Category: 37905-02-5

Regioselectivity and deuterium isotope effects in geraniol hydroxylation by the cytochrome P-450 monooxygenase from Catharanthus roseus (L.) G. Don was written by Fretz, Heinz;Woggon, Wolf Dietrich. And the article was included in Helvetica Chimica Acta in 1986.Computed Properties of C12H18O3 The following contents are mentioned in the article:

The hydroxylation of geraniol (I) by cytochrome P 450 from the subtropical plant C. roseus was optimized to give 8-hydroxygeraniol as the single product in 35% yield. Incubations of different ¹³C- and ²H-labeled geraniols revealed that H abstraction was completely regioselective in favor of the CH₃ group trans to the chain at C(6) of I. An intramol. deuterium isotope effect k_H/k_D of 8.0 was determined, suggesting that H abstraction is one of the major rate-contributing steps; however, the intramol. isotope effect was surprisingly inverse at low conversion, k_H/k_D = 0.50, indicating the existence of rate-contributing steps preceding the 1st irreversible, isotope-sensitive reaction in the sequence. This study involved multiple reactions and reactants, such as (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5Computed Properties of C12H18O3).

(2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5) belongs to esters. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Computed Properties of C12H18O3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Pharmacophore identification of ascofuranone, potent inhibitor of cyanide-insensitive alternative oxidase of Trypanosoma brucei was written by Saimoto, Hiroyuki;Kido, Yasutoshi;Haga, Yasushi;Sakamoto, Kimitoshi;Kita, Kiyoshi. And the article was included in Journal of Biochemistry in 2013.Formula: C12H18O3 The following contents are mentioned in the article:

Trypanosoma brucei is a parasite that causes human African trypanosomiasis (HAT). The parasites depend on the cyanide-insensitive trypanosome alternative oxidase (TAO) for their vital aerobic respiration. Ascofuranone (AF), a potent and specific sub-nanomolar inhibitor of the TAO quinol oxidase, is a potential novel drug with selectivity for HAT, because mammalian hosts lack the enzyme. To elucidate not only the inhibition mechanism but also the inhibitor-enzyme interaction, AF derivatives were designed and synthesized, and the structure-activity relationship was evaluated. Here the pharmacophore of AF that interacts with TAO was identified. The detailed inhibitory profiles indicated that the 1-formyl and 6-hydroxyl groups, which might contribute to intramol. hydrogen bonding and/or serve as hydrogen-bonding donors, were responsible for direct interaction with the enzyme. This study involved multiple reactions and reactants, such as (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5Formula: C12H18O3).

(2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5) belongs to esters. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.Formula: C12H18O3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

ω-Hydroxy isoprenoid bisphosphonates as linkable GGDPS inhibitors was written by Bhuiyan, Nazmul H.;Varney, Michelle L.;Bhattacharya, Deep S.;Payne, William M.;Mohs, Aaron M.;Holstein, Sarah A.;Wiemer, David F.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2019.Computed Properties of C12H18O3 The following contents are mentioned in the article:

The enzyme geranylgeranyl diphosphate synthase (GGDPS) is a potential therapeutic target for multiple myeloma. Malignant plasma cells produce and secrete large amounts of monoclonal protein, and inhibition of GGDPS results in disruption of protein geranylgeranylation which in turn impairs intracellular protein trafficking. Our previous work has demonstrated that some isoprenoid triazole bisphosphonates are potent and selective inhibitors of GGDPS. To explore the possibility of selective delivery of such compounds to plasma cells, new analogs with an ω-hydroxy group have been synthesized and examined for their enzymic and cellular activity. These studies demonstrate that incorporation of the ω-hydroxy group minimally impairs GGDPS inhibitory activity. Furthermore conjugation of one of the novel ω-hydroxy GGDPS inhibitors to hyaluronic acid resulted in enhanced cellular activity. These results will allow future studies to focus on the in vivo biodistribution of HA-conjugated GGDPS inhibitors. This study involved multiple reactions and reactants, such as (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5Computed Properties of C12H18O3).

