MedKoo Cat#: 462895 | Name: Ambrosin

Description:

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

Ambrosin is a sesquiterpene lactone and a potent NF-κβ inhibitor. It is currently being studied as a potential lead drug for Alzheimer disease therapeutics.

Chemical Structure

Ambrosin
Ambrosin
CAS#509-93-3

Theoretical Analysis

MedKoo Cat#: 462895

Name: Ambrosin

CAS#: 509-93-3

Chemical Formula: C15H18O3

Exact Mass: 246.1256

Molecular Weight: 246.31

Elemental Analysis: C, 73.15; H, 7.37; O, 19.49

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
NSC 85235; NSC85235; NSC-85235;
IUPAC/Chemical Name
(3aS,6S,6aR,9aR,9bR)-6,9a-dimethyl-3-methylene-3,3a,4,5,6,6a,9a,9b-octahydroazuleno[4,5-b]furan-2,9-dione
InChi Key
IFXGCKRDLITNAU-JHSUYXJUSA-N
InChi Code
InChI=1S/C15H18O3/c1-8-4-5-10-9(2)14(17)18-13(10)15(3)11(8)6-7-12(15)16/h6-8,10-11,13H,2,4-5H2,1,3H3/t8-,10-,11-,13+,15-/m0/s1
SMILES Code
C[C@H]1CC[C@@H]2[C@H]([C@]3([C@H]1C=CC3=O)C)OC(C2=C)=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
>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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 246.31 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: Bajwa AA, Weston PA, Gurusinghe S, Latif S, Adkins SW, Weston LA. Toxic Potential and Metabolic Profiling of Two Australian Biotypes of the Invasive Plant Parthenium Weed (Parthenium hysterophorus L.). Toxins (Basel). 2020 Jul 10;12(7):447. doi: 10.3390/toxins12070447. PMID: 32664345; PMCID: PMC7404986. 2: Khalil MNA, Choucry MA, El Senousy AS, Hassan A, El-Marasy SA, El Awdan SA, Omar FA. Ambrosin, a potent NF-κβ inhibitor, ameliorates lipopolysaccharide induced memory impairment, comparison to curcumin. PLoS One. 2019 Jul 5;14(7):e0219378. doi: 10.1371/journal.pone.0219378. PMID: 31276550; PMCID: PMC6611615. 3: Sepúlveda-Robles O, Espinoza-Gutiérrez B, Gomez-Verjan JC, Guzmán-Gutiérrez SL, De Ita M, Silva-Miranda M, Espitia-Pinzón CI, Fernández-Ramírez F, Herrera- Salazar A, Mata-Rocha M, Ortega-Hernández A, Reyes-Chilpa R. Trypanocidal and toxicological assessment in vitro and in silico of three sesquiterpene lactones from Asteraceae plant species. Food Chem Toxicol. 2019 Mar;125:55-61. doi: 10.1016/j.fct.2018.12.023. Epub 2018 Dec 18. PMID: 30572063. 4: Frajese GV, Benvenuto M, Mattera R, Giampaoli S, Ambrosin E, Bernardini R, Giganti MG, Albonici L, Dus I, Manzari V, Modesti A, Mattei M, Bei R. Electrochemically Reduced Water Delays Mammary Tumors Growth in Mice and Inhibits Breast Cancer Cells Survival In Vitro. Evid Based Complement Alternat Med. 2018 Sep 26;2018:4753507. doi: 10.1155/2018/4753507. PMID: 30402124; PMCID: PMC6196883. 5: Sotillo WS, Villagomez R, Smiljanic S, Huang X, Malakpour A, Kempengren S, Rodrigo G, Almanza G, Sterner O, Oredsson S. Anti-cancer stem cell activity of a sesquiterpene lactone isolated from Ambrosia arborescens and of a synthetic derivative. PLoS One. 2017 Sep 1;12(9):e0184304. doi: 10.1371/journal.pone.0184304. PMID: 28863191; PMCID: PMC5581169. 6: Frajese GV, Benvenuto M, Fantini M, Ambrosin E, Sacchetti P, Masuelli L, Giganti MG, Modesti A, Bei R. Potassium increases the antitumor effects of ascorbic acid in breast cancer cell lines in vitro. Oncol Lett. 2016 Jun;11(6):4224-4234. doi: 10.3892/ol.2016.4506. Epub 2016 Apr 27. PMID: 27313770; PMCID: PMC4888082. 