Gyrophoric acid

Modify Date: 2025-08-25 18:47:36

Gyrophoric acid Structure
Gyrophoric acid structure
Common Name Gyrophoric acid
CAS Number 548-89-0 Molecular Weight 468.410
Density 1.5±0.1 g/cm3 Boiling Point 693.9±55.0 °C at 760 mmHg
Molecular Formula C24H20O10 Melting Point N/A
MSDS N/A Flash Point 238.5±25.0 °C

 Use of Gyrophoric acid


Gyrophoric acid is a good ultraviolet filter in lichen populations. Gyrophoric acid shows DPPH radical scavenging activity with an IC50 value of 105.75 µg/ml[1][2].

 Names

Name 4-[4-(2,4-dihydroxy-6-methylbenzoyl)oxy-2-hydroxy-6-methylbenzoyl]oxy-2-hydroxy-6-methylbenzoic acid
Synonym More Synonyms

 Gyrophoric acid Biological Activity

Description Gyrophoric acid is a good ultraviolet filter in lichen populations. Gyrophoric acid shows DPPH radical scavenging activity with an IC50 value of 105.75 µg/ml[1][2].
Related Catalog
In Vitro Gyrophoric acid (200 μM) leads to significant decrease of mitochondrial membrane potential in ovarian cancer cells A2780 after 24 h long exposure but not in HT-29 colon adenocarcinoma cells. Gyrophoric acid significantly inhibits cell growth and affects the expression of Bcl-2, Bax and Hsp70 proteins but only on higher concentration in A375 melanoma cancer cells. Gyrophoric acid treatment on HeLa cells clearly indicates ROS production and apoptosis as form of occurred cell death. Moreover, DNA damage and changing activity of stress/survival proteins as p38MAPK, Erk1/2 and Akt mediated by Gyrophoric acid treatment confirm pro-apoptotic potential[2].
References

[1]. Kosanic M, et al. Biological activities and chemical composition of lichens from Serbia. EXCLI J. 2014;13:1226-1238. Published 2014 Nov 18.

[2]. Goga M, et al. Oxidative stress mediated by gyrophoric acid from the lichen Umbilicaria hirsuta affected apoptosis and stress/survival pathways in HeLa cells. BMC Complement Altern Med. 2019;19(1):221. Published 2019 Aug 19.

 Chemical & Physical Properties

Density 1.5±0.1 g/cm3
Boiling Point 693.9±55.0 °C at 760 mmHg
Molecular Formula C24H20O10
Molecular Weight 468.410
Flash Point 238.5±25.0 °C
Exact Mass 468.105652
PSA 170.82000
LogP 6.62
Vapour Pressure 0.0±2.3 mmHg at 25°C
Index of Refraction 1.686
InChIKey ATQPZSQVWCPVGV-UHFFFAOYSA-N
SMILES Cc1cc(OC(=O)c2c(C)cc(OC(=O)c3c(C)cc(O)cc3O)cc2O)cc(O)c1C(=O)O

 Safety Information

Hazard Codes Xi

 Gyrophoric acidBioassay

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Name: Primary cell-based high-throughput screening assay for identification of compounds th...
Source: Johns Hopkins Ion Channel Center
Target: regulator of G-protein signaling 4 isoform 2 [Homo sapiens]
External Id: JHICC_RGS_Act_HTS
Name: Effect on uncoupled photosystem 2 of spinach chloroplast assessed as inhibition of el...
Source: ChEMBL
Target: N/A
External Id: CHEMBL970895
Name: Luminescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: mu-type opioid receptor isoform MOR-1 [Homo sapiens]
External Id: OPRM1-OPRD1_AG_LUMI_1536_1X%ACT PRUN
Name: Effect on uncoupled photosystem 2 of spinach leaves chloroplast assessed as inhibitio...
Source: ChEMBL
Target: N/A
External Id: CHEMBL970894
Name: QFRET-based biochemical primary high throughput screening assay to identify exosite i...
Source: The Scripps Research Institute Molecular Screening Center
Target: disintegrin and metalloproteinase domain-containing protein 17 preproprotein [Homo sapiens]
External Id: ADAM17_INH_QFRET_1536_1X%INH PRUN
Name: Effect on uncoupled photosystem 2 of spinach chloroplast assessed as inhibition of el...
Source: ChEMBL
Target: N/A
External Id: CHEMBL970897
Name: Effect on uncoupled photosystem 2 of spinach chloroplast assessed as inhibition of el...
Source: ChEMBL
Target: N/A
External Id: CHEMBL970896
Name: Effect on uncoupled photosystem 2 of spinach leaves chloroplast assessed as inhibitio...
Source: ChEMBL
Target: N/A
External Id: CHEMBL970891
Name: Phytogrowth-inhibitory activity against Echinochloa crusgalli assessed as inhibition ...
Source: ChEMBL
Target: Echinochloa crus-galli
External Id: CHEMBL970890
Name: Fluorescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: muscarinic acetylcholine receptor M1 [Homo sapiens]
External Id: CHRM1_AG_FLUO8_1536_1X%ACT PRUN
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 Synonyms

Benzoic acid, 4-[(2,4-dihydroxy-6-methylbenzoyl)oxy]-2-hydroxy-6-methyl-, 4-carboxy-3-hydroxy-5-methylphenyl ester
4-({4-[(2,4-Dihydroxy-6-methylbenzoyl)oxy]-2-hydroxy-6-methylbenzoyl}oxy)-2-hydroxy-6-methylbenzoic acid
Gyrophoric acid
Gyrophorsaeure
p-Triorsellinsaeure
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