ChemicalBook Product Catalog Natural Products Phenylpropanoids 4-Allylpyrocatechol

4-Allylpyrocatechol

Product Name4-Allylpyrocatechol
CAS1126-61-0
MFC9H10O2
MW150.17
EINECS
MOL File1126-61-0.mol

Chemical Properties

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
solubility	DMF: 10 mg/ml DMSO: 10 mg/ml Ethanol: 10 mg/mlPBS (pH 7.2): 5 mg/ml
form	Solid
pka	9.83±0.10(Predicted)
color	White to Gray to Brown
Odor	slight creosote
BRN	1937030
InChI	InChI=1S/C9H10O2/c1-2-3-7-4-5-8(10)9(11)6-7/h2,4-6,10-11H,1,3H2
InChIKey	FHEHIXJLCWUPCZ-UHFFFAOYSA-N
SMILES	C1(O)=CC=C(CC=C)C=C1O
LogP	1.809 (est)
CAS DataBase Reference	1126-61-0

Safety Information

WGK Germany	3
RTECS	CZ9029440
HS Code	2907.29.9000

Usage And Synthesis

Chemical Properties

White to Gray to Brown powder to crystal.

Uses

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) from methyl eugenol.

in vivo

4-Allylcatechol (2-4 mg/kg, p.o., once daily for 21 days) effectively reduces cognitive deficits and mitigates oxidative stress and inflammation in Streptozotocin (HY-13753)-induced rats^[4].

Animal Model:	Alzheimer’s disease (AD) model induced by Streptozotocin (HY-13753) in rats^[4]
Dosage:	0.5, 1, 2, 4 mg/kg
Administration:	Oral gavage (p.o.), once daily for 21 days
Result:	Significantly improved cognitive function, decreased levels of TNF-α, IL-1β, IL-6, and reduced lipid peroxidation (MDA) in brain tissue.

References

[1] JITESH S. RATHEE. Antioxidant Activity of Piper betel Leaf Extract and Its Constituents[J]. Journal of Agricultural and Food Chemistry, 2006, 54 24: 9046-9054. DOI: 10.1021/jf061679e
[2] KEIJI NISHIWAKI. Structure-Activity Relationships and Docking Studies of Hydroxychavicol and Its Analogs as Xanthine Oxidase Inhibitors.[J]. Chemical & pharmaceutical bulletin, 2018, 66 7: 741-747. DOI: 10.1248/cpb.c18-00197
[3] AIYSVARIYAH RAJEDADRAM. Hydroxychavicol, a polyphenol from Piper betle leaf extract, induces cell cycle arrest and apoptosis in TP53-resistant HT-29 colon cancer cells.[J]. Journal of Zhejiang University. Science. B, 2021, 22 2: 112-122. DOI: 10.1631/jzus.b2000446
[4] ANJALI PANDEY . Modulation of Th1/Th2 cytokines and inflammatory mediators by hydroxychavicol in adjuvant induced arthritic tissues[J]. Cytokine, 2010, 49 1: Pages 114-121. DOI: 10.1016/j.cyto.2009.08.015
[5] ERIN HEATHER Andrew M M Ronald Shimmon. Organic impurity profiling of 3,4-methylenedioxymethamphetamine (MDMA) synthesised from catechol[J]. Forensic science international, 2015, 248: Pages 140-147. DOI: 10.1016/j.forsciint.2014.12.021
[6] AI-HONG YANG. Identification and analysis of the reactive metabolites related to the hepatotoxicity of safrole.[J]. Xenobiotica, 2018, 48 11: 1164-1172. DOI: 10.1080/00498254.2017.1399227

4-Allylpyrocatechol

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