Technical Data

255370
CAS Number
2753-30-2
Grade
Highly Purified
Molecular Formula
C₂₈H₃₄O₇
Molecular Weight
482.57
EU Commodity Code
38220090
Shipping Temp
RT
Storage Temp
4°C
Gedunin
(1S,3aS,4aR,4bS,5R,6aR,10aR,10bR,12aS)-5-(Acetyloxy)-1-(3-furanyl)-1,5,6,6a,7,10a,10b,11,12,12a-decahydro-4b,7,7,10a,12a-pentamethyloxireno[c]phenanthro[1,2-d]pyran-3,8(3aH,4bH)-dione; Gedunine; NSC 113497; (5α,7α,13α,14β,15β,17aα)-7-(Acetyloxy)-14,15:21,23-diepoxy-4,4,8-trimethyl-D-homo-24-nor-17-oxachola-1,20,22-triene-3,16-dione

Gedunin is a naturally occurring Hsp90 inhibitor. In vitro, Gedunin induces Hsp90-dependent client protein degradation and displays antiproliferative activity (IC50 values are 3.22, 8.84 and 16.8uM in SKBr3, MCF-7 and CaCo-2 cancer cell lines respectively). Gedunin exhibits antimalarial activity against P. falciparum (IC50 values are 0.14 and 3.1uM in parasite development and [3H]-hypoxanthine uptake assays respectively).

Synonyms
(1S,3aS,4aR,4bS,5R,6aR,10aR,10bR,12aS)-5-(Acetyloxy)-1-(3-furanyl)-1,5,6,6a,7,10a,10b,11,12,12a-decahydro-4b,7,7,10a,12a-pentamethyloxireno[c]phenanthro[1,2-d]pyran-3,8(3aH,4bH)-dione; Gedunine; NSC 113497; (5α,7α,13α,14β,15β,17aα)-7-(Acetyloxy)-14,15:21,23-diepoxy-4,4,8-trimethyl-D-homo-24-nor-17-oxachola-1,20,22-triene-3,16-dione
CAS No
2753-30-2
Molecular Formula
C₂₈H₃₄O₇
Molecular Weight
482.57
Appearance
White to off-white solid
Purity
≥97% (HPLC)
Method for Determining Identity
Proton NMR and MS
Optical Rotation
[a]D = +69.5 (c=1; Solvent: Methanol)
Elemental Analysis
%C: 68.61, %H: 7.51
Melting Point
>199°C (dec.)
Solubility
Chloroform (Slightly)
Storage and Stability
Store at -20°C under inert atmosphere. Hygroscopic, under inert atmosphere. For maximum recovery of product, centrifuge the original vial prior to removing the cap.

Intended for research use only. Not for use in human, therapeutic, or diagnostic applications.

References
1. Uddin, Shaikh J., et al., 2007. Gedunin, a limonoid from Xylocarpus granatum, inhibits the growth of CaCo-2 colon cancer cell line in vitro. Phytotherapy research : PTR. 21(8): 757-61. PMID: 17450509|2. Lee, Sung-Eun., et al., 2008. Antimalarial activity of anthothecol derived from Khaya anthotheca (Meliaceae). Phytomedicine : international journal of phytotherapy and phytopharmacology. 15(6-7): 533-5. PMID: 17913482|3. Brandt, Gary E L., et al., 2008. Gedunin, a novel hsp90 inhibitor: semisynthesis of derivatives and preliminary structure-activity relationships. Journal of medicinal chemistry. 51(20): 6495-502. PMID: 18816111
USBio References
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