vulpinic acid
benzeneacetic acid, alpha-(3-hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)-, methyl ester, (E)- (9CI)
Identification
| Name | vulpinic acid |
| IUPAC | methyl (2Z)-2-(3-hydroxy-5-oxo-4-phenylfuran-2-ylidene)-2-phenylacetate |
| CAS Number | 521-52-8 |
| EINECS | 208-314-1 |
| FDA UNII | 13N7RF6M84 |
| Molecular Formula | C19 H14 O5 |
| Molecular Weight | 322.31658000 |
| MDL Number | MFCD00075804 |
| Beilstein | 1437166 |
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 Toxicity | intraperitoneal-mouse LD50 75 mg/kg |
| 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', 'U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02804']
Safety in Use
| Category | herbicides / pesticides |
| Recommendation for vulpinic acid usage levels up to | not for fragrance use. |
| Recommendation for vulpinic acid flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
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.