4-Allylpyrocatechol

4-Allylpyrocatechol Property

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

WGK Germany 

3

RTECS 

CZ9029440

HS Code 

2907.29.9000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P322Specific measures (see …on this label).

P330Rinse mouth.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

4-Allylpyrocatechol Chemical Properties,Usage,Production

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

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