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Chemical Structure| 504-15-4 Chemical Structure| 504-15-4
Chemical Structure| 504-15-4

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Orcinol glucoside is anxiolytic agent without sedative effect. Orcinol glucoside improves depressive behaviour in CUMS rats by downregulating HPA axis hyperactivity and increasing BDNF expression and ERK1/2 phosphorylation in the hippocampus.

Synonyms: 3,5-Dihydroxytoluene; 5-Methylresorcinol; NSC 12441

4.5 *For Research Use Only !

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Product Details of Orcinol

CAS No. :504-15-4
Formula : C7H8O2
M.W : 124.14
SMILES Code : OC1=CC(C)=CC(O)=C1
Synonyms :
3,5-Dihydroxytoluene; 5-Methylresorcinol; NSC 12441
MDL No. :MFCD00002291
InChI Key :OIPPWFOQEKKFEE-UHFFFAOYSA-N
Pubchem ID :10436

Safety of Orcinol

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of Orcinol

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 504-15-4 ]

[ 504-15-4 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 74204-00-5 ]
  • [ 504-15-4 ]
  • 3
  • [ 504-15-4 ]
  • [ 22972-51-6 ]
  • [ 35482-50-9 ]
  • 4
  • [ 504-15-4 ]
  • [ 22972-51-6 ]
  • [ 22972-64-1 ]
  • 5
  • [ 504-15-4 ]
  • [ 26638-43-7 ]
  • 2-(3-hydroxy-5-methyl-phenoxysulfonyl)-benzoic acid methyl ester [ No CAS ]
  • 7
  • [ 74204-00-5 ]
  • potassium hydroxide [ No CAS ]
  • [ 504-15-4 ]
  • 8
  • [ 504-15-4 ]
  • [ 10226-29-6 ]
  • [ 560093-97-2 ]
  • 9
  • [ 504-15-4 ]
  • [ 42899-76-3 ]
  • [ 197960-44-4 ]
YieldReaction ConditionsOperation in experiment
58% With sodium hydrogencarbonate; In dichloromethane; water; at 20℃; for 48h; a) 5-Methyl-3-(3-pyridinylsulfoxy)phenol A mixture of orcinol monohydrate (1.42 g, 0.01 mol) and 3-pyridylsulfonyl chloride hydrochloride (2.13 g, 0.01 mol), as prepared in J. Am. Chem. Soc., 114:4889 (1992), in saturated aqueous sodium bicarbonate (17.5 mL) and dichloromethane (50 mL) was stirred rapidly at ambient temperature for 2 days. The dichloromethane was separated and the aqueous layer was extracted with ethyl acetate (3 x 25 mL). The ethyl acetate and dichloromethane extracts were combined and washed with brine, dried over anhydrous sodium sulfate, and evaporated to dryness. The residue was recrystallized from ether and hexane, collected by filtration, and dried under high vacuum to give 1.54 g of a white solid (58percent yield). 1H-NMR (300 MHz, CDCl3) delta 9.03 (d, 1 H), 8.88 (dd, 1 H), 8.16 (dt, 1 H), 7.5 (m, 1 H), 6.57 (d, 1 H), 6.42 (s, 1 H), 6.32 (t, 1 H), 2.24 (s, 3 H).
  • 10
  • [ 504-15-4 ]
  • [ 2689-69-2 ]
  • 1,2-dihydro-9-hydroxy-7-methyl-4-oxo-4H-thieno[2,3-c] [1]benzopyran [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 2 1,2-Dihydro-9-hydroxy-7-methyl-4-oxo-4H-thieno[2,3-c] [1]benzopyran Following a procedure similar to that described in Example 1B hereinabove, methyl 3-oxo-2,3,4,5-tetrahydrothiophene-2-carboxylate is reacted with 5-methylresorcinol to give 1,2-dihydro-9-hydroxy-7-methyl-4-oxo-4H-thieno[2,3-c] [1]benzopyran.
EXAMPLE 91 1,2-Dihydro-9-hydroxy-7-methyl-4-oxo-4H-thieno[2,3-c][1]benzopyran Following the procedure similar to that described in Example 1B hereinabove, methyl 3-oxo-2,3,4,5-tetrahydrothiophene-2-carboxylate is reacted with 5-methylresorcinol to give 1,2-dihydro-9-hydroxy-7-methyl-4-oxo-4H-thieno[2,3-c][1]benzopyran.
  • 11
  • [ 504-15-4 ]
  • [ 129112-65-8 ]
  • [ 1242243-76-0 ]
  • C30H18N6O8 [ No CAS ]
  • 12
  • [ 504-15-4 ]
  • [ 40915-37-5 ]
  • C19H24O4 [ No CAS ]
  • 13
  • [ 504-15-4 ]
  • [ 143982-40-5 ]
  • [ 109-77-3 ]
  • 2‑amino‑7‑hydroxy‑4‑(imidazo[1,2‑a]pyrimidin‑2‑yl)‑5‑methyl‑4H‑chromene‑3‑carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With sodium carbonate; In water; at 25.0℃; for 2.0h; General procedure: Imidazo[1,2-a]pyrimidine-2-carbaldehyde [40] (100 mg,0.68 mmol, 1.0 equiv.), 58 mg malononitrile (0.88 mmol, 1.3equiv.), and enolizable compounds (0.88 mmol, 1.3 equiv.)were dissolved in 5 cm3water or a mixture of water:ethylalcohol (4:1). Sodium carbonate (0.88 mmol, 93 mg, 1.3equiv.) in 2 cm3water was added and the mixture was stirredat room temperature for various times (2-7 h). The reactionprocess was monitored with thin layer chromatographyusing different ratio of hexane:ethyl acetate mixture assolvent. After completion of the reaction, the mixture waspoured into brine solution and stirred for 15 min. The resultingsolid was suction filtered using filter paper with smallpore size and washed with water. The pure products 4a-4gwere obtained by crystallization or washing with varioussolvents. Products were stored under argon atmosphere toprevent decomposition.
 

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