Category: ethers-buliding-blocks

A mechanistic study on the biosynthetic regulation of bioactive metabolite Antroquinonol from edible and medicinal mushroom Antrodia camphorata was written by Hu, Yong-Dan;Zhang, Bo-Bo;Xu, Gan-Rong;Liao, Xiang-Ru;Cheung, Peter C. K.. And the article was included in Journal of Functional Foods in 2016.Application of 605-94-7 This article mentions the following:

Antroquinonol, an important bioactive metabolite from the edible mushroom Antrodia camphorata, was difficult to be synthesized by conventional submerged fermentation The present study revealed the mechanisms related to the stimulatory effect of coenzyme Q₀, camphorwood leach liquor and soybean oil on the biosynthesis of antroquinonol. Addition of coenzyme Q₀ could up-regulate the expression of S-adenosylmethionine synthetase, affording Me group for the biosynthesis of antroquinonol. Heat shock proteins and tricarboxylic acid cycle related proteins were found to participate in the biosynthetic pathway. Camphorwood leach liquor could provide the precursor of antroquinonol by acting as donor of quinone nucleus. Soybean oil could increase the permeability of mycelial cell membrane and the extraction efficiency for the intracellular hydrophobic antroquinonol. This study advances our understanding on how stimulatory agents can be used to regulate the biosynthesis of valuable metabolites produced from mushroom mycelia and facilitate the development of submerged fermentation for potential industrial application. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Application of 605-94-7).

2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.Application of 605-94-7

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Coenzyme Q₀, a novel quinone derivative of Antrodia camphorata, induces ROS-mediated cytotoxic autophagy and apoptosis against human glioblastoma cells in vitro and in vivo was written by Yang, Hsin-Ling;Tsai, Chia-Hsuan;Shrestha, Sirjana;Lee, Chuan-Chen;Liao, Jiunn-Wang;Hseu, You-Cheng. And the article was included in Food and Chemical Toxicology in 2021.COA of Formula: C9H10O4 This article mentions the following:

Coenzyme Q₀ (CoQ₀, 2,3-dimethoxy-5-methyl-1,4-benzoquinone) derived from Antrodia camphorata exerts anticancer activities against breast, melanoma, and ovarian carcinoma. Glioblastoma multiforme is a common tumor affecting the central nervous system. This study explored anticancer properties of CoQ₀ on human glioblastoma both in vitro and in vivo, and explained the mol. mechanism behind it. CoQ₀ treatment retarded the growth and suppressed colony formation in glioblastoma (U87MG and GBM8401) cells. CoQ₀ induced apoptosis by activation of caspase-3, cleavage of PARP, and dysregulation of Bax and Bcl-2 in both cell lines. Annexin V/PI staining indicated CoQ₀ mediated necrosis and apoptosis. Interestingly, AVOs were increased trough induction of autophagy by CoQ₀, LC3-II accumulation, and p62/SQSTM1 expression, leading to death mechanism. Z-VAD-FMK has no effect on CoQ₀-induced autophagy but autophagy inhibition by 3-methyladenine (3-MA)/chloroquine (CQ) led to CoQ0-induced apoptosis. N-acetylcysteine (NAC) inhibited CoQ₀-mediated ROS production and diminished CoQ₀-induced apoptotic and autophagic cell death. Further, CoQ₀ inhibited PI3K/AKT/mTOR signaling pathways. CoQ₀ reduced the tumor burden in U87MG and GBM8401 xenografted athymic nude mice and significantly modulated tumor xenograft by inducing apoptosis and autophagy. CoQ₀ generated ROS-mediated apoptotic and autophagic cell death for effective glioblastoma treatment. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7COA of Formula: C9H10O4).

