555-66-8 Usage
Description
6-Shogaol, an aromatic constituent of ginger, is the chain-dehydroxylated analog of 6-Gingerol. It exhibits a range of pharmacological activities, including inhibition of spontaneous motor activity, antipyretic and analgesic effects, and prolonged hexobarbital-induced sleeping time. Additionally, 6-Shogaol demonstrates potent antitussive activity and influences the cortical EEG.
Uses
Used in Pharmaceutical Applications:
6-Shogaol is used as a therapeutic agent for its various pharmacological properties, such as inhibition of spontaneous motor activity, antipyretic and analgesic effects, and prolonged hexobarbital-induced sleeping time. Its potent antitussive activity and influence on the cortical EEG also contribute to its potential use in the development of medications for various conditions.
Used in Nutraceutical Applications:
6-Shogaol is used as a nutraceutical ingredient due to its potential health benefits, including its anti-inflammatory, antioxidant, and antimicrobial properties. These properties make it a valuable addition to dietary supplements and functional foods aimed at promoting overall health and well-being.
Used in Cosmetic Applications:
6-Shogaol is used as an active ingredient in the cosmetic industry for its potential anti-inflammatory and antioxidant properties. These characteristics can be beneficial in the development of skincare products designed to improve skin health, reduce inflammation, and protect against environmental stressors.
Used in Food and Beverage Industry:
6-Shogaol is used as a flavor enhancer and preservative in the food and beverage industry. Its unique aromatic properties can add depth and complexity to various food products, while its antimicrobial properties can help extend shelf life and maintain product quality.
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).
Check Digit Verification of cas no
The CAS Registry Mumber 555-66-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 5 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 555-66:
(5*5)+(4*5)+(3*5)+(2*6)+(1*6)=78
78 % 10 = 8
So 555-66-8 is a valid CAS Registry Number.
InChI:InChI=1/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/b8-7+
555-66-8Relevant articles and documents
6-Gingerol and Semisynthetic 6-Gingerdione Counteract Oxidative Stress Induced by ROS in Zebrafish
Manjunathan, Tamilvelan,Guru, Ajay,Arokiaraj, Jesu,Gopinath, Pushparathinam
, (2021/11/03)
6-Gingerol (1) is one of the major components in ginger and developing new synthetic methodologies could bring semisynthetic analogs with improved therapeutic properties. Towards this, multigram scale isolation of 6-gingerol with excellent purity was optimized using a simple and robust extraction, followed by column purification. Synthesis of 6-gingerdione, 7 from 6-gingerol was then achieved through selective –OTBDMS protection, DMP oxidation and deprotection reaction sequence for the first time. Compounds 1, 7 and 8 (dehydrozingerone) exhibited excellent cell-free antioxidant properties in DPPH, ABTS, superoxide radical scavenging assay and H2O2 assay at 10–50 μM concentrations. The hemolytic study suggests that up to 50 μM, all three compounds did not exhibit toxicity to human erythrocytes. When H2O2 treated zebrafish larvae groups (96hpf) were exposed to compounds 1, 7 and 8, it increases the SOD (19, 19.1 and 18.7 U/mg protein), CAT (18.1, 16.5, and 15.8 μmol/mg levels and decreases the lipid peroxidation level (13, 15 and 18 nmol/mg protein), respectively. In vivo ROS levels and degree of cell death were studied using DCFDA and Acridine orange assays. Compounds 1, 7 and 8 decreases the ROS and cell death level significantly. Taken together, compounds 1, 7 and 8 exhibit excellent antioxidant properties, counteract H2O2 induced oxidative stress, reduces cell death in zebrafish larvae.
Preparation method of (E)-1-(4-hydroxy-3-methoxyphenyl)-4-ene-3-decalone
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Paragraph 0029; 0038; 0040, (2018/07/15)
The invention discloses a preparation method of (E)-1-(4-hydroxy-3-methoxyphenyl)-4-ene-3-decalone and relates to the field of medicinal chemistry. The method comprises the steps as follows: 1) 4-(4-hydroxy-3-methoxyphenyl)-2-butanone is dissolved in a halogenated hydrocarbon solvent, pyrrolidine or piperidine is added at the room temperature, and the mixture reacts for 15-120 min; 2) a halogenated hydrocarbon solution of n-hexaldehyde is added, and the mixture reacts for 2-24 h; 3) an inorganic base solution is added, the mixture reacts for 1-24 h, aftertreatment is performed, and a compoundshown in formula (1) is prepared. Reactions at the room temperature are conducted with inorganic base and other weak bases, and the total yield is 78% or above. The method has mild reaction conditionsand is convenient to operate and suitable for industrial production.
Rapid synthesis method of shogaol compounds
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Paragraph 0031; 0032, (2018/03/26)
The invention relates to a rapid synthesis method of shogaol compounds. The specific reaction route is shown in the description. Compounds in formula (4) are obtained from dehydrozingerone and carbonic acid diester under the action of a base, dissolved in an organic solvent and subjected to hydrogenation reduction, key intermediate compounds shown in formula (5) are obtained and react with aliphatic aldehydes under the action of the base, and target compounds 6-shogaol in formula (1), 8-shogaol in formula (2) and 10-shogaol in formula (3) are obtained. The rapid synthesis method has the advantages that reaction yield is high, reaction conditions are mild, operation is simple and environment-friendliness is realized, and has good industrial application prospect.