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(4'-O-methyl)methyl gallate is a gallate compound derived from gallic acid, featuring a methyl group attached to the phenolic hydroxyl group at the 4' position. It has been studied for its potential antioxidant, anti-inflammatory effects, and its ability to inhibit cancer cell growth. (4'-O-methyl)methyl gallate also shows promise as a natural preservative and has potential applications in pharmaceuticals and functional foods due to its beneficial properties.

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  • 24093-81-0 Structure
  • Basic information

    1. Product Name: (4'-O-methyl)methyl gallate
    2. Synonyms: (4'-O-methyl)methyl gallate
    3. CAS NO:24093-81-0
    4. Molecular Formula: C9H10O5
    5. Molecular Weight: 198.1727
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 24093-81-0.mol
  • Chemical Properties

    1. Melting Point: 147.0 to 151.0 °C
    2. Boiling Point: 400.4°C at 760 mmHg
    3. Flash Point: 164.4°C
    4. Appearance: /
    5. Density: 1.337g/cm3
    6. Vapor Pressure: 5.51E-07mmHg at 25°C
    7. Refractive Index: 1.567
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 8?+-.0.15(Predicted)
    11. CAS DataBase Reference: (4'-O-methyl)methyl gallate(CAS DataBase Reference)
    12. NIST Chemistry Reference: (4'-O-methyl)methyl gallate(24093-81-0)
    13. EPA Substance Registry System: (4'-O-methyl)methyl gallate(24093-81-0)
  • 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: 24093-81-0(Hazardous Substances Data)

24093-81-0 Usage

Uses

Used in Antioxidant Applications:
(4'-O-methyl)methyl gallate is used as an antioxidant for its potential to combat oxidative stress and protect cells from damage, which can contribute to various health issues and the aging process.
Used in Anti-inflammatory Applications:
(4'-O-methyl)methyl gallate is used as an anti-inflammatory agent to help reduce inflammation and alleviate symptoms associated with inflammatory conditions.
Used in Cancer Therapy:
(4'-O-methyl)methyl gallate is used as an anticancer agent for its ability to inhibit the growth of cancer cells, offering a potential therapeutic approach for various types of cancer.
Used in Food and Cosmetic Preservation:
(4'-O-methyl)methyl gallate is used as a natural preservative in the food and cosmetic industries to extend the shelf life of products and maintain their quality over time.
Used in Pharmaceutical Development:
(4'-O-methyl)methyl gallate is used in the development of pharmaceuticals due to its potential health benefits and therapeutic properties, offering a promising avenue for creating new treatments and medications.
Used in Functional Food Industry:
(4'-O-methyl)methyl gallate is used in the development of functional foods for its potential to provide health benefits beyond basic nutrition, contributing to the overall wellness of consumers.

Check Digit Verification of cas no

The CAS Registry Mumber 24093-81-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,4,0,9 and 3 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 24093-81:
(7*2)+(6*4)+(5*0)+(4*9)+(3*3)+(2*8)+(1*1)=100
100 % 10 = 0
So 24093-81-0 is a valid CAS Registry Number.
InChI:InChI=1/C9H10O5/c1-13-8-6(10)3-5(4-7(8)11)9(12)14-2/h3-4,10-11H,1-2H3

24093-81-0SDS

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 Methyl 3,5-dihydroxy-4-methoxybenzoate

1.2 Other means of identification

Product number -
Other names Benzoic acid,3,5-dihydroxy-4-methoxy-,methyl 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:24093-81-0 SDS

24093-81-0Relevant articles and documents

Vanadium-Catalyzed Oxidative Intramolecular Coupling of Tethered Phenols: Formation of Phenol-Dienone Products

Gilmartin, Philip H.,Kozlowski, Marisa C.

supporting information, p. 2914 - 2919 (2020/04/10)

A mild and efficient method for the vanadium-catalyzed intramolecular coupling of tethered free phenols is described. The corresponding phenol-dienone products are prepared directly in good yields with low catalyst loadings. Electronically diverse tethered phenol precursors are well tolerated, and the catalytic method was effectively applied as the key step in syntheses of three natural products and a synthetically useful morphinan alkaloid precursor.

