CAS 122-48-5|zingerone
| Common Name | zingerone | ||
|---|---|---|---|
| CAS Number | 122-48-5 | Molecular Weight | 194.227 |
| Density | 1.1±0.1 g/cm3 | Boiling Point | 323.0±27.0 °C at 760 mmHg |
| Molecular Formula | C11H14O3 | Melting Point | 40-41 °C(lit.) |
| MSDS | ChineseUSA | Flash Point | 123.7±17.2 °C |
Names
| Name | zingerone |
|---|---|
| Synonym | More Synonyms |
zingerone BiologicalActivity
| Description | Zingerone (Vanillylacetone) is a nontoxic methoxyphenol isolated from Zingiber officinale, with potent anti-inflammatory, antidiabetic, antilipolytic, antidiarrhoeic, antispasmodic and anti-tumor[3] properties[1]. Zingerone alleviates oxidative stress and inflammation, down-regulates NF-κB mediated signaling pathways[2]. Zingerone acts as an anti-mitotic agent, and inhibits the growth of neuroblastoma cells[3]. |
|---|---|
| Related Catalog | Research Areas >>CancerResearch Areas >>Inflammation/ImmunologyResearch Areas >>Metabolic DiseaseNatural Products >>Phenols |
| Target | NF-κB[3] |
| In Vitro | Zingerone is a nontoxic methoxyphenol with potent anti-inflammatory, antidiabetic, antilipolytic, antidiarrhoeic, antispasmodic properties[1]. Zingerone (0-2 mM) decreases neruoblastoma cell survival[3]. Zingerone (0-2 mM) reduces cyclin D1 expression, increases cleavage of caspase-3 and PARP-1 in BE(2)-M17 cells[3]. |
| In Vivo | Zingerone (50, 100 mg/kg, p.o. daily for 21 days) protects against alloxan-induced diabetes via alleviation of oxidative stress and inflammation in rat[2]. Zingerone (10 mg/kg, i.p.) inhibits tumor progression through mitotic arrest, failure of cell division, and stimulation of apoptosis[3]. |
| References | [1]. Ahmad B, et al. A Review on Pharmacological Properties of Zingerone (4-(4-Hydroxy-3-methoxyphenyl)-2-butanone). ScientificWorldJournal. 2015;2015:816364. [2]. Ahmad B, et al. Zingerone (4-(4-hydroxy-3-methylphenyl) butan-2-one) protects against alloxan-induced diabetes via alleviation of oxidative stress and inflammation: Probable role of NF-kB activation. Saudi Pharm J. 2018 Dec;26(8):1137-1145. [3]. Choi JS, et al. Zingerone Suppresses Tumor Development through Decreasing Cyclin D1 Expression and Inducing Mitotic Arrest. Int J Mol Sci. 2018 Sep 19;19(9). |
Chemical & Physical Properties
| Density | 1.1±0.1 g/cm3 |
|---|---|
| Boiling Point | 323.0±27.0 °C at 760 mmHg |
| Melting Point | 40-41 °C(lit.) |
| Molecular Formula | C11H14O3 |
| Molecular Weight | 194.227 |
| Flash Point | 123.7±17.2 °C |
| Exact Mass | 194.094299 |
| PSA | 46.53000 |
| LogP | 0.64 |
| Vapour Pressure | 0.0±0.7 mmHg at 25°C |
| Index of Refraction | 1.526 |
| InChIKey | OJYLAHXKWMRDGS-UHFFFAOYSA-N |
| SMILES | COc1cc(CCC(C)=O)ccc1O |
| Storage condition | 2-8°C |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- Standard Draize test
- ROUTE OF EXPOSURE :
- Administration onto the skin
- SPECIES OBSERVED :
- Rodent - rabbit
- REFERENCE :
- FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 20,851,1982 ** ACUTE TOXICITY DATA **
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 2580 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 20,851,1982
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Administration onto the skin
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- >5 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 20,851,1982
Safety Information
| Personal Protective Equipment | Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter |
|---|---|
| Hazard Codes | Xi |
| Risk Phrases | R36/37/38 |
| Safety Phrases | S26-S36 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 2 |
| RTECS | EL8900000 |
| Packaging Group | II; III |
| Hazard Class | 4.1 |
| HS Code | 29333999 |
Customs
| HS Code | 2914509090 |
|---|---|
| Summary | HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0% |
Articles26
More Articles| Inhibition by capsaicin and its related vanilloids of compound action potentials in frog sciatic nerves. Life Sci. 92(6-7) , 368-78, (2013) Although capsaicin not only activates transient receptor potential vanilloid-1 (TRPV1) channels but also inhibits nerve conduction, the latter action has not yet been fully examined. The purpose of th... | |
| Fenugreek extract as an inducer of cellular death via autophagy in human T lymphoma Jurkat cells. BMC Complement Altern. Med. 12 , 202, (2012) Drugs used both in classical chemotherapy and the more recent targeted therapy do not have cancer cell specificity and, hence, cause severe systemic side effects. Tumors also develop resistance to suc... | |
| Targeting antioxidative signal transduction and stress response system: control of pathogenic Aspergillus with phenolics that inhibit mitochondrial function. J. Appl. Microbiol. 101(1) , 181-9, (2006) The aim of this study was to show whether antioxidative response systems are potentially useful molecular targets for control of Aspergillus fumigatus and Aspergillus flavus. Selected phenolic agents ... |
Synonyms
| UNII-4MMW850892 |
| Vanillyl acetone |
| 4-(4-Hydroxy-3-methoxyphenyl)-2-butanone |
| 4-(4-hydroxy-3-methoxyphenyl)butan-2-one |
| Zingiberone |
| 2-Butanone, 4-(4-hydroxy-3-methoxyphenyl)- |
| EINECS 204-548-3 |
| Vanillylacetone |
| MFCD00048232 |
| 3-Methoxy-4-hydroxybenzylacetone |
| 2-Butanone, 4- (4-hydroxy-3-methoxyphenyl)- |
| Zingberone |
| zingerone |
