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3,4,5-Trimethoxyphenylacetone, also known as Vanillin Acetate, is a phenylacetone derivative with a molecular formula of C12H16O4. It is a clear, colorless to yellowish liquid characterized by a sweet, floral odor. This chemical compound is widely recognized for its applications in the food industry, particularly as a flavoring agent in the production of vanilla flavoring, and has been studied for its potential antimicrobial and antioxidant properties. Furthermore, it plays a significant role in the synthesis of various pharmaceuticals and other organic compounds.

16603-18-2

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16603-18-2 Usage

Uses

Used in the Food Industry:
3,4,5-Trimethoxyphenylacetone is used as a flavoring agent for its sweet, floral odor, primarily in the production of vanilla flavoring. Its ability to mimic the aroma and taste of natural vanilla makes it a valuable ingredient in the creation of a wide range of food products.
Used in Pharmaceutical Synthesis:
3,4,5-Trimethoxyphenylacetone serves as a key intermediate in the synthesis of various pharmaceuticals and organic compounds. Its unique chemical structure allows it to be a versatile building block in the development of new drugs and medicinal agents.
Used in Antimicrobial Applications:
3,4,5-Trimethoxyphenylacetone has been studied for its potential antimicrobial properties. Its ability to inhibit the growth of certain microorganisms makes it a candidate for use in applications where controlling microbial contamination is essential, such as in food preservation or medical settings.
Used in Antioxidant Applications:
3,4,5-Trimethoxyphenylacetone has also been investigated for its antioxidant properties. Its capacity to neutralize free radicals and protect against oxidative stress could make it a valuable component in products designed to promote health and prevent cellular damage.

Check Digit Verification of cas no

The CAS Registry Mumber 16603-18-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,6,0 and 3 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 16603-18:
(7*1)+(6*6)+(5*6)+(4*0)+(3*3)+(2*1)+(1*8)=92
92 % 10 = 2
So 16603-18-2 is a valid CAS Registry Number.
InChI:InChI=1/C12H16O4/c1-8(13)5-9-6-10(14-2)12(16-4)11(7-9)15-3/h6-7H,5H2,1-4H3

16603-18-2 Well-known Company Product Price

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  • Alfa Aesar

  • (A19006)  3,4,5-Trimethoxyphenylacetone, 98%   

  • 16603-18-2

  • 5g

  • 778.0CNY

  • Detail
  • Alfa Aesar

  • (A19006)  3,4,5-Trimethoxyphenylacetone, 98%   

  • 16603-18-2

  • 25g

  • 3046.0CNY

  • Detail

16603-18-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(3,4,5-trimethoxyphenyl)propan-2-one

1.2 Other means of identification

Product number -
Other names 3,4,5-TRIMETHOXYPHENYLACETONE

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:16603-18-2 SDS

16603-18-2Relevant articles and documents

A convenient and efficient one-pot synthesis of arylacetones from (E)-3-aryl-2-methylacrylic acids by curtius rearrangement

He, Xin,Cao, Chong,Liang, Jingwei,Li, Xinyang,Zhang, Tingjian,Meng, Fanhao

, p. 386 - 390 (2017/02/10)

A convenient and efficient method was developed for the synthesis of arylacetones from (E)-3-aryl-2-methylacrylic acids through a Curtius rearrangement. The Curtius rearrangement of (E)-3-aryl-2-methylacryloyl azides and subsequent hydrolysis proceeded at mild temperatures in a two-phase medium of carbon tetrachloride and water containing a catalytic amount of tetrabutylammonium bromide to give the corresponding derivatives in 82-93% yield.

Iron-Mediated One-Pot Synthesis of 3,5-Diarylpyridines from β-Nitrostyrenes

Sathish, Manda,Chetna, Jadala,Hari Krishna, Namballa,Shankaraiah, Nagula,Alarifi, Abdullah,Kamal, Ahmed

, p. 2159 - 2165 (2016/03/15)

An operationally simple and mild one-pot protocol for the synthesis of a variety of 3,5-diarylpyridines from β-nitrostyrenes was achieved by using elemental iron. This reaction proceeds via reduction of the nitro group, resulting in in situ imine formation followed by trimolecular condensation with concomitant debenzylative aromatization. By employing this method, a series of symmetrical and unsymmetrical 3,5-diarylpyridines were synthesized with good to excellent yields. In addition, this method was also utilized for the synthesis of Sch-21418, an anti-inflammatory agent on gram scale.

Addressing challenges in palladium-catalyzed cross-couplings of aryl mesylates: Monoarylation of ketones and primary alkyl amines

Alsabeh, Pamela G.,Stradiotto, Mark

supporting information, p. 7242 - 7246 (2013/07/26)

Mor(DalPhos) for Me(sylates): Described are the first examples of ketone mono-α-arylation and primary aliphatic amine monoarylation employing aryl methanesulfonate coupling partners. A range of functionalized aryl mesylates were employed with dialkyl ketones, and also with primary and secondary amines as well as the otherwise challenging coupling partners acetone and methylamine. Ad=adamantyl. Copyright

Palladium-catalyzed mono-α-arylation of acetone with aryl imidazolylsulfonates

Ackermann, Lutz,Mehta, Vaibhav P.

supporting information; experimental part, p. 10230 - 10233 (2012/09/22)

Set the ace(tone): A palladium catalyst derived from the bidentate XantPhos ligand and Pd(OAc)2 has enabled broadly applicable mono-α-arylations of acetone to be performed with air- and moisture-stable aryl imidazolylsulfonates as most user-friendly electrophiles (see scheme). Copyright

Fe-HCl: An efficient reagent for deprotection of oximes as well as selective oxidative hydrolysis of nitroalkenes and nitroalkanes to ketones

Pradhan, Prasun K.,Dey, Sumit,Jaisankar, Parasuraman,Giri, Venkatachalam S.

