2150-46-1

Basic information

• Product Name: Methyl 2,5-dihydroxybenzoate
• Synonyms: METHYL GENTISATE;METHYL 2,5-DIHYDROXYBENZOATE;METHYL 3,6-DIHYDROXYBENZOATE;GENTISIC ACID METHYL ESTER;dihydroxybenzoic acid methyl ester;TIMTEC-BB SBB007711;RARECHEM AL BF 0043;2,5-Dihydroxybenzoic acid methyl ester
• CAS NO: 2150-46-1
• Molecular Formula: C₈H₈O₄
• Molecular Weight: 168.15
• EINECS: 218-427-8
• Product Categories: Aromatic Esters;Acids & Esters;Phenols
• Mol File: 2150-46-1.mol
• Article Data: 43

Chemical Properties

• Melting Point: 86-88 °C(lit.)
• Boiling Point: 136 °C / 1mmHg
• Flash Point: 137.6 °C
• Appearance: /
• Density: 1.354 g/cm³
• Vapor Pressure: 0.000893mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.87±0.18(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: Methyl 2,5-dihydroxybenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,5-dihydroxybenzoate(2150-46-1)
• EPA Substance Registry System: Methyl 2,5-dihydroxybenzoate(2150-46-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 2150-46-1(Hazardous Substances Data)

Usage

Description

Methyl 2,5-dihydroxybenzoate, also known as methyl gentisate, is an alkyl ester of gentisic acid. It is a skin-lightening ingredient that acts by inhibiting the melanocyte's production of tyrosinase. It is reported to show less cytotoxic and mutagenic activity than hydroquinone with a potential to inhibit melanogenesis. Methyl 2,5-dihydroxybenzoate can be naturally obtained from gentian root and has been synthesized from 2,5-dihydroxybenzoic acid. The crystal structure of the molecule was found to be planar.

Uses

Used in Cosmetics Industry:
Methyl 2,5-dihydroxybenzoate is used as a skin-lightening agent for its ability to inhibit melanocyte's production of tyrosinase, resulting in reduced melanin production and lighter skin tone.
Used in Pharmaceutical Industry:
Methyl 2,5-dihydroxybenzoate is used as a starting material in the synthesis of euonyminol, which has potential applications in the development of new drugs.
Used in Research and Development:
Methyl 2,5-dihydroxybenzoate is used in the study of its crystal structure and planar configuration, which can contribute to the understanding of its properties and potential applications in various industries.

InChI:InChI=1/C8H8O4/c1-12-8(11)5-3-2-4-6(9)7(5)10/h2-4,9-10H,1H3

Upstream product

• 67-56-1 methanol 
• 490-79-9 2,5-dihydroxybenzoic acid. 
• 77-78-1 dimethyl sulfate 
• 33757-85-6 methyl 2,5-diacetoxybenzoate 
• 99765-76-1 2-(methoxycarbonyl)-4-(methylthio)-4-(p-tolylsulfonyl)cyclohexanone 
• 79250-47-8 5-allyloxy-2-hydroxy-benzoic acid methyl ester 
• 3958-79-0 methyl 3,6-dioxocyclohexa-1,4-diene-1-carboxylate 
• 7647-01-0 hydrogenchloride 
• 67919-45-3 (+)-euryfuran 
• 4955-90-2 sodium 2,5-dihydroxybenzoate 
• 74-88-4 methyl iodide 
• 1083407-68-4 N-(benzyloxy)-5-((2-methoxyethoxy)methoxy)-2-phenoxybenzamide 
• 89-86-1 4-hydroxysalicylic acid 

Downstream Products

• 15791-90-9 2,5-dihydroxybenzohydrazide 
• 3958-79-0 methyl 3,6-dioxocyclohexa-1,4-diene-1-carboxylate 
• 52405-73-9 gentisamide 
• 61885-19-6 2,3,6-trihydroxy-benzoic acid methyl ester 
• 33757-85-6 methyl 2,5-diacetoxybenzoate 
• 61969-53-7 2,5-dihydroxy-N-(2-hydroxyethyl)benzamide 
• 63938-50-1 2,5-dihydroxy-N-methylbenzamide 
• 72955-21-6 2-(4-Hydroxy-3-methoxycarbonyl-phenoxy)-malonic acid dimethyl ester 
• 94420-55-0 methyl 2-hydroxy-5-(tetrahydropyranyloxy)benzoate 
• 137819-31-9 methyl 2-hydroxy-5-(2-hydroxyethoxy)benzoate 
• 113487-68-6 4'-hydroxy-3'-methoxycarbonylphenyl 2-benzyloxy-4-methoxy-6-methylbenzoate 
• 72826-90-5 (4aS,5R,8aS)-5-(2-Benzyloxy-ethyl)-6-methyl-1,4-dioxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carboxylic acid methyl ester 
• 124061-92-3 (4aS,5R,8aS)-5-((4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-1,4-dioxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carboxylic acid methyl ester 
• 124061-96-7 (4aS,5R,8aS)-5-((4S,5R)-5-Acetoxy-2-phenyl-[1,3]dioxan-4-yl)-1,4-dioxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carboxylic acid methyl ester 

