| Identification | More | [Name]
6-Shogaol | [CAS]
555-66-8 | [Synonyms]
6-SHOGAOL
(E)-1-(4-Hydroxy-3-methoxy-phenyl)dec-4-en-3-one
SHOGAOL
SHOGAOL, 6-
4-Decen-3-one, 1-(4-hydroxy-3-methoxyphenyl)
6-Shagaol
1-(3-Methoxy-4-hydroxyphenyl)-4-decene-3-one
1-(4-Hydroxy-3-methoxyphenyl)-4-decen-3-one | [Molecular Formula]
C17H24O3 | [MDL Number]
MFCD01736094 | [Molecular Weight]
276.37 | [MOL File]
555-66-8.mol |
| Chemical Properties | Back Directory | [Boiling point ]
427.5±35.0 °C(Predicted) | [density ]
1.0448 g/cm3(Temp: 25 °C) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) | [form ]
neat | [pka]
10.01±0.20(Predicted) | [color ]
Colourless to Light Yellow | [BRN ]
2056098 | [InChIKey]
OQWKEEOHDMUXEO-BQYQJAHWSA-N | [LogP]
3.789 (est) | [CAS DataBase Reference]
555-66-8(CAS DataBase Reference) | [NIST Chemistry Reference]
6-shogaol(555-66-8) |
| Hazard Information | Back Directory | [Uses]
[6]-Shogaol is an aromatic constituent of ginger and the chain-dehydroxylated analog of [6]-Gingerol. [6]-Shogaol has activity very similar to [6]-Gingerol and produced an inhibition of spontaneous motor activity, antipyretic and analgesic effects, and prolonged hexobarbital-induced sleeping time. [6]-Shogaol also has potent antitussive activity and affected the cortical EEG. | [Definition]
ChEBI: [6]-Shogaol is a monomethoxybenzene, a member of phenols and an enone. | [Anticancer Research]
6-Shogaol is the dehydrated product of 6-gingerol, extracted from the rhizome ofginger. Treatment of HCC cell line with 6-shogaol resulted in cells with apoptoticphenotypes, which showed signs of cell and nuclear shrinkage as well as substantialchromatin condensation. De-phosphorylation of PERK and activation of theexpression of CHOP initiate caspase cascade reaction inducing apoptosis inHCC. Two-dimensional gel electrophoretic analysis of proteome revealed that in response to the treatment with 6-shogaol, a significant stimulation was observed inproteins related to the ER stress, signifying that apoptosis induced by 6-shogoal didinvolve ER stress. Cells showed marked rise in the UPR target expression, HSP70,Grp94, Grp78/Bip and the other ER chaperones on exposure to 6-shogoal in a time-dependentmanner, which elicited activation of caspase-3 and degradation of polyADP ribose polymerase (PARP). Various ER chaperone proteins improve adaptationof cancer cells to hypoxic environment and aid in developing resistance againstanticancer therapy (Zorzi and Bonvini 2011; Urra et al. 2016). Screening of specificinhibitors of Grp78 as antitumour agents (Hu et al. 2012; Liu et al. 2013; Venkatesanet al. 2015) implies that inhibition of Grp78/Bip is a very promising anticancerstrategy. HCC cells are selectively killed by 6-shogaol in the absence of anynoticeable toxic consequence on normal healthy cells and very little toxicity asstudied on SMMC7721 xenograft mice. Administration of 6-shogaol and salubrinaltogether for distinct time intervals resulted in significant increase in ER stress in thecell. It appears that 6-shogaol in combination with salubrinal has great therapeuticvalue against various malignancies including HCC (Hu et al. 2012). |
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