Structure via PubChem · Public domain (PubChem)
orcinol
Sign in to saveAlso known as 3-Hydroxy-5-methylphenol, Orcin, 5-Methyl-1,3-dihydroxybenzene, 1,3-Dihydroxy-5-methylbenzene
Orcinol is an organic compound with the formula CH3C6H3(OH)2. It occurs in many species of lichens including Roccella tinctoria and Lecanora. Orcinol has been detected in the "toxic glue" of the ant species Camponotus saundersi. It is a colorless solid. It is related to resorcinol, 1,3-C6H4(OH)2.
Chemical data
- Formula
- C7H8O2
- Molecular weight
- 124.14 g/mol
- IUPAC name
- 5-methylbenzene-1,3-diol
- SMILES
- CC1=CC(=CC(=C1)O)O
- InChIKey
- OIPPWFOQEKKFEE-UHFFFAOYSA-N
- XLogP
- 1.6
- Polar surface area
- 40.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
415 papers- Orcinol glucoside targeted p38 as an agonist to promote osteogenesis and protect glucocorticoid-induced osteoporosis.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2023
- Production of the antidepressant orcinol glucoside in Yarrowia lipolytica with yields over 6,400-fold higher than plant extraction.PLoS biology · 2023
- Orcinol and resorcinol induce local ordering of water molecules near the liquid-vapor interface.Environmental science: atmospheres · 2022
- Orcinol gentiobioside inhibits RANKL-induced osteoclastogenesis by promoting apoptosis and suppressing autophagy via the JNK1 signaling.Journal of ethnopharmacology · 2024
- Orcinol Glucoside Facilitates the Shift of MSC Fate to Osteoblast and Prevents Adipogenesis via Wnt/β-Catenin Signaling Pathway [Retraction].Drug design, development and therapy · 2023
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 124.052429
Show 6 more facts
- described by source
- Brockhaus and Efron Encyclopedic Dictionary
- chemical formula
- C₇H₈O₂
- canonical SMILES
- CC1=CC(=CC(=C1)O)O
- melting point
- 107
- Commons category
- Orcinol
- boiling point
- 288.5
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Synthesis and reactions
- Production from shale oil
- See also
- References
Orcinol is an organic compound with the formula CH3C6H3(OH)2. It occurs in many species of lichens including Roccella tinctoria and Lecanora. Orcinol has been detected in the "toxic glue" of the ant species Camponotus saundersi. It is a colorless solid. It is related to resorcinol, 1,3-C6H4(OH)2.
== Synthesis and reactions== Orcinol was first prepared by dehydroacetic acid, a conversion that involved ring-opening of the pyrone to a triketone. This early experiment helped establish the rich condensation chemistry of polyketides. It can be obtained by fusing extract of aloes with potash, followed by acidification.
Excerpted from Wikipedia’s “orcinol” article, available under the CC BY-SA 4.0 licence.