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555-66-8 Usage

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.

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+

555-66-8 Well-known Company Product Price

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  • Sigma-Aldrich

  • (39303)  [6]-Shogaol  analytical standard

  • 555-66-8

  • 39303-10MG

  • 6,165.90CNY

  • Detail

555-66-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name (E)-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one

1.2 Other means of identification

Product number -
Other names Shogaol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:555-66-8 SDS

555-66-8Synthetic route

ethyl 5-(4-hydroxy-3-methoxyphenyl)-3-oxopentanoate

ethyl 5-(4-hydroxy-3-methoxyphenyl)-3-oxopentanoate

hexanal
66-25-1

hexanal

[6]-shogaol
555-66-8

[6]-shogaol

Conditions
ConditionsYield
With sodium hydroxide In dimethyl sulfoxide at 0℃; for 0.5h;75%
Conditions
ConditionsYield
With potassium fluoride; C50H34F12O6 In toluene at 25℃; for 192h; Inert atmosphere; Resolution of racemate; enantioselective reaction;A n/a
B 48%
Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene Heating;
With potassium carbonate; methyl iodide In methanol at 20℃; for 48h;
hexanal
66-25-1

hexanal

zingerone

zingerone

[6]-shogaol
555-66-8

[6]-shogaol

Conditions
ConditionsYield
With potassium hydroxide; diethyl ether
Dehydrozingerone
1080-12-2

Dehydrozingerone

[6]-shogaol
555-66-8

[6]-shogaol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: H2 / Raney-Ni / -10 °C
2: (i) nBuLi, iPr2NH, THF, (ii) /BRN= 1209232/
3: TiCl4 / CH2Cl2 / -78 °C
4: TsOH / benzene / Heating
View Scheme
Multi-step reaction with 3 steps
1: sodium hydride / Reflux
2: hydrogen / acetone
3: sodium hydroxide / dimethyl sulfoxide / 0.5 h / 0 °C
View Scheme
4-(4-hydroxy-3-methoxyphenyl)-2-butanone
122-48-5

4-(4-hydroxy-3-methoxyphenyl)-2-butanone

[6]-shogaol
555-66-8

[6]-shogaol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (i) nBuLi, iPr2NH, THF, (ii) /BRN= 1209232/
2: TiCl4 / CH2Cl2 / -78 °C
3: TsOH / benzene / Heating
View Scheme
2-Methoxy-1-trimethylsilanyloxy-4-(3-trimethylsilanyloxy-but-3-enyl)-benzene
60101-00-0

2-Methoxy-1-trimethylsilanyloxy-4-(3-trimethylsilanyloxy-but-3-enyl)-benzene

[6]-shogaol
555-66-8

[6]-shogaol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TiCl4 / CH2Cl2 / -78 °C
2: TsOH / benzene / Heating
View Scheme
vanillin
121-33-5

vanillin

[6]-shogaol
555-66-8

[6]-shogaol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: BF3-Et2O / CH2Cl2
2: H2 / Raney-Ni / -10 °C
3: (i) nBuLi, iPr2NH, THF, (ii) /BRN= 1209232/
4: TiCl4 / CH2Cl2 / -78 °C
5: TsOH / benzene / Heating
View Scheme
[6]-shogaol
555-66-8

[6]-shogaol

1-(4'-hydroxy-3'-methoxyphenyl)-4-decen-3-ol

1-(4'-hydroxy-3'-methoxyphenyl)-4-decen-3-ol

Conditions
ConditionsYield
Stage #1: [6]-shogaol With cerium(III) chloride heptahydrate In methanol at -78℃; for 0.166667h;
Stage #2: With methanol; sodium tetrahydroborate at -78℃; for 0.5h;
100%
[6]-shogaol
555-66-8

[6]-shogaol

[6]-paradol
27113-22-0

[6]-paradol

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 20℃;98%
[6]-shogaol
555-66-8

