zingerone

Names

[ CAS No. ]:
122-48-5

[ Name ]:
zingerone

[Synonym ]:
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

Biological Activity

[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 >> Cancer

Research Areas >> Inflammation/Immunology

Research Areas >> Metabolic Disease

Natural 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).

[Related Small Molecules]

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

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: EL8900000

CHEMICAL NAME :: 2-Butanone, 4-(4-hydroxy-3-methoxyphenyl)-

CAS REGISTRY NUMBER :: 122-48-5

BEILSTEIN REFERENCE NO. :: 2051099

LAST UPDATED :: 199701

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C11-H14-O3

MOLECULAR WEIGHT :: 194.25

HEALTH HAZARD DATA

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

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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%

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