gyrophoric acid
triorsellinic acid
Identification
| Name | gyrophoric acid |
| IUPAC | 4-[4-(2,4-dihydroxy-6-methylbenzoyl)oxy-2-hydroxy-6-methylbenzoyl]oxy-2-hydroxy-6-methylbenzoic acid |
| CAS Number | 548-89-0 |
| FDA UNII | BAQ44A6C6H |
| Molecular Formula | C24 H20 O10 |
| Molecular Weight | 468.41540000 |
| Nikkaji Number | J227.841C |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 693.90 °C. @ 760.00 mm Hg (est) |
| Flash Point | 461.00 °F. TCC ( 238.50 °C. ) (est) |
| logP (o/w) | 6.620 (est) |
| Soluble in | water, 0.01792 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for gyrophoric acid usage levels up to | not for fragrance use. |
| Recommendation for gyrophoric acid flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
benzoic acid, 4-[(2,4-dihydroxy-6-methylbenzoyl)oxy]-2-hydroxy-6-methyl-, 4-carboxy-3-hydroxy-5-methylphenyl ester
4-(4-
carboxy-3-hydroxy-5-methyl phenoxycarbonyl)-3-hydroxy-5-methyl phenyl 2,4-dihydroxy-6-methyl benzoate
4-[4-(2,4-
dihydroxy-6-methylbenzoyl)oxy-2-hydroxy-6-methylbenzoyl]oxy-2-hydroxy-6-methylbenzoic acid
4-({4-[(2,4-
dihydroxy-6-methylbenzoyl)oxy]-2-hydroxy-6-methylbenzoyl}oxy)-2-hydroxy-6-methylbenzoic acid
triorsellinic acid
PubMed:
Lichen secondary metabolites as DNA-interacting agents.
PubMed:
UV-protectant metabolites from lichens and their symbiotic partners.
PubMed:
Lichenic extracts and metabolites as UV filters.
PubMed:
Lichen secondary metabolites are responsible for induction of apoptosis in HT-29 and A2780 human cancer cell lines.
PubMed:
Antioxidant and antimicrobial properties of some lichens and their constituents.
PubMed:
Larvicidal activity of some secondary lichen metabolites against the mosquito Culiseta longiareolata Macquart (Diptera: Culicidae).
PubMed:
Variable responses of different human cancer cells to the lichen compounds parietin, atranorin, usnic acid and gyrophoric acid.
PubMed:
PTP1B inhibitory effects of tridepside and related metabolites isolated from the Antarctic lichen Umbilicaria antarctica.
PubMed:
Antiproliferative effects on tumour cells and promotion of keratinocyte wound healing by different lichen compounds.
PubMed:
Antimicrobial activity of extracts of the lichen Xanthoparmelia pokornyi and its gyrophoric and stenosporic acid constituents.
PubMed:
Cytotoxic and apoptotic effects on hepatocytes of secondary metabolites obtained from lichens.
PubMed:
Effect of lichen metabolites on thylakoid electron transport and photophosphorylation in isolated spinach chloroplasts.
PubMed:
A revised structure for (-)-dihydropertusaric acid, a gamma-butyrolactone acid from the lichen punctelia microsticta
PubMed:
Lichen metabolites. 2. Antiproliferative and cytotoxic activity of gyrophoric, usnic, and diffractaic acid on human keratinocyte growth.
PubMed:
Lichen metabolites. 1. Inhibitory action against leukotriene B4 biosynthesis by a non-redox mechanism.