3D Mol Similar

xanthatin

: Iupac Name：(3aR,7S,8aS)-7-methyl-3-methylidene-6-[(E)-3-oxobut-1-enyl]-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one; CAS No.: 26791-73-1; Molecular Weight：246.306; Modify Date.: 2022-11-05 22:28; Introduction: Xanthatin is isolated from?Xanthium strumarium?leaves. Xanthatin exhibits strong antitumor activities against a variety of cancer cells through apoptosis?persuasion?and shows anti-inflammatory activities by inhibiting?PGE2?synthesis and?5-lipoxygenase?activity[1]. Xanthatin is a potent and orally active inhibitor of VEGFR2 kinase activity with an IC50 of 3.8 μM and prominently blocks the phosphorylation of VEGFR2 at Tyr951 site. Xanthatin inhibits angiogenesis and has the potential for t View more+

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1. Names and Identifiers

: 1.1 Name; xanthatin; 1.2 Synonyms; (-)-Xanthatin (3aR,7S,8aS)-3,3a,4,7,8,8a-Hexahydro-7-methyl-3-methylene-6-[(1E)-3-oxo-1-buten-1-yl]-2H-cyclohepta[b]furan-2-one 2H-Cyclohepta[b]furan-2-one, 3,3a,4,7,8,8a-hexahydro-7-methyl-3-methylene-6-(3-oxo-1-buten-1-yl)- 2H-Cyclohepta[b]furan-2-one, 3,3a,4,7,8,8a-hexahydro-7-methyl-3-methylene-6-(3-oxo-1-butenyl)-, [3aR-(3aα,7β,8aβ)]- 2H-Cyclohepta[b]furan-2-one, 3,3a,4,7,8,8a-hexahydro-7-methyl-3-methylene-6-[(1E)-3-oxo-1-buten-1-yl]-, (3aR,7S,8aS)- 2H-Cyclohepta[b]furan-2-one, 3,3a,4,7,8,8a-hexahydro-7-methyl-3-methylene-6-[(1E)-3-oxo-1-butenyl]-, (3aR,7S,8aS)- 2H-Cyclohepta[b]furan-2-one,3,3a,4,7,8,8a-hexahydro-7-methyl-3-methylene-6-(3-oxo-1-butenyl)-, [3aR-(3aa,7b,8ab)]- 2H-Cyclohepta[b]furan-2-one,3,3a,4,7,8,8a-hexahydro-7-methyl-3-methylene-6-(3-oxo-1-butenyl)-,(3aR,7S,8aS)- (9CI) 3-Cycloheptene-1-acetic acid, 7-hydroxy-5-methyl-a-methylene-4-(3-oxo-1-butenyl)-, g-lactone (7CI) 3-Cycloheptene-1-acetic acid, 7-hydroxy-5-methyl-α-methylene-4-(3-oxo-1-butenyl)-, γ-lactone 7-Methyl-3-methylene-6-(3-oxo-1-buten-1-yl)-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one Xanthatin (6CI); View all

1.3 CAS No.: 26791-73-1

1.4 CID: 5281511

1.5 Molecular Formula: C15H18O3 (isomer)

1.6 Inchi: InChI=1S/C15H18O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h4-6,9,13-14H,3,7-8H2,1-2H3/b5-4+/t9-,13+,14-/m0/s1

1.7 InChIkey: RBRPTFMVULVGIC-ZTIIIDENSA-N

1.8 Canonical Smiles: CC1CC2C(CC=C1C=CC(=O)C)C(=C)C(=O)O2

1.9 Isomers Smiles: C[C@H]1C[C@H]2[C@H](CC=C1/C=C/C(=O)C)C(=C)C(=O)O2

2. Properties

2.1 Density: 1.1

2.1 Melting point: 114.5-115°

2.1 Boiling point: 444.3°Cat760mmHg

2.1 Refractive index: 1.528

2.1 Flash Point: 199.2°C

2.1 Precise Quality: 246.12600

2.1 PSA: 43.37000

2.1 logP: 2.58570

2.1 Color/Form: Cryst.

3. Use and Manufacturing

3.1 Purification Methods: Crystallise xanthatin from MeOH, aqueous MeOH, EtOH or aqueous EtOH. UV: 213 and 275nm (max 7300). The 2,4-dinitrophenylhydrazone has m 240o(dec) (twice recrystallised from CHCl3/MeOH). [Geissman et al. J Am Chem Soc 76 685 1954, Deuel & Geissman J Am Chem Soc 79 3778 1957, Beilstein 17 III/IV 6221, 17/1 V 305.] xanthatinSupplier

4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

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5. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

6. Other Information

6.0 Purification Methods: Crystallise xanthatin from MeOH, aqueous MeOH, EtOH or aqueous EtOH. UV: 213 and 275nm (max 7300). The 2,4-dinitrophenylhydrazone has m 240o(dec) (twice recrystallised from CHCl3/MeOH). [Geissman et al. J Am Chem Soc 76 685 1954, Deuel & Geissman J Am Chem Soc 79 3778 1957, Beilstein 17 III/IV 6221, 17/1 V 305.]

7. Computational chemical data

Molecular Weight: 246.306g/mol
Molecular Formula: C₁₅H₁₈O₃
Compound Is Canonicalized: True
XLogP3-AA: 2.1
Exact Mass: 246.125594432
Monoisotopic Mass: 246.125594432
Complexity: 456
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 43.4
Heavy Atom Count: 18
Defined Atom Stereocenter Count: 3
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceBwMAAAAAAAAAAAAAAAAAAAASAAAAAAAAAABAAAAACAAAAAGgAAAAAADRSggAICCAAABACIAqDSCAAAAAAgAAAICAEAAEgIBBIAIQACAAAEwAAIoYOKyOCOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

8. Question & Answer

What are the properties and uses of Xanthium strumarium? Dec 28 2019
The genus Xanthium is widely distributed around the world. These plants are known for their chemical composition, mainly consisting of sesquiterpene lactones. This study focuses on Xanthium strumarium..

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2H-Cyclohepta[b]furan-2-one,3,3a,4,7,8,8a-hexahydro-7-methyl-3-methylene-6-(3-oxo-1-buten-1-yl)-,(3aR,7S,8aS)-

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