Ethyl 2,4-dihydroxy-6-methylbenzoate

Bezeichnung:Ethyl 2,4-dihydroxy-6-methylbenzoate

CAS-Nr2524-37-0

Englisch Name:Ethyl 2,4-dihydroxy-6-methylbenzoate

CBNumberCB1400139

SummenformelC10H12O4

Molgewicht196.2

MOL-Datei2524-37-0.mol

Ethyl 2,4-dihydroxy-6-methylbenzoate physikalisch-chemischer Eigenschaften

Schmelzpunkt	129-132 °C(lit.)
Siedepunkt	293.08°C (rough estimate)
Dichte	1.2166 (rough estimate)
Brechungsindex	1.5430 (estimate)
storage temp.	Sealed in dry,Room Temperature
Löslichkeit	Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Aggregatzustand	powder to crystal
pka	8.27±0.23(Predicted)
Farbe	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 Datenbank	2524-37-0(CAS DataBase Reference)
EPA chemische Informationen	Benzoic acid, 2,4-dihydroxy-6-methyl-, ethyl ester (2524-37-0)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-37/39
WGK Germany	3
HS Code	2916399090

Gefahreninformationscode (GHS)

Ethyl 2,4-dihydroxy-6-methylbenzoate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Definition
ChEBI: 2,4-dihydroxy-6-methylbenzoic acid ethyl ester is a 4-hydroxybenzoate ester.
Allgemeine Beschreibung
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.
Synthese
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].
Einzelnachweise
[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 Upstream-Materialien And Downstream Produkte

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