6-Shogaol

Product Name: 6-Shogaol
CAS No.: 555-66-8
Chemical Name: 6-Shogaol
Synonyms: SHOGAOL;6-SHOGAOL;6-Shagaol;SHOGAOL, 6-;6-gingerenol;6-Shogaol-RM;6-Shogaol USP/EP/BP;[6]-Shogaol D5 (Major);TIANFU-CHEM - 6-Shogaol;1-(4-Hydroxy-3-methoxyphenyl)-4-decen-3-one
CBNumber: CB4748322
Molecular Formula: C17H24O3
Formula Weight: 276.37
MOL File: 555-66-8.mol

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6-Shogaol Property

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)
form: Liquid
color: Colourless to Light Yellow
Odor: 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 DataBase Reference: 555-66-8(CAS DataBase Reference)
NIST Chemistry Reference: 6-shogaol(555-66-8)

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Safety

Hazard Codes: Xn
Risk Statements: 22
WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SMB00311
Product name: [6]-Shogaol
Purity: ≥90% (HPLC)
Packaging: 50mg
Price: $947
Updated: 2024/03/01

Sigma-Aldrich

Product number: 39303
Product name: [6]-Shogaol
Purity: analytical standard
Packaging: 10mg
Price: $740
Updated: 2024/03/01

Cayman Chemical

Product number: 11901
Product name: 6-Shogaol
Purity: ≥95%
Packaging: 1mg
Price: $44
Updated: 2024/03/01

Cayman Chemical

Product number: 11901
Product name: 6-Shogaol
Purity: ≥95%
Packaging: 5mg
Price: $172
Updated: 2024/03/01

Cayman Chemical

Product number: 11901
Product name: 6-Shogaol
Purity: ≥95%
Packaging: 10mg
Price: $321
Updated: 2024/03/01

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6-Shogaol Chemical Properties,Usage,Production

Chemical Properties

White crystalline powder. B.P. higher than 300℃. Very slightly soluble in water, soluble in alcohol and oils.

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.

Application

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".

Preparation

6-Shogaol is prepared by condensation of Vanillin with Acetone, followed by hydrogenation. The resulting ketone is then condensed with Hexaldehyde under conditions which inactivate the hydroxyl group during the reaction.

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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6-Shogaol Suppliers

Canada 2 China 225 France 1 Germany 2 India 5 Japan 1 United Kingdom 4 United States 20 Global 260

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View Lastest Price from 6-Shogaol manufacturers

Hebei Weibang Biotechnology Co., Ltd

Product: 6-Shogaol 555-66-8
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 500000kg
Release date: 2024-11-01

Hebei Mojin Biotechnology Co., Ltd

Product: 3-Isothioureidopropionic acid 555-66-8
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 50000KG/month
Release date: 2023-10-16

Shanghai Standard Technology Co., Ltd.

Product: 6-Shogaol 555-66-8
Price: US $0.00/ml
Min. Order: 0.1ml
Purity: ≥98%(HPLC)
Supply Ability: 100 ml
Release date: 2020-03-05

555-66-8, 6-ShogaolRelated Search:

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

(E)-1-(4-Hydroxy-3-methoxy-phenyl)dec-4-en-3-one

6-SHOGAOL

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

6-Shogaol USP/EP/BP

[6]-Shogaol D5 (Major)

TIANFU-CHEM - 6-Shogaol

1-(4-Hydroxy-3-methoxyphenyl)dec-4-en-3-one

6-gingerenol

6-Shogaol-RM

555-66-8

chemical reagent

pharmaceutical intermediate

phytochemical

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reference standards from Chinese medicinal herbs (TCM).

standardized herbal extract