[6]-shogaol

O-acetylsalicyloyl chloride
5538-51-2

O-acetylsalicyloyl chloride

6-shogaol aspirinate

6-shogaol aspirinate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 2h;93%
methanol
67-56-1

methanol

[6]-shogaol
555-66-8

[6]-shogaol

5-methoxy-1-(4'-hydroxy-3'-methoxyphenyl)decan-3-one

5-methoxy-1-(4'-hydroxy-3'-methoxyphenyl)decan-3-one

Conditions
ConditionsYield
With sodium methylate at 0℃; for 4h; Michael Addition;90%
N-acetylcystein
616-91-1

N-acetylcystein

[6]-shogaol
555-66-8

[6]-shogaol

5-N-acetylcysteinyl-[6]-shogaol

5-N-acetylcysteinyl-[6]-shogaol

Conditions
ConditionsYield
With sodium hydrogencarbonate In methanol; water at 20℃; for 72h; Reagent/catalyst; Solvent; Temperature; Michael Addition;80%
GLUTATHIONE
70-18-8

GLUTATHIONE

[6]-shogaol
555-66-8

[6]-shogaol

5-glutathiol-[6]-shogaol

5-glutathiol-[6]-shogaol

Conditions
ConditionsYield
With sodium hydrogencarbonate In methanol; water at 20℃; for 3h; Michael Addition;80%
[6]-shogaol
555-66-8

[6]-shogaol

thymin
65-71-4

thymin

1-(1-(4-hydroxy-3-methoxyphenyl)-3-oxodecan-5-yl)-5-methylpyrimidine-2,4-(1H,3H)-dione

1-(1-(4-hydroxy-3-methoxyphenyl)-3-oxodecan-5-yl)-5-methylpyrimidine-2,4-(1H,3H)-dione

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide at 20℃; for 24h; Michael Addition;67%
[6]-shogaol
555-66-8

[6]-shogaol

(1E,4E)-1-(4'-hydroxy-3'-methoxyphenyl)-deca-1,4-dien-3-one

(1E,4E)-1-(4'-hydroxy-3'-methoxyphenyl)-deca-1,4-dien-3-one

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 0 - 20℃; for 3.5h;62%
L-Cysteine
52-90-4

L-Cysteine

[6]-shogaol
555-66-8

[6]-shogaol

5-cysteinyl-[6]-shogaol

5-cysteinyl-[6]-shogaol

Conditions
ConditionsYield
With sodium hydrogencarbonate In methanol; water at 20℃; for 24h; Michael Addition;60%
[6]-shogaol
555-66-8

[6]-shogaol

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

5-methylthio-1-(4'-hydroxy-3'-methoxyphenyl)decan-3-one

5-methylthio-1-(4'-hydroxy-3'-methoxyphenyl)decan-3-one

Conditions
ConditionsYield
In tetrahydrofuran; water at 20℃; for 6h; Michael Addition;60%
3-methylpyridin-2-ylamine
1603-40-3

3-methylpyridin-2-ylamine

[6]-shogaol
555-66-8

[6]-shogaol

1-(4-hydroxy-3-methoxyphenyl)-5-(3-methylpyridin-2-ylamino)decan-3-one

1-(4-hydroxy-3-methoxyphenyl)-5-(3-methylpyridin-2-ylamino)decan-3-one

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide at 20℃; for 24h; Michael Addition;57%
2-Amino-4-methylpyridine
695-34-1

2-Amino-4-methylpyridine

[6]-shogaol
555-66-8

[6]-shogaol

1-(4-hydroxy-3-methoxyphenyl)-5-(4-methylpyridin-2-ylamino)decan-3-one

1-(4-hydroxy-3-methoxyphenyl)-5-(4-methylpyridin-2-ylamino)decan-3-one

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide at 20℃; for 24h; Michael Addition;54%
(5-methyl-pyridin-2-yl)amine
1603-41-4

