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4-HYDROXYPHENOXYACETIC ACID, also known as (4-Hydroxyphenoxy)acetic acid, is an organic compound that forms a polyaromatic anionic compound RG-13577 when combined with formaldehyde ammonium salt. 4-HYDROXYPHENOXYACETIC ACID mimics synthetic heparin and specifically binds to vascular smooth muscle cells (SMCs), inhibiting their proliferative growth. The carboxyl groups in the molecules of 4-HYDROXYPHENOXYACETIC ACID are held together by R22(8) hydrogen bonds. It is an off-white to beige fine crystalline powder.

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  • 1878-84-8 Structure
  • Basic information

    1. Product Name: 4-HYDROXYPHENOXYACETIC ACID
    2. Synonyms: 2-(4-Hydroxyphenoxy)acetic acid;2-(4-Hydroxyphenoxy)ethanoic acid, 4-(Carboxymethoxy)phenol;4-HYDROXYPHENOXYACETIC ACID;(P-HYDROXYPHENOXY)ACETIC ACID;(4-hydroxyphenoxy)-aceticaci;4-Hydroxyphenoxyacetic acid, 98+%
    3. CAS NO:1878-84-8
    4. Molecular Formula: C8H8O4
    5. Molecular Weight: 168.15
    6. EINECS: 217-525-8
    7. Product Categories: Carbonyl Compounds;Carboxylic Acids;Phenoxyacetic Acids and Alcohols (substituted);C8
    8. Mol File: 1878-84-8.mol
  • Chemical Properties

    1. Melting Point: 154-157 °C(lit.)
    2. Boiling Point: 372.6°Cat760mmHg
    3. Flash Point: 158.3°C
    4. Appearance: Off-white to beige/Fine Crystalline Powder
    5. Density: 1.367g/cm3
    6. Vapor Pressure: 3.27E-06mmHg at 25°C
    7. Refractive Index: N/A
    8. Storage Temp.: N/A
    9. Solubility: soluble in Methanol
    10. BRN: 1952779
    11. CAS DataBase Reference: 4-HYDROXYPHENOXYACETIC ACID(CAS DataBase Reference)
    12. NIST Chemistry Reference: 4-HYDROXYPHENOXYACETIC ACID(1878-84-8)
    13. EPA Substance Registry System: 4-HYDROXYPHENOXYACETIC ACID(1878-84-8)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36
    4. WGK Germany: 3
    5. RTECS:
    6. TSCA: Yes
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 1878-84-8(Hazardous Substances Data)

1878-84-8 Usage

Uses

Used in Enzyme Inhibition:
4-HYDROXYPHENOXYACETIC ACID is used as an inhibitor for 4-hydroxyphenylpyruvate dioxygenase, a key enzyme involved in various metabolic pathways. It acts as a transient intermediate and substrate analogue, helping in the design, synthesis, and evaluation of inhibitors.
Used in Pharmaceutical Research:
4-HYDROXYPHENOXYACETIC ACID is used as a reagent in the preparation of compounds with anti-HIV and kinesin Eg5 inhibitory activities. It is also utilized in QSAR (Quantitative Structure-Activity Relationship) and modeling studies of triazolothiadiazole and triazolothiadiazine derivatives.
Used in Chemical Synthesis:
In the chemical industry, 4-HYDROXYPHENOXYACETIC ACID is used in the synthesis of thiadiazolotriazin-4-ones, which have been studied for their mosquito-larvicidal and antibacterial properties.
Used in Drug Development:
4-HYDROXYPHENOXYACETIC ACID plays a role in the development of drugs targeting vascular smooth muscle cells, as it forms the polyaromatic anionic compound RG-13577, which has potential applications in treating conditions related to the proliferation of these cells.

Check Digit Verification of cas no

The CAS Registry Mumber 1878-84-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,7 and 8 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1878-84:
(6*1)+(5*8)+(4*7)+(3*8)+(2*8)+(1*4)=118
118 % 10 = 8
So 1878-84-8 is a valid CAS Registry Number.
InChI:InChI=1/C8H8O4/c9-6-1-3-7(4-2-6)12-5-8(10)11/h1-4,9H,5H2,(H,10,11)/p-1

1878-84-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Alfa Aesar

  • (A12940)  4-Hydroxyphenoxyacetic acid, 98+%   

  • 1878-84-8

  • 5g

  • 690.0CNY

  • Detail
  • Alfa Aesar

  • (A12940)  4-Hydroxyphenoxyacetic acid, 98+%   

  • 1878-84-8

  • 25g

  • 2778.0CNY

  • Detail
  • Alfa Aesar

  • (A12940)  4-Hydroxyphenoxyacetic acid, 98+%   

  • 1878-84-8

  • 100g

  • 9554.0CNY

  • Detail

1878-84-8SDS

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 2-(4-hydroxyphenoxy)acetic acid

1.2 Other means of identification

Product number -
Other names 4-(Carboxymethoxy)phenol

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:1878-84-8 SDS

1878-84-8Relevant articles and documents

Diradicals Photogeneration from Chloroaryl-Substituted Carboxylic Acids

Di Terlizzi, Lorenzo,Protti, Stefano,Ravelli, Davide,Fagnoni, Maurizio

, (2022/04/09)