A Regio- and Diastereoselective Anodic Aryl–Aryl Coupling in the Biomimetic Total Synthesis of (?)-Thebaine

Lipp, Alexander,Ferenc, Dorota,Gütz, Christoph,Geffe, Mario,Vierengel, Nina,Schollmeyer, Dieter,Sch?fer, Hans J.,Waldvogel, Siegfried R.,Opatz, Till

supporting information, p. 11055 - 11059 (2018/08/21)

The biosynthesis of thebaine is based on the regioselective, intramolecular, oxidative coupling of (R)-reticuline. For decades, chemists have sought to mimic this coupling by using stoichiometric oxidants. However, all approaches to date have suffered from low yields or the formation of undesired regioisomers. Electrochemistry would represent a sustainable alternative in this respect but all attempts to accomplish an electrochemical synthesis of thebaine have failed so far. Herein, a regio- and diastereoselective anodic coupling of 3′,4′,5′-trioxygenated laudanosine derivatives is presented, which finally enables electrochemical access to (?)-thebaine.

Synthesis and cytotoxic activities of hexyl-esters derivatives of gallic acid against MCF-7 cell line

Paramita, Rafika Indah,Arsianti, Ade,Radji, Maksum

, p. 295 - 300 (2018/03/21)

Gallic acid is found in many plants, fruits, and foods where the anti-cancer activity is found. However, gallic acid has a problem on the high polarity and low bio availability. So, it takes molecular modifications in order to increase its lipophilicity, which is expected to increase bio availability and cytotoxic activity of gallic acid. Hexyl esters derivatives of gallic acid were synthesized and characterized by spectrometer 1H-NMR, 13C-NMR, mass spectrometry and infrared spectrophotometer (FTIR). All compounds were then evaluated for cytotoxic activity on MCF-7 cell line using MTT method. Compound cis-2′-hexenyl-3,4,5-trimethoxygallate (19) had the lowest IC50 value compared with gallic acid and other derivatives hexyl esters. IC50 value of cis-2′-hexenyl-3,4,5-trimethoxygallate (19) is 14.48 μg/ml. Compound (19) also has approached with IC50 values of gossypol as a positive control. Compound (19) is a potential compound to inhibit growth of MCF-7 cell line.

Synthesis and in vitro antimalarial activity of alkyl esters of gallate as a growth inhibitor of plasmodium falciparum

Arsianti, Ade,Astuty, Hendri,Fadilah,Simadibrata, Daniel Martin,Adyasa, Zoya Marie,Amartya, Daniel,Bahtiar, Anton,Tanimoto, Hiroki,Kakiuchi, Kiyomi

, p. 655 - 662 (2018/05/28)

This study is aimed to synthesize alkyl esters gallate and determine its in vitro antimalarial activity against parasite Plasmodium falciparum. Fourteen compounds of alkyl esters gallate were synthesized by esterification of the carboxyl group of gallic acid with a series of alkyl alcohols, as well as methoxylation of the hydroxy groups on the aromatic ring of gallic acid. Antimalarial activity of the synthesized alkyl esters gallate were expressed by IC50 value, with gallic acid as an original compound and artemisin as a positive control. Compared to gallic acid, eleven synthesized compounds of alkyl esters gallate, have a greater antimalarial activity against Plasmodium falciparum. On the other hand, three compounds, that are propyl gallate, butyl gallate and trimethoxy methyl gallate, showed a lower antimalarial activity. Moreover, compared to gallic acid (IC50: 194.86 mM) and artemisin (IC50: 0.5 mM), two synthesized compounds of alkyl gallates, namely methyl gallate and hexyl gallate exhibited the stronger antimalarial activity against Plasmodium falciparum, with IC50 value of 0.03 mM and 0.11 mM, respectively. Our result clearly demonstrated that methyl gallate and hexyl gallate as a promising candidate for the new antimalarial agents.

