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 |
DescriptionCurator'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
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| The COP9 signalosome mediates transcriptional and metabolic response to hormones, oxidative stress protection and cell wall rearrangement during fungal development. | 2010-11 |
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| Aspergillus oryzae type III polyketide synthase CsyA is involved in the biosynthesis of 3,5-dihydroxybenzoic acid. | 2010-08-15 |
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| The chemical constituents of endophytic fungus Trichoderma sp. MFF-1. | 2010-07 |
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| Insights into bacterial 6-methylsalicylic acid synthase and its engineering to orsellinic acid synthase for spirotetronate generation. | 2010-05-28 |
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| In vitro antitumour activity of orsellinates. | 2010-04-02 |
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| Molecular genetic analysis of the orsellinic acid/F9775 gene cluster of Aspergillus nidulans. | 2010-03 |
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| Molecular structural studies of lichen substances with antimicrobial, antiproliferative, and cytotoxic effects from Parmelia subrudecta. | 2010 |
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| Structure and cytotoxicity of arnamial and related fungal sesquiterpene aryl esters. | 2009-10 |
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| Structural characterization of CalO2: a putative orsellinic acid P450 oxidase in the calicheamicin biosynthetic pathway. | 2009-01 |
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| Ancient horizontal gene transfer from bacteria enhances biosynthetic capabilities of fungi. | 2009 |
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| Radical-scavenging activity of orsellinates. | 2008-11 |
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| Synthesis of an advanced intermediate for (+)-pillaromycinone. Staunton-Weinreb annulation revisited. | 2008-07-03 |
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| Plant phenolics regulate neoplastic cell growth and survival: a quantitative structure-activity and biochemical analysis. | 2007-11 |
|
| Platelet activating factor-induced neuronal apoptosis is initiated independently of its G-protein coupled PAF receptor and is inhibited by the benzoate orsellinic acid. | 2007-10 |
|
| Ozoroalide, a new macrolide from Ozoroa insignis. | 2007-07 |
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| Cytotoxic activity of orsellinates. | 2006-12-02 |
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| Synthesis of gerfelin and related analogous compounds. | 2006-10 |
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| Pigment chemistry, taxonomy and phylogeny of the Hypoxyloideae (Xylariaceae). | 2006-09 |
|
| The genus Pyrenomyxa and its affinities to other cleistocarpous Hypoxyloideae as inferred from morphological and chemical traits. | 2006-04-07 |
|
| Inhibition of nitric oxide production in RAW 264.7 cells by azaphilones from xylariaceous fungi. | 2006-01 |
|
| A short synthetic route to biologically active (+/-)-daurichromenic acid as highly potent anti-HIV agent. | 2005-11-07 |
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| Total synthesis of CRM646-A and -B, two fungal glucuronides with potent heparinase inhibition activities. | 2005-10-28 |
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| Globosumones A-C, cytotoxic orsellinic acid esters from the Sonoran desert endophytic fungus Chaetomium globosum. | 2005-05 |
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| Chromenes of polyketide origin from Peperomia villipetiola. | 2005-03 |
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| New azaphilones from the inedible mushroom Hypoxylon rubiginosum. | 2004-07 |
|
| Total synthesis of the antiallergic naphtho-alpha-pyrone tetraglucoside, cassiaside C(2), isolated from cassia seeds. | 2003-08-08 |
|
| Characterization of the biosynthetic gene cluster for the oligosaccharide antibiotic, Evernimicin, in Micromonospora carbonacea var. africana ATCC39149. | 2001-12 |
|
| [Studies on chemical constituents of Umbilicaria esculenta (Miyoshi) minks]. | 2001-09 |
Patents
Sample Use Guides
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
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admin
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Edited
Mon Mar 31 18:56:58 GMT 2025
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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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