trans-4-Hydroxycinnamic acid

Names

[ CAS No. ]:
501-98-4

[ Name ]:
trans-4-Hydroxycinnamic acid

[Synonym ]:
4-Hydroxy cinnamic acid
(2E)-3-(4-Hydroxyphenyl)acrylic acid
trans-p-Cumaric Acid
EINECS 231-000-0
3-(4-Hydroxy-phenyl)-acrylic acid
trans-p-Coumaric Acid
2-propenoic acid, 3-(4-hydroxyphenyl)-
E-4-Hydroxycinnamic Acid
(E)-3-(4-Hydroxyphenyl)acrylic acid
2-Propenoic acid, 3-(4-hydroxyphenyl)-, (2E)-
4-Coumaric acid
trans-4-Hydroxycinnamic Acid
p-Hydroxycinnamic acid,predominantly trans
MFCD00004399
4-Hydroxycinnamic acid

Biological Activity

[Description]:

p-Coumaric acid is the abundant isomer of cinnamic acid which has antitumor and anti-mutagenic activities.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

Natural Products >> Phenylpropanoids

[References]

[1]. Jaganathan SK, et al. Events associated with apoptotic effect of p-Coumaric acid in HCT-15 colon cancer cells. World J Gastroenterol. 2013 Nov 21;19(43):7726-34.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
346.1±17.0 °C at 760 mmHg

[ Melting Point ]:
214ºC

[ Molecular Formula ]:
C₉H₈O₃

[ Molecular Weight ]:
164.158

[ Flash Point ]:
177.3±17.4 °C

[ Exact Mass ]:
164.047348

[ PSA ]:
57.53000

[ LogP ]:
1.88

[ Vapour Pressure ]:
0.0±0.8 mmHg at 25°C

[ Index of Refraction ]:
1.660

[ Water Solubility ]:
soluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GD9095000

CHEMICAL NAME :: Cinnamic acid, p-hydroxy-, (E)-

CAS REGISTRY NUMBER :: 501-98-4

BEILSTEIN REFERENCE NO. :: 2207381

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C9-H8-O3

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2850 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: GNRIDX Gendai no Rinsho. (Tokyo, Japan) V.1-10, 1967-76(?). Volume(issue)/page/year: 3,675,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1160 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: GNRIDX Gendai no Rinsho. (Tokyo, Japan) V.1-10, 1967-76(?). Volume(issue)/page/year: 3,675,1969

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
GD9095000

[ HS Code ]:
2918290000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918290000

[ Summary ]:
HS: 2918290000 other carboxylic acids with phenol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) VAT:17.0% MFN tariff:6.5% General tariff:30.0%

Articles

Hydroxycinnamic acids used as external acceptors of electrons: an energetic advantage for strictly heterofermentative lactic acid bacteria.

Appl. Environ. Microbiol. 80(24) , 7574-82, (2014)

The metabolism of hydroxycinnamic acids by strictly heterofermentative lactic acid bacteria (19 strains) was investigated as a potential alternative energy route. Lactobacillus curvatus PE5 was the mo...

Antimicrobial activity of natural products from the flora of Northern Ontario, Canada.

Pharm. Biol. 53(6) , 800-6, (2015)

The number of multidrug resistant (MDR) microorganisms is increasing and the antimicrobial resistance expressed by these pathogens is generating a rising global health crisis. In fact, there are only ...

Effect of selected Saccharomyces cerevisiae yeast strains and different aging techniques on the polysaccharide and polyphenolic composition and sensorial characteristics of Cabernet Sauvignon red wines.

J. Sci. Food Agric. 95 , 2132-44, (2015)

The objective of this work was to study the effect of two Saccharomyces cerevisiae yeast strains with different capabilities of polysaccharide liberation during alcoholic fermentation in addition to s...