122-48-5

122-48-5 structure

Name: zingerone
Chemical Name: zingerone
CAS Number: 122-48-5
Molecular Formula: C₁₁H₁₄O₃
Molecular Weight: 194.227
Catalog: Biochemical Chinese herbal medicine ingredients
Create Date: 2018-06-21 11:23:27
Modify Date: 2024-01-02 19:44:34
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].

Name	zingerone
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

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).

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

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

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

Precursor 8
1080-12-2 121-33-5 78-94-4 90-05-1
61152-59-8 39886-78-7 458-36-6 290820-47-2
DownStream 7
39728-80-8 77334-06-6 77398-90-4 56700-87-9
61152-58-7 61152-62-3 6302-60-9

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%