2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.COA of Formula: C9H10O4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

The synthesis of 1-haloalkyl-1,3,4,5-tetrahydro-2-benzoxepins was written by TenBrink, Ruth E.;McCall, John M.. And the article was included in Journal of Heterocyclic Chemistry in 1981.Category: ethers-buliding-blocks This article mentions the following:

Short, efficient routes to several 7,8-dimethoxy-1-haloalkyl-1,3,4,5-tetrahydro-2-benzoxepins were developed. These benzoxepins were prepared by the Lewis acid-catalyzed condensation of Cl(CH₂)₃CH(OEt)₂ or BrCH₂CH(OEt)₂ with 3,4-(MeO)₂C₆H₃(CH₂)₃OH. This condensation was facilitated by Me substitution on the propanol. In an alternate route, 3,4-(MeO)₂C₆H₃CH₂CH₂CO₂Et was acylated with ClCH₂CH₂COCl. The adduct was reduced with LiAlH₄. The resultant 3-[2-(3-chloro-1-hydroxypropyl)-4,5-dimethoxyphenyl]propanol was dehydrated to the corresponding tetrahydrobenzoxepin. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Category: ethers-buliding-blocks).

3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. But on the other hand, ethers undergo cleavage by reaction with acids. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.Category: ethers-buliding-blocks

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Quantitative structure activity relationship of inhibitors of glycolic acid oxidase was written by Singh, Pashupati Prasad;Kumar, Pragnesh;Marfatia, K.;Singh, Rajesh Kumar. And the article was included in Medicinal Chemistry: An Indian Journal in 2006.Electric Literature of C9H10O4 This article mentions the following:

In order to avoid trial and error method in selecting a suitable drug, QSAR methods have provided a rational basis to the design of enzyme inhibitors. 90 Derivatives of enzyme inhibitors, whose inhibitory potencies in term of PI₅₀ are reported, have been used as study material for QSAR study. These derivatives are divided into five groups: (1) substituted glycolic acids, (2) substituted oxyacetic acids, (3) substituted glyoxylic acids, (4) substituted-3-hydroxy-1H pyrrole-2,5-diones derivatives, (5) 4-heterocyclic substituted 3-hydroxy-1H-pyrrole-2,5-diones derivatives The QSAR study and MLR anal. have been collectively made, because the potency is reported in one unit and the target enzyme glycolic acid oxidase (GAO) is common to all. The study has been made with the help of seven descriptors in different combinations: (1) Heat of formation (ΔH_f), (2) HOMO energy (3) LUMO energy, (4) Absolute hardness (η) (5) Mol. weight (MW), (6) Electronegativity (χ) (7) Total energy (TE). This is perhaps for the first time when inhibitory potency has been related with quantum mech. parameters, without any significance to structure of compounds The values of descriptors have been obtained with the help of PC MODEL software using the semiempirical PM3 Hamiltonian. 32 Multi linear regression models using different combinations of descriptors have been developed using the project leader program associated with CAChe software. The predicted activity is close to the observed activity and the correlation coefficient is above 0.80. The best QSAR models are obtained by MLR anal. using the combinations, (i) heat of formation, mol. weight and electronegativity, (ii) mol. wight, total energy and electronegativity. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Electric Literature of C9H10O4).

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. But on the other hand, ethers undergo cleavage by reaction with acids. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).Electric Literature of C9H10O4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Complexation and structural studies of a sulfonamide aza-15-crown-5 derivative was written by Ioannidis, Marie;Gentleman, Alexander S.;Ho, Lam;Lincoln, Stephen F.;Sumby, Christopher J.. And the article was included in Inorganic Chemistry Communications in 2010.COA of Formula: C10H21NO4 This article mentions the following:

