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SODIUM 2-(4-METHOXYPHENOXY)PROPIONATE, also known as Lactisole, is a taste modulator derived from the sodium salt of racemic 2(4 methoxyphenoxy) propionic acid. It is found in coffee beans and has the ability to inhibit the perception of sweetness in humans, while not affecting the taste in rats. Lactisole is a potent inhibitor of the sweetness of sucrose and other sweeteners, and it has been affirmed as a GRAS (Generally Recognized As Safe) flavor by FEMA (Flavor and Extract Manufacturers Association) with the number 3773.

13794-15-5

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13794-15-5 Usage

Uses

Used in Food Industry:
SODIUM 2-(4-METHOXYPHENOXY)PROPIONATE is used as a taste modulator for reducing the perception of sweetness in various food products. This application helps in creating a more balanced taste profile and allows for the reduction of sugar content in products without compromising on taste.
Used in Pharmaceutical Industry:
SODIUM 2-(4-METHOXYPHENOXY)PROPIONATE is used as a research tool for studying the mechanisms of taste perception, particularly the sweet taste receptors. This application aids in the development of new drugs and therapies targeting taste-related disorders and conditions.
Used in Flavor and Fragrance Industry:
SODIUM 2-(4-METHOXYPHENOXY)PROPIONATE is used as a flavor enhancer to modify and improve the taste of various products in the flavor and fragrance industry. This application helps in creating unique and appealing taste experiences for consumers.
Used in Research and Development:
SODIUM 2-(4-METHOXYPHENOXY)PROPIONATE is used as a research compound for studying the effects of taste modulation on human perception and behavior. This application contributes to the understanding of taste biology and the development of new taste-related products and technologies.

Biochem/physiol Actions

As a taste modulator, the sodium salt inhibits the perception of sweetness in humans, but not in rats.

Check Digit Verification of cas no

The CAS Registry Mumber 13794-15-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,7,9 and 4 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 13794-15:
(7*1)+(6*3)+(5*7)+(4*9)+(3*4)+(2*1)+(1*5)=115
115 % 10 = 5
So 13794-15-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H12O4.Na/c1-7(10(11)12)14-9-5-3-8(13-2)4-6-9;/h3-7H,1-2H3,(H,11,12);/q;+1/p-1

13794-15-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name (±)-2-(p-Methoxyphenoxy)propionic acid

1.2 Other means of identification

Product number -
Other names SODIUM 2-(4-METHOXYPHENOXY)PROPIONATE

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:13794-15-5 SDS

13794-15-5Synthetic route

ethyl 2-(4-methoxyphenoxy)propanoate
111479-08-4, 958238-90-9

ethyl 2-(4-methoxyphenoxy)propanoate

2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water at 0℃; for 4h;99%
Stage #1: ethyl 2-(4-methoxyphenoxy)propanoate With water; potassium hydroxide In ethanol for 0.75h; Reflux;
Stage #2: With hydrogenchloride In water
92%
Stage #1: ethyl 2-(4-methoxyphenoxy)propanoate With sodium hydroxide In methanol; water at 20℃; for 12h;
Stage #2: With hydrogenchloride In water
89%
4-methoxy-phenol
150-76-5

4-methoxy-phenol

2-Bromopropionic acid
598-72-1

2-Bromopropionic acid

2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 80℃; for 24h;81%
With sodium hydroxide for 1h; Heating;77%
With sodium hydroxide
2-chloro-propionic acid methyl ester
17639-93-9

2-chloro-propionic acid methyl ester

4-methoxy-phenol
150-76-5

4-methoxy-phenol

2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

Conditions
ConditionsYield
With sodium hydroxide79%
With water; potassium iodide; sodium hydroxide at 60 - 90℃; for 12h; Reagent/catalyst; Temperature; Large scale;14.28 kg
2-(4-Methoxyphenoxy)propionsaeuremethylester
69033-92-7

2-(4-Methoxyphenoxy)propionsaeuremethylester

2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

Conditions
ConditionsYield
With water; lithium hydroxide In tetrahydrofuran
(±)-2-(p-methoxyphenoxy)propionic acid sodium salt

