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Cas Database

23513-14-6

23513-14-6

Identification

  • Product Name:3-Decanone,5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (5S)-

  • CAS Number: 23513-14-6

  • EINECS:607-241-6

  • Molecular Weight:294.391

  • Molecular Formula: C17H26O4

  • HS Code:29145090

  • Mol File:23513-14-6.mol

Synonyms:3-Decanone,5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (S)-;3-Decanone,5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (S)-(+)- (8CI);(+)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone;(+)-[6]-Gingerol;(S)-(+)-[6]Gingerol;(S)-[6]Gingerol;[6]-Gingerol;Gingerol;(5S)-5-Hydroxy-1-(4-hydroxy-3-methoxy-phenyl)decan-3-one;

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Safety information and MSDS view more

  • Pictogram(s):Xn

  • Hazard Codes:Xn

  • Signal Word:Danger

  • Hazard Statement:H301 Toxic if swallowedH315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:(+)-[6]-Gingerol
  • Packaging:100mg
  • Price:$ 1135
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:[6]-Gingerol
  • Packaging:5mg
  • Price:$ 173.9
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:[6]-Gingerol ≥98% (HPLC)
  • Packaging:5mg
  • Price:$ 217
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:[6]-Gingerol ≥98% (HPLC)
  • Packaging:10mg
  • Price:$ 419
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:[6]-Gingerol analytical standard
  • Packaging:10mg
  • Price:$ 475
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  • Manufacture/Brand:JR MediChem
  • Product Description:6-Gingerol(NewProduct) 98%
  • Packaging:500mg
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  • Manufacture/Brand:JR MediChem
  • Product Description:6-Gingerol(NewProduct) 98%
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  • Manufacture/Brand:DC Chemicals
  • Product Description:6-Gingerol >98%,StandardReferencesGrade
  • Packaging:20 mg
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  • Manufacture/Brand:CSNpharm
  • Product Description:6-Gingerol
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  • Manufacture/Brand:CSNpharm
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Relevant articles and documentsAll total 28 Articles be found

Discovery and Characterization of Pure RhlR Antagonists against Pseudomonas aeruginosa Infections

Nam, SangJin,Ham, So-Young,Kwon, Hongmok,Kim, Han-Shin,Moon, Suhyun,Lee, Jeong-Hoon,Lim, Taehyeong,Son, Sang-Hyun,Park, Hee-Deung,Byun, Youngjoo

, p. 8388 - 8407 (2020/09/21)

Pseudomonas aeruginosa (P. aeruginosa) is an opportunistic human pathogen that forms biofilms and produces virulence factors via quorum sensing (QS). Blocking the QS system in P. aeruginosa is an excellent strategy to reduce biofilm formation and the production of virulence factors. RhlR plays an essential role in the QS system of P. aeruginosa. We synthesized 55 analogues based on the chemical structure of 4-gingerol and evaluated their RhlR inhibitory activities using the cell-based reporter strain assay. Comprehensive structure-activity relationship studies identified the alkynyl ketone 30 as the most potent RhlR antagonist. This compound displayed selective RhlR antagonism over LasR and PqsR, strong inhibition of biofilm formation, and reduced production of virulence factors in P. aeruginosa. Furthermore, the survival rate of Tenebrio molitor larvae treated with 30 in vivo greatly improved. Therefore, compound 30, a pure RhlR antagonist, can be utilized for developing QS-modulating molecules in the control of P. aeruginosa infections.

GINGEROL DERIVATIVE HAVING INHIBITORY ACTIVITY AGAINST BIOFILM FORMATION AND PHARMACEUTICAL COMPOSITION COMPRISING SAME AS EFFECTIVE INGREDIENT FOR PREVENTING OR TREATING BIOFILM-CAUSED INFECTION SYMPTOM

-

Paragraph 0032; 0051-0052; 0055-0056, (2020/09/22)

The present invention relates to a gingerol derivative having inhibitory activity against biofilm formation and a pharmaceutical composition for preventing or treating infections caused by biofilms including the gingerol derivative as an active ingredient. The gingerol derivative of the present invention exhibits significantly improved binding affinity for LasR and inhibitory activity against biofilm formation. Therefore, the gingerol derivative of the present invention can act on various membrane surfaces where biofilms tend to form and can effectively inhibit the formation of the corresponding biofilms. In addition, the use of the pharmaceutical composition according to the present invention can fundamentally prevent or treat a variety of infections caused by biofilms due to the presence of the gingerol derivative in the pharmaceutical composition.

