Ethyl 2,4-dihydroxy-6-methylbenzoate
- CAS NO.:2524-37-0
- Empirical Formula: C10H12O4
- Molecular Weight: 196.2
- MDL number: MFCD00010821
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-10-31 13:32:20
What is Ethyl 2,4-dihydroxy-6-methylbenzoate?
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).
Properties of Ethyl 2,4-dihydroxy-6-methylbenzoate
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 |
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 for Ethyl 2,4-dihydroxy-6-methylbenzoate
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Ethyl 2,4-dihydroxy-6-methylbenzoate
InChIKey | UQSRXQMIXSZGLA-UHFFFAOYSA-N |
SMILES | C(OCC)(=O)C1=C(C)C=C(O)C=C1O |
Abamectin manufacturer
Ralington Pharma
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