6622-76-0

Basic information

• Product Name: Methyl tiglate
• Synonyms: TIGLIC ACID METHYL ESTER;METHYL E-2,3-DIMETHYLACRYLATE;METHYL-TRANS-2-METHYL-2-BUTENOATE;METHYL TIGLATE;(E)-2-Methyl-but-2-enoicacidmethylester;2-Butenoic acid, 2-methyl-, methyl ester, (E)-;2-Butenoicacid,2-methyl-,methylester,(2E)-;2-Carbomethoxy-2-butene, (E)-
• CAS NO: 6622-76-0
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.14
• EINECS: 229-575-8
• Product Categories: Aromatic Esters
• Mol File: 6622-76-0.mol

Chemical Properties

• Melting Point: 37.22°C (estimate)
• Boiling Point: 137-138 °C758 mm Hg(lit.)
• Flash Point: 95 °F
• Appearance: colourless liquid
• Density: 0.95 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.436(lit.)
• Storage Temp.: Flammables area
• Water Solubility: Soluble in alcohol, water 3813 mg/L @ 25°C (est).
• Stability: Stable. Flammable. Incompatible with strong oxidising agents.
• Merck: 14,9433
• BRN: 1720455
• CAS DataBase Reference: Methyl tiglate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl tiglate(6622-76-0)
• EPA Substance Registry System: Methyl tiglate(6622-76-0)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 2
• RTECS: EM9254600
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 6622-76-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Methyl tiglate is used as a reactant for the elaboration of conjugated alkenes, which are essential in the synthesis of various organic compounds. Its ability to insert into a vinylic C-H bond allows for the formation of new chemical bonds and the creation of complex molecular structures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, methyl tiglate may be utilized as a building block for the development of new drugs or drug candidates. Its role in the synthesis of conjugated alkenes can contribute to the discovery of novel therapeutic agents with unique properties and potential applications in medicine.
Used in Material Science:
Methyl tiglate can also be employed in material science for the development of advanced materials with specific properties. The synthesis of conjugated alkenes using methyl tiglate can lead to the creation of new polymers, coatings, or other materials with improved characteristics for various applications.

Synthesis Reference(s)

Journal of the American Chemical Society, 108, p. 3016, 1986 DOI: 10.1021/ja00271a034

InChI:InChI=1/C6H10O2/c1-4-5(2)6(7)8-3/h4H,1-3H3/b5-4+

Upstream product

• 186581-53-3 diazomethane 
• 80-62-6 methacrylic acid methyl ester 
• 91-22-5 quinoline 
• 815-75-8 3-chloro-2-methyl-butyric acid methyl ester 
• 82504-42-5 methyl (2-chloromethyl)butanoate 
• 67-56-1 methanol 
• 80-59-1 Tiglic acid 
• 6028-38-2 (E)-2-methyl-2-butenamide 
• 64-17-5 ethanol 
• 3586-58-1 2-methylenebutyric acid 
• 74-88-4 methyl iodide 
• 4111-08-4 2-hydroxy-2-methyl-butyronitrile 
• 15081-13-7 3-methyl-4,4-bis-methylsulfanyl-but-3-en-2-ol 
• 102710-80-5 3-Methanesulfonyloxy-2-methyl-butyric acid methyl ester 