7: Saeed ME, Abdelgadir H, Sugimoto Y, Khalid HE, Efferth T. Cytotoxicity of 35 medicinal plants from Sudan towards sensitive and multidrug-resistant cancer cells. J Ethnopharmacol. 2015 Nov 4;174:644-58. doi: 10.1016/j.jep.2015.07.005. Epub 2015 Jul 10. PMID: 26165828. 8: Ambrosini E, Remoli ME, Giacomini E, Rosicarelli B, Serafini B, Lande R, Aloisi F, Coccia EM. Astrocytes produce dendritic cell-attracting chemokines in vitro and in multiple sclerosis lesions. J Neuropathol Exp Neurol. 2005 Aug;64(8):706-15. doi: 10.1097/01.jnen.0000173893.01929.fc. PMID: 16106219. 9: Ambrosini E, Aloisi F. Chemokines and glial cells: a complex network in the central nervous system. Neurochem Res. 2004 May;29(5):1017-38. doi: 10.1023/b:nere.0000021246.96864.89. PMID: 15139300. 10: Ambrosino C, Nebreda AR. Cell cycle regulation by p38 MAP kinases. Biol Cell. 2001 Sep;93(1-2):47-51. doi: 10.1016/s0248-4900(01)01124-8. PMID: 11730321. 11: Dirsch VM, Stuppner H, Vollmar AM. Cytotoxic sesquiterpene lactones mediate their death-inducing effect in leukemia T cells by triggering apoptosis. Planta Med. 2001 Aug;67(6):557-9. doi: 10.1055/s-2001-16478. PMID: 11509981. 12: Ambrosini A, Bresciani L, Brunello N, Racagni G. Cyclic GMP inhibition of metabotropic glutamate receptor-induced phosphoinositide hydrolysis in mesencephalic neurons. Neuropharmacology. 1996;35(11):1641-3. doi: 10.1016/s0028-3908(96)00109-8. PMID: 9025113. 13: Hejchman E, Haugwitz RD, Cushman M. Synthesis and cytotoxicity of water- soluble ambrosin prodrug candidates. J Med Chem. 1995 Aug 18;38(17):3407-10. doi: 10.1021/jm00017a025. PMID: 7650694. 14: Abou Basha LM, el Sayad MH, Allam AF, Osman MM. The effect of Ambrosia maritima (Damsissa) on the viability of Lymnaea cailliaudi; an experimental study. J Egypt Soc Parasitol. 1994 Dec;24(3):513-7. PMID: 7844416. 15: Massari S, Folena E, Ambrosin V, Schiavo G, Colonna R. pH-dependent lipid packing, membrane permeability and fusion in phosphatidylcholine vesicles. Biochim Biophys Acta. 1991 Aug 26;1067(2):131-8. doi: 10.1016/0005-2736(91)90034-6. PMID: 1878366. 16: Alard F, Stievenart C, Vanparys P, Thilemans L, Geerts S. Toxicity and mutagenicity of the molluscicidal plant Ambrosia maritima L. Drug Chem Toxicol. 1991;14(4):353-73. doi: 10.3109/01480549109011639. PMID: 1811958. 17: Bernardi P, Angrilli A, Ambrosin V, Azzone GF. Activation of latent K+ uniport in mitochondria treated with the ionophore A23187. J Biol Chem. 1989 Nov 15;264(32):18902-6. PMID: 2509471. 18: el-Sawy MF, el-Hamd ZM, Loutfy NF, el Masry S, Abdel-Gualil MZ. Ambrosia maritima a larvicide and pupacide for Anopheles pharoensis ambrosin as an effective insecticide. I. Laboratory experimentation. J Egypt Soc Parasitol. 1986 Jun;16(1):57-64. PMID: 3722901. 19: El Sawy MF, Duncan J, Marshall TF, Bassiouny HK, Shehata MA. The molluscicidal properties of Ambrosia maritima L. (compositae). 1. Design for a molluscicide field trial. Tropenmed Parasitol. 1983 Mar;34(1):11-4. PMID: 6845414. 20: Hausen BM. Die Parthenium hysterophorus-Allergie. Ein Unkraut-Problem in Indien [Parthenium hysterophorus allergy. A weed problem in India (author's transl)]. Derm Beruf Umwelt. 1978;26(4):115-20. German. PMID: 755653.