An aza-15-crown-5 derivative, N-[4-(phenyldiazo)benzenesulfonyl]-aza-15-crown-5, 1 was synthesized from com. available starting materials in 55% yield. Compound 1, which contains a sulfonamide link between the crown ether macroring and the azobenzene, readily binds alkali metals in buffered ethanol-water (75:25 volume/volume, pH 6.66). Titration data for both sodium and potassium were readily fitted to a 1:1 metal ion/ligand binding model to obtain stability constants (log K) of 4.7 ± 0.4 and 4.8 ± 0.2 dm³ mol^-1, resp. The authors also studied the structures of 1 and the sodium perchlorate salt of 1, [Na(1)(H₂O)]₂(ClO₄)₂, which were determined by x-ray crystallog. [Na(1)(H₂O)]₂(ClO₄)₂ is a dimer in the solid state whereby a sulfonamide oxygen atom from one of the [Na(1)(H₂O)] cations provides solvation of the adjacent macroring bound sodium cation. In the crystal structure, binding of a water mol. to the sodium cation is supported by hydrogen bonding to the sulfonamide oxygen, which represents a supramol. lariat ether-like interaction. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3COA of Formula: C10H21NO4).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil. Ethers feature bent C–O–C linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141 pm. The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.COA of Formula: C10H21NO4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthesis and cytotoxic activity of substituted hexahydro-2H-4,6-(epoxymethano)chromen-8(5H)-ones obtained from (-)-verbenone was written by Il’ina, I. V.;Pokrovsky, M. A.;Mikhalchenko, O. S.;Korchagina, D. V.;Volcho, K. P.;Pokrovsky, A. G.;Salakhutdinov, N. F.. And the article was included in Russian Chemical Bulletin in 2015.Application In Synthesis of 3-Hydroxy-5-methoxybenzaldehyde This article mentions the following:

A number of compounds with a substituted hexahydro-2H-4,6-(epoxymethano)chromen-8(5H)-one framework, I [R¹ = R⁴ = H, R² = H, OMe, R³ = OMe; R¹ = H, R² = R³ = R⁴ = OMe; R¹ = R² = R³ = OMe, R⁴ = H; R¹ = H, R² = R⁴ = OMe, R³ = OH; R¹ = R⁴ = H, R² = OH, R³ = OMe; R¹ = R⁴ = H, R² = OMe, R³ = OH], was synthesized starting from monoterpenoid (-)-verbenone and aromatic aldehydes containing methoxy and hydroxy groups. Cytotoxic activity of these compounds on human tumor cell lines was studied for the first time. Compounds containing three methoxy groups in each aromatic ring were found to be the most promising for further studies. In the experiment, the researchers used many compounds, for example, 3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8Application In Synthesis of 3-Hydroxy-5-methoxybenzaldehyde).

3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. Ethers feature bent C–O–C linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141 pm. The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.Application In Synthesis of 3-Hydroxy-5-methoxybenzaldehyde

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthesis of dialkyl acetals of N,N-dialkylaminoacetaldehydes was written by Kazaryan, L. Z.;Tagmazyan, K. Ts.;Vardanyan, Ts. Kh.. And the article was included in Armyanskii Khimicheskii Zhurnal in 1968.COA of Formula: C10H21NO3 This article mentions the following:

The tabulated RCH2CH(OR1)2 were prepared by stirring a mixture of 0.1 mole H2N(CH2)6NH2 and 0.1 mole of the bromoacetaldehyde dialkyl acetal in 30 ml. MeOH 18 hrs. at 50-60°, distilling MeOH, neutralizing the Et2O-extracted residue with dilute cold aqueous alkali, separating from it the oily layer, and removing Et2O from the combined dried oily layer and Et2O extract of the aqueous HCl-extracted Et2O extract (small amounts of the bis(dialkyl acetal) were also isolated by distillation) or by stirring 0.3 mole of the amine and 0.15 mole of the bromoacetaldehyde dialkyl acetal as 65-70° for 6 hrs. In the experiment, the researchers used many compounds, for example, 4-(2,2-Diethoxyethyl)morpholine (cas: 3616-59-9COA of Formula: C10H21NO3).