(±)-2-(p-methoxyphenoxy)propionic acid sodium salt

2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

Conditions
ConditionsYield
With phosphoric acid82%
4-methoxy-phenol
150-76-5

4-methoxy-phenol

2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 88 percent / sodium hydride / tetrahydrofuran / 14 h / 20 °C
2: 99 percent / potassium hydroxide / ethanol; H2O / 4 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: NaH / hexamethylphosphoric acid triamide; tetrahydrofuran / 60 °C
2: 82 percent / 85percent H3PO4
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C / Inert atmosphere
2: water; sodium hydroxide / tetrahydrofuran / 3 h / 80 °C / Inert atmosphere
View Scheme
4-methoxy-phenol
150-76-5

4-methoxy-phenol

(R,S)-2-chloropropionic acid
598-78-7

(R,S)-2-chloropropionic acid

2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

Conditions
ConditionsYield
With sodium hydroxide In water for 20h; Heating;
4-methoxy-phenol
150-76-5

4-methoxy-phenol

tetraethylene glycol ditoluene-p-sulphonate or tetraethylene glycol dimethanesulphonate

tetraethylene glycol ditoluene-p-sulphonate or tetraethylene glycol dimethanesulphonate

2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / acetone / 10 h / Heating
2: 10 percent sodium hydroxide / H2O / Heating
View Scheme
4-methoxy-phenol
150-76-5

4-methoxy-phenol

Ethyl 2-bromopropionate
535-11-5, 41978-69-2

Ethyl 2-bromopropionate

2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

2-(4'-methoxyphenoxy)propanoic acid chloride
92818-05-8

2-(4'-methoxyphenoxy)propanoic acid chloride

Conditions
ConditionsYield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 6h; Inert atmosphere;99%
With thionyl chloride In N,N-dimethyl-formamide for 1h; Heating;69%
With thionyl chloride at 90℃; for 1.5h;
With oxalyl dichloride; N-methyl-N-phenylformamide In dichloromethane at 20℃; for 5h;
With thionyl chloride at 74℃; for 2h; Inert atmosphere;
2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

5-amino-2-(pyridin-4-yl)-1,3-benzoxazole
349609-85-4

5-amino-2-(pyridin-4-yl)-1,3-benzoxazole

2-(4-methoxyphenoxy)-N-(2-(pyridine-4-yl)benzo[d]oxazol-5-yl)propanamide
1434516-80-9

2-(4-methoxyphenoxy)-N-(2-(pyridine-4-yl)benzo[d]oxazol-5-yl)propanamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 12h; Inert atmosphere;73%
2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

A

carbon monoxide
201230-82-2

carbon monoxide

B

acetaldehyde
75-07-0

acetaldehyde

C

4-methoxy-phenol
150-76-5

4-methoxy-phenol

Conditions
ConditionsYield
at 326.85℃; Kinetics;
2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

butan-1-ol
71-36-3

butan-1-ol

(R)-2-(4-Methoxy-phenoxy)-propionic acid butyl ester

(R)-2-(4-Methoxy-phenoxy)-propionic acid butyl ester

Conditions
ConditionsYield
With L-alanin; Candida rugosa lipase In di-isopropyl ether at 37℃; for 59h;
2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

2-(4-methoxyphenoxy)acetic acid
1877-75-4

2-(4-methoxyphenoxy)acetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 17 percent / 2,6-lutidine; LiClO4 / acetonitrile / Electrochemical reaction
2: 65 percent / aq. NaOH / 16 h / 80 °C
View Scheme
2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

α-(4-methoxyphenoxy)-2-methylpropionic acid
17509-54-5

α-(4-methoxyphenoxy)-2-methylpropionic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 17 percent / 2,6-lutidine; LiClO4 / acetonitrile / Electrochemical reaction
2: 70 percent / NaOH; H2O / acetone / 18 h / 20 °C
View Scheme
2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

3,3-dimethyl-1,4-dioxospiro[4.5]deca-6,9-diene-2,8-dione
65110-04-5

3,3-dimethyl-1,4-dioxospiro[4.5]deca-6,9-diene-2,8-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 17 percent / 2,6-lutidine; LiClO4 / acetonitrile / Electrochemical reaction
2: 70 percent / NaOH; H2O / acetone / 18 h / 20 °C
3: 24 percent Chromat. / LiClO4 / acetonitrile / Electrochemical reaction
View Scheme
Multi-step reaction with 3 steps
1: 17 percent / 2,6-lutidine; LiClO4 / acetonitrile / Electrochemical reaction
2: 70 percent / NaOH; H2O / acetone / 18 h / 20 °C
3: 61 percent / pyridine; LiClO4 / acetonitrile; H2O / Electrochemical reaction
View Scheme
2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

