atranorin
parmelin
Identification
| Name | atranorin |
| IUPAC | (3-hydroxy-4-methoxycarbonyl-2,5-dimethylphenyl)3-formyl-2,4-dihydroxy-6-methylbenzoate |
| CAS Number | 479-20-9 |
| EINECS | 207-527-7 |
| FDA UNII | 450U2VJ2VG |
| Molecular Formula | C19 H18 O8 |
| Molecular Weight | 374.34606000 |
| MDL Number | MFCD00016597 |
| Nikkaji Number | J12.600D |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 195.00 °C. @ 760.00 mm Hg |
| Boiling Point | 535.70 °C. @ 760.00 mm Hg (est) |
| Flash Point | 373.00 °F. TCC ( 189.30 °C. ) (est) |
| logP (o/w) | 6.140 (est) |
| Soluble in | water, 0.02303 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| 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 atranorin usage levels up to | not for fragrance use. |
| Recommendation for atranorin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
antranoric acid
atranoric acid
atranorine
benzoic acid, 3-formyl-2,4-dihydroxy-6-methyl-, 3-hydroxy-4- (methoxycarbonyl)-2,5-dimethylphenyl ester
benzoic acid, 3-formyl-2,4-dihydroxy-6-methyl-, 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester (9CI)
3-
formyl-2,4-dihydroxy-6-methylbenzoic acid 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester
3-
hydroxy-4-(methoxycarbonyl)-2,5-dimethyl phenyl 3-formyl-2,4-dihydroxy-6-methyl benzoate
3-
hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl 3-formyl-2,4-dihydroxy-6-methylbenzoate
(3-
hydroxy-4-methoxycarbonyl-2,5-dimethylphenyl)3-formyl-2,4-dihydroxy-6-methylbenzoate
methyl 1-(3-formyl-2,4-dihydroxy-6-methylphenylcarbonyloxy)-3-hydroxy-2,5-dimethyl-4-benzenecarboxylate
parmelin
parmelin acid
iso
phthalaldehydic acid, 2,4-dihydroxy-6-methyl-, 4-ester with methyl 3,6-dimethyl-b-resorcylate (8CI)
usnarin
usnarin acid
PubMed:
Clastogenic effect of atranorin, evernic acid, and usnic acid on human lymphocytes.
PubMed:
Redox properties and cytoprotective actions of atranorin, a lichen secondary metabolite.
PubMed:
Variable responses of different human cancer cells to the lichen compounds parietin, atranorin, usnic acid and gyrophoric acid.
PubMed:
Antinociceptive activity of atranorin in mice orofacial nociception tests.
PubMed:
Antimicrobial and antibiofilm activity of secondary metabolites of lichens against methicillin-resistant Staphylococcus aureus strains from cystic fibrosis patients.
PubMed:
Depsides: lichen metabolites active against hepatitis C virus.
PubMed:
Ecological implication of variation in the secondary metabolites in Parmelioid lichens with respect to altitude.
PubMed:
Purification, physicochemical properties, thermal analysis and antinociceptive effect of atranorin extracted from Cladina kalbii.
PubMed:
Contact allergy to atranorin in lichens and perfumes.
PubMed:
The antimicrobial activity of extracts of the lichen Cladonia foliacea and its (-)-usnic acid, atranorin, and fumarprotocetraric acid constituents.
PubMed:
Antimicrobial activity of extracts of chemical races of the lichen Pseudevernia furfuracea and their physodic acid, chloroatranorin, atranorin, and olivetoric acid constituents.
PubMed:
The sensitizing capacity of atranorin.
PubMed:
Enzymatic production of atranorin: a component of the oak moss absolute by immobilized lichen cells.
PubMed:
Identification of atranorin and related potential allergens in oakmoss absolute by high-performance liquid chromatography-tandem mass spectrometry using negative ion atmospheric pressure chemical ionization.
PubMed:
Secondary metabolites of the lichen Hypogymnia physodes (L.) Nyl. and their presence in spruce (Picea abies (L.) H. Karst.) bark.
PubMed:
Airborne contact dermatitis from atranorin.