(2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5) belongs to esters. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Computed Properties of C12H18O3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Chemical transformation of terpenoids. X. Ionophoretic activities of macrocyclic lactone epoxides synthesized from geraniol was written by Shibuya, Hirotaka;Ohashi, Kazuyoshi;Narita, Norihiko;Ishida, Toshimasa;Kitagawa, Isao. And the article was included in Chemical & Pharmaceutical Bulletin in 1994.Quality Control of (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate The following contents are mentioned in the article:

Two coronand-type 18-membered lactone epoxides, i.e., geranyl dimeric lactone diepoxide (GL₂E₂, I) and tetraepoxide (GL₂E₄, II), were synthesized from geraniol as diastereomeric mixtures Among them, II was shown to exhibit ion-transport activity for Ca²⁺ ion in the test using a W-07 (liquid-membrane type) apparatus and ion-permeation activities for Ca²⁺ and K⁺ ions across the human erythrocyte membrane. Isolation of six component diastereomers of II was effected by HPLC separation of two diastereomeric tetraepoxides, III and IV which were prepared from two diepoxides I. The relative stereostructures of these diastereomers were determined by a combination of X-ray diffraction and ¹H-NMR analyses. Among the six diastereomers, S₂-sym. V exhibited the strongest ion-transport activity for Ca²⁺ ion while C₂-sym. GL₂E₄-6 VI exhibited the strongest ion-permeation activity for Ca²⁺ ion across the human erythrocyte membrane. This study involved multiple reactions and reactants, such as (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5Quality Control of (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate).

(2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Quality Control of (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

An alternative route to cyclic terpenes by reductive cyclization in iridoid biosynthesis was written by Geu-Flores, Fernando;Sherden, Nathaniel H.;Courdavault, Vincent;Burlat, Vincent;Glenn, Weslee S.;Wu, Cen;Nims, Ezekiel;Cui, Yuehua;O’Connor, Sarah E.. And the article was included in Nature (London, United Kingdom) in 2012.Reference of 37905-02-5 The following contents are mentioned in the article:

The iridoids comprise a large family of distinctive bicyclic monoterpenes that possess a wide range of pharmacol. activities, including anticancer, anti-inflammatory, antifungal and antibacterial activities. Addnl., certain iridoids are used as sex pheromones in agriculturally important species of aphids, a fact that has underpinned innovative and integrated pest management strategies. To harness the biotechnol. potential of this natural product class, the enzymes involved in the biosynthetic pathway must be elucidated. Here we report the discovery of iridoid synthase, a plant-derived enzyme that generates the iridoid ring scaffold, as evidenced by biochem. assays, gene silencing, coexpression anal. and localization studies. In contrast to all known monoterpene cyclases, which use geranyl diphosphate as substrate and invoke a cationic intermediate, iridoid synthase uses the linear monoterpene 10-oxogeranial as substrate and probably couples an initial NAD(P)H-dependent reduction step with a subsequent cyclization step via a Diels-Alder cycloaddition or a Michael addition Our results illustrate how a short-chain reductase was recruited as cyclase for the production of iridoids in medicinal plants. Furthermore, we highlight the prospects of using unrelated reductases to generate artificial cyclic scaffolds. Beyond the recognition of an alternative biochem. mechanism for the biosynthesis of cyclic terpenes, we anticipate that our work will enable the large-scale heterologous production of iridoids in plants and microorganisms for agricultural and pharmaceutical applications. This study involved multiple reactions and reactants, such as (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5Reference of 37905-02-5).

(2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Reference of 37905-02-5

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Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Selective allylic hydroxylation of acyclic terpenoids by CYP154E1 from Thermobifida fusca YX was written by Bogazkaya, Anna M.;von Buehler, Clemens J.;Kriening, Sebastian;Busch, Alexandrine;Seifert, Alexander;Pleiss, Juergen;Laschat, Sabine;Urlacher, Vlada B.. And the article was included in Beilstein Journal of Organic Chemistry in 2014.Recommanded Product: (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate The following contents are mentioned in the article:

