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  • Product Name: 6-Shogaol
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555-66-8

555-66-8 structure
555-66-8 structure
  • Name: 6-Shogaol
  • Chemical Name: (E)-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one
  • CAS Number: 555-66-8
  • Molecular Formula: C17H24O3
  • Molecular Weight: 276.371
  • Catalog: Biochemical Chinese herbal medicine ingredients
  • Create Date: 2018-08-04 10:43:46
  • Modify Date: 2024-01-02 19:07:02
  • 6-shogaol, an active compound isolated from Ginger (Zingiber officinale Rosc), exhibits a variety of biological activities including anticancer, anti-inflammation, and anti-oxidation.
Name (E)-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one
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
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
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.
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
Storage condition 2-8°C

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

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