Relevant articles and documents

Synthesis of methyl 3,6-dioxo-endo-tricyclo[6.2.1.0 2,7]undeca-4,9-diene-2-carboxylate as synthetic intermediate for conduritol deravatives

Gentisic acid reacted with methyl iodide in HMPA to give 94% of the corresponding methyl ester. Its oxidation with Ag2O in toluene afforded 57% of methoxycarbonylbenzoquinone as yellow crystals. Reaction of the latter with cyclopentadiene resulted in formation of methyl 3,6-dioxotricyclo[6.2.1.02,7]undeca-4,9-diene-2-carboxylate (21%).

STEREOCONTROLLED SYNTHESIS OF CLERODIN HOMOLOG - A SYNTHETIC APPROACH TO STRUCTURE-ACTIVITY RELATIONSHIPS -

In order to elucidate the structure-activity relationships of the antifeeding diterpenes having a neo-clerodane skeleton, clerodin homolog 5 was stereoselectively synthetized through 18 steps via a key intermediate 11.Perhydrofurofuran ring in the synthesized homolog was more unstable than that of the natural product, and gave a tri-MeOH adduct 3 in a similar behavior to that of the model compound 1 and 2.

Macrocyclic pentamers functionalised around their periphery as potential building blocks

The elaboration of a five-fold symmetric macrocyclic aromatic pentamer bearing peripheral benzyloxy and hydroxyl groups is described. These could be used to explore further functionalisation for use as pentagonal building blocks. The internal fluorine-substituted macrocycle has been prepared via a one-pot procedure which is an improvement on the stepwise chain growth approach reported in the literature.

Studies on quinones. Part 35: Access to antiprotozoal active euryfurylquinones and hydroquinones

(+)-Euryfuran adds regiospecifically to activated monosubstituted 1,4-benzoquinones under mild conditions to give the corresponding Michael adducts which, depending on the quinone substituent, undergo in situ redox reactions to the respective euryfurylbenzoquinones. One of these Michael adducts undergoes a facile stereoselective cyclisation under oxidant conditions to afford a naphthofuro[4,3-c]benzopyran derivative. The in vitro activities of the obtained euryfurylquinones and hydroquinones against Leishmania amazonensis are described.

A Structure-Reactivity Relationship of the Tandem Asymmetric Dihydroxylation on a Biologically Relevant Diene: Influence of Remote Stereocenters on Diastereofacial Selectivity

The Sharpless asymmetric dihydroxylation (AD) finds widespread use in natural product and drug molecule syntheses, in part, due to its efficiency and predictability. However, the tandem AD of dienes is much less studied, but important in complex molecular synthesis. Herein, a biologically relevant tandem AD is reported, and several anomalies are discovered with the accepted model. These include the formation of unpredicted diastereoisomers, with matched and mismatched stereocenters contradicting the Sharpless mnemonic device. From a structural analysis of the tandem AD, we present a strategy to improve asymmetric induction in sterically hindered alkenes using double diastereodifferentiation from a 9-bond distant stereocenter. A theoretical justification for the unpredicted stereoselectivity, accounting for the influence of steric hindrance and pre-installed chirality, is proposed.

Mechanistic Studies of the Deslongchamps Annulation

The Cs2CO3-mediated annulations ("Deslongchamps annulations") of three spirocyclic benzoquinone monoketals 5b-d with an ester or acyl substituent at C-2 to two tert-butyl esters of λδ-unsaturated β-ketocarboxyl acids ("Nazarov reagents" 2a,b) were monitored 1H NMR spectroscopically. This revealed that a primary product, by all likelihood the Michael adduct, forms fast and prior to the appearance of the Deslongchamps adduct. These primary products form reversibly. This was proved by two crossover and four scavenging experiments. Therein, components already incorporat.