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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
Structure of ORSELLINIC ACID

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)

HIDE SMILES / InChI

Description
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.

Originator

Sources: Bulletin de la Societe Chimique de France 45, 116. From: J. Am. Chem. Soc. 8(1), 21 1886.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Synthesis of an advanced intermediate for (+)-pillaromycinone. Staunton-Weinreb annulation revisited.
2008 Jul 3
Structural characterization of CalO2: a putative orsellinic acid P450 oxidase in the calicheamicin biosynthetic pathway.
2009 Jan
Molecular structural studies of lichen substances with antimicrobial, antiproliferative, and cytotoxic effects from Parmelia subrudecta.
2010
The chemical constituents of endophytic fungus Trichoderma sp. MFF-1.
2010 Jul
The COP9 signalosome mediates transcriptional and metabolic response to hormones, oxidative stress protection and cell wall rearrangement during fungal development.
2010 Nov
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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.
Name Type Language
ORSELLINIC ACID
Common Name English
4,6-DIHYDROXY-O-TOLUIC ACID
Common Name English
2,4-DIHYDROXY-6-METHYLBENZENECARBOXYLIC ACID
Systematic Name English
O-ORSELLINIC ACID
MI  
Common Name English
ORCINOLCARBOXYLIC ACID
Common Name English
6-METHYL-.BETA.-RESORCYLIC ACID
Common Name English
2,4-DIHYDROXY-6-METHYLBENZOIC ACID
Systematic Name English
O-ORSELLINIC ACID [MI]
Common Name English
Code System Code Type Description
WIKIPEDIA
ORSELLINIC ACID
Created by admin on Fri Dec 15 17:55:19 GMT 2023 , Edited by admin on Fri Dec 15 17:55:19 GMT 2023
PRIMARY
PUBCHEM
68072
Created by admin on Fri Dec 15 17:55:19 GMT 2023 , Edited by admin on Fri Dec 15 17:55:19 GMT 2023
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MERCK INDEX
m8247
Created by admin on Fri Dec 15 17:55:19 GMT 2023 , Edited by admin on Fri Dec 15 17:55:19 GMT 2023
PRIMARY Merck Index
MESH
C501612
Created by admin on Fri Dec 15 17:55:19 GMT 2023 , Edited by admin on Fri Dec 15 17:55:19 GMT 2023
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FDA UNII
11XLA0494B
Created by admin on Fri Dec 15 17:55:19 GMT 2023 , Edited by admin on Fri Dec 15 17:55:19 GMT 2023
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CAS
480-64-8
Created by admin on Fri Dec 15 17:55:19 GMT 2023 , Edited by admin on Fri Dec 15 17:55:19 GMT 2023
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CHEBI
32807
Created by admin on Fri Dec 15 17:55:19 GMT 2023 , Edited by admin on Fri Dec 15 17:55:19 GMT 2023
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EPA CompTox
DTXSID20197385
Created by admin on Fri Dec 15 17:55:19 GMT 2023 , Edited by admin on Fri Dec 15 17:55:19 GMT 2023
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