Allylic alcs. are valuable precursors in the synthesis of pharmaceutical intermediates, agrochems. and natural products. Regioselective oxidation of parental alkenes is a challenging task for chem. catalysts and requires several steps including protection and deprotection. Many cytochrome P 450 enzymes are known to catalyze selective allylic hydroxylation under mild conditions. Here, we describe CYP154E1 from Thermobifida fusca YX that enables this type of oxidation Several acyclic terpenoids were tested as possible substrates for CYP154E1, and the regio- and chemo-selectivity of their oxidation was investigated. Using a previously established bioinformatics approach we identified position 286 in the active site of CYP154E1 which is putatively involved in substrate binding and thereby might have an effect on enzyme selectivity. To tune regio- and chemo-selectivity of the enzyme three mutants at position 286 were constructed and used for substrate oxidation All formed products were analyzed with GC-MS and identified using chem. synthesized authentic samples and known compounds as references Best regioselectivity towards geraniol and nerol was observed with the wild type enzyme mainly leading to 8-hydroxy derivatives (8-hydroxygeraniol or 8-hydroxynerol) with high selectivity (100% and 96% resp.). Highest selectivities during the oxidation of geranylacetone and nerylacetone were observed with the following variants: V286F led mainly to 7-hydroxygeranylacetone (60% of the total product) and V286A produced predominantly 12-hydroxynerylacetone (75% of total product). Thus, CYP154E1 and its mutants expand the tool-box for allylic hydroxylation in synthetic chem. This study involved multiple reactions and reactants, such as (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5Recommanded Product: (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate).

(2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5) belongs to esters. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Recommanded Product: (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Preparation of domoic acid analogues using a bioconversion system, and their toxicity in mice was written by Maeno, Yukari;Kotaki, Yuichi;Terada, Ryuta;Hidaka, Masafumi;Cho, Yuko;Konoki, Keiichi;Yotsu-Yamashita, Mari. And the article was included in Organic & Biomolecular Chemistry in 2021.Recommanded Product: (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate The following contents are mentioned in the article:

Domoic acid (1, DA), a member of the natural kainoid family, is a potent agonist of ionotropic glutamate receptors in the central nervous system. The chem. synthesis of DA and its derivatives requires considerable effort to establish a pyrrolidine ring containing three contiguous stereocenters. Recently, a biosynthetic cyclase for DA, DabC, was identified. This enzyme cyclizes the linear precursor of isodomoic acid A (IA) to IA, a bioactive DA analog. In this study, we developed a bioconversion system to obtain DA analogs from linear substrates prepared by simple chem. synthesis using DabC expressed in Escherichia coli, in vivo. Three IA analogs with various substitutions at the C7′-geranyl terminus were prepared using this system: two minor natural analogs, 7′-methyl-IA (5) and 7′-hydroxy-IA (6), and one new unnatural analog, 7′-amide-IA (7). In addition, the toxicity of these DA analogs in mice was examined by intracerebroventricular injection. Most of the mice injected with 5 (3 nmol) and 6 (3 nmol) did not show any adverse symptoms, whereas the mice injected with 7 (3 nmol) showed typical symptoms induced by DA (1, 0.7 nmol) and IA (2, 3 nmol). These results suggest that the 7′-carbonyl group in the side chain of IA (2) is crucial for its toxicity. The docking studies of DA, IA (2), 5, 6, and 7 to GluK1 supported these results. This study involved multiple reactions and reactants, such as (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5Recommanded Product: (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate).

(2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Recommanded Product: (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Structure-Odor Relationship Study on Geraniol, Nerol, and Their Synthesized Oxygenated Derivatives was written by Elsharif, Shaimaa Awadain;Buettner, Andrea. And the article was included in Journal of Agricultural and Food Chemistry in 2018.Safety of (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate The following contents are mentioned in the article:

Despite being isomers having the same citrus-like, floral odor, geraniol, 1, and nerol, 3, show different odor thresholds. To date, no systematic studies are at hand elucidating the structural features required for their specific odor properties. Therefore, starting from these two basic structures and their corresponding esters, namely, geranyl acetate, 2, and neryl acetate, 4, a total of 12 oxygenated compounds were synthesized and characterized regarding retention indexes (RI), mass spectrometric (MS), and NMR (NMR) data. All compounds were individually tested for their odor qualities and odor thresholds in air (OT). Geraniol, the Z-isomer, with an OT of 14 ng/L, was found to be more potent than its E-isomer, nerol, which has an OT of 60 ng/L. However, 8-oxoneryl acetate was the most potent derivative within this study, exhibiting an OT of 8.8 ng/L, whereas 8-oxonerol was the least potent with an OT of 493 ng/L. Interestingly, the 8-oxo derivatives smell musty and fatty, whereas the 8-hydroxy derivatives show odor impressions similar to those of 1 and 3. 8-Carboxygeraniol was found to be odorless, whereas its E-isomer, 8-carboxynerol, showed fatty, waxy, and greasy impressions. Overall, we observed that oxygenation on C-8 affects mainly the odor quality, whereas the E/Z position of the functional group on C-1 affects the odor potency. This study involved multiple reactions and reactants, such as (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5Safety of (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate).

