2-hydroxychavicol

1,2-benzenediol, 4-(2-propenyl)-

CAS: 1126-61-0 C9 H10 O2 MW: 150.17710000

Identification

Name2-hydroxychavicol
IUPAC4-prop-2-enylbenzene-1,2-diol
CAS Number1126-61-0
FDA UNIISearch
Molecular FormulaC9 H10 O2
Molecular Weight150.17710000
MDL NumberMFCD01548379
Nikkaji NumberJ126.217C
Beilstein1937030
XlogP30.80 (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 SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for 2-hydroxychavicol usage levels up tonot for fragrance use.
Recommendation for 2-hydroxychavicol flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

betel leaf oil

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.