Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H8O4 |
Molecular Weight | 168.1467 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=C(C(O)=O)C(O)=CC(O)=C1
InChI
InChIKey=AMKYESDOVDKZKV-UHFFFAOYSA-N
InChI=1S/C8H8O4/c1-4-2-5(9)3-6(10)7(4)8(11)12/h2-3,9-10H,1H3,(H,11,12)
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/15921417Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/28422496 | https://www.ncbi.nlm.nih.gov/pubmed/19782562 | https://www.ncbi.nlm.nih.gov/pubmed/29311513
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15921417
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/28422496 | https://www.ncbi.nlm.nih.gov/pubmed/19782562 | https://www.ncbi.nlm.nih.gov/pubmed/29311513
Orsellinic acid is a common salicylic acid unit in the biosynthesis of secondary metabolites in actinomycetes, fungi, and lichens, formally isolated from Chaetomium cochliodes in 1959. Orsellinic acid is a key biosynthetic intermediate of many depside metabolites in lichen and fungi. Orsellinic acid is also an important polar co-metabolite present in many fungi, notably Trichomonacea, however, its contribution to overall bioactivity is not well understood. Orsellinic acid is a useful standard for bioassay and analytical techniques for dereplication of common cometabolites.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL335 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19782562 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Synthesis of an advanced intermediate for (+)-pillaromycinone. Staunton-Weinreb annulation revisited. | 2008 Jul 3 |
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Structural characterization of CalO2: a putative orsellinic acid P450 oxidase in the calicheamicin biosynthetic pathway. | 2009 Jan |
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Molecular structural studies of lichen substances with antimicrobial, antiproliferative, and cytotoxic effects from Parmelia subrudecta. | 2010 |
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The chemical constituents of endophytic fungus Trichoderma sp. MFF-1. | 2010 Jul |
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The COP9 signalosome mediates transcriptional and metabolic response to hormones, oxidative stress protection and cell wall rearrangement during fungal development. | 2010 Nov |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29311513
Inhibition of the diphenolase activity of mushroom tyrosinase was evaluated using L-DOPA as the substrate.2The test compounds (Orsellinic acid, compound 4) were first dissolved in dimethyl sulfoxide (DMSO) at 10.0 mM. For analysis of samples 4–14, 0.1 mL of sample solution in DMSO was combined with 1.5 mL of sodium phosphate buffer. Each resulting solution was then mixed with 0.2 mL of L-DOPA (3.5 mM) and 0.2 mL of tyrosinase (10 μg/mL). The mixtures were homogenized and incubated for 5 min at 30°C. Absorbances were measured at 475 nm to monitor the formation of dopachrome (ε=3700 M−1 cm−1) using a Spectrum 220 spectrophotometer.
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ORSELLINIC ACID
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68072
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m8247
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C501612
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11XLA0494B
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480-64-8
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32807
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DTXSID20197385
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SUBSTANCE RECORD