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)
Molecular Formula | C8H8O4 |
Molecular Weight | 168.1467 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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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[Studies on chemical constituents of Umbilicaria esculenta (Miyoshi) minks]. | 2001 Sep |
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Total synthesis of the antiallergic naphtho-alpha-pyrone tetraglucoside, cassiaside C(2), isolated from cassia seeds. | 2003 Aug 8 |
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Chromenes of polyketide origin from Peperomia villipetiola. | 2005 Mar |
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The genus Pyrenomyxa and its affinities to other cleistocarpous Hypoxyloideae as inferred from morphological and chemical traits. | 2005 Sep-Oct |
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Inhibition of nitric oxide production in RAW 264.7 cells by azaphilones from xylariaceous fungi. | 2006 Jan |
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Synthesis of gerfelin and related analogous compounds. | 2006 Oct |
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Pigment chemistry, taxonomy and phylogeny of the Hypoxyloideae (Xylariaceae). | 2006 Sep |
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Cytotoxic activity of orsellinates. | 2006 Sep-Oct |
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Molecular structural studies of lichen substances with antimicrobial, antiproliferative, and cytotoxic effects from Parmelia subrudecta. | 2010 |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:55:19 GMT 2023
by
admin
on
Fri Dec 15 17:55:19 GMT 2023
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Record UNII |
11XLA0494B
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Record Status |
Validated (UNII)
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Record Version |
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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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