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Cas Database

10538-51-9

10538-51-9

Identification

Synonyms:Cinnamicacid, 2,5-dimethoxy- (6CI,7CI,8CI);3-(2,5-Dimethoxyphenyl)acrylic acid;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 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 view more

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  • Manufacture/Brand:TRC
  • Product Description:(E)-3-(2,5-Dimethoxyphenyl)acrylicacid
  • Packaging:250mg
  • Price:$ 55
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2,5-Dimethoxycinnamic Acid >97.0%(T)
  • Packaging:10g
  • Price:$ 62
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2,5-Dimethoxycinnamic acid 99.0%
  • Packaging:5 g
  • Price:$ 23
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2,5-Dimethoxycinnamic acid 99.0%
  • Packaging:25 g
  • Price:$ 77
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2,5-Dimethoxycinnamic acid, predominantly trans 99%
  • Packaging:100g
  • Price:$ 286
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2,5-Dimethoxycinnamic acid, predominantly trans 99%
  • Packaging:25g
  • Price:$ 106
  • Delivery:In stock
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  • Manufacture/Brand:Frontier Specialty Chemicals
  • Product Description:2,5-Dimethoxycinnamic Acid 99%
  • Packaging:5g
  • Price:$ 28
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  • Manufacture/Brand:Crysdot
  • Product Description:3-(2,5-Dimethoxyphenyl)acrylicacid 98%
  • Packaging:500g
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  • Manufacture/Brand:Chemenu
  • Product Description:3-(2,5-Dimethoxyphenyl)acrylicacid 95+%
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:2,5-Dimethoxycinnamic acid
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Relevant articles and documentsAll total 10 Articles be found

Physico-chemical properties of new liquid crystals incorporating a lactone ring

Morita, Yuki,Tasaka, Takeyasu,Yamaguchi, Remuto,Okamoto, Hiroaki,Takenaka, Shunsuke

, p. 209/[2075]-220/[2086] (2005)

Synthesis and physico-chemical properties of 4-alkoxyphenyl and 4-alkoxybiphenyl-4′-yl 2H-pyran-2-one-5-carboxylates, 2H-chromen-2-one-6- yl 4-alkoxybenzoates and 4-alkoxybiphenyl-4′-carboxylates, and 2H-chromen-2-one-7-yl 4-alkoxybenzoates and 4-alkoxybiphenyl-4′- carboxylates are described. Terminal 2H-pyran-2-one and chronten-2-one cores are effective in enhancing liquid crystalline properties. The layer structure was examined by a small angle X-ray measurement, and the results are discussed in terms of the molecular structure. The polar effect of the terminal lactone group is recognized in the thermal properties and the layer structure of smectic A (SmA) phase.

Controlling reactivity in the Fujiwara–Moritani reaction: Examining solvent effects and the addition of 1,3-dicarbonyl ligands on the oxidative coupling of electron rich arenes and acrylates

Jones, Roderick C.

supporting information, (2019/12/25)

A palladium-catalysed direct alkenation of electron rich arenes in the presence of K2S2O8 with an acetic acid/1,4-dioxane solvent combination has been developed. The 1,4-dioxane co-solvent dramatically influences the rate of reaction, giving selectively disubstituted alkenes, while the addition of acetylacetone ligands was shown to increase site selectivity for the alkenation of monofunctionalized arenes. The participation of these carbonyl ligands has been confirmed by ESI-MS studies, with some key in situ intermediates in the catalytic cycle identified. A variety of electron rich arenes and olefinic substrates can be utilised in the direct oxidative coupling to give disubstituted alkenes in moderate to good yields.

Synthesis, preliminarily biological evaluation and molecular docking study of new Olaparib analogues as multifunctional PARP-1 and cholinesterase inhibitors

Gao, Cheng-Zhi,Dong, Wei,Cui, Zhi-Wen,Yuan, Qiong,Hu, Xia-Min,Wu, Qing-Ming,Han, Xianlin,Xu, Yao,Min, Zhen-Li

, p. 150 - 162 (2018/11/30)

