125-46-2CC(=O)c1c(O)c(C)c(O)c2c1OC1=CC(=O)C(C(C)=O)C(=O)C12CCUCUKLJLRRAKFN-UHFFFAOYSA-N7-Hydroxy-(S)-usnate is a member of benzofurans.
125-46-2DTXSID0040123CHEMBL1375951CHEBI:2264... yellowish /colored/ pigment.
Yellow orthorombic prisms from acetone
Crystalline yellow solid
Solubility at 25 °C (g/100 ml): acetone, 0.77; ethyl acetate, 0.88; fural, 7.32; furfuryl alcohol, 1.21
Solubility at 25 °C (g/100 ml): water, <0.01
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Danger
H301 (70.2%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P273, P301+P316, P301+P317, P321, P330, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 94 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Chemical: 1,3(2H,9bH)-Dibenzofurandione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-
1,3(2H,9bH)-Dibenzofurandione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
The physiological effects of usnic acid /was investigated/ in two cultured species of the lichen alga Trebouxia. Exposing Trebouxia to the sodium salt of usnic acid resulted in the inhibition of growth and photosynthesis, an incr in membrane permeability and immobilization of zoospore. /Usnic acid, sodium salt/
The mechanism of action expressed by usnic acid remains speculative. (+)-Usnic acid has been shown to be an uncoupler of oxidative phosphorylation in mouse-liver mitochondria at levels of 1 uM.
The accumulation of usnic acid can be stimulated by the inhibition of photosynthesis, suggesting a possible role of glucose in regulating enzymes of phenol synthesis.
Experiments show that usnic acid is an allelopathic agent, inhibiting moss spore germination and that its effectiveness is pH dependent.
In vitro, usnic acid has a slight inhibitory action against leukotriene biosynthesis in bovine polymorphonuclear leukocytes by a specific enzyme interaction rather than acting as an antioxidant against the peroxidation process, or as a scavenger, or even as a source of free radicals.
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Agents used to treat trichomonas infections.
Antibacterial compound present in lichens; [Merck Index] Used as preservative and antibiotic (folk remedy); [HSDB] Used as a topical antibiotic; Workers exposed to lichens (forestry and horticulture) may develop allergic contact dermatitis. [Kanerva, p. 1845]
Ingesting herbal remedies [Category: Food & Drugs]
Medicine: antibiotic /SRP: folk remedy/
Preservative
Usnic acid is effective in vitro against ...anerobic bacteria.
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불러오는 중…
Pale yellow silky needles; slightly soluble in water /Sodium salt dihydrate/
Occurs in nature in both the d- and l-forms as well as a racemic mixture.
Crystalline, yellow solid. Insoluble in water; slightly soluble in alcohol and ether.
Several cases of clinically apparent acute liver injury have been attributed to commercial dietary supplements that contain usnic acid. “LipoKinetix” was one such supplement advertised as a weight loss and body building supplement. Each tablet contained sodium usniate (100 mg), norephedrine (25 mg), diiodothyronine (100 mg), yohimbine (3 mg) and caffeine (100 mg). The product has been linked to multiple instances of acute liver injury. The time to onset was 2 to 12 weeks and the clinical presentation resembled acute viral hepatitis with onset of fatigue and nausea, followed by jaundice. The pattern of serum enzyme elevations was hepatocellular, with marked elevations in serum ALT and minimal increases in alkaline phosphatase levels. Liver biopsy demonstrated acute hepatocellular necrosis and inflammation. Immunoallergic features (fever, rash and eosinophilia) were not common and autoantibodies were usually not present. Recovery was rapid with stopping the dietary supplement, but some cases were severe and led to acute liver failure and either death or need for emergency liver transplantation. Instances of acute hepatitis have also been reported with other multi-ingredient dietary supplements that contain usnic acid, but much more rarely than with LipoKinetix which was withdrawn from distribution after a FDA warning letter. Rare instances of hepatotoxicity have also been reported with use of lichen based teas known as Kombucha tea, but whether these were due to usnic acid or another contaminant of the tea was not shown.
The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=125-46-2]
Usnic acid is one of the most common and abundant lichen metabolites.
Usnic acid is widely distributed in species of Cladonia (Cladoniaceae),Usnea (Usneaceae), Lecanora (Lecanoraceae), Ramalina (Ramalinaceae), Evernia, Parmelia (Parmeliaceae) and other lichen species.
