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)
물리적 상태	Liquid
색상	무색~연황색
냄새	Mild, warm-herbaceous, sweet odor
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

화학적 성질
White crystalline powder. B.P. higher than 300℃. Very slightly soluble in water, soluble in alcohol and oils.
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.
주요 응용
Shogaol has little or no application in perfumery, and very little interest to the flavor industry, but it is included in this work mainly for the purpose of elucidating the problems apparently existing around the description of the odorand flavor of "Zingerone".
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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