Introduction：Basic information about Ethyl 2,4-dihydroxy-6-methylbenzoate CAS 2524-37-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Ethyl 2,4-dihydroxy-6-methylbenzoate Basic information
| Product Name: | Ethyl 2,4-dihydroxy-6-methylbenzoate |
| Synonyms: | 4-ETHOXYCARBONYL-5-METHYLRESORCINOL;4-CARBETHOXY-5-METHYLRESORCINOL;ETHYL 2,4-DIHYDROXY-6-METHYLBENZOATE, 98 %;2,4-dihydroxy-6-methyl-benzoicaciethylester;ETHYL 2,4-DIHYDROXY-6-METHYLBENZOATE;2,4-DIHYDROXY-6-METHYLBENZOIC ACID ETHYL ESTER;2-CARBETHOXY-3,5-DIHYDROXYTOLUENE;2-ETHOXYCARBONYL-3,5-DIHYDROXYTOLUENE |
| CAS: | 2524-37-0 |
| MF: | C10H12O4 |
| MW: | 196.2 |
| EINECS: | |
| Product Categories: | Inhibitors;C10 to C11;Carbonyl Compounds;Esters;Aromatic Esters |
| Mol File: | 2524-37-0.mol |
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Ethyl 2,4-dihydroxy-6-methylbenzoate Chemical Properties
| Melting point | 129-132 °C(lit.) |
| Boiling point | 293.08°C (rough estimate) |
| density | 1.2166 (rough estimate) |
| refractive index | 1.5430 (estimate) |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. |
| pka | 8.27±0.23(Predicted) |
| form | powder to crystal |
| color | White to Gray to Brown |
| InChI | InChI=1S/C10H12O4/c1-3-14-10(13)9-6(2)4-7(11)5-8(9)12/h4-5,11-12H,3H2,1-2H3 |
| InChIKey | UQSRXQMIXSZGLA-UHFFFAOYSA-N |
| SMILES | C(OCC)(=O)C1=C(C)C=C(O)C=C1O |
| LogP | 2.910 (est) |
| CAS DataBase Reference | 2524-37-0(CAS DataBase Reference) |
| EPA Substance Registry System | Benzoic acid, 2,4-dihydroxy-6-methyl-, ethyl ester (2524-37-0) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-37/39 |
| WGK Germany | 3 |
| TSCA | TSCA listed |
| HS Code | 2916399090 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
Ethyl 2,4-dihydroxy-6-methylbenzoate Usage And Synthesis
| Description | Ethyl orsellinate is a lichen metabolite and a derivative of lecanoric acid (Item No. 22710) that has antiproliferative activities.1,2 It inhibits the proliferation of human Hep-2 larynx carcinoma, MCF-7 breast cancer, and 786-0 kidney carcinoma cells, as well as B16-F10 murine melanoma and non-cancerous Vero cells (IC50s = 31.2, 70.3, 47.5, 64.8, and 28.1 µg/ml, respectively).2 Ethyl orsellinate is toxic to brine shrimp (A. salina) with an LC50 value of 495 µM.3WARNING This product is not for human or veterinary use. |
| Definition | ChEBI: 2,4-dihydroxy-6-methylbenzoic acid ethyl ester is a 4-hydroxybenzoate ester. |
| General Description | Ethyl 2,4-dihydroxy-6-methylbenzoate is also referred as ethyl orsellinate. It was isolated from chloroform extract of Peltigera aphthosa. It is one of the product formed during alcoholyses of lecanoric acid. |
| Synthesis | The stem bark of Illicium difengpi (5.0?kg) was powdered and extracted three times with aqueous ethanol (ethanol/water 8:2) under reflux. The solvent was then evaporated under reduced pressure to obtain a dry residue (150?g). The residue was suspended in water (2?L) and extracted successively with petroleum ether (3 × 2?L), EtOAc (3 × 2?L) and BuOH (3 × 2?L), affording 5?g, 70?g, and 40?g, respectively, of each dried fraction. The EtOAc fraction was subjected to silica gel column chromatography using gradient elution (CH2Cl2/CH3OH, 200:1 to 2:1, v/v) to give four main fractions, of which was purified by successive silica gel column chromatography (CH2Cl2/CH3OH, 100:1→20:1); 2,4-dihy-droxy-6-methyl-benzoic acid ethyl ester (Ethyl 2,4-dihydroxy-6-methylbenzoate) was obtained from the fraction eluted by CH2Cl2/CH3OH (40:1)[1]. |
| Structure and conformation | The mol-ecular structure of Ethyl 2,4-dihydroxy-6-methylbenzoate contains a methyl group, two hydroxyl groups, and a carboeth-oxy group, which are attached to C2, C4, C6 and C7 of the central benzene ring, respectively. An intra-molecular O3—H3···O1 hydrogen bond stabilizes the mol-ecular conformation. In the crystal, O4—H4···O3i and C3—H3A···O4ii hydrogen bonds link the mol-ecules into double strands parallel to the direction. In the solid state, the compound also forms offset slanted stacks of alternating inversion-related mol-ecules along the a-axis direction[1]. |
| References | [1] Xiong, Huiping , et al. "Crystal structure of the ethyl 2,4-dihydroxy-6-methylbenzoate from Illicium difengpi K.I.B et K.I.M. " IUCrData 12(2018). |
Ethyl 2,4-dihydroxy-6-methylbenzoate Preparation Products And Raw materials
| Raw materials | Chloroform-->Poly(vinyl alcohol)-->2,4-DIHYDROXY-6-METHYLBENZOIC ACID-->ETHYL 3,5-DIBROMO-2,4-DIHYDROXY-6-METHYLBENZOATE |
| Preparation Products | 2-(2-Oxopropyl)-7-hydroxy-5-methyl-4H-1-benzopyran-4-one-->2 4-DIHYDROXY-6-METHYLBENZALDEHYDE |
