EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes

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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CAS Number: 19683-98-8Picture of molecule3D/inchi
FDA UNII: Search
XlogP3-AA:0.60 (est)
Molecular Weight:296.36328000
Formula:C16 H24 O5
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:antidandruff, antimicrobial agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
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Pubchem Patents:Search
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)
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: antidandruff agents
antimicrobial agents
BOC Sciences
For experimental / research use only.
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
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
Experientia. Vol. 44, Pg. 611, 1988.

Inhalation Toxicity:
Not determined
Safety in Use Information:
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.
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 :29739
National Institute of Allergy and Infectious Diseases:Data
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):29739
Pubchem (sid):134992397
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
KEGG (GenomeNet):C09674
HMDB (The Human Metabolome Database):HMDB38120
VCF-Online:VCF Volatile Compounds in Food
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
 lettuce seed
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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)-(-)-


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].
sesquiterpene isolated from culture filtrate of fungus pseudorotium ovalis; shows antitumor activity. Found in lettuce seeds
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