(4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one

• ChemBase ID: 155794
• Molecular Formular: C15H22O5
• Molecular Mass: 282.33218
• Monoisotopic Mass: 282.1467238
• SMILES: C[C@@H]1CC[C@H]2[C@H](C(=O)O[C@H]3[C@]42[C@H]1CCC(O3)(OO4)C)C
• Canonical SMILES: O=C1O[C@@H]2OC3(C)CC[C@@H]4[C@]2([C@H]([C@H]1C)CC[C@H]4C)OO3
• InChI: InChI=1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14?,15-/m1/s1
• InChIKey: BLUAFEHZUWYNDE-DCJAHCNHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecan-10-one
• IUPAC Traditional name: (4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecan-10-one
• Synonyms: Arteannuin; Qinghaosu; Artemisinin

Database IDs

• CAS Number: 63968-64-9
• MDL Number: MFCD00081057
• PubChem SID: 162249932; 24862236
• PubChem CID: 452191

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.114058
• LogD (pH = 7.4): 3.114058
• Log P: 3.114058
• Molar Refractivity: 68.6817 cm^3
• Polarizability: 28.359936 Å^3
• Polar Surface Area: 53.99 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 156-157 °C(lit.)
• Optical Rotation: [α]20/D +76°, c = 0.5 in methanol

Safety Information

• RTECS: KD4170000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C15H22O5

DETAILS

Sigma Aldrich - 361593

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Packaging
100 mg in glass bottle
Biochem/physiol Actions
Artemisinin (Qinghaosu), a sesquiterpene lactone, is a highly active anti-malarial (falciparum malaria) drug. Artemisinin is also an anthelmintic (parasitic worm) effective against the blood fluke, schistosomiasis.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 361593.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.