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MedKoo Cat#: 581551 | Name: Deacetylgedunin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Deacetylgedunin is a limonoid that is the 7-deacetyl derivative of gedunin. It has been isolated from Azadirachta indica.

Chemical Structure

Deacetylgedunin
Deacetylgedunin
CAS#10314-90-6

Theoretical Analysis

MedKoo Cat#: 581551

Name: Deacetylgedunin

CAS#: 10314-90-6

Chemical Formula: C26H32O6

Exact Mass: 440.2199

Molecular Weight: 440.54

Elemental Analysis: C, 70.89; H, 7.32; O, 21.79

Price and Availability

This product was removed for the commercial reasons.
Related CAS #
No Data
Synonym
Deacetylgedunin; 7-Deacetylgedunin; 7-Desacetylgedunin; 7-Deacetyl Genudin; NSC 309912; NSC309912; NSC-309912
IUPAC/Chemical Name
(1S,3aS,4aR,4bS,5R,6aR,10aR,10bR,12aS)-1-(furan-3-yl)-5-hydroxy-4b,7,7,10a,12a-pentamethyl-1,5,6,6a,7,10a,10b,11,12,12a-decahydronaphtho[2,1-f]oxireno[2,3-d]isochromene-3,8(3aH,4bH)-dione
InChi Key
HCEYJYMNIQHPPK-DXTZDJJUSA-N
InChi Code
InChI=1S/C26H32O6/c1-22(2)16-12-18(28)25(5)15(23(16,3)9-7-17(22)27)6-10-24(4)19(14-8-11-30-13-14)31-21(29)20-26(24,25)32-20/h7-9,11,13,15-16,18-20,28H,6,10,12H2,1-5H3/t15-,16+,18-,19+,20-,23-,24+,25+,26-/m1/s1
SMILES Code
C[C@@]12CC[C@@H]3[C@]4(C=CC(=O)C([C@@H]4C[C@H]([C@]3([C@@]15[C@H](O5)C(=O)O[C@H]2C6=COC=C6)C)O)(C)C)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 440.54 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Chen JY, Zhu GY, Su XH, Wang R, Liu J, Liao K, Ren R, Li T, Liu L. 7-deacetylgedunin suppresses inflammatory responses through activation of Keap1/Nrf2/HO-1 signaling. Oncotarget. 2017 Jul 5;8(33):55051-55063. doi: 10.18632/oncotarget.19017. eCollection 2017 Aug 15. PubMed PMID: 28903401; PubMed Central PMCID: PMC5589640. 2: Akihisa T, Nishimoto Y, Ogihara E, Matsumoto M, Zhang J, Abe M. Nitric Oxide Production-Inhibitory Activity of Limonoids from Azadirachta indica and Melia azedarach. Chem Biodivers. 2017 Jun;14(6). doi: 10.1002/cbdv.201600468. Epub 2017 May 23. PubMed PMID: 28145090. 3: Sarigaputi C, Sangpech N, Palaga T, Pudhom K. Suppression of inducible nitric oxide synthase pathway by 7-deacetylgedunin, a limonoid from Xylocarpus sp. Planta Med. 2015 Mar;81(4):312-9. doi: 10.1055/s-0034-1396308. Epub 2015 Feb 25. PubMed PMID: 25714725. 4: Pereira TB, Rocha E Silva LF, Amorim RC, Melo MR, Zacardi de Souza RC, Eberlin MN, Lima ES, Vasconcellos MC, Pohlit AM. In vitro and in vivo anti-malarial activity of limonoids isolated from the residual seed biomass from Carapa guianensis (andiroba) oil production. Malar J. 2014 Aug 13;13:317. doi: 10.1186/1475-2875-13-317. PubMed PMID: 25124944; PubMed Central PMCID: PMC4138406. 5: Miranda Júnior RN, Dolabela MF, da Silva MN, Póvoa MM, Maia JG. Antiplasmodial activity of the andiroba (Carapa guianensis Aubl., Meliaceae) oil and its limonoid-rich fraction. J Ethnopharmacol. 2012 Aug 1;142(3):679-83. doi: 10.1016/j.jep.2012.05.037. Epub 2012 May 31. PubMed PMID: 22659195. 6: Ravangpai W, Sommit D, Teerawatananond T, Sinpranee N, Palaga T, Pengpreecha S, Muangsin N, Pudhom K. Limonoids from seeds of Thai Xylocarpus moluccensis. Bioorg Med Chem Lett. 2011 Aug 1;21(15):4485-9. doi: 10.1016/j.bmcl.2011.06.010. Epub 2011 Jun 16. PubMed PMID: 21733687. 7: da Silva VP, Oliveira RR, Figueiredo MR. Isolation of limonoids from seeds of Carapa guianensis Aublet (Meliaceae) by high-speed countercurrent chromatography. Phytochem Anal. 2009 Jan-Feb;20(1):77-81. doi: 10.1002/pca.1100. PubMed PMID: 19003936. 8: Hay AE, Ioset JR, Ahua KM, Diallo D, Brun R, Hostettmann K. Limonoid orthoacetates and antiprotozoal compounds from the roots of Pseudocedrela kotschyi. J Nat Prod. 2007 Jan;70(1):9-13. PubMed PMID: 17253841. 9: Senthil Nathan S, Kalaivani K, Sehoon K, Murugan K. The toxicity and behavioural effects of neem limonoids on Cnaphalocrocis medinalis (Guenée), the rice leaffolder. Chemosphere. 2006 Mar;62(8):1381-7. Epub 2005 Sep 27. PubMed PMID: 16194558. 10: Senthil Nathan S, Kalaivani K, Chung PG, Murugan K. Effect of neem limonoids on lactate dehydrogenase (LDH) of the rice leaffolder, Cnaphalocrocis medinalis (Guenée) (Insecta: Lepidoptera: Pyralidae). Chemosphere. 2006 Mar;62(8):1388-93. Epub 2005 Sep 12. PubMed PMID: 16154614. 11: Nathan SS, Kalaivani K, Murugan K. Effects of neem limonoids on the malaria vector Anopheles stephensi Liston (Diptera: Culicidae). Acta Trop. 2005 Oct;96(1):47-55. PubMed PMID: 16112073.