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(2E)-3-(5-methyl-2-furyl)acrylic acid, also known as 2E-3-(5-methyl-2-furanyl)acrylic acid, is an organic compound characterized by the molecular formula C8H8O3. It is a derivative of acrylic acid, featuring a furan ring substitution at the 2-position, with an additional methyl group at the 5-position of the furan ring. (2E)-3-(5-methyl-2-furyl)acrylic acid exhibits a yellowish appearance and is widely recognized for its unique properties, making it a versatile component in various industries, including pharmaceuticals, flavorings, fragrances, polymer manufacturing, and as a precursor for other organic compounds.

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  • 14779-25-0 Structure
  • Basic information

    1. Product Name: (2E)-3-(5-methyl-2-furyl)acrylic acid
    2. Synonyms: (2E)-3-(5-methyl-2-furyl)acrylic acid;2-Propenoic acid,3-(5-Methyl-2-furanyl)-
    3. CAS NO:14779-25-0
    4. Molecular Formula: C8H8O3
    5. Molecular Weight: 152.15
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 14779-25-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 262.6°C at 760 mmHg
    3. Flash Point: 112.6°C
    4. Appearance: /
    5. Density: 1.225g/cm3
    6. Vapor Pressure: 0.00546mmHg at 25°C
    7. Refractive Index: 1.571
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: (2E)-3-(5-methyl-2-furyl)acrylic acid(CAS DataBase Reference)
    11. NIST Chemistry Reference: (2E)-3-(5-methyl-2-furyl)acrylic acid(14779-25-0)
    12. EPA Substance Registry System: (2E)-3-(5-methyl-2-furyl)acrylic acid(14779-25-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 14779-25-0(Hazardous Substances Data)

14779-25-0 Usage

Uses

Used in Pharmaceutical Industry:
(2E)-3-(5-methyl-2-furyl)acrylic acid is utilized as an active pharmaceutical ingredient for the development of new drugs, leveraging its unique chemical structure to target specific biological pathways and treat various medical conditions.
Used in Flavoring and Fragrance Industry:
(2E)-3-(5-methyl-2-furyl)acrylic acid serves as a key component in the creation of flavorings and fragrances, adding distinct scents and tastes to a range of consumer products, from food and beverages to cosmetics and perfumes.
Used in Polymer Manufacturing:
(2E)-3-(5-methyl-2-furyl)acrylic acid is employed as a monomer in the synthesis of polymers, contributing to the development of materials with specific properties tailored for various applications, such as coatings, adhesives, and plastics.
Used as a Precursor in Organic Chemistry:
In the realm of organic chemistry, (2E)-3-(5-methyl-2-furyl)acrylic acid is used as a starting material for the preparation of other organic compounds, enabling the synthesis of a diverse array of molecules with potential applications in various fields.
Used in Chemical Industry for Synthesis:
(2E)-3-(5-methyl-2-furyl)acrylic acid is applied in the chemical industry for the synthesis of a variety of compounds, showcasing its versatility and importance in the creation of new chemical entities for different uses.

Check Digit Verification of cas no

The CAS Registry Mumber 14779-25-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,7,7 and 9 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 14779-25:
(7*1)+(6*4)+(5*7)+(4*7)+(3*9)+(2*2)+(1*5)=130
130 % 10 = 0
So 14779-25-0 is a valid CAS Registry Number.
InChI:InChI=1/C8H8O3/c1-6-2-3-7(11-6)4-5-8(9)10/h2-5H,1H3,(H,9,10)/b5-4+

14779-25-0SDS

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 (E)-3-(5-methylfuran-2-yl)prop-2-enoic acid

1.2 Other means of identification

Product number -
Other names (2E)-3-(5-methylfuran-2-yl)prop-2-enoic acid

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:14779-25-0 SDS

14779-25-0Relevant articles and documents

Process for the preparation of fatty acids

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Paragraph 0134-0141, (2020/09/04)

The invention discloses a method for preparing fatty acid. The method comprises the following steps: providing a first reactant which is a furan compound containing an carbonyl group; providing a second reactant which is a compound containing a carboxyl group, an ester group or an anhydride group and can participate in a condensation reaction with the carbonyl group of the first reactant; allowingthe first reactant and the second reactant to participate in a first condensation reaction, and allowing a C=O bond of the carbonyl group of the first reactant to be connected with alpha carbon of the carbonyl group of the second reactant and to be converted into a C=C bond so as to form a condensation product; and carrying out a second-step reaction under hydrogen pressure in the presence of a co-catalytic system of a hydrogenation catalyst and Lewis acid, opening a furan ring of the condensation product, carrying out hydrodeoxygenation at the same time, removing all oxygen except for oxygenin the carboxyl group, and allowing a carbon chain to be saturated so as to obtain the fatty acid.