A series of new Olaparib derivatives was designed and synthesized, and their inhibitory activities against poly (ADP-ribose) polymerases-1 (PARP-1) enzyme and cancer cell line MDA-MB-436 in vitro were evaluated. The results showed that compound 5l exhibited the most potent inhibitory effects on PARP-1 enzyme (16.10 ± 1.25 nM) and MDA-MB-436 cancer cell (11.62 ± 2.15 μM), which was close to that of Olaparib. As a PARP-1 inhibitor had been reported to be viable to neuroprotection, in order to search for new multitarget-directed ligands (MTDLs) for the treatment of Alzheimer’s disease (AD), the inhibitory activities of the synthesized compounds against the enzymes AChE (from electric eel) and BChE (from equine serum) were also tested. Compound 5l displayed moderate BChE inhibitory activity (9.16 ± 0.91 μM) which was stronger than neostigmine (12.01 ± 0.45 μM) and exhibited selectivity for BChE over AChE to some degree. Molecular docking studies indicated that 5l could bind simultaneously to the catalytic active of PARP-1, but it could not interact well with huBChE. For pursuit of PARP-1 and BChE dual-targeted inhibitors against AD, small and flexible non-polar groups introduced to the compound seemed to be conducive to improving its inhibitory potency on huBChE, while keeping phthalazine-1-one moiety unchanged which was mainly responsible for PARP-1 inhibitory activity. Our research gave a clue to search for new agents based on AChE and PARP-1 dual-inhibited activities to treat Alzheimer’s disease.

Design, synthesis, and docking studies of afatinib analogs bearing cinnamamide moiety as potent EGFR inhibitors

Tu, Yuanbiao,Ouyang, Yiqiang,Xu, Shan,Zhu, Yan,Li, Gen,Sun, Chao,Zheng, Pengwu,Zhu, Wufu

, p. 1495 - 1503 (2016/03/15)

Two series of afatinib derivatives bearing cinnamamide moiety (10a-n and 11a-h) were designed, synthesized and evaluated for the IC50 values against four cancer cell lines (A549, PC-3, MCF-7 and Hela). Two selected compounds (10e, 10k) were further evaluated for the inhibitory activity against EGFR and VEGFR2/KDR kinases. Seven of the compounds showed excellent cytotoxicity activity and selectivity with the IC50 values in single-digit μM to nanomole range. Three of them are equal to more active than positive control afatinib against one or more cell lines. The most promising compound 10k showed the best activity against A549, PC-3, MCF-7 and Hela cancer cell lines and EGFR kinase, with the IC50 values of 0.07 ± 0.02 μM, 7.67 ± 0.97 μM, 4.65 ± 0.90 μM and 4.83 ± 1.28 μM, which were equal to more active than afatinib (0.05 ± 0.01 μM, 4.1 ± 2.47 μM, 5.83 ± 1.89 μM and 6.81 ± 1.77 μM), respectively. Activity of compounds 10e (IC50 9.1 nM) and 10k (IC50 3.6 nM) against EGFR kinase were equal to the reference compound afatinib (IC50 1.6 nM). Structure-activity relationships (SARs) and docking studies indicated that replacement of the aqueous solubility 4-(dimethylamino)but-2-enamide group by cinnamamide moiety didn't decrease the antitumor activity. The results suggested that methoxy substitution had a significant impact on the activity and methoxy substituted on C-4 or C-2,3,4 position was benefit for the activity.

Process route upstream and downstream products

Process route

malonic acid
141-82-2

malonic acid

2,5-dimethoxybenzaldehyde
93-02-7

2,5-dimethoxybenzaldehyde

2,5-dimethoxycinnamic acid
10538-51-9

2,5-dimethoxycinnamic acid

Conditions
Conditions Yield
With piperidine; pyridine; at 50 - 85 ℃; for 5h; Reflux;
94%
With piperidine; pyridine; at 50 ℃; for 4.5h; Reflux;
92%
With piperidine; pyridine;
85%
With piperidine; pyridine; hydrogenchloride; In water; Heating;
75%
With pyridine; ammonium acetate; at 85 ℃; for 5h; Darkness;
67.26%
With piperidine; In ethanol; for 6h;
With piperidine; pyridine; for 6h; Reflux;
With piperidine; pyridine; for 20h; Reflux;
With pyridine; ammonium acetate; at 85 ℃; for 5h;
acrylic acid
79-10-7

