| Identification | More | [Name]
2,4-DIHYDROXY-6-METHYLBENZOIC ACID ETHYL ESTER | [CAS]
2524-37-0 | [Synonyms]
2,4-DIHYDROXY-6-METHYLBENZOIC ACID ETHYL ESTER
2-CARBETHOXY-3,5-DIHYDROXYTOLUENE
2-ETHOXYCARBONYL-3,5-DIHYDROXYTOLUENE
4-CARBETHOXY-5-METHYLRESORCINOL
4-ETHOXYCARBONYL-5-METHYLRESORCINOL
ETHYL 2,4-DIHYDROXY-6-METHYLBENZOATE
2,4-dihydroxy-6-methyl-benzoicaciethylester
ETHYL 2,4-DIHYDROXY-6-METHYLBENZOATE, 98 %
2,4-DIHYDROXY-6-METHYLBENZOIC ACID ETHYL ESTER 98+%
Ethyl orsellinate | [Molecular Formula]
C10H12O4 | [MDL Number]
MFCD00010821 | [Molecular Weight]
196.2 | [MOL File]
2524-37-0.mol |
| Chemical Properties | Back Directory | [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. | [form ]
powder to crystal | [pka]
8.27±0.23(Predicted) | [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 Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [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 |
| Hazard Information | Back Directory | [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. | [Uses]
Ethyl 2,4-dihydroxy-6-methylbenzoate is used as use organically synthesized intermediates. | [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]. | [storage]
Store at -20°C | [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). |
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