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Isoferulic acid

Isoferulic acid structure

CAS No:
537-73-5
Formula:
C10H10O4
Chemical Name:
Isoferulic acid
Synonyms:
2-Propenoic acid,3-(3-hydroxy-4-methoxyphenyl)-;Cinnamic acid,3-hydroxy-4-methoxy-;3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid;Hesperetic acid;Isoferulic acid;3-Hydroxy-4-methoxycinnamic acid;NSC 51987;4-Methoxycaffeic acid;4-O-Methylcaffeic acid
Categories:
Flavors and Fragrances > Synthetic Fragrances

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.

Isoferulic acid Basic Attributes

Molecular Weight：

194.18

Exact Mass：

194.18

BRN：

2212760

EC Number：

208-676-0

HScode：

29189090

Characteristics

PSA：

66.8

XLogP3：

1.5

Appearance：

Solid

Density：

1.3±0.1 g/cm3

Melting Point：

125 °C @ Solvent: Ethyl acetate

Boiling Point：

410.2°C at 760 mmHg

Flash Point：

167.6±19.4 °C

Refractive Index：

1.627

Water Solubility：

soluble in ethanol and methanol.

Storage Conditions：

-20°C Freezer

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-37/39-24/25

RTECS Number：

UD3365400

Marks：

Hazard note：

Irritant

Stability/Shelf Life：

Stable under normal temperatures and pressures.

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

Isoferulic acid Use and Manufacturing

Methods of Manufacturing

To a suspension of isovanillin (1) (152 mg, 1.00 mmol) and malonic acid (416 mg, 4.00 mmol) in toluene (5 mL) were added EtTo a solution of isovanillin (1) (22.81g, 150mmol) and malonic acid (62.44g, 600mmol) in pyridine (150mL) was added 1, 8-diazabicyclo(5.4.0)undec-7-ene (DBU, 34.26g). The stirred reaction solution was heated at reflux for 4h, then cooled to room temperature. The cooled reaction mixture was poured into a solution (500mL) of concentrated HCl and ice (v/v=1:1) and the resulting precipitate was filtered and washed with acidified water to give a crude product. The crude product was dissolved in aqueous NaOH (1M, 200mL) and extracted with CHTo a suspension of finely powdered 3-hydroxy-4-methoxycinnamic acid (4.83 g, 24.9 mmol) in acetic acid (80 ml) was added a solution of bromine (4.05 g, 1.30 ml, 25.4 mmol) in acetic acid (11 ml) dropwise. The acid gradually went into solution and produced HBr. The resulting solution was poured into water (1 l) and the dark pink precipitate filtered off and recrystallized twice from 30percent ethanol in water to give 15 as fine white crystals (1.6 g, 28percent). m.p. 95-6° C. (lit. 95-6° C.); Rf=0.32 (SiO2 petrol:EtOAc 7:3), deltaH (400 MHz) 3.92 (3H, s, OCH3), 5.63 (1H, s, OH), 6.64 (1H, d, J=13.9, olefinic H), 6.78 (1H, dd, J=8.3, 1.9, H-4), 6.81 (1H, d, J=8.3, H-3), 6.93 (1H, d, J=1.9, H-6), 7.01 (1H, d, J=13.9, olefinic H).

Uses

3-Hydroxy-4-methoxycinnamic Acid (Isoferulic acid) is a hypoglycemic agent.

Computed Properties

Molecular Weight:194.18
XLogP3:1.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:194.05790880
Monoisotopic Mass:194.05790880
Topological Polar Surface Area:66.8
Heavy Atom Count:14
Complexity:224
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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CAS No.: 537-73-5

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Guide of Isoferulic acid

Description
Basic Attributes
Characteristics
Safety Information
Use and Manufacturing
Computed Properties
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Isoferulic acid

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