With the aim of generating new, thermally inaccessible diradicals, potentially able to induce a double-strand DNA cleavage, the photochemistry of a set of chloroaryl-substituted carboxylic acids in polar media was investigated. The photoheterolytic cleavage of the Ar?Cl bond occurred in each case to form the corresponding triplet phenyl cations. Under basic conditions, the photorelease of the chloride anion was accompanied by an intramolecular electron-transfer from the carboxylate group to the aromatic radical cationic site to give a diradical species. This latter intermediate could then undergo CO2 loss in a structure-dependent fashion, according to the stability of the resulting diradical, or abstract a hydrogen atom from the medium. In aqueous environment at physiological pH (pH=7.3), both a phenyl cation and a diradical chemistry was observed. The mechanistic scenario and the role of the various intermediates (aryl cations and diradicals) involved in the process was supported by computational analysis.

Design, synthesis, molecular docking and 3D-QSAR studies of potent inhibitors of enoyl-acyl carrier protein reductase as potential antimycobacterial agents

More, Uttam A.,Joshi, Shrinivas D.,Aminabhavi, Tejraj M.,Gadad, Andanappa K.,Nadagouda, Mallikarjuna N.,Kulkarni, Venkatrao H.

, p. 199 - 218 (2014/01/06)

In order to develop a lead antimycobacterium tuberculosis compound, a series of 52, novel pyrrole hydrazine derivatives have been synthesized and screened which target the essential enoyl-ACP reductase. The binding mode of the compounds at the active site of enoyl-ACP reductase was explored using surflex-docking method. The binding model suggests one or two hydrogen bonding interactions between pyrrole hydrazones and InhA enzyme. Highly active compound 5r (MIC 0.2 μg/mL) showed hydrogen bonding interactions with Tyr158 and NAD+ in the same manner as those of ligands PT70 and triclosan. The CoMFA and CoMSIA models generated with database alignment were the best in terms of overall statistics. The predictive ability of the CoMFA and CoMSIA models was determined using a test set of 13 compounds, which gave predictive correlation coefficients (rpred2) of 0.896 and 0.930, respectively.

Antimalarial activity enhancement in hydroxymethylcarbonyl (HMC) isostere-based dipeptidomimetics targeting malarial aspartic protease plasmepsin

Hidaka, Koushi,Kimura, Tooru,Ruben, Adam J.,Uemura, Tsuyoshi,Kamiya, Mami,Kiso, Aiko,Okamoto, Tetsuya,Tsuchiya, Yumi,Hayashi, Yoshio,Freire, Ernesto,Kiso, Yoshiaki

scheme or table, p. 10049 - 10060 (2009/04/07)

Plasmepsin (Plm) is a potential target for new antimalarial drugs, but most reported Plm inhibitors have relatively low antimalarial activities. We synthesized a series of dipeptide-type HIV protease inhibitors, which contain an allophenylnorstatine-dimethylthioproline scaffold to exhibit potent inhibitory activities against Plm II. Their activities against Plasmodium falciparum in the infected erythrocyte assay were largely different from those against the target enzyme. To improve the antimalarial activity of peptidomimetic Plm inhibitors, we attached substituents on a structure of the highly potent Plm inhibitor KNI-10006. Among the derivatives, we identified alkylamino compounds such as 44 (KNI-10283) and 47 (KNI-10538) with more than 15-fold enhanced antimalarial activity, to the sub-micromolar level, maintaining their potent Plm II inhibitory activity and low cytotoxicity. These results suggest that auxiliary substituents on a specific basic group contribute to deliver the inhibitors to the target Plm.

FUNCTIONALIZED DIPHENOLICS AND ABSORBABLE POLYMERS THEREFROM

-

Page/Page column 20, (2008/06/13)

The present invention relates to dephenolic compounds, an example of which is shown below, which are functionalized, and polymers formed from the same. Polymers formed from the functionalized diphenolics are expected to have controllable degradation profiles, enabling them to release an active component over a desired time range. The polymers are also expected to be useful in a variety of medical applications.

Design, synthesis, and evaluation of postulated transient intermediate and substrate analogues as inhibitors of 4-hydroxyphenylpyruvate dioxygenase

Lin, Yun-Loung,Huang, Jian-Lin,Wu, Chung-Shieh,Liu, Hung-Ge,Yang, Ding-Yah

, p. 1709 - 1713 (2007/10/03)

An epoxybenzoquinone, 4-hydroxyphenoxypropionic acid, and 2-hydroxy-3-phenyl-3-butenoic acid derivatives have been designed, synthesized, and evaluated for in vitro inhibition activity against 4-hydroxyphenylpyruvate dioxygenase (4-HPPD) from pig liver by the spectrophotometric enol-borate method. The biological data demonstrated that neither epoxybenzoquinone ester nor 2-hydroxy-3-phenyl-3-butenoic acid is an inhibitor of 4-HPPD. The most potent 4-HPPD inhibitor tested was 3-hydroxy-4-phenyl-2(5H)-furanone with an IC50 value of 0.5 μM, which may serve as a lead compound for further design of more potent 4-HPPD inhibitors.

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