(5-methyl-pyridin-2-yl)amine

[6]-shogaol
555-66-8

[6]-shogaol

1-(4-hydroxy-3-methoxyphenyl)-5-(5-methylpyridin-2-ylamino)decan-3-one

1-(4-hydroxy-3-methoxyphenyl)-5-(5-methylpyridin-2-ylamino)decan-3-one

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide at 20℃; for 24h; Michael Addition;50%
Conditions
ConditionsYield
With benzyltri(n-butyl)ammonium chloride; potassium hydroxide In chloroform; water at 20℃; for 6.5h;44%
5-bromouracil
51-20-7

5-bromouracil

[6]-shogaol
555-66-8

[6]-shogaol

5-bromo-1-(1-(4-hydroxy-3-methoxyphenyl)-3-oxodecan-5-yl)-pyrimidine-2,4-(1H,3H)-dione

5-bromo-1-(1-(4-hydroxy-3-methoxyphenyl)-3-oxodecan-5-yl)-pyrimidine-2,4-(1H,3H)-dione

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide at 20℃; for 24h; Michael Addition;43%
[6]-shogaol
555-66-8

[6]-shogaol

5-(6-amino-9H-purin-9-yl)-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
1311378-31-0

5-(6-amino-9H-purin-9-yl)-1-(4-hydroxy-3-methoxyphenyl)decan-3-one

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide at 20℃; for 24h; Michael Addition;38%
With caesium carbonate In methanol; water at 20℃; for 72h; Michael-type reaction;36%
diethyl ether
60-29-7

diethyl ether

[6]-shogaol
555-66-8

[6]-shogaol

platinum black

platinum black

dihydroshogaol

dihydroshogaol

Conditions
ConditionsYield
Hydrogenation;
[6]-shogaol
555-66-8

[6]-shogaol

2-methoxy-4-(5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-oxodecyl)phenyl methanesulfonate

2-methoxy-4-(5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-oxodecyl)phenyl methanesulfonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dimethyl sulfoxide / 24 h / 20 °C
2: triethylamine / dichloromethane / 2 h / 0 - 20 °C
View Scheme
[6]-shogaol
555-66-8

[6]-shogaol

2-methoxy-4-(5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-oxodecyl)phenyl 4-methylbenzenesulfonate

2-methoxy-4-(5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-oxodecyl)phenyl 4-methylbenzenesulfonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dimethyl sulfoxide / 24 h / 20 °C
2: triethylamine / dichloromethane / 2 h / 0 - 20 °C
View Scheme
[6]-shogaol
555-66-8

[6]-shogaol

2-methoxy-4-(5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-oxodecyl)phenyl 6-chloronicotinate

2-methoxy-4-(5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-oxodecyl)phenyl 6-chloronicotinate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dimethyl sulfoxide / 24 h / 20 °C
2: triethylamine / dichloromethane / 2 h / 0 - 20 °C
View Scheme
[6]-shogaol
555-66-8

[6]-shogaol

C38H42N2O9

C38H42N2O9

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dimethyl sulfoxide / 24 h / 20 °C
2: triethylamine / dichloromethane / 2 h / 0 - 20 °C
View Scheme
[6]-shogaol
555-66-8

[6]-shogaol

4-(5-(3-(furan-2-carbonyl)-5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-oxodecyl)-2-methoxyphenyl furan-2-carboxylate

4-(5-(3-(furan-2-carbonyl)-5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-oxodecyl)-2-methoxyphenyl furan-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dimethyl sulfoxide / 24 h / 20 °C
2: triethylamine / dichloromethane / 2 h / 0 - 20 °C
View Scheme

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.

Rapid synthesis method of shogaol compounds

-

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.

Kinetic Resolution of β-Hydroxy Carbonyl Compounds via Enantioselective Dehydration Using a Cation-Binding Catalyst: Facile Access to Enantiopure Chiral Aldols

Paladhi, Sushovan,Hwang, In-Soo,Yoo, Eun Jeong,Ryu, Do Hyun,Song, Choong Eui

supporting information, p. 2003 - 2006 (2018/04/16)

A practical and highly enantioselective nonenzymatic kinetic resolution of racemic β-hydroxy carbonyl (aldol) compounds through enantioselective dehydration process was developed using a cation-binding Song's oligoethylene glycol (oligoEG) catalyst with p

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