artemisitene
(3R-(3alpha,5abeta,6beta,8abeta,12beta,12aR*))-octahydro-3,6-dimethyl-9-methylene-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one
Identification
| Name | artemisitene |
| CAS Number | 101020-89-7 |
| FDA UNII | Search |
| Molecular Formula | C15 H20 O5 |
| Molecular Weight | 280.32040000 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 417.51 °C. @ 760.00 mm Hg (est) |
| Flash Point | 367.00 °F. TCC ( 185.90 °C. ) (est) |
| logP (o/w) | 0.733 (est) |
| Soluble in | water, 59.65 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| 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']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for artemisitene usage levels up to | not for fragrance use. |
| Recommendation for artemisitene flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
(3R-(3alpha,5abeta,6beta,8abeta,12beta,12aR*))-
octahydro-3,6-dimethyl-9-methylene-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one
PubMed:
Anti-plasmodial polyvalent interactions in Artemisia annua L. aqueous extract--possible synergistic and resistance mechanisms.
PubMed:
A rapid method for the determination of artemisinin and its biosynthetic precursors in Artemisia annua L. crude extracts.
PubMed:
Cytotoxic activity of secondary metabolites derived from Artemisia annua L. towards cancer cells in comparison to its designated active constituent artemisinin.
PubMed:
Production of Artemisinin and Related Sesquiterpenes in Japanese Artemisia annua During a Vegetation Period.
PubMed:
From artemisinin to new artemisinin antimalarials: biosynthesis, extraction, old and new derivatives, stereochemistry and medicinal chemistry requirements.
PubMed:
Quantitation of artemisinin and its biosynthetic precursors in Artemisia annua L. by high performance liquid chromatography-electrospray quadrupole time-of-flight tandem mass spectrometry.
PubMed:
Oxidative stress response of tumor cells: microarray-based comparison between artemisinins and anthracyclines.
PubMed:
Recent advances in artemisinin and its derivatives as antimalarial and antitumor agents.
PubMed:
Structure-activity relationships of the antimalarial agent artemisinin. 8. design, synthesis, and CoMFA studies toward the development of artemisinin-based drugs against leishmaniasis and malaria.
PubMed:
Structure-activity relationships of the antimalarial agent artemisinin. 7. Direct modification of (+)-artemisinin and in vivo antimalarial screening of new, potential preclinical antimalarial candidates.
PubMed:
C-16 artemisinin derivatives and their antimalarial and cytotoxic activities: syntheses of artemisinin monomers, dimers, trimers, and tetramers by nucleophilic additions to artemisitene.
PubMed:
Acid catalyzed Michael additions to artemisitene.
PubMed:
Microbial metabolism of artemisitene.
PubMed:
Stereochemistry-dependent cytotoxicity of some artemisinin derivatives.
PubMed:
Correlation of antimalarial activity of artemisinin derivatives with binding affinity with ferroprotoporphyrin IX.
PubMed:
Immunoquantitative analysis of artemisinin from Artemisia annua using polyclonal antibodies.
PubMed:
Artemisinin, Related Sesquiterpenes, and Essential Oil in Artemisia annua During a Vegetation Period in Vietnam.
PubMed:
Synthesis and antimalarial activity of some 9-substituted artemisinin derivatives.
PubMed:
Cytotoxicity of artemisinin-related endoperoxides to Ehrlich ascites tumor cells.
PubMed:
In vitro chloroquine resistant Plasmodium falciparum in Calcutta and its sensitivity to qinghaosu (artemisitene).
PubMed:
Conversion of artemisinin (qinghaosu) to iso-artemisitene and to 9-epi-artemisinin1.
PubMed:
Artemisitene, a New Sesquiterpene Lactone Endoperoxide from Artemisia annua.