1-oxaspiro(2,5)octan-6-one, 4-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-4-hydroxy-5-methoxy-, (1S,2R,3S,4R,5S)-(-)-

CAS: 19683-98-8 C16 H24 O5 MW: 296.36328000

Identification

Nameovalicin
IUPAC7-hydroxy-8-methoxy-7-[2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-4-oxaspiro[2.5]octan-2-one
CAS Number19683-98-8
FDA UNIISearch
Molecular FormulaC16 H24 O5
Molecular Weight296.36328000

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 447.51 °C. @ 760.00 mm Hg (est)
Flash Point 323.00 °F. TCC ( 161.70 °C. ) (est)
logP (o/w) -0.136 (est)
Soluble in water, 87.11 mg/L @ 25 °C (est)

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesantidandruff agents

No sensory data available

Safety Information

Oral/Parenteral Toxicityintraperitoneal-guinea pig LD50 5500 ug/kg
Dermal Toxicityskin-guinea pig LD50 200 ug/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryantidandruff, antimicrobial agents
Recommendation for ovalicin usage levels up tonot for fragrance use.
Recommendation for ovalicin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

lettuce seed

Synonyms

(1S,2R,3S,4R,5S)-(-)-4-(1,2- epoxy-1,5-dimethyl-4-hexenyl)-4-hydroxy-5-methoxy-1-oxaspiro(2,5)octan-6-one graphinone 7- hydroxy-8-methoxy-7-[2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-4-oxaspiro[2.5]octan-2-one 1-oxa spiro(2,5)octan-6-one, 4-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-4-hydroxy-5-methoxy-, (1S,2R,3S,4R,5S)-(-)- PubMed: Polyketides from the littoral plant associated fungus Pseudallescheria boydii. PubMed: Ovalicin ameliorates compound 48/80-induced atopic dermatitis-related symptoms. PubMed: Syntheses of fumagillin and ovalicin. PubMed: In vivo activity of cationic immune stimulating complexes (PLUSCOMs). PubMed: Total syntheses of (+/-)-ovalicin, C4(S *)-isomer, and its C5-analogs and anti-trypanosomal activities. PubMed: A Diels-Alder approach to (-)-ovalicin. PubMed: New bioactive sesquiterpenes from Ripartites metrodii and R. tricholoma. PubMed: Structure of the angiogenesis inhibitor ovalicin bound to its noncognate target, human Type 1 methionine aminopeptidase. PubMed: Antimicrosporidial activities of fumagillin, TNP-470, ovalicin, and ovalicin derivatives in vitro and in vivo. PubMed: Methionine aminopeptidase 2 and cancer. PubMed: Concise enantio- and diastereoselective total syntheses of fumagillol, RK-805, FR65814, ovalicin, and 5-demethylovalicin. PubMed: Synthesis of ovalicin starting from D-mannose. PubMed: Structural basis for the functional differences between type I and type II human methionine aminopeptidases. PubMed: Investigations into microsporidian methionine aminopeptidase type 2: a therapeutic target for microsporidiosis. PubMed: Synthesis and biological evaluation of novel fumagillin and ovalicin analogues. PubMed: A single amino acid residue defines the difference in ovalicin sensitivity between type I and II methionine aminopeptidases. PubMed: Development of Protacs to target cancer-promoting proteins for ubiquitination and degradation. PubMed: Fumagalone, a reversible inhibitor of type 2 methionine aminopeptidase and angiogenesis. PubMed: Methionine aminopeptidase 2 is a new target for the metastasis-associated protein, S100A4. PubMed: QSAR of the inhibition of angiogenesis by TNP-470 and ovalicin analogues: another example of an allosteric interaction. PubMed: Protacs: chimeric molecules that target proteins to the Skp1-Cullin-F box complex for ubiquitination and degradation. PubMed: Structure and function of the methionine aminopeptidases. PubMed: Selective inhibition of amino-terminal methionine processing by TNP-470 and ovalicin in endothelial cells. PubMed: Antifungal activities of antineoplastic agents: Saccharomyces cerevisiae as a model system to study drug action. PubMed: Mer-f3, 12-hydroxy-ovalicin, produced by Metarrhizium sp. f3. PubMed: Molecular recognition of angiogenesis inhibitors fumagillin and ovalicin by methionine aminopeptidase 2. PubMed: Synthetic analogues of TNP-470 and ovalicin reveal a common molecular basis for inhibition of angiogenesis and immunosuppression. PubMed: The anti-angiogenic agent fumagillin covalently modifies a conserved active-site histidine in the Escherichia coli methionine aminopeptidase. PubMed: Methionine aminopeptidase (type 2) is the common target for angiogenesis inhibitors AGM-1470 and ovalicin. PubMed: Chlovalicin, a new cytocidal antibiotic produced by Sporothrix sp. FO-4649. II. Physicochemical properties and structural elucidation. PubMed: Chlovalicin, a new cytocidal antibiotic produced by Sporothrix sp. FO-4649. I. Taxonomy, fermentation, isolation and biological activities. PubMed: The history of cyclosporin A (Sandimmune) revisited: another point of view. PubMed: Enhanced toxicity of the immunosuppressant ovalicin upon application to the skin. PubMed: On the mode of action of the immunosuppressive sesquiterpene ovalicin. PubMed: On the mechanism of action of the cytostatic drug anguidine and of the immunosuppressive agent ovalicin, two sesquiterpenes from fungi. PubMed: Application of deuterium magnetic resonance to biosynthetic studies. 1. Biosynthesis of ovalicin. PubMed: Application of carbon-13 magnetic resonance to isoprenoid biosynthesis. II. Ovalicin and the use of doubly labeled mevalonate. PubMed: Letter: Application of carbon-13 magnetic resonance to isoprenoid biosynthesis. I. Ovalicin. PubMed: Immunosuppressive effects of ovalicin-semicarbazone. PubMed: [Structure of ovalicin]. PubMed: Effect of the immunosuppressive agent ovalicin on the kinetics of antibody formation. PubMed: Immunosuppressive effect of a new antibiotic: ovalicin. PubMed: Immunosuppressive and specific antimitotic effects of ovalicin. PubMed: [Isolation and structure elucidation of ovalicin].