4-methoxy-phenol
150-76-5

4-methoxy-phenol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 17 percent / 2,6-lutidine; LiClO4 / acetonitrile / Electrochemical reaction
2: 65 percent / aq. NaOH / 16 h / 80 °C
3: 23 percent / 2,6-lutidine; LiClO4 / acetonitrile / Electrochemical reaction
View Scheme
2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

A

p-benzoquinone
106-51-4

p-benzoquinone

B

2-butenyl cobaloxime complex

2-butenyl cobaloxime complex

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 17 percent / 2,6-lutidine; LiClO4 / acetonitrile / Electrochemical reaction
2: 65 percent / aq. NaOH / 16 h / 80 °C
3: 12 percent / 2,6-lutidine; LiClO4 / acetonitrile / Electrochemical reaction
View Scheme
Multi-step reaction with 3 steps
1: 17 percent / 2,6-lutidine; LiClO4 / acetonitrile / Electrochemical reaction
2: 70 percent / NaOH; H2O / acetone / 18 h / 20 °C
3: 7 percent Chromat. / LiClO4 / acetonitrile / Electrochemical reaction
View Scheme
2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

ethyl 2-(4-methoxyphenoxy)propanoate
111479-08-4, 958238-90-9

ethyl 2-(4-methoxyphenoxy)propanoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 17 percent / 2,6-lutidine; LiClO4 / acetonitrile / Electrochemical reaction
2: 65 percent / aq. NaOH / 16 h / 80 °C
3: 23 percent / 2,6-lutidine; LiClO4 / acetonitrile / Electrochemical reaction
4: KI; K2CO3 / acetone / 22 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 17 percent / 2,6-lutidine; LiClO4 / acetonitrile / Electrochemical reaction
2: KI; K2CO3 / acetone / 22 h / Heating
View Scheme
2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

4'-methyl-2,6-di-tert-butylphenyl 2-(4
92817-70-4

4'-methyl-2,6-di-tert-butylphenyl 2-(4"methoxyphenoxy)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 69 percent / SOCl2 / dimethylformamide / 1 h / Heating
2: 45 percent / 1.5 M n-BuLi / tetrahydrofuran; hexane / -78 °C
View Scheme
2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

4'-methyl-2',6'-di-tert-butylphenyl (2RS,3SR)-3-hydroxy-2-methyl-2-(4
92817-81-7

4'-methyl-2',6'-di-tert-butylphenyl (2RS,3SR)-3-hydroxy-2-methyl-2-(4"-methoxyphenoxy)-3-benzenepropanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 69 percent / SOCl2 / dimethylformamide / 1 h / Heating
2: 45 percent / 1.5 M n-BuLi / tetrahydrofuran; hexane / -78 °C
3: LDA / tetrahydrofuran / 0.5 h / -78 °C
View Scheme
2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

4'-methyl-2',6'-di-tert-butylphenyl (2RS,3SR)-2,4-dimethyl-3-hydroxy-2-(4
92817-80-6

4'-methyl-2',6'-di-tert-butylphenyl (2RS,3SR)-2,4-dimethyl-3-hydroxy-2-(4"-methoxyphenoxy)hexanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 69 percent / SOCl2 / dimethylformamide / 1 h / Heating
2: 45 percent / 1.5 M n-BuLi / tetrahydrofuran; hexane / -78 °C
3: LDA / tetrahydrofuran / 0.5 h / -78 °C
View Scheme
2-(4-methoxyphenoxy)propanoic acid
13794-15-5

2-(4-methoxyphenoxy)propanoic acid

4'-methyl-2',6'-di-tert-butylphenyl (2RS,3RS)-2,4-dimethyl-3-hydroxy-2-(4
92817-79-3

4'-methyl-2',6'-di-tert-butylphenyl (2RS,3RS)-2,4-dimethyl-3-hydroxy-2-(4"-methoxyphenoxy)hexanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 69 percent / SOCl2 / dimethylformamide / 1 h / Heating
2: 45 percent / 1.5 M n-BuLi / tetrahydrofuran; hexane / -78 °C
3: LDA / tetrahydrofuran / 0.5 h / -78 °C
View Scheme

13794-15-5Relevant articles and documents

Access to Optically Enriched α-Aryloxycarboxylic Esters via Carbene-Catalyzed Dynamic Kinetic Resolution and Transesterification

Liu, Bin,Song, Runjiang,Xu, Jun,Majhi, Pankaj Kumar,Yang, Xing,Yang, Song,Jin, Zhichao,Chi, Yonggui Robin

supporting information, p. 3335 - 3338 (2020/04/30)

Optically active α-aryloxycarboxylic acids and their derivatives are important functional molecules. Disclosed here is a carbene-catalyzed dynamic kinetic resolution and transesterification reaction for access to this class of molecules with up to 99% yields and 99:1 er values. Addition of a chiral carbene catalyst to the ester substrate leads to two diastereomeric azolium ester intermediates that can quickly epimerize to each other and thus allows for effective dynamic kinetic resolution to be realized. The optically enriched ester products from our reaction can be quickly transformed to chiral herbicides and other bioactive molecules.

Alkali-sensitive ring opening cucurbituril and application thereof

-

Paragraph 0017; 0018, (2018/08/04)

The invention discloses alkali-sensitive ring opening cucurbituril. A structural formula of the alkali-sensitive ring opening cucurbituril is shown. The alkali-sensitive ring opening cucurbituril hasthe advantages that the alkali-sensitive ring opening cucurbituril can be used as a supermolecular medicine carrier and is provided with large ring cryptand with inner cavities, the ring rigidity of large rings can be reduced by means of ring opening, and accordingly the alkali-sensitive ring opening cucurbituril is extremely high in host-guest bonding capacity; the alkali-sensitive ring opening cucurbituril is excellent in alkali sensitivity, contains carboxylic acid groups and can be used as the medicine carrier to be widely applied to medicine delivery paths, and the water solubility and the stability of insoluble medicines can be greatly improved; the alkali-sensitive ring opening cucurbituril can be used as an alkali-sensitive carrier, medicines can be released in alkaline environments such as small intestines in human bodies, accordingly, effects of releasing the medicines in a sustained and controlled manner can be realized, and irritation of the medicines on gastric mucosas canbe prevented.

Highly Enantioselective Hydrogenation of Amides via Dynamic Kinetic Resolution Under Low Pressure and Room Temperature

Rasu, Loorthuraja,John, Jeremy M.,Stephenson, Elanna,Endean, Riley,Kalapugama, Suneth,Clément, Roxanne,Bergens, Steven H.

supporting information, p. 3065 - 3071 (2017/03/11)

High-throughput screening and lab-scale optimization were combined to develop the catalytic system trans-RuCl2((S,S)-skewphos)((R,R)-dpen), 2-PrONa, and 2-PrOH. This system hydrogenates functionalized α-phenoxy and related amides at room temperature under 4 atm H2 pressure to give chiral alcohols with up to 99% yield and in greater than 99% enantiomeric excess via dynamic kinetic resolution.

A 2 - (4-methoxyphenoxy) process for industrial production of sodium propionate

-

Paragraph 0029; 0030, (2016/10/07)

The invention relates to the technical field of a preparation method of a compound, and especially relates to an industrial production method of a sweetness inhibitor 2-(4-methoxyphenoxy)sodium propionate. The method comprises the following steps: taking methoxyphenol and methyl 2-chloropropionate as raw materials, under the effect of sodium hydroxide and a catalyst, taking water as a solvent, reacting for 6-24 hours at the temperature of 60-90 DEG C to obtain the product 2-(4-methoxyphenoxy)propionic acid; placing the 2-(4-methoxyphenoxy)propionic acid and sodium hydroxide in ethanol, heating, and reacting to obtain 2-(4-methoxyphenoxy)sodium propionate. According to the invention, water is taken as a solvent, the impurity in the generated product can be effectively removed, the synthesis and purification treatment processes are simple, the purity of the product is high, and the industrial production method is suitable for industrial production of 2-(4-methoxyphenoxy)sodium propionate.

Optimization of benzoxazole-based inhibitors of Cryptosporidium parvum inosine 5′-monophosphate dehydrogenase

Gorla, Suresh Kumar,Kavitha, Mandapati,Zhang, Minjia,Chin, James En Wai,Liu, Xiaoping,Striepen, Boris,Makowska-Grzyska, Magdalena,Kim, Youngchang,Joachimiak, Andrzej,Hedstrom, Lizbeth,Cuny, Gregory D.

, p. 4028 - 4043 (2013/06/27)

Cryptosporidium parvum is an enteric protozoan parasite that has emerged as a major cause of diarrhea, malnutrition, and gastroenteritis and poses a potential bioterrorism threat. C. parvum synthesizes guanine nucleotides from host adenosine in a streamlined pathway that relies on inosine 5′-monophosphate dehydrogenase (IMPDH). We have previously identified several parasite-selective C. parvum IMPDH (CpIMPDH) inhibitors by high-throughput screening. In this paper, we report the structure-activity relationship (SAR) for a series of benzoxazole derivatives with many compounds demonstrating CpIMPDH IC50 values in the nanomolar range and >500-fold selectivity over human IMPDH (hIMPDH). Unlike previously reported CpIMPDH inhibitors, these compounds are competitive inhibitors versus NAD +. The SAR study reveals that pyridine and other small heteroaromatic substituents are required at the 2-position of the benzoxazole for potent inhibitory activity. In addition, several other SAR conclusions are highlighted with regard to the benzoxazole and the amide portion of the inhibitor, including preferred stereochemistry. An X-ray crystal structure of a representative E·IMP·inhibitor complex is also presented. Overall, the secondary amine derivative 15a demonstrated excellent CpIMPDH inhibitory activity (IC 50 = 0.5 ± 0.1 nM) and moderate stability (t1/2 = 44 min) in mouse liver microsomes. Compound 73, the racemic version of 15a, also displayed superb antiparasitic activity in a Toxoplasma gondii strain that relies on CpIMPDH (EC50 = 20 ± 20 nM), and selectivity versus a wild-type T. gondii strain (200-fold). No toxicity was observed (LD 50 > 50 μM) against a panel of four mammalian cells lines.

Design, synthesis, and pharmacological effects of structurally simple ligands for MT1 and MT2 melatonin receptors

Carocci, Alessia,Catalano, Alessia,Lovece, Angelo,Lentini, Giovanni,Duranti, Andrea,Lucini, Valeria,Pannacci, Marilou,Scaglione, Francesco,Franchini, Carlo

experimental part, p. 6496 - 6511 (2010/10/02)

A series of phenoxyalkyl and phenylthioalkyl amides were prepared as melatoninergic ligands. Modulation of affinity of the newly synthesized compound by applying SARs around the terminal amide moiety, the alkyl chain, and the methoxy group on the aromatic ring provides compounds with nanomolar affinity for both melatonin receptor subtypes. Affinity towards MT1 and MT2 receptors were modulated also exploiting chirality. The investigation of intrinsic activity revealed that all the tested compounds behave as full or partial agonists.

A great improvement of the enantioselectivity of lipase-catalyzed hydrolysis and esterification using co-solvents as an additive

Nishigaki, Tomohiro,Yasufuku, Yoshitaka,Murakami, Sayuri,Ebara, Yasuhito,Ueji, Shin-Ichi

experimental part, p. 617 - 622 (2009/04/11)

Addition of co-solvents such as tetrahydrofuran resulted in a great improvement of the enantioselectivity of lipase-catalyzed hydrolysis of butyl 2-(4-substituted phenoxy)propanoates in an aqueous buffer solution. On the other hand, lipase lyophilized from an aqueous solution containing the co-solvents catalyzed highly enantioselective esterification of 2-(4-substituted phenoxy)propionic acids, 2-(4-isobutylphenyl)propionic acid (ibuprofen), and 2-(6-methoxy-2-naph-thyl)propionic acid (naproxen) in an organic solvent. An increase in the E value up to two orders of magnitude was observed for some substrates. The origin of the enantioselectivity enhancement caused by the co-solvent addition was mainly attributed to a significant deceleration in the initial reaction rate for the incorrectly binding enantiomer, as compared with that for the correctly binding enantiomer. From the results of FT-1R, CD, and ESR spectra, the co-solvent addition was also found to bring about a partial destruction of the tertiary structure of lipase.

Chlorination of 2-phenoxypropanoic acid with NCP in aqueous acetic acid: Using a novel ortho-para relationship and the para/meta ratio of substituent effects for mechanism elucidation

Segurado, Manuel A. P.,Reis, Joao Carlos R.,De Oliveira, Jaime D. Gomes,Kabilan, Senthamaraikannan,Shanthi, Manohar

, p. 5327 - 5336 (2008/02/07)

(Graph Presented) Rate constants were measured for the oxidative chlorodehydrogenation of (R,S)-2-phenoxypropanoic acid and nine ortho-, ten para- and five meta-substituted derivatives using (R,S)-1-chloro-3-methyl-2,6- diphenylpiperidin-4-one (NCP) as chlorinating agent. The kinetics was run in 50% (v/v) aqueous acetic acid acidified with perchloric acid under pseudo-first-order conditions with respect to NCP at temperature intervals of 5 K between 298 and 318 K, except at the highest temperature for the meta derivatives. The dependence of rate constants on temperature was analyzed in terms of the isokinetic relationship (IKR). For the 20 reactions studied at five different temperatures, tne isokinetic temperature was estimated to be 382 K, which suggests the preferential involvement of water molecules in the rate-determining step. The dependence of rate constants on meta and para substitution was analyzed using the tetralinear extension of the Hammett equation. The parameter λ for the para/meta ratio of polar substituent effects was estimated to be 0.926, and its electrostatic modeling suggests the formation of an activated complex bearing an electric charge near the oxygen atom belonging to the phenoxy group. A new approach is introduced for examining the effect of ortho substituents on reaction rates. Using IKR-determined values of activation enthalpies for a set of nine pairs of substrates with a given substituent, a linear correlation is found between activation enthalpies of ortho and para derivatives. The correlation is interpreted in terms of the selectivity of the reactant toward para- or ortho-monosubstituted substrates, the slope of which being related to the ortho effect. This slope is thought to be approximated by the ratio of polar substituent effects from ortho and para positions in benzene derivatives. Using the electrostatic theory of through-space interactions and a dipole length of 0.153 nm, this ratio was calculated at various positions of a charged reaction center along the benzene C1-C4 axis, being about 2.5 near the ring and decreasing steeply with increasing distance until reaching a minimum value of -0.565 at 1.3 nm beyond the aromatic ring. Activation enthalpies and entropies were estimated for substrates bearing the isoselective substituent in either ortho and para positions, being demonstrated that they are much different from the values for the parent substrate. The electrophilic attack on the phenolic oxygen atom by the protonated chlorinating agent is proposed as the rate-determining step, this step being followed by the fast rearrangement of the intermediate thus formed, leading to products containing chlorine in the aromatic ring.

TRIAZOLE, OXADIAZOLE AND THIADIAZOLE DERIVATIVE AS PPAR MODULATORS FOR THE TREATMENT OF DIABETES

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Page/Page column 82, (2008/06/13)

The present invention is directed to compounds represented by the following structural formula, Formula (I): wherein: (a) X is selected from the group consisting of a single bond, O, S, S(O)2 and N; (b) U is an aliphatic linker; (c) Y is selected from the group consisting of O, C, S, NH and a single bond; (d) W is N, O or S; (e) E is C(R3)(R4)A or A and wherein; (f) A is selected from the group consisting of carboxyl, tetrazole, C1-C6 alkylnitrile, carboxamide, sulfonamide and acylsufonamide. The other substituents are defined in the claims; the compounds are modulators of peroxisome proleferator activated receptors (PPARs) and are useful for the treatment of diabetes and other metabolic disorders.

Microbial deracemization of α-substituted carboxylic acids: Substrate specificity and mechanistic investigation

Kato, Dai-Ichiro,Mitsuda, Satoshi,Ohta, Hiromichi

, p. 7234 - 7242 (2007/10/03)

A new enzymatic method for the preparation of optically active α-substituted carboxylic acids is reported. This technique is called deracemization reaction, which provides us with a route to obtain the enantiomerically pure compounds, theoretically in 100% yield starting from the racemic mixture. This means that the synthesis of a racemate is almost equal to the synthesis of the optically active compound, and this concept is entirely different from the commonly accepted one in the asymmetric synthesis. Using the growing cell system of Nocardia diaphanozonaria JCM3208, racemates of 2-aryl- and 2-aryloxypropanoic acid are deracemized smoothly and (R)-form-enriched products are recovered in high chemical yield (>50%). In addition, using optically active starting compounds and deuterated derivatives as well as inhibitors, we have disclosed the fact that a new type of enzyme takes part in this biotransformation, and that the reaction proceeds probably via the same mechanism as that in rat liver.

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