PubMed:
Larvicidal activity of some secondary lichen metabolites against the mosquito Culiseta longiareolata Macquart (Diptera: Culicidae).
PubMed:
Atranorin and oak moss contact allergy.
PubMed:
Lichen secondary metabolites as DNA-interacting agents.
PubMed:
Lichen secondary metabolites are responsible for induction of apoptosis in HT-29 and A2780 human cancer cell lines.
PubMed:
Antimalarial drug interactions of compounds isolated from Kigelia africana (Bignoniaceae) and their synergism with artemether, against the multidrug-resistant W2mef Plasmodium falciparum strain.
PubMed:
Growth promoting effects of some lichen metabolites on probiotic bacteria.
PubMed:
Biosynthesis of lichen depsides, lecanoric acid and atranorin.
PubMed:
Light screening in lichen cortices can be quantified by chlorophyll fluorescence techniques for both reflecting and absorbing pigments.
PubMed:
Effect of vicanicin and protolichesterinic acid on human prostate cancer cells: role of Hsp70 protein.
PubMed:
Platismatia glaucia and Pseudevernia furfuracea lichens as sources of antioxidant, antimicrobial and antibiofilm agents.
PubMed:
Biological activities and chemical composition of lichens from Serbia.
PubMed:
β-Orcinol-type depsides from the lichen Thamnolia vermicularis.
PubMed:
Dereplication of depsides from the lichen Pseudevernia furfuracea by centrifugal partition chromatography combined to 13C nuclear magnetic resonance pattern recognition.
PubMed:
A new depside from Usnea aciculifera growing in Vietnam.
PubMed:
Biologically active components of a Papua New Guinea analgesic and anti-inflammatory lichen preparation.
PubMed:
UV-protectant metabolites from lichens and their symbiotic partners.
PubMed:
Antibacterial and antioxidant activity of lichen species Ramalina roesleri.
PubMed:
Cytotoxic evaluation of phenolic compounds from lichens against melanoma cells.
PubMed:
In vitro antiplasmodial activity and cytotoxicity of crude extracts and compounds from the stem bark of Kigelia africana (Lam.) Benth (Bignoniaceae).
PubMed:
Chemical composition of three Parmelia lichens and antioxidant, antimicrobial and cytotoxic activities of some their major metabolites.
PubMed:
Isolation, characterization and antifungal activity of major constituents of the Himalayan lichen Parmelia reticulata Tayl.
PubMed:
Chemical constituents of Stereospermum acuminatissimum and their urease and α-chymotrypsin inhibitions.
PubMed:
Chemical Composition, Antioxidant, and Antimicrobial Activities of Lichen Umbilicaria cylindrica (L.) Delise (Umbilicariaceae).
PubMed:
A study of lipid secretion from the lichen symbionts, ascomycetous fungus Myelochroa leucotyliza and green alga Trebouxia sp.
PubMed:
Lichen acids as uncouplers of oxidative phosphorylation of mouse-liver mitochondria.
PubMed:
Sensitivity of Xanthoria parietina to UV-A: role of metabolic modulators.
PubMed:
Physiological responses of root-less epiphytic plants to acid rain.
PubMed:
Light might regulate divergently depside and depsidone accumulation in the lichen Parmotrema hypotropum by affecting thallus temperature and water potential.
PubMed:
Solubilization of poorly soluble lichen metabolites for biological testing on cell lines.
PubMed:
Photoprotector capacity of lichen metabolites assessed through the inhibition of the 8-methoxypsoralen photobinding to protein.
PubMed:
Chemical constituents of the lichen, Candelaria concolor: a complete NMR and chemical degradative investigation.
PubMed:
Antimycobacterial activity of lichen substances.
PubMed:
Identification of crystalline material found in the thallus of the lichen, Myelochroa leucotyliza.
PubMed:
Photosensitivity and allergy to aromatic lichen acids, Compositae oleoresins and other plant substances.
PubMed:
Quantitative determination of secondary metabolites in Cladina stellaris and other lichens by micellar electrokinetic chromatography.
PubMed:
Production of phenolics by immobilized cells of the lichen Pseudevernia furfuracea: the role of epiphytic bacteria.
