Isoferulic acid

Names

[ CAS No. ]:
537-73-5

[ Name ]:
Isoferulic acid

[Synonym ]:
3'-hydroxy-4'-methoxy cinnamic acid
Hesperitinic acid
trans-Isoferulic acid
2-Propenoic acid, 3-(3-hydroxy-4-methoxyphenyl)-, (2E)-
RARECHEM BK HW 0093
trans-3-hydroxy-4-methoxycinnamic acid
3-Hydroxy-4-MethoxycinnaMic Acid
3-(3-Hydroxy-4-methoxyphenyl)acrylic acid
3-Hydroxy-4-methoxycinnamic
Isoferulic acid
HESPERETINIC ACID
Isoferulate
MFCD00004391
EINECS 208-676-0
Isoferulic
Caffeic acid 4-methyl ether
(2E)-3-(3-Hydroxy-4-methoxyphenyl)acrylic acid
3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid
Hesperetic acid
(2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid
3-hydroxy-4-methoxy-Cinnamic acid

Biological Activity

[Description]:

3-Hydroxy-4-methoxycinnamic acid (Isoferulic acid) is a cinnamic acid derivative that has antidiabetic activity. 3-Hydroxy-4-methoxycinnamic acid binds to and activates α1-adrenergic receptors (IC50=1.4 µM) to enhance secretion of β-endorphin (EC50=52.2 nM) and increase glucose use.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor

Research Areas >> Metabolic Disease

Natural Products >> Phenylpropanoids

[References]

[1]. Liu IM, et al. Mediation of beta-endorphin by isoferulic acid to lower plasma glucose in streptozotocin-induced diabetic rats. J Pharmacol Exp Ther. 2003 Dec;307(3):1196-204.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
410.2±35.0 °C at 760 mmHg

[ Melting Point ]:
230 °C (dec.)(lit.)

[ Molecular Formula ]:
C₁₀H₁₀O₄

[ Molecular Weight ]:
194.184

[ Flash Point ]:
167.6±19.4 °C

[ Exact Mass ]:
194.057907

[ PSA ]:
66.76000

[ LogP ]:
1.56

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.627

[ Storage condition ]:
-20?C Freezer

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UD3365400

CHEMICAL NAME :: 2-Propenoic acid, 3-(3-hydroxy-4-methoxyphenyl)-

CAS REGISTRY NUMBER :: 537-73-5

BEILSTEIN REFERENCE NO. :: 2212760

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C10-H10-O4

MOLECULAR WEIGHT :: 194.20

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 7900 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

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: 95,539,1975

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 8100 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

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: 95,539,1975

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-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-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
UD3365400

[ HS Code ]:
29189090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918990090

[ Summary ]:
2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

A metabolite profiling approach to identify biomarkers of flavonoid intake in humans.

J. Nucl. Med. 139 , 2309-14, (2009)

Flavonoids are phytochemicals that are widespread in the human diet. Despite limitations in their bioavailability, experimental and epidemiological data suggest health benefits of flavonoid consumptio...

Development of a targeted method for twenty-three metabolites related to polyphenol gut microbial metabolism in biological samples, using SPE and UHPLC-ESI-MS/MS.

Talanta 128 , 221-30, (2014)

An increasing number of studies have concerned the profiling of polyphenol microbial metabolites, especially in urine or plasma, but only a few have regarded their accurate quantification. This study ...

Ion-pairing reversed-phase liquid chromatography fractionation in combination with isotope labeling reversed-phase liquid chromatography–mass spectrometry for comprehensive metabolome profiling

J. Chromatogr. A. 1218(23) , 3689-94, (2011)

We report a novel two-dimensional (2D) separation strategy aimed at improving the detectability of liquid chromatography mass spectrometry (LC–MS) for metabolome analysis. It is based on the use of io...

Related Compounds

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