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gyrophoric acid
triorsellinic acid

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Name:4-[4-(2,4-dihydroxy-6-methylbenzoyl)oxy-2-hydroxy-6-methylbenzoyl]oxy-2-hydroxy-6-methylbenzoic acid
CAS Number: 548-89-0Picture of molecule3D/inchi
FDA UNII: BAQ44A6C6H
Nikkaji Web:J227.841C
XlogP3-AA:5.60 (est)
Molecular Weight:468.41540000
Formula:C24 H20 O10
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:
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PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Gyrophoric acid 0.98
Odor: characteristic
Use: Gyrophoric acid isolated from the herbs of Parmelia tinctorum Despr. anti-tumor; anti-cancer; antibacterial; antimicrobial; anti-proliferative/cytotoxic effect
Carbosynth
For experimental / research use only.
Gyrophoric Acid
Coompo
For experimental / research use only.
Gyrophoric Acid from Plants ≥96%
 
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 gyrophoric acid usage levels up to:
 not for fragrance use.
 
Recommendation for gyrophoric 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 :135728
National Institute of Allergy and Infectious Diseases:Data
4-[4-(2,4-dihydroxy-6-methylbenzoyl)oxy-2-hydroxy-6-methylbenzoyl]oxy-2-hydroxy-6-methylbenzoic acid
Chemidplus:0000548890
 
References:
 4-[4-(2,4-dihydroxy-6-methylbenzoyl)oxy-2-hydroxy-6-methylbenzoyl]oxy-2-hydroxy-6-methylbenzoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):135728
Pubchem (sid):135090828
 
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
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
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
 

Articles:

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.
 
Notes:
a tridepside isolated from parmelia nepalensis.
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