Downstream Products

• 6028-38-2 (E)-2-methyl-2-butenamide 
• 57090-73-0 2,3-Dimethyl-4,4-diphenylbuttersaeuremethylester 
• 99865-15-3 2-(1-Phenylethyl)acrylic acid 
• 98066-39-8 1-Phenyl-1-allencarbonsaeure-methylester 
• 141956-92-5 3-(3,5-Dioxo-4-phenyl-[1,2,4]triazolidin-1-yl)-2-methylene-butyric acid methyl ester 
• 104286-59-1 4--2-methylbut-2-en-4-olide 
• 73213-61-3 methyl boninenalate 
• 23009-73-6 trans-1-chloro-2-methylbut-2-ene 
• 72450-34-1 methyl 2-hydroxy-2-methyl-3-oxobutanoate 
• 104286-63-7 4-(p-formylphenoxy)-2-methylbut-2-en-4-olide 
• 104286-61-5 methyl (Z)-4-(p-formylphenoxy)-2-methylbut-2-enoate 
• 104286-60-4 methyl (E)-4-(p-formylphenoxy)-2-methylbut-2-enoate 
• 126824-96-2 threo-2-methyl-3-(phenylthio)butanoic acid methyl ester 
• 126824-96-2 erythro-2-methyl-3-(phenylthio)butanoic acid methyl ester 

Relevant articles and documents

Lewis Acid Catalysis of the Ene Addition of Chloral and Bromal to Olefins; Stereochemical and Mechanistic Studies

The Lewis acid catalysed ene additions of chloral and bromal to alkenes are completely regiospecific, moderately regioselective, and often highly stereoselective.Diastereoselectivity in the addition to (-)-β-pinene was a function of the Lewis acid, and with TiCl4 essentially quantitative asymmetric induction was observed.The stereochemical phenomena are explained satisfactory by assuming the active enophiles possess transoid structures such as (1), that a concerted or rapid stepwise mechanism operates, and that product formation occurs predominantly through the least hindered encounter complex of the olefin and (1).In the case of 2-methylbut-2-ene, however, there is some evidence for an additional stereoelectronic contribution, the 'cis-effect'.Stereochemical assignements are supported by X-ray structural data.Ketones, hydrohalogenated ene adducts, or rearrangement products are formed (mainly in the addition to olefins of moderate reactivity) indicating the participation of Friedel-Crafts type dipolar intermediates.The ene adducts themselves could be formed via dipolar intermediates or in competing 'concerted' reactions; the stepwise mechanism must operate in some reactions because of the observation of Wagner-Meerwein rearrangements.Olefin reactivity over the series, measured by the competitive technique, towards chloral-AlCl3 showed a ca. 900-fold variation in rate; 'ene' reactivity decreases more steeply.

Synthesis and Biomimetic Rearrangement of a Chiral Diterpene Dioxide

As part of a biomimetic approach towards the marine triterpene teurilene (2), the synthesis of the chiral diepoxide 3 is described.Aiming at the synthesis of the squalene tetraepoxide 1, double Sharpless epoxidation led to the intermediate bisglycidic alcohol 7 being subject to a stereochemical analysis.

Gastric cytoprotective activity of 2-cyclopenten-1-one and related compounds

The cytoprotective activity of the isolated functional groups of several sesquiterpene lactones is reported. Among them the highest activity is shown by α-methylen-γ-butyrolactone and 2-cyclopenten-1-one. The activity shown by those Michael acceptors with a β carbon hindered by an alkyl substituent was always lower or almost null. A three-way mechanism of action is proposed: a) reduced glutathione synthesis, b) prostaglandin synthesis and c) mucosal glycoprotein synthesis.

Well-defined polymers from biosourced monomers: The case of 2-(methacryloyloxy)ethyl tiglate

Tiglic acid esters are naturally derived olefins of pleasant odor but incapable of undergoing free-radical polymerization due to the steric hindrances conferred by the β-methyl group. In an effort to incorporate these green olefins in well-defined (co)polymers, we first established that methyl tiglate, the simplest tiglic acid ester, could not be polymerized using controlled polymerization techniques either, and we then introduced it in a methacrylate monomer, 2-(methacryloyloxy)ethyl tiglate (MAET), which could smoothly undergo group transfer polymerization (GTP) to yield linear polymers of narrow molecular weight distributions. Subsequently, amphiphilic and double-hydrophobic block copolymers, as well as a star polymer of MAET were obtained by its sequential GTP with 2-(dimethylamino)ethyl methacrylate, methyl methacrylate, and ethylene glycol dimethacrylate, respectively. Finally, polyMAET was selectively oxidized.

