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p-Hydroxy-cinnamic acid

Names

[ CAS No. ]:
7400-08-0

[ Name ]:
p-Hydroxy-cinnamic acid

[Synonym ]:
p-Hydroxycinnamic acid
b-[4-Hydroxyphenyl]acrylic Acid
E-4-HydroxycinnamicAcid
2-Propenoic acid, 3-(4-hydroxyphenyl)-, (2E)-
4-Coumaric acid
4-Hydroxycinnamic acid
p-Hydroxycinnamic acid, trans
2-Propenoic acid, 3- (4-hydroxyphenyl)-
(2E)-3-(4-Hydroxyphenyl)acrylic acid
(E)-4-Hydroxycinnamic acid
EINECS 231-000-0
trans-p-hydroxycinnamic acid
PARA-HYDROXYCINNAMIC ACID
p-coumaric acid
hydroxycinnamic acid
p-Coumaric acid, trans
trans-4-hydroxycinnamic acid
trans-4-coumaric acid
trans-p-Coumaric Acid
(2E)-3-(4-hydroxyphenyl)prop-2-enoic acid
β-[4-hydroxyphenyl]acrylic acid
p-Hydroxy-cinnamic acid
(E)-p-hydroxycinnamic acid
β-(4-Hydroxyphenyl)acrylic acid
MFCD00004399

Biological Activity

[Description]:

p-Hydroxycinnamic acid, a common dietary phenol, could inhibit platelet activity, with IC50s of 371 μM, 126 μM for thromboxane B2 production and lipopolysaccharide-induced prostaglandin E2 generation, respectively.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Prostaglandin Receptor
Natural Products >> Acids and Aldehydes
Research Areas >> Others

[Target]

PGE2:126 μM (IC50)

TXB2:371 μM (IC50)

Human Endogenous Metabolite


[In Vitro]

p-Hydroxycinnamic acid (p-Coumaric acid), is a ubiquitous plant metabolite with antioxidant and anti-inflammatory properties. p-Hydroxycinnamic acid (500 μM and 1 mM) reduces ADP-induced platelet aggregation (55•2 (SE 4•01) % and 35•6 (SE 2•35) % relative to basal level, respectively). p-Hydroxycinnamic acid is able to modify platelet function, a shear-inducing device that simulates primary haemostasis. p-Hydroxycinnamic acid interferes also with arachidonic acid cascade, reducing thromboxane B2 production and lipopolysaccharide-induced prostaglandin E2 generation (IC50 371 and 126 μM, respectively)[1].

[References]

[1]. Luceri C, et al. p-Coumaric acid, a common dietary phenol, inhibits platelet activity in vitro and in vivo. Br J Nutr. 2007 Mar;97(3):458-63.


[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]:
1.3±0.1 g/cm3

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

[ Melting Point ]:
212-214ºC

[ 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

[ Storage condition ]:
-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GD9094000
CHEMICAL NAME :
Cinnamic acid, p-hydroxy-
CAS REGISTRY NUMBER :
7400-08-0
BEILSTEIN REFERENCE NO. :
2207383
LAST UPDATED :
199701
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C9-H8-O3
MOLECULAR WEIGHT :
164.17
WISWESSER LINE NOTATION :
QV1U1R DQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
657 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 104,793,1984 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2800 mg/kg
SEX/DURATION :
male 56 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands Reproductive - Fertility - mating performance (e.g. # sperm positive females per # females mated; # copulations per # estrus cycles)
REFERENCE :
CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 23,677,1981
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
35 mg/kg
SEX/DURATION :
female 6 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
REFERENCE :
IJEBA6 Indian Journal of Experimental Biology. (Publications & Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.1- 1963- Volume(issue)/page/year: 16,1285,1978
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
50 mg/kg
SEX/DURATION :
female 6 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - abortion
REFERENCE :
CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 20,49,1979
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
9600 mg/kg
SEX/DURATION :
female 12 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
REFERENCE :
SCIEAS Science. (American Assoc. for the Advancement of Science, 1333 H St., NW, Washington, DC 20005) V.1- 1895- Volume(issue)/page/year: 195,575,1977

Safety Information

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S22-S26-S36/37/39

[ WGK Germany ]:
2

[ RTECS ]:
GD9095000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds