6-Shogaol

한글명:6-Shogaol

카스 번호555-66-8

상품명:6-Shogaol

CBNumberCB4748322

분자식C17H24O3

포뮬러 무게276.37

MOL 파일555-66-8.mol

화학적 성질

끓는 점	427.5±35.0 °C(Predicted)
밀도	1.0448 g/cm3(Temp: 25 °C)
저장 조건	Keep in dark place,Inert atmosphere,2-8°C
용해도	클로로포름(약간 용해됨), 에틸아세테이트(약간 용해됨), 메탄올(약간 용해됨)
용해도	클로로포름(약간), 에틸아세테이트(약간), 메탄올(약간)에 용해됨
산도 계수 (pKa)	10.01±0.20(Predicted)
색상	무색~연황색
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 데이터베이스	555-66-8(CAS DataBase Reference)
NIST	6-shogaol(555-66-8)

위험 및 안전 성명

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WGK 독일

NFPA 704:

	3
0		0

그림문자(GHS)

6-Shogaol 화학적 특성, 용도, 생산

용도
[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.
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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