MnO2as a terminal oxidant in Wacker oxidation of homoallyl alcohols and terminal olefins

Fernandes, Rodney A.,Ramakrishna, Gujjula V.,Bethi, Venkati

, p. 6115 - 6125 (2020/10/27)

Efficient and mild reaction conditions for Wacker-type oxidation of terminal olefins of less explored homoallyl alcohols to β-hydroxy-methyl ketones have been developed by using a Pd(ii) catalyst and MnO2 as a co-oxidant. The method involves mild reaction conditions and shows good functional group compatibility along with high regio- and chemoselectivity. While our earlier system of PdCl2/CrO3/HCl produced α,β-unsaturated ketones from homoallyl alcohols, the present method provided orthogonally the β-hydroxy-methyl ketones. No overoxidation or elimination of benzylic and/or β-hydroxy groups was observed. The method could be extended to the oxidation of simple terminal olefins as well, to methyl ketones, displaying its versatility. An application to the regioselective synthesis of gingerol is demonstrated.

6-gingerol derivative and its preparation and application

-

Paragraph 0093-0095; 0113-0116, (2019/10/07)

A 6-gingerol derivative and its preparation and application are provided. That derivative has the following structure. The derivative of the present invention has antitumor activity and inhibit effect on tumor cells. In addition, the chemical properties o

METHOD FOR PREPARING HIGHLY ENANTIO-ENRICHED GINGEROLS

-

Paragraph 0056-0061; 0133, (2019/12/25)

Disclosed is a method for preparing a chiral Gingerol compound. To prepare the chiral Gingerol compound, a racemic Gingerol compound is treated with kinetic resolution in the presence of a chiral catalyst compound and an alkali metal fluoride so a chiral Gingerol compound with high optical purity can be prepared. An oligo ethylene glycol-derived compound including an oligo ethylene glycol functional group, a basic part, and a hydroxy functional group of a binol derivative, an acidic part, can be used as a chiral catalyst compound.COPYRIGHT KIPO 2020

Process route upstream and downstream products

Process route

4-(3-methoxy-4-trimethylsilyloxyphenyl)butan-2-one
56700-87-9

4-(3-methoxy-4-trimethylsilyloxyphenyl)butan-2-one

hexanal
66-25-1

hexanal

4-(4-hydroxy-3-methoxyphenyl)-2-butanone
122-48-5

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

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)butane
39728-80-8

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)butane

4-hydroxy-3-(4-hydroxy-3-methoxybenzyl)nonan-2-one
77333-91-6

4-hydroxy-3-(4-hydroxy-3-methoxybenzyl)nonan-2-one

Conditions
Conditions Yield
With hydrogenchloride; lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1.) -78 deg C, 1 h, THF, 2.) ether;
(5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
1360109-87-0

(5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-1-(4-hydroxy-3-methoxyphenyl)decan-3-one

Conditions
Conditions Yield
With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 6h; Inert atmosphere;
87%
With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;
87%
Conditions
Conditions Yield
With potassium fluoride; C50H34F12O6; In toluene; at 25 ℃; for 192h; stereoselective reaction;
48%
Conditions
Conditions Yield
With potassium fluoride; C50H34F12O6; In toluene; at 25 ℃; for 192h; enantioselective reaction; Inert atmosphere; Resolution of racemate;
48%
(S,E)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dec-1-en-3-one
1186501-32-5

(S,E)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dec-1-en-3-one

Conditions
Conditions Yield
With palladium 10% on activated carbon; hydrogen; triethylamine; In ethyl acetate; for 4h;
90%
3-<4-(benzyloxy)-3-methoxyphenyl>propan-1-ol
57371-44-5

3-<4-(benzyloxy)-3-methoxyphenyl>propan-1-ol

Conditions
Conditions Yield
Multi-step reaction with 9 steps
1: 81 percent / CrO3, pyridine / CH2Cl2 / Ambient temperature
2: 80 percent / BF3*OEt2 / CH2Cl2 / 1.5 h / 0 °C
4: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature
5: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature
6: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight
7: 76 percent / LiAlH4 / diethyl ether / 48 h / Heating
8: MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C
9: p-toluenesulfonic acid / ethanol / 2 h / 55 °C
With pyridine; chromium(VI) oxide; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; calcium carbonate; methyl iodide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; chloroform; water; acetonitrile;
Multi-step reaction with 4 steps
1: 76 percent / pyridine / 16 h / 5 °C
2: 86 percent / NaI / acetone / 21 h / Ambient temperature
4: 1.) B(OH)3, H2, 2.) H2 / 1.) Raney Ni, 2.) 10 percent Pd/C / 1.) MeOH-H2O 5-1, 3.5 h, room temp., 2.) MeOH, 40 min, room temp.
With hydrogen; boric acid; sodium iodide; palladium on activated charcoal; nickel; In pyridine; acetone;
Multi-step reaction with 12 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C
1.2: 1 h / 20 °C
2.1: zinc; ammonium chloride / tetrahydrofuran; water / 4 h / 0 - 20 °C
3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C
3.2: 6 h / 20 °C
4.1: AD-mix-β / water; tert-butyl alcohol / 24 h / 0 °C
5.1: triphenylphosphine; diethylazodicarboxylate / benzene / 18 h / Reflux
6.1: magnesium / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere
6.2: 0 - 20 °C
7.1: 1H-imidazole / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere
8.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 5 h / 20 °C / 2068.65 Torr
9.1: potassium carbonate / acetone / 3 h / 20 °C / Reflux
10.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 °C
11.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 5 h / 20 °C / 2068.65 Torr
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
With 1H-imidazole; oxalyl dichloride; palladium 10% on activated carbon; AD-mix-β; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; sodium hydrogencarbonate; potassium carbonate; ammonium chloride; Dess-Martin periodane; magnesium; dimethyl sulfoxide; triphenylphosphine; zinc; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetone; tert-butyl alcohol; benzene; 4.1: |Sharpless Asymmetric Epoxidation;
(S)-1-[3-Methoxy-4-(tetrahydro-pyran-2-yloxy)-phenyl]-5-(tetrahydro-pyran-2-yloxy)-decan-3-one