(2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Safety of (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthesis of Cembranoid Analogues through Ring-Closing Metathesis of Terpenoid Precursors: A Challenge Regarding Ring-Size Selectivity was written by Heidt, Tanja;Baro, Angelika;Koehn, Andreas;Laschat, Sabine. And the article was included in Chemistry – A European Journal in 2015.Formula: C12H18O3 The following contents are mentioned in the article:

A systematic study on ring-closing metathesis with Grubbs II catalyst to cembranoid macrocycles is described. Acyclic terpenoids I [X = OTBS, H, OH, etc.; R = Me, Et, iPr, etc., R¹ = H, Me, Et, etc.] with a functional group X in the homoallylic position relative to an RCM active terminus and substituents R, R¹ directly attached to the other terminal double bond were prepared from geraniol derived trienes and fragments that are based on bromoalkenes and di-Me malonate. Such terpenoids were suitable precursors, despite the presence of competing double bonds in their framework. The size of R and R¹ is crucial for successful macrocyclization. Whereas small alkyl substituents at the double bond directed the RCM towards six-membered ring formation, cross metathesis leading to dimers dominated for bulkier alkyl groups. A similar result was obtained for precursors without functional group X. In the case of unsym. substituted terpenoid precursor I [R = Et, R¹ = Me] with homoallylic OTBS or OMe group, the RCM could be controlled towards formation of macrocyclic cembranoids, which were isolated with excellent E-selectivity. The role of the substituents was further studied by quantum chem. calculations of simplified model substrates. Based on these results a mechanistic rationale is proposed. This study involved multiple reactions and reactants, such as (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5Formula: C12H18O3).

(2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Formula: C12H18O3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Multi-target-directed design, syntheses, and characterization of fluorescent bisphosphonate derivatives as multifunctional enzyme inhibitors in mevalonate pathway was written by Gao, Jinbo;Liu, Jinggong;Qiu, Yongge;Chu, Xiusheng;Qiao, Yuqin;Li, Ding. And the article was included in Biochimica et Biophysica Acta, General Subjects in 2013.Product Details of 37905-02-5 The following contents are mentioned in the article:

Mevalonate pathway is an important cellular metabolic pathway present in all higher eukaryotes and many bacteria. Four enzymes in mevalonate pathway, including MVK, PMK, MDD, and FPPS, play important regulatory roles in cholesterol biosynthesis and cell proliferation. The following methods were used: cloning, expression and purification of enzymes in mevalonate pathway, organic syntheses of multifunctional enzyme inhibitors, measurement of their IC₅₀ values for above four enzymes, kinetic studies of enzyme inhibitions, mol. modeling studies, cell viability tests, and fluorescence microscopy. We report our multi-target-directed design, syntheses, and characterization of two blue fluorescent bisphosphonate derivatives compounds 15 and 16 as multifunctional enzyme inhibitors in mevalonate pathway. These two compounds had good inhibition to all these four enzymes with their IC₅₀ values at nanomolar to micromolar range. Kinetic and mol. modeling studies showed that these two compounds could bind to the active sites of all these four enzymes. The fluorescence microscopy indicated that these two compounds could easily get into cancer cells. Multifunctional enzyme inhibitors are generally more effective than single enzyme inhibitors, with fewer side effects. Our results showed that these multifunctional inhibitors could become lead compounds for further development for the treatment of soft-tissue tumors and hypercholesteremia. This study involved multiple reactions and reactants, such as (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5Product Details of 37905-02-5).

(2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Product Details of 37905-02-5

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics