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MedKoo Cat#: 551023 | Name: Azadirone

Description:

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

Azadirone, a limonoid tetranortriterpene, induces death receptors and sensitizes human cancer cells to tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) through a p53 protein-independent mechanism. Azadirone can sensitize cancer cells to tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) through ROS-ERK-CHOP-mediated up-regulation of DR5 and DR4 signaling, down-regulation of cell survival proteins, and up-regulation of proapoptotic proteins.

Chemical Structure

Azadirone
Azadirone
CAS#30002-86-9

Theoretical Analysis

MedKoo Cat#: 551023

Name: Azadirone

CAS#: 30002-86-9

Chemical Formula: C28H36O4

Exact Mass: 436.2614

Molecular Weight: 436.59

Elemental Analysis: C, 77.03; H, 8.31; O, 14.66

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Azadirone
IUPAC/Chemical Name
[(5R,7R,8R,9R,10R,13S,17R)-17-(furan-3-yl)-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-7-yl] acetate
InChi Key
XXIKKMLIDXLAIK-RFKFVWFBSA-N
InChi Code
InChI=1S/C28H36O4/c1-17(29)32-24-15-22-25(2,3)23(30)10-13-27(22,5)21-9-12-26(4)19(18-11-14-31-16-18)7-8-20(26)28(21,24)6/h8,10-11,13-14,16,19,21-22,24H,7,9,12,15H2,1-6H3/t19-,21+,22-,24+,26-,27+,28-/m0/s1
SMILES Code
CC(O[C@@H]1C[C@@]2([H])C(C)(C)C(C=C[C@]2(C)[C@@]3([H])CC[C@@]4(C)[C@H](C5=COC=C5)CC=C4[C@]13C)=O)=O
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
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 436.59 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: 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. 2: Akihisa T, Horiuchi M, Matsumoto M, Ogihara E, Ishii K, Zhang J. Melanogenesis-Inhibitory Activities of Isomeric C-seco Limonoids and Deesterified Limonoids. Chem Biodivers. 2016 Oct;13(10):1410-1421. doi: 10.1002/cbdv.201600100. PubMed PMID: 27450797. 3: Kushwaha P, Khedgikar V, Haldar S, Gautam J, Mulani FA, Thulasiram HV, Trivedi R. Azadirachta indica triterpenoids promote osteoblast differentiation and mineralization in vitro and in vivo. Bioorg Med Chem Lett. 2016 Aug 1;26(15):3719-24. doi: 10.1016/j.bmcl.2016.05.076. Epub 2016 May 27. PubMed PMID: 27317644. 4: Gupta SC, Francis SK, Nair MS, Mo YY, Aggarwal BB. Azadirone, a limonoid tetranortriterpene, induces death receptors and sensitizes human cancer cells to tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) through a p53 protein-independent mechanism: evidence for the role of the ROS-ERK-CHOP-death receptor pathway. J Biol Chem. 2013 Nov 8;288(45):32343-56. doi: 10.1074/jbc.M113.455188. Epub 2013 Sep 27. PubMed PMID: 24078627; PubMed Central PMCID: PMC3820870. 5: Koriem KM. Review on pharmacological and toxicologyical effects of oleum azadirachti oil. Asian Pac J Trop Biomed. 2013 Oct;3(10):834-40. doi: 10.1016/S2221-1691(13)60165-3. Epub 2013 Sep 4. Review. PubMed PMID: 24075352; PubMed Central PMCID: PMC3761146. 6: Chianese G, Yerbanga SR, Lucantoni L, Habluetzel A, Basilico N, Taramelli D, Fattorusso E, Taglialatela-Scafati O. Antiplasmodial triterpenoids from the fruits of neem, Azadirachta indica. J Nat Prod. 2010 Aug 27;73(8):1448-52. doi: 10.1021/np100325q. PubMed PMID: 20669933. 7: Mitsui K, Saito H, Yamamura R, Fukaya H, Hitotsuyanagi Y, Takeya K. Apotirucallane and tirucallane triterpenoids from Cedrela sinensis. Chem Pharm Bull (Tokyo). 2007 Oct;55(10):1442-7. PubMed PMID: 17917286. 8: Siddiqui BS, Tariq Ali S, Kashif Ali S. A new flavanoid from the flowers of Azadirachta indica. Nat Prod Res. 2006 Mar;20(3):241-5. PubMed PMID: 16401554. 9: Huerta A, Medina P, Smagghe G, Castañera P, Viñuela E. Topical toxicity of two acetonic fractions of Trichilia havanensis Jacq. and four insecticides to larvae and adults of Chrysoperla carnea (Stephens) (Neuroptera: Chrysopidae). Commun Agric Appl Biol Sci. 2003;68(4 Pt A):277-86. PubMed PMID: 15149120. 10: Nanduri S, Thunuguntla SS, Nyavanandi VK, Kasu S, Kumar PM, Ram PS, Rajagopal S, Kumar RA, Deevi DS, Rajagopalan R, Venkateswarlu A. Biological investigation and structure-activity relationship studies on azadirone from Azadirachta indica A. Juss. Bioorg Med Chem Lett. 2003 Nov 17;13(22):4111-5. PubMed PMID: 14592518. 11: Siddiqui S, Faizi S, Siddiqui BS, Ghiasuddin. Constituents of Azadirachta indica: isolation and structure elucidation of a new antibacterial tetranortriterpenoid, mahmoodin, and a new protolimonoid, naheedin. J Nat Prod. 1992 Mar;55(3):303-10. PubMed PMID: 1593280.