(S)-1-[3-Methoxy-4-(tetrahydro-pyran-2-yloxy)-phenyl]-5-(tetrahydro-pyran-2-yloxy)-decan-3-one

Conditions
Conditions Yield
With toluene-4-sulfonic acid; In ethanol; at 55 ℃; for 2h; Yield given;
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6,537-98-4

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Conditions
Conditions Yield
Multi-step reaction with 13 steps
1: 98 percent / H2, NaOH / 10percent Pd/C / H2O / 12 h / 22501.8 Torr
2: 98 percent / conc.H2SO4 / Heating
3: 1) NaH, 2) tetrabutylammonium iodide / 1) THF, 0 deg C, 0.5 h, 2) 0 deg C
4: 95 percent / LiAlH4 / diethyl ether / 0 °C
5: 81 percent / CrO3, pyridine / CH2Cl2 / Ambient temperature
6: 80 percent / BF3*OEt2 / CH2Cl2 / 1.5 h / 0 °C
8: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature
9: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature
10: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight
11: 76 percent / LiAlH4 / diethyl ether / 48 h / Heating
12: MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C
13: p-toluenesulfonic acid / ethanol / 2 h / 55 °C
With pyridine; chromium(VI) oxide; sodium hydroxide; lithium aluminium tetrahydride; sulfuric acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; calcium carbonate; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; chloroform; water; acetonitrile;
3-methoxy-4-(phenylmethoxy)benzaldehyde
2426-87-1

3-methoxy-4-(phenylmethoxy)benzaldehyde

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1: 75 percent / NaH / 1,2-dimethoxy-ethane / 24 h / Heating
2: 86 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 18 h / Ambient temperature
3: 76 percent / pyridine / 16 h / 5 °C
4: 86 percent / NaI / acetone / 21 h / Ambient temperature
6: 1.) B(OH)3, H2, 2.) H2 / 1.) Raney Ni, 2.) 10 percent Pd/C / 1.) MeOH-H2O 5-1, 3.5 h, room temp., 2.) MeOH, 40 min, room temp.
With lithium aluminium tetrahydride; hydrogen; boric acid; sodium hydride; sodium iodide; palladium on activated charcoal; nickel; In tetrahydrofuran; pyridine; 1,2-dimethoxyethane; diethyl ether; acetone;
Multi-step reaction with 6 steps
1.1: triphenylphosphine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere
2.1: ethylmagnesium bromide / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere
3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere
3.2: 4 h / -78 - 20 °C
4.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
5.1: hydrogen; palladium(II) hydroxide / benzene / 5 h / 20 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere
With n-butyllithium; ethylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; palladium(II) hydroxide; dimethyl sulfoxide; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; dichloromethane; benzene; 1.1: Corey-Fuchs reaction;
ethyl 3-(4-(benzyloxy)-3-methoxy)propanoate
186895-24-9

ethyl 3-(4-(benzyloxy)-3-methoxy)propanoate

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: 86 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 18 h / Ambient temperature
2: 76 percent / pyridine / 16 h / 5 °C
3: 86 percent / NaI / acetone / 21 h / Ambient temperature
5: 1.) B(OH)3, H2, 2.) H2 / 1.) Raney Ni, 2.) 10 percent Pd/C / 1.) MeOH-H2O 5-1, 3.5 h, room temp., 2.) MeOH, 40 min, room temp.
With lithium aluminium tetrahydride; hydrogen; boric acid; sodium iodide; palladium on activated charcoal; nickel; In tetrahydrofuran; pyridine; diethyl ether; acetone;

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