vulpinic acid

benzeneacetic acid, alpha-(3-hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)-, methyl ester, (E)- (9CI)

CAS: 521-52-8 C19 H14 O5 MW: 322.31658000

Identification

Namevulpinic acid
IUPACmethyl (2Z)-2-(3-hydroxy-5-oxo-4-phenylfuran-2-ylidene)-2-phenylacetate
CAS Number521-52-8
EINECS208-314-1
FDA UNII13N7RF6M84
Molecular FormulaC19 H14 O5
Molecular Weight322.31658000
MDL NumberMFCD00075804
Beilstein1437166

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 568.80 °C. @ 760.00 mm Hg (est)
Flash Point 411.00 °F. TCC ( 210.30 °C. ) (est)
logP (o/w) 2.540 (est)
Soluble in water, 10.59 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral Toxicityintraperitoneal-mouse LD50 75 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02804']

Safety in Use

Categoryherbicides / pesticides
Recommendation for vulpinic acid usage levels up tonot for fragrance use.
Recommendation for vulpinic acid flavor usage levels up tonot for flavor use.

No supplier data available

Potential Uses

None Found

Natural Occurrence

found in nature

Synonyms

acetic acid, (3-hydroxy-5-oxo-4-phenyl-2(5H)-furylidene)phenyl-, methyl ester benzeneacetic acid, alpha-(3-hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)-, methyl ester, (E)- (9CI) delta(sup 2(5H),alpha)- furanacetic acid, 3-hydroxy-5-oxo-alpha,4-diphenyl-, methyl ester delta2(5H),alpha- furanacetic acid, 3-hydroxy-5-oxo-alpha,4-diphenyl-, methyl ester (8CI) 2,4- hexadienedioic acid, 3,4-dihydroxy-2,5-diphenyl-, mono-gamma-lactone, methyl ester 3- hydroxy-5-oxo-alpha,4-diphenyl-delta(sup 2(5H),alpha)-furan acetic acid methyl ester methyl (2Z)-2-(3-hydroxy-5-oxo-4-phenylfuran-2-ylidene)-2-phenylacetate methyl 2-(3,5-dioxo-4-phenyl-2-furylidene)-2-phenylacetate vulpinic acid methyl ester PubMed: Sensitivity of Xanthoria parietina to UV-A: role of metabolic modulators. PubMed: Chemical constituents of the lichen, Candelaria concolor: a complete NMR and chemical degradative investigation. PubMed: Antiproliferative effects on tumour cells and promotion of keratinocyte wound healing by different lichen compounds. PubMed: 3-Aryltetronic acids: efficient preparation and use as precursors for vulpinic acids. PubMed: Suzuki cross-coupling reactions of gamma-alkylidenebutenolides: application to the synthesis of vulpinic acid. PubMed: A bioactive triterpenoid and vulpinic acid derivatives from the mushroom Scleroderma citrinum. PubMed: Two novel ravenelones from the edible mushroom Pulveroboletus ravenelii. PubMed: Chemical and biological investigation of the fungus Pulveroboletus ravenelii. PubMed: Lichen acids as uncouplers of oxidative phosphorylation of mouse-liver mitochondria. PubMed: In vitro activities of the lichen secondary metabolites vulpinic acid, (+)-usnic acid, and (-)-usnic acid against aerobic and anaerobic microorganisms. PubMed: Induction of murine cytochrome P4503A by the lichen constituents usnic and vulpinic acids. PubMed: Antibacterial and antiproliferative activities of vulpinic acids in vitro. PubMed: Note on the action of vulpinic acid.