Photocatalytic decarboxylative alkenylation of α-amino and α-hydroxy acid-derived redox active esters by NaI/PPh3 catalysis

Fu, Ming-Chen,Fu, Yao,Shang, Rui,Wang, Ya-Ting,Zhao, Bin

supporting information, p. 2495 - 2498 (2020/03/06)

Herein, we report the photocatalytic decarboxylative alkenylation reactions of N-(acyloxy)phthalimide derived from α-amino and α-hydroxy acids with 1,1-diarylethene, and with cinnamic acid derivatives through double decarboxylation, using sodium iodide and triphenylphosphine as redox catalysts. The reaction proceeds under mild irradiation conditions with visible blue light (440 nm or 456 nm) in an acetone solvent without recourse to transition-metal or organic dye based photoredox catalysts. The reaction proceeds via photoactivation of a transiently self-assembled chromophore from N-(acyloxy)phthalimide and NaI/PPh3. Solvation plays a crucial role in the reactivity.

Palladium(II)-Catalyzed Oxidative Decarboxylative [2 + 2 + 1] Annulation of Cinnamic Acids with Alkynes: Access to Polysubstituted Pentafulvenes

Peng, Shiyong,Chen, Nuan,Zhang, Hong,He, Min,Li, Hongguang,Lang, Ming,Wang, Jian

supporting information, p. 5589 - 5593 (2020/07/08)

An unprecedented palladium(II)-catalyzed oxidative decarboxylative [2 + 2 + 1] annulation of cinnamic acids with alkynes has been developed for the synthesis of polysubstituted pentafulvenes. Ag2CO3 and DMSO are essential for the reaction. This protocol features readily available starting materials, a wide substrate scope, and moderate to excellent yields. Moreover, various significant frameworks can be easily obtained from the late-stage transformations of pentafulvenes via oxidation, reduction, and Scholl-type reaction.

Synthesis of heteroleptic pentavalent antimonials bearing heterocyclic cinnamate moieties and their biological studies

Sarwar, Sidra,Iftikhar, Tuba,Rauf, Muhammad Khawar,Badshah, Amin,Waseem, Durdana,Tahir, Muhammad Nawaz,Khan, Khalid Mohammed,Khan, Gul Majid

, p. 12 - 19 (2018/02/23)

In the search of new drugs with high therapeutic efficacy, antimony (V) dicarboxylates bearing cinnamate moieties with general formula [SbR3(O2CR′)2] have been synthesized and characterized by spectroscopic techniques like FTIR, multinuclear (1H and 13C) NMR and single crystal X-ray diffraction. The organic moieties (R) in the complexes are phenyl and p-tolyl while the carboxylates are heterocyclic acrylates. In the crystal structure of [Sb(phenyl)3(O2CC2H2C4H3O)2] (1), [Sb(phenyl)3(O2CC2H2C4H3S)2] (3), [Sb(p-tolyl)3(O2CC2H2C4H3S)2] (5) and [Sb(p-tolyl)3(O2CC2H2C4H2O(CH3))2] (6), antimony was found to adopt a distorted trigonal bipyramidal geometry and was monomeric with phenyl or p-tolyl groups at equatorial and carboxylate ligands at axial positions. Furthermore, biological activities of carboxylates and their corresponding complexes were conducted including antileishmanial activity (against Leishmania tropica KWH23 parasite), anticancer (against HepG2 cell line), antibacterial (against Staphylococcus aureus, E. coli, P. aeruginosa and K. pneumoniae) and α-amylase inhibition potentials. Results show that compounds (4), (5) and (6) are significantly cytotoxic against cancer cells (median inhibitory concentration (IC50): 7.44, 4.61, 5.0 μg/mL respectively) and leishmania parasite (IC50: 1.75, 0.03 and 0.02 μg/mL respectively). Results of biological activities suggest these complexes as attractive therapeutic agents for further in vivo studies except α-amylase inhibition.

A METHOD FOR THE SITE-SPECIFIC ENZYMATIC LABELLING OF NUCLEIC ACIDS IN VITRO BY INCORPORATION OF UNNATURAL NUCLEOTIDES

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Paragraph 00176, (2015/02/25)

Provided herein are analogs of unnatural nucleotides bearing predominantly hydrophobic nucleobase analogs that form unnatural base pairs during DNA polymerase- mediated replication of DNA or RNA polymerase-mediated transcription of RNA. In this manner, the unnatural nucleobases can be introduced in a site-specific way into oligonucleotides (single or double stranded DNA or RNA), where they can provide for site-specific cleavage, or can provide a reactive linker than can undergo functionalization with a cargo -bearing reagent by means of reaction with a primary amino group or by means of click chemistry with an alkyne group of the unnatural nucleobase linker.

