Basic information
- CAS
1126-61-0- Standard SMILES
C=CCc1ccc(O)c(O)c1- InChIKey
FHEHIXJLCWUPCZ-UHFFFAOYSA-N- Molecular formula
- C9H10O2
- Average molar mass
- 150.17 g/mol
- Monoisotopic mass
- 150.06807956
Overview
4-allylpyrocatechol has been reported in Dracaena cambodiana, Alpinia officinarum, and other organisms with data available.
Names & identifiers
- Preferred name
- Hydroxychavicol
- IUPAC
- 4-prop-2-enylbenzene-1,2-diol
- English name
- 4-Allylpyrocatechol
- Molecular formula
- C9H10O2
- Molecular weight
- 150.17
Names & synonyms
1126-61-0Hydroxychavicol2-Hydroxychavicol4-prop-2-enylbenzene-1,2-diol1,2-Benzenediol, 4-(2-propenyl)-DTXSID20150112FG58C4J9BRRefChem:923136DTXCID40726034-Allylpyrocatechol4-allylbenzene-1,2-diol4-allylcatechol
Show more names
HYDROXYCHAVICOL(P)4-Allyl-1,2-benzenediol4-DIHYDROXY-ALLYLBENZENE1,2-Dihydroxy-4-allylbenzene4-Allylcatechol, 10 mM in DMSO
3,4-dihydroxy-allylbenzene4-(prop-2-en-1-yl)benzene-1,2-diolMFCD01548379CCRIS 15244-allylbenzene-1,2-d4-(2-propenyl)-1,2-benzenediolUNII-FG58C4J9BR4-Allyl-1,2-dihydroxybenzene
Database identifiers
- CAS
1126-61-0- PubChem CID
- 70775
- DTXSID
DTXSID20150112- ChEMBL
CHEMBL111134- UNII
- FG58C4J9BR
- EC Number
- 683-143-7
- Nikkaji
- J126.217C
Properties
Computed structural properties
- XLogP
- 0.8
- Topological polar surface area
- 40.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 134
Experimental & physicochemical properties
Collision Cross Section121.58 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 42 to · 42.0 to 46.0 °C
- Boiling point
- 123 °C/2mmHg · 123°C/2mmHg(lit.)
- Density
- 1.148 · 1.148±0.06 g/cm3(Predicted)
- Flash point
- 141 ℃ · 141℃
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- 10 mg/mlDMSO: · DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 5 mg/ml
- form
- Solid
- pka
- 9.83 · 9.83±0.10(Predicted)
- color
- White to Gray to Brown
- Odor
- slight creosote
- BRN
- 1937030 · 1937030
- InChI
- InChI=1S/C9H10O2/c1-2-3-7-4-5-8(10)9(11)6-7/h2,4-6,10-11H,1,3H2
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (33.3%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P317, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (33.3%)
Safety data
- wgk
- 3
- rtecs
- CZ9029440
- hs_code
- 2907.29.9000
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H312
- Precautionary statements
- P264-P270-P301+P312-P330-P501-P280-P302+P352-P312-P322-P363-P501
Chemistry & industry
Pharmacology
Metabolism/MetabolitesHydroxychavicol is a known human metabolite of eugenol.
Applications
Uses4-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 methods
Preparation4-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.
Upstream & downstream products
Downstream products
Suppliers100 total
Related reactions
3 records
Compound notes
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