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lobaric acid
11H-dibenzo(b,e)(1,4)dioxepin-7-carboxylic acid, 8-hydroxy-3-methoxy-11-oxo-1-(1-oxopentyl)-6-pentyl-

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Name:3-hydroxy-9-methoxy-6-oxo-7-pentanoyl-1-pentylbenzo[b][1,4]benzodioxepine-2-carboxylic acid
CAS Number: 522-53-2Picture of molecule3D/inchi
FDA UNII: Search
Nikkaji Web:J11.718H
MDL:MFCD00597234
XlogP3-AA:6.10 (est)
Molecular Weight:456.49176000
Formula:C25 H28 O8
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 667.90 °C. @ 760.00 mm Hg (est)
Flash Point: 438.00 °F. TCC ( 225.70 °C. ) (est)
logP (o/w): 7.070 (est)
Soluble in:
 water, 0.007725 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Lobaric acid ≥95%
Odor: characteristic
Use: Lobaric acid is a metabolite isolated from the lichen Stereocaulon alpinum. It exhibits potent in vitro inhibitory effects on a
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for lobaric acid usage levels up to:
 not for fragrance use.
 
Recommendation for lobaric acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :73157
National Institute of Allergy and Infectious Diseases:Data
3-hydroxy-9-methoxy-6-oxo-7-pentanoyl-1-pentylbenzo[b][1,4]benzodioxepine-2-carboxylic acid
Chemidplus:0000522532
 
References:
 3-hydroxy-9-methoxy-6-oxo-7-pentanoyl-1-pentylbenzo[b][1,4]benzodioxepine-2-carboxylic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):73157
Pubchem (sid):135029816
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 parmelia
Search PMC Picture
 stereocaulon
Search PMC Picture
 
Synonyms:
11H-dibenzo(b,e)(1,4)dioxepin-7-carboxylic acid, 8-hydroxy-3-methoxy-11-oxo-1-(1-oxopentyl)-6-pentyl-
8-hydroxy-3-methoxy-11-oxo-1-(1-oxopentyl)-6-pentyl-11H-dibenzo(b,e)(1,4)dioxepin-7-carboxylic acid
8-hydroxy-3-methoxy-11-oxo-1-pentanoyl-6-pentyl-11H-dibenzo[b,e][1,4]dioxepine-7-carboxylic acid
3-hydroxy-9-methoxy-6-oxo-7-pentanoyl-1-pentylbenzo[b][1,4]benzodioxepine-2-carboxylic acid
 usnetic acid
 

Articles:

PubMed:UV-protectant metabolites from lichens and their symbiotic partners.
PubMed:Sekikaic acid and lobaric acid target a dynamic interface of the coactivator CBP/p300.
PubMed:Lobarin from the Sumatran lichen, Stereocaulon halei.
PubMed:Cytotoxic activity and antioxidant capacity of purified lichen metabolites: an in vitro study.
PubMed:Antioxidant activity of some lichen metabolites.
PubMed:Antimitotic activity of lobaric acid and a new benzofuran, sakisacaulon A from Stereocaulon sasakii.
PubMed:Protein tyrosine phosphatase 1B inhibitory effects of depsidone and pseudodepsidone metabolites from the Antarctic lichen Stereocaulon alpinum.
PubMed:Eubacterium rangiferina, a novel usnic acid-resistant bacterium from the reindeer rumen.
PubMed:Spectroscopic and photochemical properties of the lichen compound lobaric acid.
PubMed:Anti-proliferative lichen compounds with inhibitory activity on 12(S)-HETE production in human platelets.
PubMed:Anti-proliferative effects of lichen-derived lipoxygenase inhibitors on twelve human cancer cell lines of different tissue origin in vitro.
PubMed:Antimycobacterial activity of lichen metabolites in vitro.
PubMed:Anti-proliferative effects of lichen-derived inhibitors of 5-lipoxygenase on malignant cell-lines and mitogen-stimulated lymphocytes.
PubMed:Effect of lobaric acid on cysteinyl-leukotriene formation and contractile activity of guinea pig taenia coli.
PubMed:Inhibitory effects of the lichen metabolite lobaric acid on arachidonate metabolism in vitro.
 
Notes:
inhibits formation of leukotrienes c4, d4, and e4; also reduces muscle contraction.
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