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HomeProduct name list4-Allylpyrocatechol

4-Allylpyrocatechol

Synonym(s):1,2-Dihydroxy-4-allylbenzene;4-(2-Propenyl)-1,2-benzenediol;4-Allyl-1,2-benzenediol;4-Allylcatechol;Allylpyrocatechol

4-Allylpyrocatechol Structural

What is 4-Allylpyrocatechol?

Chemical properties

White to Gray to Brown powder to crystal.

The Uses of 4-Allylpyrocatechol

4-Allylpyrocatechol (other name: hydroxychavicol), isolated from Piper betle leaves, has been reported as an antimicrobial, antioxidant, and anti-inflammatory agent. In 2009, it was reported as a more potent xanthine oxidase (XO) inhibitor than allopurinol, which is clinically used for the treatment of hyperuricemia.
4-Allylpyrocatechol is an antioxidant found in Piper Betel leaf extract. It is widely used as mouth freshener. It is a phenolic compound, considered to be effective against indomethacin-gastropathy.

Preparation

4-allylpyrocatechol is readily obtained from precursors such as eugenol or methyl eugenol – two natural products predominately extracted from the essential oils of Syzygium aromaticum flower buds (commonly known as clove buds) by hydrodistillation.
8.00 g EugTES (21 mmol) was dissolved in 10 mL of THF and purged with N2 for 45 minutes. The solution was then transferred, under N2, to a reaction vessel containing HCl solution, and mixed rapidly. The reaction proceeded quickly and completion was confirmed via thin layer chromatography. The organic layer was extracted into CH2Cl2 and then washed with H2O, followed by drying and filtration. The solvent was removed via vacuum to recover the pure product as a white solid (Yield, 54%).
Synthesis of 4-allylpyrocatechol (EugOH)
Synthesis of 4-allylpyrocatechol (EugOH) from methyl eugenol.

Properties of 4-Allylpyrocatechol

Melting point: 42.0 to 46.0 °C
Boiling point: 123°C/2mmHg(lit.)
Density  1.148±0.06 g/cm3(Predicted)
Flash point: 141℃
storage temp.  Sealed in dry,2-8°C
form  Solid
form  neat
pka 9.83±0.10(Predicted)
color  White to Gray to Brown
Odor slight creosote
BRN  1937030
CAS DataBase Reference 1126-61-0

Safety information for 4-Allylpyrocatechol

Computed Descriptors for 4-Allylpyrocatechol

InChIKey FHEHIXJLCWUPCZ-UHFFFAOYSA-N

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