/HUMAN EXPOSURE STUDIES/ ... Usnic acid gave negative patch test reactions in subjects found to be allergic to lichen substances. ... Positive test reactions against usnic acid in 0.35% of tested patients.
/HUMAN EXPOSURE STUDIES/ Two forest workers affected with allergic contact dermatitis, which occurred only during work in forest areas, showed positive patch test reactions to lichens containing usnic acid and to isolated usnic acid. Lichens are plants composed of fungi living in symbiosis with algae. Usnic acid, one of the lichenic acids which accumulates in lichenized fungi, is a monobasic acid with dibenzofuran structure and antibiotic properties. Dibenzofuran is chemically related to furocoumarans. Lichens are plentiful in temperate zone forests and allergy to usnic acid represents some part of the "cedar-poisoning" problem in British Columbia. Geographical distribution of lichens containing usnic acid suggests that allergy to usnic acid will be found to be more common than presently recognized.
/SIGNS AND SYMPTOMS/ The only reported adverse effects /concerning usnic acid toxicity in humans/ are local irritation and allergic contact dermatitis, sometimes accompanied by conjunctivitis.
/SPECIAL STUDIES/ In vitro challenges were /conducted/ on primary and continuously cultured cells /to determine/ the cytotoxic action of usnic acid alone or as a component of oral care formulations. The cell strains KB human epidermoid and gingival keratinocytes and fibroblasts (taken from human biopsies), usnic acid alone or as part of a formulation did not /result/ in any sign of cytotoxicity. ...
For more Human Toxicity Excerpts (Complete) data for USNIC ACID (6 total), please visit the HSDB record page.
/LABORATORY ANIMALS: Acute Exposure/ The sensitizing potency of the most common lichen substances were determined in Guinea pigs by a modified Freunds' complete adjuvant (FCA) test. ... The sensitizing potency of (-) and (+)-usnic acid was weak. The (-) stereoisomer was found to be twice as active as its counterpart.
/LABORATORY ANIMALS: Acute Exposure/ Sodium usneate administered iv to anesthetized cats at doses of 10 mg/kg led to an augmented rate of metabolism with symptoms such as hyperventilation, increased oxygen consumption and rise in body temperature. /Sodium usneate/
/LABORATORY ANIMALS: Acute Exposure/ Mice were treated orally with aqueous suspensions of (+)-usnic acid in a single dose of either 100 or 200 mg/kg. The effects on femur cells and proteins and on nucleic acids of liver cells were studied 24-72 hr after treatment. (+)-Usnic acid was found to affect the proliferation of polychromatic erythrocytes possibly by interference with RNA biosynthesis. The slight increase in the micronucleated polychromatic erythrocytes without affecting DNA synthesis suggests an effect of usnic acid on spindle apparatus.
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Feeding experiments in ... animals have shown usnic acid to be toxic in high doses. The development of ataxia in sheep and cattle, leading to paralysis of the extremities in severe cases, was attributed to usnic acid following consumption of lichen Parmelia molliuscula.
For more Non-Human Toxicity Excerpts (Complete) data for USNIC ACID (7 total), please visit the HSDB record page.
/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
LD50 Dog iv 40 mg/kg
LD50 Rabbit iv 30 mg/kg
LD50 Rat iv 30 mg/kg
LD50 Rabbit oral 500 mg/kg
For more Non-Human Toxicity Values (Complete) data for USNIC ACID (6 total), please visit the HSDB record page.
1,3(2H,9bH)-Dibenzofurandione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-: ACTIVE
Antibacterial substance found in lichens. Isolation from varieties of Usnea barbata.
용도Usnic acid is a major metabolite from a number of lichen and fungal species and is perhaps one of the longest known microbial metabolites, first isolated in 1844. Usnic acid exhibits a broad range of biological activity, indeed it is easier to list the bioassays in which it does not exhibit activity. More often than not, potency is low and of limited value. Usnic acid is an important metabolite for dereplication in discovery research programs.
정의ChEBI: A member of the class of dibenzofurans that is dibenzo[b,d]furan-1(9bH)-one substituted by acetyl groups at positions 2 and 6, hydroxy groups at positions 3 and 7 and methyl groups at positions 8 and 9b.