Methyl 2,5-dihydroxybenzoate

Base Information

• Chemical Name: Methyl 2,5-dihydroxybenzoate
• CAS No.: 2150-46-1
• Molecular Formula: C8H8O4
• Molecular Weight: 168.149
• Hs Code.: 29182900
• European Community (EC) Number: 218-427-8
• NSC Number: 618316
• UNII: LS28B004KM
• DSSTox Substance ID: DTXSID80175841
• Nikkaji Number: J80.402I
• Wikidata: Q27283153
• Pharos Ligand ID: NBK2HR5SLS48
• ChEMBL ID: CHEMBL1978880
• Mol file: 2150-46-1.mol

Synonyms:methyl gentisate

Chemical Property of Methyl 2,5-dihydroxybenzoate

Chemical Property:

• Vapor Pressure: 0.000893mmHg at 25°C
• Melting Point: 86-88 °C(lit.)
• Refractive Index: 1.587
• Boiling Point: 328.2 °C at 760 mmHg
• PKA: 9.87±0.18(Predicted)
• Flash Point: 137.6 °C
• PSA: 66.76000
• Density: 1.354 g/cm³
• LogP: 0.88440
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 168.04225873
• Heavy Atom Count: 12
• Complexity: 168

Purity/Quality:

99% ^*data from raw suppliers

Methyl 2,5-dihydroxybenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: COC(=O)C1=C(C=CC(=C1)O)O
• Uses: methyl gentisate is also known as methyl dihydroxybenzoate. It is a skin-lightening ingredient that acts by inhibiting the melanocyte’s production of tyrosinase. It can be naturally obtained from gentian root. Methyl 2,5-dihydroxybenzoate (methyl gentisate) may be used as a starting material in the synthesis of euonyminol.

Technology Process of Methyl 2,5-dihydroxybenzoate

There total 17 articles about Methyl 2,5-dihydroxybenzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

2,5-dihydroxybenzoic acid. (490-79-9) + methyl iodide (74-88-4) → Methyl 2,5-dihydroxybenzoate (2150-46-1)

Guidance literature:

With potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 40 ℃;

DOI:10.1081/SCC-200046532

Reference yield: 97.0%

methanol (67-56-1) + 2,5-dihydroxybenzoic acid. (490-79-9) → Methyl 2,5-dihydroxybenzoate (2150-46-1)

Guidance literature:

With sulfuric acid; for 48h; Reflux;

DOI:10.1021/ol802679p DOI:10.1021/ja100579z

Reference yield: 95.0%

methyl 2,5-diacetoxybenzoate (33757-85-6) → Methyl 2,5-dihydroxybenzoate (2150-46-1)

Guidance literature:

silica gel; toluene-4-sulfonic acid; In water; toluene; at 80 ℃; for 6h;

DOI:10.1055/s-1989-27277

upstream raw materials:

methanol

2,5-dihydroxybenzoic acid.

dimethyl sulfate

methyl 2,5-diacetoxybenzoate

Downstream raw materials:

2,5-dihydroxybenzohydrazide

methyl 3,6-dioxocyclohexa-1,4-diene-1-carboxylate

gentisamide

2,3,6-trihydroxy-benzoic acid methyl ester

Refernces

• 1、 Borges, Rosivaldo S.,Castle, Steven L.. "The antioxidant properties of salicylate derivatives: A possible new mechanism of anti-inflammatory activity". . p. 4808 - 4811. Retrieved 2015.
• 2、 Kojima,Kato. "Stereocontrolled synthesis of clerodin homolog. A synthetic approach to structure-activity relationships". . p. 2527 - 2538. Retrieved 1981.
• 3、 Martic, Sanela,Brennan, John D.,Brook, Michael A.,Ackloo, Suzanne,Nagy, Noemi. "Towards the development of a covalently tethered MALDI system - A study of allyl-modified MALDI matrixes". . p. 66 - 76. Retrieved 2007.
• 4、 Dissanayake, Isuru,Hart, Jacob D.,Becroft, Emma C.,Sumby, Christopher J.,Newton, Christopher G.. "Bisketene Equivalents as Diels-Alder Dienes". supporting information. p. 13328 - 13333. Retrieved 2020/09/03.
• 5、 -. "APOPTOSIS SIGNAL-REGULATING KINASE INHIBITORS AND USES THEREOF". Paragraph 00281. . Retrieved 2019/04/09.