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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

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

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
[Studies on chemical constituents of Umbilicaria esculenta (Miyoshi) minks].
2001 Sep
Total synthesis of the antiallergic naphtho-alpha-pyrone tetraglucoside, cassiaside C(2), isolated from cassia seeds.
2003 Aug 8
Chromenes of polyketide origin from Peperomia villipetiola.
2005 Mar
The genus Pyrenomyxa and its affinities to other cleistocarpous Hypoxyloideae as inferred from morphological and chemical traits.
2005 Sep-Oct
Inhibition of nitric oxide production in RAW 264.7 cells by azaphilones from xylariaceous fungi.
2006 Jan
Synthesis of gerfelin and related analogous compounds.
2006 Oct
Pigment chemistry, taxonomy and phylogeny of the Hypoxyloideae (Xylariaceae).
2006 Sep
Cytotoxic activity of orsellinates.
2006 Sep-Oct
Molecular structural studies of lichen substances with antimicrobial, antiproliferative, and cytotoxic effects from Parmelia subrudecta.
2010
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:55:19 GMT 2023
Edited
by admin
on Fri Dec 15 17:55:19 GMT 2023
Record UNII
11XLA0494B
Record Status Validated (UNII)
Record Version
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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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY