2-hydroxychavicol
1,2-benzenediol, 4-(2-propenyl)-
Identification
| Name | 2-hydroxychavicol |
| IUPAC | 4-prop-2-enylbenzene-1,2-diol |
| CAS Number | 1126-61-0 |
| FDA UNII | Search |
| Molecular Formula | C9 H10 O2 |
| Molecular Weight | 150.17710000 |
| MDL Number | MFCD01548379 |
| Nikkaji Number | J126.217C |
| Beilstein | 1937030 |
| XlogP3 | 0.80 (est) |
Regulatory
Physical Properties
| Appearance | colorless crystalline needles (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Refractive Index | 1.56000 @ 29.00 °C., 1.56890 @ 7.50 °C. |
| Melting Point | 48.00 to 49.00 °C. @ 760.00 mm Hg |
| Boiling Point | 147.00 to 149.00 °C. @ 10.00 mm Hg, 156.00 to 158.00 °C. @ 16.00 mm Hg |
| Vapor Pressure | 0.001000 mmHg @ 25.00 °C. (est) |
| Flash Point | 287.00 °F. TCC ( 141.70 °C. ) (est) |
| logP (o/w) | 1.809 (est) |
| Soluble in | alcohol |
Organoleptic Properties
| Odor Description | slight creosote |
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for 2-hydroxychavicol usage levels up to | not for fragrance use. |
| Recommendation for 2-hydroxychavicol flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
4-
allyl catechol
4-
allyl pyrocatechol
4-
allyl-1,2-benzenediol
4-
allyl-benzene-1,2-diol
4-
allylbenzene-1,2-diol
4-
allylcatechol
4-
allylpyrocatechol
1,2-
benzenediol, 4-(2-propen-1-yl)-
1,2-
benzenediol, 4-(2-propenyl)-
3,4-
dihydroxy-allylbenzene
2-
hydroxy chavicol
hydroxychavicol
4-(
prop-2-en-1-yl)benzene-1,2-diol
4-
prop-2-enyl benzene-1,2-diol
4-
prop-2-enylbenzene-1,2-diol
4-(2-
propenyl)-1,2-benzene diol
PubMed:
Growth inhibitory response and ultrastructural modification of oral-associated candidal reference strains (ATCC) by Piper betle L. extract.
PubMed:
Synergistic apoptosis of CML cells by buthionine sulfoximine and hydroxychavicol correlates with activation of AIF and GSH-ROS-JNK-ERK-iNOS pathway.
PubMed:
A new hydroxychavicol dimer from the roots of Piper betle.
PubMed:
Piper betel leaf extract: anticancer benefits and bio-guided fractionation to identify active principles for prostate cancer management.
PubMed:
Identification of hydroxychavicol and its dimers, the lipase inhibitors contained in the Indonesian spice, Eugenia polyantha.
PubMed:
Antimycobacterial activity of constituents from Foeniculum vulgare var. dulce grown in Mexico.
PubMed:
Hydroxychavicol, a Piper betle leaf component, induces apoptosis of CML cells through mitochondrial reactive oxygen species-dependent JNK and endothelial nitric oxide synthase activation and overrides imatinib resistance.
PubMed:
Simultaneous estimation of hydroxychavicol and chlorogenic acid from Piper betel L. through RP-HPLC.
PubMed:
Physiologically based biokinetic model of bioactivation and detoxification of the alkenylbenzene methyleugenol in rat.
PubMed:
Hydroxychavicol inhibits immune responses to mitigate cognitive dysfunction in rats.
PubMed:
In vitro antifungal activity of hydroxychavicol isolated from Piper betle L.
PubMed:
Modulation of Th1/Th2 cytokines and inflammatory mediators by hydroxychavicol in adjuvant induced arthritic tissues.
PubMed:
Biotransformation and cytotoxic effects of hydroxychavicol, an intermediate of safrole metabolism, in isolated rat hepatocytes.
PubMed:
Hydroxychavicol: a potent xanthine oxidase inhibitor obtained from the leaves of betel, Piper betle.
PubMed:
Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent.
PubMed:
Hydroxychavicol, a novel betel leaf component, inhibits platelet aggregation by suppression of cyclooxygenase, thromboxane production and calcium mobilization.
PubMed:
Hydroxychavicol modulates benzo[a]pyrene-induced genotoxicity through induction of dihydrodiol dehydrogenase.
PubMed:
Reactive oxygen species are crucial for hydroxychavicol toxicity toward KB epithelial cells.
PubMed:
Elevated expression of cyclooxygenase (COX)-2 in oral squamous cell carcinoma--evidence for COX-2 induction by areca quid ingredients in oral keratinocytes.
PubMed:
Isolation and structural elucidation of some glycosides from the rhizomes of smaller galanga (Alpinia officinarum Hance).
PubMed:
Inducing the cell cycle arrest and apoptosis of oral KB carcinoma cells by hydroxychavicol: roles of glutathione and reactive oxygen species.
PubMed:
Enhanced hydroxychavicol-induced cytotoxic effects in glutathione-depleted HepG2 cells.
PubMed:
Role of oxidative DNA damage in hydroxychavicol-induced genotoxicity.
PubMed:
Hydroxychavicol: a new anti-nitrosating phenolic compound from betel leaf.
PubMed:
Protective effect of hydroxychavicol, a phenolic component of betel leaf, against the tobacco-specific carcinogens.
PubMed:
Hydroxychavicol: a new phenolic antimutagen from betel leaf.