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 |
|---|---|---|
| Characterization of the biosynthetic gene cluster for the oligosaccharide antibiotic, Evernimicin, in Micromonospora carbonacea var. africana ATCC39149. | 2001 Dec |
|
| [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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| New azaphilones from the inedible mushroom Hypoxylon rubiginosum. | 2004 Jul |
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| Chromenes of polyketide origin from Peperomia villipetiola. | 2005 Mar |
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| Globosumones A-C, cytotoxic orsellinic acid esters from the Sonoran desert endophytic fungus Chaetomium globosum. | 2005 May |
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| Total synthesis of CRM646-A and -B, two fungal glucuronides with potent heparinase inhibition activities. | 2005 Oct 28 |
|
| The genus Pyrenomyxa and its affinities to other cleistocarpous Hypoxyloideae as inferred from morphological and chemical traits. | 2005 Sep-Oct |
|
| Synthesis of gerfelin and related analogous compounds. | 2006 Oct |
|
| 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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| Ozoroalide, a new macrolide from Ozoroa insignis. | 2007 Jul |
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| Synthesis of an advanced intermediate for (+)-pillaromycinone. Staunton-Weinreb annulation revisited. | 2008 Jul 3 |
|
| Radical-scavenging activity of orsellinates. | 2008 Nov |
|
| Ancient horizontal gene transfer from bacteria enhances biosynthetic capabilities of fungi. | 2009 |
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| Structural characterization of CalO2: a putative orsellinic acid P450 oxidase in the calicheamicin biosynthetic pathway. | 2009 Jan |
|
| Structure and cytotoxicity of arnamial and related fungal sesquiterpene aryl esters. | 2009 Oct |
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| Molecular structural studies of lichen substances with antimicrobial, antiproliferative, and cytotoxic effects from Parmelia subrudecta. | 2010 |
|
| Aspergillus oryzae type III polyketide synthase CsyA is involved in the biosynthesis of 3,5-dihydroxybenzoic acid. | 2010 Aug 15 |
|
| In vitro antitumour activity of orsellinates. | 2010 Jan-Feb |
|
| The chemical constituents of endophytic fungus Trichoderma sp. MFF-1. | 2010 Jul |
|
| Molecular genetic analysis of the orsellinic acid/F9775 gene cluster of Aspergillus nidulans. | 2010 Mar |
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| Insights into bacterial 6-methylsalicylic acid synthase and its engineering to orsellinic acid synthase for spirotetronate generation. | 2010 May 28 |
|
| 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
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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