PubMed:
Antimycobacterial activity of lichen metabolites in vitro.
PubMed:
Photohemolytic activity of lichen metabolites.
PubMed:
Lichen metabolites modulate hydrogen peroxide and nitric oxide in mouse macrophages.
PubMed:
Chemistry of the lichen Hypogymnia physodes transplanted to an industrial region.
PubMed:
An investigation of the allergenic constituents of Cladonia stellaris (Opiz) Pous & Vezda ('silver moss', 'reindeer moss' or 'reindeer lichen').
PubMed:
Metabolites from the Lichen Ochrolechia parella growing under two different heliotropic conditions.
PubMed:
Metabolites of Pseudevernia furfuracea (L.) Zopf. and their inhibition potential of proteolytic enzymes.
PubMed:
Phytochemical investigation of the Australian lichens Ramalina glaucescens and Xanthoria parietina.
PubMed:
Characterization of a non-reducing polyketide synthase gene from lichen Dirinaria applanata.
PubMed:
Is a low content in atranol/chloroatranol safe in oak moss-sensitized individuals?
PubMed:
Antimicrobial activity of extracts of the lichen Parmelia sulcata and its salazinic acid constituent.
PubMed:
Lupane triterpenoids from Acacia mellifera with cytotoxic activity.
PubMed:
Ozone reactivity and free radical scavenging behavior of phenolic secondary metabolites in lichens exposed to chronic oxidant air pollution from Mexico City.
PubMed:
Lichen substances affect metal adsorption in Hypogymnia physodes.
PubMed:
A study of the genetic variability of Rhizoplaca chrysoleuca using DNA sequences and secondary metabolic substances.
PubMed:
Identification and quantitation of allelochemicals from the lichen Lethariella canariensis: phytotoxicity and antioxidative activity.
PubMed:
Contact allergy to oak moss: search for sensitizing molecules using combined bioassay-guided chemical fractionation, GC-MS, and structure-activity relationship analysis.
PubMed:
Lichen metabolites. 2. Antiproliferative and cytotoxic activity of gyrophoric, usnic, and diffractaic acid on human keratinocyte growth.
PubMed:
Preparation of an oakmoss absolute with reduced allergenic potential.
PubMed:
Chemical Constituents of the Lichen Ramalina hierrensis.
PubMed:
Contact sensitivity to oak moss.
PubMed:
The Utilization of Urea by the Lichen Cladonia sandstedei.
PubMed:
Perfume allergy due to oak moss and other lichens.
PubMed:
Contact allergy due to lichens in patients with a history of photosensitivity.
PubMed:
First Report of Heterodermia squamulosa (Lichenized Ascomycota, Physciaceae) in South Korea.
PubMed:
Beta-orcinol metabolites from the lichen Hypotrachyna revoluta.
PubMed:
Antifungal constituents from the Chinese moss Homalia trichomanoides.
PubMed:
Comparison of elicitation potential of chloroatranol and atranol--2 allergens in oak moss absolute.
PubMed:
Culture studies and secondary compounds of six Ramalina species.
PubMed:
Phenolic constituents from the lichen Parmotrema stuppeum (Nyl.) Hale and their antioxidant activity.
PubMed:
Allergy to lichen acids in a fragrance.
PubMed:
Lichen metabolites. 1. Inhibitory action against leukotriene B4 biosynthesis by a non-redox mechanism.
PubMed:
Lichen biodeterioration of the Convento de la Peregrina, Sahagún, Spain.
PubMed:
Sequestration of lichen compounds by lichen-feeding members of the Arctiidae (Lepidoptera).
PubMed:
Sequestration of lichen compounds by three species of terrestrial snails.
PubMed:
Contact dermatitis from oak moss.
PubMed:
The occurrence of lichen phenolics in the photobiont cells of Evernia prunastri.
PubMed:
Contact sensitivity to lichens and compositae in Frullania dermatitis.
PubMed:
Photosensitivity to oak moss.
PubMed:
Purification and Properties of the Constitutive Arginase of Evernia prunastri.
PubMed:
Photosensitivity and allergy to aromatic lichen acids, Compositae oleoresins and other plant substances.