, p. 913 - 922 (2007/10/03)

Fe-HCl mixture was found to selectively perform oxidative hydrolysis of the nitroalkenes 1a-j and nitroalkanes 2a-j to the ketones 3a-j. Also, the reagent was observed to deprotect the oximes 7a-j to carbonyl compounds 8a-j in excellent yields.

1,3-Diarylprop-2-en-1-ones, compositions containing them and use thereof

-

, (2008/06/13)

1,3-Diarylprop-2-en-1-ones and derivatives, compositions containing them, manufacturing process and use. Substituted 1,3-diarylprop-2-en-1-ones with therapeutic activity may be used in oncology.

2,4-Diaminothienopyrimidine Analogues of Trimetrexate and Piritrexim as Potential Inhibitors of Pneumocystis Carinii and Toxoplasma gondii Dihydrofolate Reductase

Rosowsky, Andre,Mota, Clara E.,Wright, Joel E.,Freisheim, James H.,Heusner, James J.,et al.

, p. 3103 - 3112 (2007/10/02)

A series of eight previously undescribed 2,4-diaminothienopyrimidine analogues of the potent dihydrofolate reductase (DHFR) inhibitors trimetrexate (TMQ) and piritrexim (PTX) were synthesized as potential drugs against Pneumocystis carinii and Toxoplasma gondii, which are major causes of severe opportunistic infections in AIDS patients. 2,4-Diamino-5-methyl-6-(aryl/aralkyl)thienopyrimidines with 3,4,5-trimethoxy or 2,5-dimethoxy substitution in the aryl/aralkyl moiety and 2,4-diamino-5-(aryl/aralkyl)thienopyrimidines with 2,5-dimethoxy substitution in the aryl/aralkyl moiety were obtained by reaction of the corresponding 2-amino-3-cyanothiophenes with chloroformamidine hydrochloride.The aryl group in the 5,6-disubstituted analogues was either attached directly to the hetero ring or was separated from it by one or two carbons, whereas the aryl group in the 5-monosubstituted analogues was separated from the hetero ring by two or three carbons. 2-Amino-3-cyano-5-methyl-6-(aryl/alkyl)thiophene intermediates for the preparation of the 5,6-disubstituted analogues were prepared from ω-aryl-2-alkylidenemalononitriles and sulfur in the presence of a secondary amine, and 2-amino-3-cyano-4-(aryl/aralkyl)thiophene intermediates for the preparation of the 5-monosubstituted analogues were obtained from ω-aryl-1-chloro-2-alkylidenemalononitriles and sodium hydrosulfide.Synthetic routes to the heterofore unknown ylidenemalononitriles, and the ketone precursors thereof, were developed.The final products were tested in vitro as inhibitors of DHFR from Pneumocystis carinii, Toxoplasma gondii, rat liver, beef liver, and Lactobacillus casei.A select number of previously known 2,4-diaminothienopyrimidines lacking the 3,4,5-trimethoxyphenyl and 2,5-dimethoxyphenyl substitution pattern of TMQ and PTX, respectively, were also tested for comparison.None of the compounds was as potent as TMQ or PTX, and while some of them showed some selectivity in their binding to Pneumocystis carinii and Toxoplasma gondii versus rat liver DHFR, this effect was not deemed large enough to warrant further preclinical evaluation.

Intramolecular Oxidative Coupling of Aromatic Compounds. V. para-para Diphenolic Oxidative Coupling as a Possible Route to the Eupodienone Skeleton

Carroll, Anthony R.,Krauss, Adrian S.,Taylor, Walter C.

, p. 277 - 292 (2007/10/02)

The synthesis of (2RS,3RS)-1,4-bis(4-hydroxy-3,5-dimethoxyphenyl)-2,3-dimethylbutan-1-one (9) is described.Diphenolic oxidative coupling of (9) gave the unstable dienone (24), which decomposed in methanol to give what is believed to be the acetal (26).Syn

Reduction of Ketene Dithioacetal S,S-Dioxides with Sodium Borohydride and Its Application to a Convenient Synthesis of Alkyl Arylmethyl Ketones

Ogura, Katsuyuki,Ohtsuki, Kazuo,Takahashi, Kazumasa,Iida, Hirotada

, p. 1597 - 1598 (2007/10/02)

The C-C double bond of a ketene dithioacetal S,S-dioxide was found to undergo reduction with sodium borohydride.This fact provides an efficient synthetic route from an aromatic aldehyde to an alkyl arylmethyl ketone using methylthiomethyl p-totyl sulfone.

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