Bioinspired Total Synthesis of Bussealin e

Twigg, David G.,Baldassarre, Leonardo,Frye, Elizabeth C.,Galloway, Warren R. J. D.,Spring, David R.

supporting information, p. 1597 - 1599 (2018/03/23)

The first total synthesis of bussealin E, a natural product with a unique cycloheptadibenzofuran scaffold, is reported. A strategy inspired by a proposed biosynthesis was employed whereby a diphenylpropane derivative underwent an oxidative phenolic coupling to forge the tetracyclic ring system. The synthesis of the diphenylpropane featured a key sp2-sp3 Hiyama coupling between a vinyldisiloxane and a benzylic bromide.

Ruthenium-Catalyzed Hydroarylation and One-Pot Twofold Unsymmetrical C?H Functionalization of Arenes

Ghosh, Koushik,Ramesh, E.,Rit, Raja K.,Sahoo, Akhila K.

supporting information, p. 7821 - 7825 (2016/07/07)

A methyl phenyl sulfoximine (MPS) is used as a directing group in the ruthenium-catalyzed intramolecular hydroarylation of alkene-tethered benzoic acid derivatives to afford dihydrobenzofurans and indolines in good to excellent yields. A one-pot, unsymmetrical, twofold C?H functionalization involving intramolecular C?C and intermolecular C?C/C?N bond formations is successfully demonstrated by using a single set of catalytic reaction conditions, which is unprecedented thus far. A novel isoquinolone-bearing dihydrobenzofuran is constructed through an unsymmetrical twofold C?H functionalization.

Chalcone derivative, preparing method, pharmaceutical composition and application

-

Paragraph 0096; 0097, (2017/02/09)

The invention relates to a chalcone derivative, a preparing method, a pharmaceutical composition and application, provides a compound with the general formula I, and pharmaceutically-acceptable salt or solvate or polymorphic substances or metabolites or prodrugs of the compound, and further provides a preparing method of the compound of the structure shown in the general formula I, a pharmaceutical composition including the substance, and application of the substance in preparing medicine for treating or preventing inflammation. The general formula I is shown in the description, wherein R1, R2, R3, R4, R5, R6, R7, R8 and R9 are H, substituted or unsubstituted C1-C4 alkyl, hydroxyl, alkoxy, amino, halogen, C1-C4 substituted acylamino and C1-C4 acyl; R11 and R12 are substituted or unsubstituted C1-C4 alkyl.

3,5-dihydroxy-4-trifluoromethoxybenzyl alcohol (3,5-dihydro x y-4-metho x ybenzylalcohol) synthesis method (by machine translation)

-

Paragraph 0023-0027, (2017/04/11)

PROBLEM TO BE SOLVED: earpick not derived from a so-called new antioxidant and anti-oxidant composition 3,5-dihydroxy-4-efficient trifluoromethoxybenzyl alcohol, to provide a method for synthesizing high purity. SOLUTION: subgallate dimethyl formamide suc

Cross-coupling reaction of saccharide-based alkenyl boronic acids with aryl halides: The synthesis of bergenin

Parkan, Kamil,Pohl, Radek,Kotora, Martin

supporting information, p. 4414 - 4419 (2014/05/06)

A convenient synthetic pathway enabling D-glucal and D-galactal pinacol boronates to be prepared in good isolated yields was achieved. Both pinacol boronates were tested in a series of cross-coupling reactions under Suzuki-Miyaura cross-coupling conditions to obtain the corresponding aryl, heteroaryl, and alkenyl derivatives in high isolated yields. This methodology was applied to the formal synthesis of the glucopyranoside moiety of papulacandin D and the first total synthesis of bergenin. Building blocks with boron: A convenient synthetic route to D-glucal and D-galactal pinacol boronates was developed, and the boronates were used in cross-coupling reactions to generate the corresponding aryl, heteroaryl, and alkenyl derivatives in high yields (see scheme). This methodology was applied to the formal synthesis of the glucopyranoside moiety of papulacandin D and the total synthesis of bergenin.

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