4-(2,2-Diethoxyethyl)morpholine (cas: 3616-59-9) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.COA of Formula: C10H21NO3

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Cp*Co(III)-Catalyzed Enantioselective Hydroarylation of Unactivated Terminal Alkenes via C-H Activation was written by Liu, Yan-Hua;Xie, Pei-Pei;Liu, Lei;Fan, Jun;Zhang, Zhuo-Zhuo;Hong, Xin;Shi, Bing-Feng. And the article was included in Journal of the American Chemical Society in 2021.COA of Formula: C8H9IO This article mentions the following:

Enantioselective hydroarylation of unactivated terminal alkenes RCH=CH₂ (R = n-hexyl, benzyl, cyclohexylmethyl, etc.) constitutes a prominent challenge in organic chem. Synthesis of Cp*Co(III)-catalyzed asym. hydroarylation of unactivated aliphatic terminal alkenes assisted by a new type of tailor-made amino acid ligands. Critical to the chiral induction was the engaging of a novel noncovalent interaction (NCI), which has seldomly been disclosed in C-H activation area, arising from the mol. recognition among the organocobalt(III) intermediate, the coordinated alkene and the well-designed chiral ligand. A broad range of C2 alkylated indoles were obtained in high yields and excellent enantioselectivities. DFT calculations revealed the reaction mechanism and elucidated the origins of chiral induction in the stereodetermining alkene insertion step. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2COA of Formula: C8H9IO).

4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.COA of Formula: C8H9IO

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Studies on the fat-soluble chemical constituents in stalk and leaf of fistular onion was written by Zhang, Geng;Zhou, Yinbo;Zhang, Changgong;Liu, Jingyou;Cheng, Lu. And the article was included in Zhongguo Yaoshi (Wuhan, China) in 2010.Category: ethers-buliding-blocks This article mentions the following:

The objective of this paper was to compare the difference of the chem. constituents between stalk and leaf of fistular onion. The stalk and leaf of fistular onion were extracted by supercritical CO₂ fluid resp., and then isolated by silica gel column chromatog. to obtain seven components with different polarities. Then four components of them were analyzed by GC-MS combined with computer database anal. The types of chem. constituents of stalk and leaf of fistular onion were basically similar, but there were more chem. materials in fistular onion stalk. The systematic research on the difference of the chem. constituents between stalk and leaf of fistular onion was significant for the development of them. In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3Category: ethers-buliding-blocks).

N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Category: ethers-buliding-blocks

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Encapsulation effect on the in vitro bioaccessibility of sacha inchi oil (Plukenetia volubilis L.) by soft capsules composed of gelatin and cactus mucilage biopolymers was written by Otalora, Maria Carolina;Camelo, Robinson;Wilches-Torres, Andrea;Cardenas-Chaparro, Agobardo;Castano, Jovanny A. Gomez. And the article was included in Polymers (Basel, Switzerland) in 2020.Application of 111-77-3 This article mentions the following:

Sacha inchi (Plukenetia volubilis L.) seed oil is a rich source of polyunsaturated fatty acids (PUFAs) that are beneficial for human health, whose nutritional efficacy is limited because of its low water solubility and labile bioaccessibility (compositional integrity). In this work, the encapsulation effect, using blended softgels of gelatin (G) and cactus mucilage (CM) biopolymers, on the PUFAs’ bioaccessibility of P. volubilis seed oil was evaluated during in vitro simulated digestive processes (mouth, gastric, and intestinal). Gas chromatog.-mass spectrometry (GC-MS) and gas chromatog. with a flame ionization detector (GC-FID) were used for determining the chem. composition of P. volubilis seed oil both before and after in vitro digestion. The most abundant compounds in the undigested samples were α-linolenic, linoleic, and oleic acids with 59.23, 33.46, and 0.57 (g/100 g), resp. The bioaccessibility of α-linolenic, linoleic, and oleic acid was found to be 1.70%, 1.46%, and 35.8%, resp., along with the presence of some oxidation products. G/CM soft capsules are capable of limiting the in vitro bioaccessibility of PUFAs because of the low mucilage ratio in their matrix, which influences the enzymic hydrolysis of gelatin, thus increasing the release of the polyunsaturated content during the simulated digestion. In the experiment, the researchers used many compounds, for example, 2-(2-Methoxyethoxy)ethanol (cas: 111-77-3Application of 111-77-3).

2-(2-Methoxyethoxy)ethanol (cas: 111-77-3) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. But on the other hand, ethers undergo cleavage by reaction with acids. Ethers feature bent C–O–C linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141 pm. The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.Application of 111-77-3

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem