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Ethyl 3-hydroxyphenylacetate is a light yellow liquid that serves as a valuable synthetic intermediate in the development of innovative anti-inflammatory agents.

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  • 22446-38-4 Structure
  • Basic information

    1. Product Name: ethyl 3-hydroxyphenylacetate
    2. Synonyms: (3-Hydroxyphenyl)acetic acid ethyl ester;3-Hydroxyphenylacetic acid ethyl ester;3-Hydroxy-benzeneacetic Acid Ethyl Ester;Ethyl 2-(3-Hydroxyphenyl)acetate
    3. CAS NO:22446-38-4
    4. Molecular Formula: C10H12O3
    5. Molecular Weight: 180.2005
    6. EINECS: N/A
    7. Product Categories: Aromatics
    8. Mol File: 22446-38-4.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 179°C/12mmHg(lit.)
    3. Flash Point: 123.6 °C
    4. Appearance: /
    5. Density: 1.146 g/cm3
    6. Vapor Pressure: 0.00104mmHg at 25°C
    7. Refractive Index: 1.5220 to 1.5270
    8. Storage Temp.: Refrigerator
    9. Solubility: N/A
    10. PKA: 9.75±0.10(Predicted)
    11. Stability: Store in Freezer
    12. CAS DataBase Reference: ethyl 3-hydroxyphenylacetate(CAS DataBase Reference)
    13. NIST Chemistry Reference: ethyl 3-hydroxyphenylacetate(22446-38-4)
    14. EPA Substance Registry System: ethyl 3-hydroxyphenylacetate(22446-38-4)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 22446-38-4(Hazardous Substances Data)

22446-38-4 Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 3-hydroxyphenylacetate is utilized as a synthetic intermediate for the preparation of novel anti-inflammatory agents, contributing to the advancement of treatments targeting inflammation-related conditions.

Check Digit Verification of cas no

The CAS Registry Mumber 22446-38-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,4,4 and 6 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 22446-38:
(7*2)+(6*2)+(5*4)+(4*4)+(3*6)+(2*3)+(1*8)=94
94 % 10 = 4
So 22446-38-4 is a valid CAS Registry Number.
InChI:InChI=1/C10H12O3/c1-2-13-10(12)7-8-4-3-5-9(11)6-8/h3-6,11H,2,7H2,1H3

22446-38-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name ethyl 2-(3-hydroxyphenyl)acetate

1.2 Other means of identification

Product number -
Other names 3-hydroxyphenylacetic acid ethyl ester

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:22446-38-4 SDS

22446-38-4Relevant articles and documents

A new route for the synthesis of the repaglinide key intermediate 3-ethoxy-4-ethoxycarbonylphenylacetic acid

Zhang, Yue,Liu, Tingting,Niu, Zhaohuan,Fu, Yajing,Yang, Jixia,Song, Yongxing,Zhao, Shuchun

, p. 506 - 510 (2016)

A new method is described for manufacturing 3-ethoxy-4-ethoxycarbonylphenylacetic acid, which is a key intermediate of the antidiabetic drug repaglinide, starting from 3-hydroxyphenylacetic acid and involving esterification, formylation, oxidation, etherification and selective hydrolysis. The effect of reaction temperature, time, solvent and substrate ratios on the yield were studied in detail and the optimal conditions are presented in the paper. The new method makes the scale-up operation easier and the environmental problems are fewer. The impurities in the intermediate of the new route were also determined. Characterisation of the product and intermediates involved was achieved by FTIR, 1H NMR, 13C NMR, HRMS and DSC.

Discovery of 2-(3,5-difluoro-4-methylsulfonaminophenyl)propanamides as potent TRPV1 antagonists

Kim, Changhoon,Ann, Jihyae,Lee, Sunho,Sun, Wei,Blumberg, Peter M.,Frank-Foltyn, Robert,Bahrenberg, Gregor,Stockhausen, Hannelore,Christoph, Thomas,Lee, Jeewoo

, p. 2539 - 2542 (2018/06/07)

A series of A-region analogues of 2-(3-fluoro-4-methylsufonamidophenyl) propanamide 1 were investigated as TRPV1 antagonists. The analysis of structure-activity relationship indicated that a fluoro group at the 3- (or/and) 5-position and a methylsulfonamido group at the 4-position were optimal for antagonism of TRPV1 activation by capsaicin. The most potent antagonist 6 not only exhibited potent antagonism of activation of hTRPV1 by capsaicin, low pH and elevated temperature but also displayed highly potent antagonism of activation of rTRPV1 by capsaicin. Further studies demonstrated that antagonist 6 blocked the hypothermic effect of capsaicin in vivo, consistent with its in vitro mechanism, and it showed promising analgesic activity in the formalin animal model.

Phosphonate-based irreversible inhibitors of human γ-glutamyl transpeptidase (GGT). GGsTop is a non-toxic and highly selective inhibitor with critical electrostatic interaction with an active-site residue Lys562 for enhanced inhibitory activity

Kamiyama, Akane,Nakajima, Mado,Han, Liyou,Wada, Kei,Mizutani, Masaharu,Tabuchi, Yukiko,Kojima-Yuasa, Akiko,Matsui-Yuasa, Isao,Suzuki, Hideyuki,Fukuyama, Keiichi,Watanabe, Bunta,Hiratake, Jun

supporting information, p. 5340 - 5352 (2016/10/24)

γ-Glutamyl transpeptidase (GGT, EC 2.3.2.2) that catalyzes the hydrolysis and transpeptidation of glutathione and its S-conjugates is involved in a number of physiological and pathological processes through glutathione metabolism and is an attractive phar

1,2,3-Triazole-containing uracil derivatives with excellent pharmacokinetics as a novel class of potent human deoxyuridine triphosphatase inhibitors

