ovalicin
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)-(-)-
 
Notes:
sesquiterpene isolated from culture filtrate of fungus pseudorotium ovalis; shows antitumor activity. Found in lettuce seeds
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7-hydroxy-8-methoxy-7-[2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-4-oxaspiro[2.5]octan-2-one (Click)
CAS Number: 19683-98-8Picture of molecule
XlogP3-AA: 0.60 (est)
Molecular Weight: 296.36328000
Formula: C16 H24 O5
NMR Predictor: Predict (works with chrome or firefox)
Category: antidandruff, antimicrobial agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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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)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antidandruff agents
antimicrobial agents
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Suppliers:
 None found
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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:
intraperitoneal-guinea pig LD50  5500 ug/kg
Experientia. Vol. 44, Pg. 611, 1988.

intravenous-guinea pig LD50  7 mg/kg
Experientia. Vol. 44, Pg. 611, 1988.

intraperitoneal-mouse LD50  160 mg/kg
"CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 6, Pg. 63, 1981.

intravenous-mouse LD50  > 100 mg/kg
Experientia. Vol. 44, Pg. 611, 1988.

intravenous-rat LD50  > 200 mg/kg
Experientia. Vol. 44, Pg. 611, 1988.

Dermal Toxicity:
skin-guinea pig LD50 200 ug/kg
BEHAVIORAL: EXCITEMENT BEHAVIORAL: IRRITABILITY BEHAVIORAL: FLUID INTAKE
Experientia. Vol. 44, Pg. 611, 1988.

Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: antidandruff, antimicrobial agents
Recommendation for ovalicin usage levels up to:
 not for fragrance use.
 
Recommendation for ovalicin flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 29739
National Institute of Allergy and Infectious Diseases: Data
 7-hydroxy-8-methoxy-7-[2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-4-oxaspiro[2.5]octan-2-one
Chemidplus: 0019683988
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References:
 7-hydroxy-8-methoxy-7-[2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-4-oxaspiro[2.5]octan-2-one
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 29739
Pubchem (sid): 134992397
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
KEGG (GenomeNet): C09674
HMDB (The Human Metabolome Database): HMDB38120
FooDB: FDB017345
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 lettuce seed
Search Trop  Picture
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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-oxaspiro(2,5)octan-6-one, 4-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-4-hydroxy-5-methoxy-, (1S,2R,3S,4R,5S)-(-)-
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Articles:
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].
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