CAS 555-66-8|6-Shogaol

Introduction：Basic information about CAS 555-66-8|6-Shogaol, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. 6-Shogaol BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Articles26
7. Synonyms

Common Name	6-Shogaol
CAS Number	555-66-8	Molecular Weight	276.371
Density	1.0±0.1 g/cm3	Boiling Point	427.5±35.0 °C at 760 mmHg
Molecular Formula	C₁₇H₂₄O₃	Melting Point	/
MSDS	ChineseUSA	Flash Point	150.3±19.4 °C
Symbol	GHS07	Signal Word	Warning

Names

Name	(E)-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one
Synonym	More Synonyms

6-Shogaol BiologicalActivity

Description	6-shogaol, an active compound isolated from Ginger (Zingiber officinale Rosc), exhibits a variety of biological activities including anticancer, anti-inflammation, and anti-oxidation.
Related Catalog	Signaling Pathways >>Autophagy >>AutophagyNatural Products >>FlavonoidsResearch Areas >>Cancer
In Vitro	6-shogaol has anticancer activity against several cell lines[1]. 6-shogaol is identified to be cytotoxic in various cell lines, with KB (IC50=7.4±2.2 μM) and HL60 (IC50=7.9±2.0 μM) cells most susceptible to 6-shogaol[2]. 6-shogaol (IC50=8 μM) has much stronger growth inhibitory effects than 6-gingerol (IC50=150 μM) on HCT-116 human colon cancer cells[3]. 6-shogaol stimulates phosphorylations of mitogen-activated protein kinases (MAPKs) such as ERK, JNK, and p38. Moreover, the 6-shogaol-induced expressions of Nrf2 and HO-1 are attenuated by treatments of SB202190 (a p38 specific inhibitor) and LY294002 (an Akt specific inhibitor)[4].
In Vivo	The 6-shogaol decreases the diethylnitrosamine (DEN)-mediated elevations of serum aspartate transaminase and alanine transaminase as well as the DEN-induced hepatic lipid peroxidation. Inductions of Nrf2 and HO-1 by 6-shogaol are also confirmed in the mice. The administration of 6-shogaol to the mice also restores the DEN-reduced activity and protein expression of hepatic antioxidant enzymes such as superoxide dismutase, glutathione peroxidase and catalase[4].
Cell Assay	The effects of 6-shogaol on the viability of HepG2 cells are determined by a MTT assay after 24 h treatment. The data are expressed as percent cell viability compared to that of control. The concentrations of the treatments 6-shogaol varied from 10 to 100 μg/mL[4].
Animal Admin	Mice: Male Balb/c mice are treated with 6-shogaol-rich ginger extracts (10 and 100 mg/kg b.w.) or silymarin (100 mg/kg b.w.), a positive control, and challenged with diethyl-nitrosoamine (DEN, 30 mg/kg b.w.) 3 days per week for 3 weeks[4].
References	[1]. Semwal RB, et al. Gingerols and shogaols: Important nutraceutical principles from ginger. Phytochemistry. 2015 Sep;117:554-68. [2]. Peng F, et al. Cytotoxic, cytoprotective and antioxidant effects of isolated phenolic compounds from fresh ginger. Fitoterapia. 2012 Apr;83(3):568-85. [3]. Sang S, et al. Increased growth inhibitory effects on human cancer cells and anti-inflammatory potency of shogaols from Zingiber officinale relative to gingerols. J Agric Food Chem. 2009 Nov 25;57(22):10645-50. [4]. Bak MJ, et al. 6-shogaol-rich extract from ginger up-regulated the antioxidant defense systems in cells and mice. Molecules. 2012 Jul 4;17(7):8037-55.

Chemical & Physical Properties

Density	1.0±0.1 g/cm3
Boiling Point	427.5±35.0 °C at 760 mmHg
Molecular Formula	C₁₇H₂₄O₃
Molecular Weight	276.371
Flash Point	150.3±19.4 °C
Exact Mass	276.172546
PSA	46.53000
LogP	3.85
Vapour Pressure	0.0±1.1 mmHg at 25°C
Index of Refraction	1.522
InChIKey	OQWKEEOHDMUXEO-BQYQJAHWSA-N
SMILES	CCCCCC=CC(=O)CCc1ccc(O)c(OC)c1
Storage condition	2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: HE2097000

CHEMICAL NAME :: 4-Decen-3-one, 1-(4-hydroxy-3-methoxyphenyl)-

CAS REGISTRY NUMBER :: 555-66-8

LAST UPDATED :: 199410

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C17-H24-O3

MOLECULAR WEIGHT :: 276.41

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 687 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 109 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 50900 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Escherichia coli

DOSE/DURATION :: 700 umol/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 122,87,1983

Safety Information

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H302
Hazard Codes	Xn
Risk Phrases	22
RIDADR	NONH for all modes of transport

Articles26

Update on the chemopreventive effects of ginger and its phytochemicals.

Crit. Rev. Food Sci. Nutr 51(6) , 499-523, (2011)

The rhizomes of Zingiber officinale Roscoe (Zingiberaceae), commonly known as ginger, is one of the most widely used spice and condiment. It is also an integral part of many traditional medicines and ...

In vitro antioxidant and anti-inflammatory activities of 1-dehydro-[6]-gingerdione, 6-shogaol, 6-dehydroshogaol and hexahydrocurcumin.

Food Chem. 135(2) , 332-7, (2012)

Hexahydrocurcumin, 1-dehydro-[6]-gingerdione, 6-dehydroshogaol and 6-shogaol were evaluated for their antioxidant and anti-inflammatory activities in the present study. The relative antioxidant potenc...

6-Shogaol inhibits breast and colon cancer cell proliferation through activation of peroxisomal proliferator activated receptor γ (PPARγ).

Cancer Lett. 336(1) , 127-39, (2013)

6-Shogaol has been shown to possess many antitumor properties including inhibition of cancer cell growth, inhibition of cancer metastasis, induction of apoptosis in cancer cells and induction of cance...

Synonyms

(E)-1-(4-Hydroxy-3-methoxy-phenyl)-dec-4-en-3-one

(4E)-1-(4-Hydroxy-3-methoxyphenyl)dec-4-en-3-one

6-Shogaol

Trans-6-Shogaol

MFCD01736094

4-Decen-3-one, 1-(4-hydroxy-3-methoxyphenyl)

Shogaol

4-Decen-3-one, 1-(4-hydroxy-3-methoxyphenyl)-, (4E)-

(4E)-1-(4-Hydroxy-3-methoxyphenyl)-4-decen-3-one

[6]-Shogaol

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