Miyakoshi, Hitoshi,Miyahara, Seiji,Yokogawa, Tatsushi,Endoh, Kanji,Muto, Toshiharu,Yano, Wakako,Wakasa, Takeshi,Ueno, Hiroyuki,Chong, Khoon Tee,Taguchi, Junko,Nomura, Makoto,Takao, Yayoi,Fujioka, Akio,Hashimoto, Akihiro,Itou, Kenjirou,Yamamura, Keisuke,Shuto, Satoshi,Nagasawa, Hideko,Fukuoka, Masayoshi

supporting information; experimental part, p. 6427 - 6437 (2012/09/22)

Deoxyuridine triphosphatase (dUTPase) has emerged as a potential target for drug development as a 5-fluorouracil-based combination chemotherapy. We describe the design and synthesis of a novel class of human dUTPase inhibitors, 1,2,3-triazole-containing u

PURINE DERIVATIVES USEFUL AS HSP90 INHIBITORS

-

Page/Page column 127-128, (2011/04/26)

The present application provides substituted purine derivatives and related compounds of the formulas shown. These com ounds are useful as inhibitors of HSP90, and hence in the treatment of related diseases. (Formulae) Z1-Z3, Xa-Xc, X2, X4, Y and R are as defined in the specification.

Receptor activity and conformational analysis of 5′-halogenated resiniferatoxin analogs as TRPV1 ligands

Lim, Kwang Su,Kang, Dong Wook,Kim, Yong Soo,Kim, Myeong Seop,Park, Seul-Gi,Choi, Sun,Pearce, Larry V.,Blumberg, Peter M.,Lee, Jeewoo

scheme or table, p. 299 - 302 (2011/02/27)

A series of 5′-halogenated resiniferatoxin analogs have been investigated in order to examine the effect of halogenation in the A-region on their binding and the functional pattern of agonism/antagonism for rat TRPV1 heterologously expressed in Chinese hamster ovary cells. Halogenation at the 5-position in the A-region of RTX and of 4-amino RTX shifted the agonism of parent compounds toward antagonism. The extent of antagonism was greater as the size of the halogen increased (I > Br > Cl > F) while the binding affinities were similar, as previously observed for our potent agonists. In this series, 5-bromo-4-amino RTX (39) showed very potent antagonism with K i (ant) = 2.81 nM, which was thus 4.5-fold more potent than 5′-iodo RTX, previously reported as a potent TRPV1 antagonist. Molecular modeling analyses with selected agonists and the corresponding halogenated antagonists revealed a striking conformational difference. The 3-methoxy of the A-region in the agonists remained free to interact with the receptor whereas in the case of the antagonists, the compounds assumed a bent conformation, permitting the 3-methoxy to instead form an internal hydrogen bond with the C4-hydroxyl of the diterpene.

Halogenation of 4-hydroxy/amino-3-methoxyphenyl acetamide TRPV1 agonists showed enhanced antagonism to capsaicin

Kang, Dong Wook,Kim, Yong Soo,Lim, Kwang Su,Kim, Myeong Seop,Pearce, Larry V.,Pavlyukovets, Vladimir A.,Tao, Andy K.,Lang-Kuhs, Krystle A.,Blumberg, Peter M.,Lee, Jeewoo

experimental part, p. 8092 - 8105 (2011/01/13)

As an extension of our analysis of the effect of halogenation on thiourea TRPV1 agonists, we have now modified selected 4-hydroxy(or 4-amino)-3- methoxyphenyl acetamide TRPV1 agonists by 5- or 6-halogenation on the aromatic A-region and evaluated them for potency for TRPV1 binding and regulation and for their pattern of agonism/antagonism (efficacy). Halogenation shifted the functional activity at TRPV1 toward antagonism with a greater extent of antagonism as the size of the halogen increased (I > Br > Cl), as previously observed for the thiourea series. The extent of antagonism was greater for halogenation at the 5-position than at the 6-position, in contrast to SAR for the thiourea series. In this series, compounds 55 and 75 showed the most potent antagonism, with Ki (ant) = 2.77 and 2.19 nM, respectively, on rTRPV1 expressed in Chinese hamster ovary cells. The compounds were thus ca. 40-60-fold more potent than 6′-iodononivamide.

Vanilloid Receptor Ligands, Pharmaceutical Compositions Containing Them, Process for Making Them, and Use Thereof for Treating Pain and Other Conditions

-

Page/Page column 40; 49; 52-53, (2009/07/03)

Vanilloid receptor ligand compounds corresponding to formula I: pharmaceutical compositions containing such compounds, a process for producing such compounds, and methods of using such compounds for treating or inhibiting pain and various other disorders or conditions.

CYCLIC DIARYL ETHER COMPOUNDS AS ANTAGONISTS OF PROSTAGLANDIN D2 RECEPTORS

-

Page/Page column 95, (2009/10/09)

Described herein are compounds that are antagonists of PGD2 receptors. Also described are pharmaceutical compositions and medicaments that include the antagonists of PGD2 receptors described herein, as well as methods of using such antagonists of PGD2 receptors, alone and in combination with other compounds, for treating respiratory, cardiovascular, and other PGD2-dependent or PGD2-mediated conditions or diseases.

AMINOALKYLPHENYL ANTAGONISTS OF PROSTAGLANDIN D2 RECEPTORS

-

Page/Page column 104, (2009/12/27)

Described herein are compounds that are antagonists of PGD2 receptors. Also described are pharmaceutical compositions and medicaments that include the compounds described herein that are antagonists of PGD2 receptors. Also described herein are methods of using such antagonists of PGD2 receptors, alone and in combination with other compounds, for treating respiratory, cardiovascular, and other PGD2-dependent or PGD2-mediated conditions or diseases.

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