(+)-Epoxysuberosin

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Category Others
Catalog number BBF-04724
CAS 80368-68-9
Molecular Weight 260.29
Molecular Formula C15H16O4
Purity >95% by HPLC

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Description

(+)-Epoxylinolein is a coumarin isolated from Hesperethusa crenulata. Epoxy Suberosin has anti-Leishmania activity.

Specification

Synonyms Epoxysuberosin, (+)-
Storage Store at -20°C
IUPAC Name 6-[[(2R)-3,3-dimethyloxiran-2-yl]methyl]-7-methoxychromen-2-one
Canonical SMILES CC1(C(O1)CC2=C(C=C3C(=C2)C=CC(=O)O3)OC)C
InChI InChI=1S/C15H16O4/c1-15(2)13(19-15)7-10-6-9-4-5-14(16)18-12(9)8-11(10)17-3/h4-6,8,13H,7H2,1-3H3/t13-/m1/s1
InChI Key JZRVCRZHZQXYDH-CYBMUJFWSA-N

Properties

Appearance Crystalline Solid
Boiling Point 411.2±45.0°C (Predicted)
Density 1.223±0.06 g/cm3 (Predicted)
Solubility Soluble in ethanol, methanol, DMF, DMSO

Reference Reading

1. Employing Pressurized Hot Water Extraction (PHWE) to Explore Natural Products Chemistry in the Undergraduate Laboratory
Curtis C Ho, Bianca J Deans, Jeremy Just, Gregory G Warr, Shane Wilkinson, Jason A Smith, Alex C Bissember J Vis Exp. 2018 Nov 7;(141). doi: 10.3791/58195.
A recently developed pressurized hot water extraction (PHWE) method which utilizes an unmodified household espresso machine to facilitate natural products research has also found applications as an effective teaching tool. Specifically, this technique has been used to introduce second- and third-year undergraduates to aspects of natural products chemistry in the laboratory. In this report, two experiments are presented: the PHWE of eugenol and acetyleugenol from cloves and the PHWE of seselin and (+)-epoxysuberosin from the endemic Australian plant species Correa reflexa. By employing PHWE in these experiments, the crude clove extract, enriched in eugenol and acetyleugenol, was obtained in 4-9% w/w from cloves by second-year undergraduates and seselin and (+)-epoxysuberosin were isolated in yields of up to 1.1% w/w and 0.9% w/w from C. reflexa by third-year students. The former exercise was developed as a replacement for the traditional steam distillation experiment providing an introduction to extraction and separation techniques, while the latter activity featured guided-inquiry teaching methods in an effort to simulate natural products bioprospecting. This primarily derives from the rapid nature of this PHWE technique relative to traditional extraction methods that are often incompatible with the time constraints associated with undergraduate laboratory experiments. This rapid and practical PHWE method can be used to efficiently isolate various classes of organic molecules from a range of plant species. The complementary nature of this technique relative to more traditional methods has also been demonstrated previously.

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