Natural-like replication of an unnatural base pair for the expansion of the genetic alphabet and biotechnology applications

Li, Lingjun,Degardin, Melissa,Lavergne, Thomas,Malyshev, Denis A.,Dhami, Kirandeep,Ordoukhanian, Phillip,Romesberg, Floyd E.

supporting information, p. 826 - 829 (2014/02/14)

We synthesized a panel of unnatural base pairs whose pairing depends on hydrophobic and packing forces and identify dTPT3-dNaM, which is PCR amplified with a natural base pair-like efficiency and fidelity. In addition, the dTPT3 scaffold is uniquely tolerant of attaching a propargyl amine linker, resulting in the dTPT3PA-dNaM pair, which is amplified only slightly less well. The identification of dTPT3 represents significant progress toward developing an unnatural base pair for the in vivo expansion of an organism's genetic alphabet and for a variety of in vitro biotechnology applications where it is used to site-specifically label amplified DNA, and it also demonstrates for the first time that hydrophobic and packing forces are sufficient to mediate natural-like replication.

Synthesis and sar study of diarylpentanoid analogues as new anti-inflammatory agents

Leong, Sze Wei,Mohd Faudzi, Siti Munirah,Abas, Faridah,Mohd Aluwi, Mohd Fadhlizil Fasihi,Rullah, Kamal,Wai, Lam Kok,Abdul Bahari, Mohd Nazri,Ahmad, Syahida,Tham, Chau Ling,Shaari, Khozirah,Lajis, Nordin H.

, p. 16058 - 16081 (2015/01/08)

A series of ninety-seven diarylpentanoid derivatives were synthesized and evaluated for their anti-inflammatory activity through NO suppression assay using interferone gamma (IFN-γ)/lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. Twelve compounds (9, 25, 28, 43, 63, 64, 81, 83, 84, 86, 88 and 97) exhibited greater or similar NO inhibitory activity in comparison with curcumin (14.7 ± 0.2 μM), notably compounds 88 and 97, which demonstrated the most significant NO suppression activity with IC50 values of 4.9 ± 0.3 μM and 9.6 ± 0.5 μM, respectively. A structure-activity relationship (SAR) study revealed that the presence of a hydroxyl group in both aromatic rings is critical for bioactivity of these molecules. With the exception of the polyphenolic derivatives, low electron density in ring-A and high electron density in ring-B are important for enhancing NO inhibition. Meanwhile, pharmacophore mapping showed that hydroxyl substituents at both meta- and para-positions of ring-B could be the marker for highly active diarylpentanoid derivatives.

Design, synthesis and in vitro antibacterial/antifungal evaluation of novel 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7(1-piperazinyl)quinoline-3-carboxylic acid derivatives

Yu, Zhiyi,Shi, Guanying,Sun, Qiu,Jin, Hong,Teng, Yun,Tao, Ke,Zhou, Guoping,Liu, Wei,Wen, Fang,Hou, Taiping

scheme or table, p. 4726 - 4733 (2010/01/06)

A series of 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7(1-piperazinyl)quinoline-3-carboxylic acid (norfloxacin) derivatives were prepared according to the principle of combinating bioactive substructures and tested for their activities against five plant pathogenic bacteria and three fungi in vitro. The preliminary bioassays indicated that almost all synthesized target compounds retained the antibacterial activities of norfloxacin and had some antifungal activities as carboxylic acid amide compounds. The activities of compounds 1 and 22 against Xanthomonas oryzae were better than norfloxacin and all tested compounds had better antibacterial activities as compared to the agricultural streptomycin sulfate (a commercial bactericide) against X. oryzae, Xanthomonas axonopodis and Erwinia aroideae. Additionally, compounds 2 and 20 displayed good antifungal activities against Rhizoctonia solani and their inhibition of growth reached 83% and 94% respectively at the concentration of 200 mg/L.

Esters of 17 α-ethynyl 19-nor-testosterone and 17 α-ethynyl-18-homo-19-nor-testosterone and pharmaceutical compositions containing the same

-

, (2008/06/13)

Esters of 17 α-ethynyl 19-nor-testosterone and 17 α-ethynyl-18-homo-19-nor-testosterone and the 3-oximes thereof having long-active contraceptive activity.

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