide | Adenosine triphosphate | 4-Acetamidophenol | Prostaglandin E1 | Dehydroepiandrosterone | Corticosterone | Progesterone | Docosahexaenoic Acid | NAD+

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
265.0±0.0 °C at 760 mmHg

[ Melting Point ]:
133ºC

[ Molecular Formula ]:
C9H8O2

[ Molecular Weight ]:
148.159

[ Flash Point ]:
189.5±9.6 °C

[ Exact Mass ]:
148.052429

[ PSA ]:
37.30000

[ LogP ]:
2.41

[ Vapour Pressure ]:
0.0±0.5 mmHg at 25°C

[ Index of Refraction ]:
1.616

[ Stability ]:
Stable. Combustible. Incompatible with strong oxidizing agents.

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GD7800000
CHEMICAL NAME :
Cinnamic acid
CAS REGISTRY NUMBER :
621-82-9
LAST UPDATED :
199701
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C9-H8-O2
MOLECULAR WEIGHT :
148.17
WISWESSER LINE NOTATION :
QV1U1R

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
REFERENCE :
FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 16,687,1978 ** ACUTE TOXICITY DATA **
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 16,687,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 112,53,1973
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
GISAAA Gigiena i Sanitariya. For English translation, see HYSAAV. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1- 1936- Volume(issue)/page/year: 46(1),94,1981
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
160 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 16,687,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
380 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 19,617,1969
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
VPITAR Voprosy Pitaniya. Problems of Nutrition. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1-10, 1932-41; V.11- 1952- Volume(issue)/page/year: 33(5),48,1974 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 82933 No. of Facilities: 87 (estimated) No. of Industries: 2 No. of Occupations: 10 No. of Employees: 22012 (estimated)

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36

[ WGK Germany ]:
1

[ RTECS ]:
GD7850000

[ HS Code ]:
2916190090

Synthetic Route

Precursor & DownStream

Customs

[ HS Code ]: 2916399090

[ Summary ]:
2916399090 other aromatic monocarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%


Related Compounds