Second-Generation meta-Phenolsulfonic Acid-Formaldehyde Resin as a Catalyst for Continuous-Flow Esterification

A second-generation m-phenolsulfonic acid-formaldehyde resin (PAFR II) catalyst was prepared by condensation polymerization of sodium m-phenolsulfonate and paraformaldehyde in an aqueous H2SO4 solution. This reusable, robust acid resin catalyst was improved in both catalytic activity and stability, maintaining the characteristics of the previous generation catalyst (p-phenolsulfonic acid-formaldehyde resin). PAFR II was applied in the batchwise and continuous-flow direct esterification without water removal and provided higher product yields in continuous-flow esterification than any other commercial ion-exchanged acid catalyst tested.

The acylated piperazine compound and use thereof

The present invention relates to acylated piperazine compound and its use, further relates to the pharmaceutical composition. The compound of the invention or the pharmaceutical composition can be used as dipeptidyl peptidase - IV (DPP - IV) inhibitors.

BIPOLAR TRANS CAROTENOID SALTS AND USES THEREOF

PROBLEM TO BE SOLVED: To provide compounds useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans. SOLUTION: There is provided a compound which has a structure represented by YZ-TCRO-ZY and is not trans sodium crocetinate [where, Y is a cation; Z is a polar group which is associated with the cation; and TCRO is trans carotenoid skeleton], and preferably, Y is a monovalent metal ion selected from the group consisting of Na+, K+ and Li+, or is an organic cation selected from the group consisting of R4 N+ and R3S+ [R is H, or CnH2n+1(n is 1 to 10)]. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT

Characterization of the Saffron Derivative Crocetin as an Inhibitor of Human Lactate Dehydrogenase 5 in the Antiglycolytic Approach against Cancer

Inhibition of lactate dehydrogenase (LDH) represents an innovative approach to tackle cancer because this peculiar glycolytic metabolism is characteristic of most invasive tumor cells. An investigation into the biological properties of saffron extracts led to the discover of their LDH-inhibition properties. In particular, the most important saffron components, crocetin, was found to inhibit LDH (IC50 = 54.9 ± 4.7 μM). This carotenoid was independently produced by chemical synthesis, and its LDH-inhibition properties manifested via its antiproliferative activity against two glycolytic cancer cell lines (A549 and HeLa, IC50 = 114.0 ± 8.0 and 113.0 ± 11.1 μM, respectively). The results described in this article suggest that saffron may be a helpful alimentary component in the prevention of cancer that potentially contributes to the efficacy of approved cancer therapies.

3-PHOSPHOGLYCERATE DEHYDROGENASE INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

BIPOLAR TRANS CAROTENOID SALTS AND THEIR USE

PROBLEM TO BE SOLVED: To provide trans carotenoid salt compounds useful for improving the diffusibility of oxygen between red blood cells and a body tissue in mammalian including human being, a method for producing them, a method for solubilizing them, and a method for using them. SOLUTION: There are provided compounds represented by the following formula, and are compounds not being trans sodium crocetinate: YZ-TCRO-ZY[Y denotes a cation; Z denotes a polar group coupled to the cation; TCRO denotes a trans carotenoid skeleton; preferably, as follows; Y denotes the monovalent metal ion of Na+,K+ or Li+ or R4 N+ or R3S+;R denotes H or CnH2n+1;n denotes the integer of 1 to 10;Z denotes a carboxyl group, a sulfuric acid group, a mono-phosphoric acid group, a di-phosphoric acid group, or a tri-phosphoric acid group; and TCRO denotes a group using isopronoid in which the single bond and double bond of straight chain carbon and carbon as exemplified by the following formula is repeated (X respectively independently denotes H, a straight chain/branched carbon chain substituted/non-substituted with 1 to 10C halogen or a halogen)]. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPO&INPIT