acrylic acid

1,4-dimethoxybezene
150-78-7

1,4-dimethoxybezene

2,5-dimethoxycinnamic acid
10538-51-9

2,5-dimethoxycinnamic acid

Conditions
Conditions Yield
With dipotassium peroxodisulfate; palladium diacetate; In 1,4-dioxane; acetic acid; at 80 ℃; for 24h;
51%
acetic anhydride
108-24-7

acetic anhydride

2,5-dimethoxybenzaldehyde
93-02-7

2,5-dimethoxybenzaldehyde

2,5-dimethoxycinnamic acid
10538-51-9

2,5-dimethoxycinnamic acid

Conditions
Conditions Yield
With sodium acetate; at 180 ℃;
methyl iodide
74-88-4

methyl iodide

2,5-dimethoxycinnamic acid
10538-51-9

2,5-dimethoxycinnamic acid

Conditions
Conditions Yield
With methanol; Verseifen des gebildeten Esters mit Kalilauge;
1,4-dimethoxybezene
150-78-7

1,4-dimethoxybezene

2,5-dimethoxycinnamic acid
10538-51-9

2,5-dimethoxycinnamic acid

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: benzene; AlCl3 / man erhitzt dann auf 35-40grad und leitet 4 Stdn. HCl durch die Fluessigkeit; man zersetzt das Reaktionsprodukt erst mit Eiswasser, dann durch Destillation mit Wasserdampf
2: sodium acetate / 180 °C
With aluminium trichloride; sodium acetate; benzene;
o-Coumaric acid
614-60-8

o-Coumaric acid

2,5-dimethoxycinnamic acid
10538-51-9

2,5-dimethoxycinnamic acid

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: alkali; potassium persulfate / Erhitzen des Reaktionsproduktes mit Salzsaeure
2: NaOH-solution
With sodium hydroxide; potassium peroxomonosulphate;
2,5-dihydroxycinnamic acid
636-01-1

2,5-dihydroxycinnamic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

2,5-dimethoxycinnamic acid
10538-51-9

2,5-dimethoxycinnamic acid

Conditions
Conditions Yield
With sodium hydroxide;
2,5-dimethoxycinnamic acid
10538-51-9

2,5-dimethoxycinnamic acid

Conditions
Conditions Yield
Id, Malons.;
2,5-dimethoxycinnamic acid
10538-51-9

2,5-dimethoxycinnamic acid

4,7-dimethoxyindan-1-one
52428-09-8

4,7-dimethoxyindan-1-one

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 2068.65 Torr
2.1: thionyl chloride; N,N-dimethyl-formamide / 5 h / Reflux
2.2: 0.83 h / -5 °C
With thionyl chloride; palladium 10% on activated carbon; hydrogen; N,N-dimethyl-formamide; In ethyl acetate;
Multi-step reaction with 3 steps
1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 48 h / 23 °C
2: thionyl chloride; N,N-dimethyl-formamide / 2 h / 23 °C / Inert atmosphere
3: aluminum (III) chloride / dichloromethane / 0.17 h / 0 °C / Inert atmosphere
With aluminum (III) chloride; thionyl chloride; palladium 10% on activated carbon; hydrogen; N,N-dimethyl-formamide; In dichloromethane; ethyl acetate;
Multi-step reaction with 2 steps
1: palladium 10% on activated carbon; hydrogen / 760.05 Torr
2: phosphorus pentoxide; methanesulfonic acid / dichloromethane / 19 h / 20 °C
With methanesulfonic acid; phosphorus pentoxide; palladium 10% on activated carbon; hydrogen; In dichloromethane;
2,5-dimethoxycinnamic acid
10538-51-9

2,5-dimethoxycinnamic acid

3-(2,5-dimethoxyphenyl)propanoic acid
10538-49-5

3-(2,5-dimethoxyphenyl)propanoic acid

Conditions
Conditions Yield
With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 23 ℃; for 48h;
99%
With palladium 10% on activated carbon; hydrogen; In ethyl acetate; under 2068.65 Torr;
98%
With hydrogen;
95%
With borane-ammonia complex; In methanol; water; at 20 ℃; for 90h; Time; chemoselective reaction; Catalytic behavior;
95%
With potassium hydroxide; bei der elektrolytischen Reduktion;
With palladium 10% on activated carbon; hydrogen; under 760.051 Torr;

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