6-Shogaol Chemical Properties

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)

pka

10.01±0.20(Predicted)

color 

Colourless to Light Yellow

BRN 

2056098

InChI

InChI=1S/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3

InChIKey

OQWKEEOHDMUXEO-BQYQJAHWSA-N

SMILES

C(C1=CC=C(O)C(OC)=C1)CC(=O)C=CCCCCC

LogP

3.789 (est)

CAS DataBase Reference

555-66-8(CAS DataBase Reference)

NIST Chemistry Reference

6-shogaol(555-66-8)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

6-Shogaol Usage And Synthesis

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).

6-Shogaol(555-66-8)Related Product Information

• 4-Methoxyphenylacetone
• Glycitein
• PHENYL VALERATE
• CHLOROPHOSPHONAZO III
• 1-Decene
• (Trifluoromethoxy)benzene
• p-Anisidine
• p-Anisaldehyde
• Anisole
• 3-Methoxybenzaldehyde
• Phenylacetic acid
• Oxygen
• 8-SHOGAOL
• 6-Shogaol
• Ginger Constituent Mixture+6-gingerol and 6-shogaol
• SHOGAOL, 6-(P)
• SHOGAOL, 6-(PRIMARY STANDARD)
• Methoxy