6-Shogaol
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- CAS-Nr.
- 555-66-8
- Englisch Name:
- 6-Shogaol
- Synonyma:
- SHOGAOL;6-SHOGAOL;6-Shagaol;SHOGAOL, 6-;6-gingerenol;6-Shogaol USP/EP/BP;[6]-Shogaol D5 (Major);TIANFU-CHEM - 6-Shogaol;1-(4-Hydroxy-3-methoxyphenyl)-4-decen-3-one;1-(4-Hydroxy-3-methoxyphenyl)dec-4-en-3-one
- CBNumber:
- CB4748322
- Summenformel:
- C17H24O3
- Molgewicht:
- 276.37
- MOL-Datei:
- 555-66-8.mol
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6-Shogaol Eigenschaften
- Siedepunkt:
- 427.5±35.0 °C(Predicted)
- Dichte
- 1.0448 g/cm3(Temp: 25 °C)
- storage temp.
- Keep in dark place,Inert atmosphere,2-8°C
- Löslichkeit
- Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
- pka
- 10.01±0.20(Predicted)
- Aggregatzustand
- Liquid
- Farbe
- Colourless to Light Yellow
- Geruch (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 Datenbank
- 555-66-8(CAS DataBase Reference)
- NIST chemische Informationen
- 6-shogaol(555-66-8)
Sicherheit
- Risiko- und Sicherheitserklärung
- Gefahreninformationscode (GHS)
| Kennzeichnung gefährlicher |
Xn |
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| R-Sätze: |
22 |
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| WGK Germany |
3 |
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| Bildanzeige (GHS) |
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| Alarmwort |
Warnung |
| Gefahrenhinweise |
| Code |
Gefahrenhinweise |
Gefahrenklasse |
Abteilung |
Alarmwort |
Symbol |
P-Code |
| H302 |
Gesundheitsschädlich bei Verschlucken. |
Akute Toxizität oral |
Kategorie 4 |
Warnung |
![GHS hazard pictograms]() src="/GHS07.jpg" width="20" height="20" /> |
P264, P270, P301+P312, P330, P501 |
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| Sicherheit |
| P261 |
Einatmen von Staub vermeiden. |
| P280 |
Schutzhandschuhe/Schutzkleidung/Augenschutz tragen. |
| P301+P312 |
BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen. |
| P302+P352 |
BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen. |
| P305+P351+P338 |
BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen. |
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6-Shogaol Chemische Eigenschaften,Einsatz,Produktion Methoden
Chemische Eigenschaften
White crystalline powder. B.P. higher than 300℃. Very slightly soluble in water, soluble in alcohol and oils.
Verwenden
[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.
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".
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 Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
6-Shogaol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.
Global( 253)Lieferanten
555-66-8()Verwandte Suche:
- (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
- 555-66-8
- chemical reagent
- pharmaceutical intermediate
- phytochemical
- Miscellaneous Natural Products
- The group of Ginerols
- Aromatics
- Intermediates & Fine Chemicals
- Pharmaceuticals
- reference standards from Chinese medicinal herbs (TCM).
- standardized herbal extract
