Bullatacin | CAS#123123-32-0 | fatty acid lactone

MedKoo Cat#: 598803 | Name: Bullatacin

Description:

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

Bullatacin is a bis(tetrahydrofuranoid) fatty acid lactone found in some fruits from Annonaceae family. It is a member of the class of compounds known as acetogenins.

Chemical Structure

Bullatacin

CAS#123123-32-0

Theoretical Analysis

MedKoo Cat#: 598803

Name: Bullatacin

CAS#: 123123-32-0

Chemical Formula: C37H66O7

Exact Mass: 622.4809

Molecular Weight: 622.92

Elemental Analysis: C, 71.34; H, 10.68; O, 17.98

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Bullatacin; LI 12105; LI-12105; LI12105 Rolliniastatin 2; Squamocin G; Annonareticin; ( )-Bullatacin;

IUPAC/Chemical Name

(S)-3-((2R,13R)-2,13-dihydroxy-13-((2R,2'R,5S,5'R)-5'-((S)-1-hydroxyundecyl)octahydro-[2,2'-bifuran]-5-yl)tridecyl)-5-methylfuran-2(5H)-one

InChi Key

MBABCNBNDNGODA-BAVRERFOSA-N

InChi Code

InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-9-8-10-13-16-19-30(38)27-29-26-28(2)42-37(29)41/h26,28,30-36,38-40H,3-25,27H2,1-2H3/t28-,30+,31-,32+,33+,34-,35+,36+/m0/s1

SMILES Code

CCCCCCCCCC[C@H](O)[C@@H](CC1)O[C@H]1[C@H](O2)CC[C@H]2[C@H](O)CCCCCCCCCC[C@@H](O)CC3=C[C@H](C)OC3=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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 622.92 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.

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 Y, Chen JW, Liu SJ, Xu CL, Xu HQ, Cai BC, Li X, Ju WZ. Determination of bullatacin in rat plasma by liquid chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 May 15;897:94-7. doi: 10.1016/j.jchromb.2012.03.044. Epub 2012 Apr 11. PubMed PMID: 22534655. 2: Shi JF, Wu P, Jiang ZH, Wei XY. Synthesis and tumor cell growth inhibitory activity of biotinylated annonaceous acetogenins. Eur J Med Chem. 2014 Jan;71:219-28. doi: 10.1016/j.ejmech.2013.11.012. Epub 2013 Nov 15. PubMed PMID: 24308999. 3: Chih HW, Chiu HF, Tang KS, Chang FR, Wu YC. Bullatacin, a potent antitumor annonaceous acetogenin, inhibits proliferation of human hepatocarcinoma cell line 2.2.15 by apoptosis induction. Life Sci. 2001 Aug 3;69(11):1321-31. PubMed PMID: 11521756. 4: Morré DJ, de Cabo R, Farley C, Oberlies NH, McLaughlin JL. Mode of action of bullatacin, a potent antitumor acetogenin: inhibition of NADH oxidase activity of HeLa and HL-60, but not liver, plasma membranes. Life Sci. 1995;56(5):343-8. PubMed PMID: 7837933. 5: Liang YJ, Zhang X, Dai CL, Zhang JY, Yan YY, Zeng MS, Chen LM, Fu LW. Bullatacin triggered ABCB1-overexpressing cell apoptosis via the mitochondrial-dependent pathway. J Biomed Biotechnol. 2009;2009:867123. doi: 10.1155/2009/867123. Epub 2009 Jul 21. PubMed PMID: 19639048; PubMed Central PMCID: PMC2715821. 6: Hui YH, Rupprecht JK, Liu YM, Anderson JE, Smith DL, Chang CJ, McLaughlin JL. Bullatacin and bullatacinone: two highly potent bioactive acetogenins from Annona bullata. J Nat Prod. 1989 May-Jun;52(3):463-77. PubMed PMID: 2778448. 7: Chiu HF, Chih TT, Hsian YM, Tseng CH, Wu MJ, Wu YC. Bullatacin, a potent antitumor Annonaceous acetogenin, induces apoptosis through a reduction of intracellular cAMP and cGMP levels in human hepatoma 2.2.15 cells. Biochem Pharmacol. 2003 Feb 1;65(3):319-27. PubMed PMID: 12527325. 8: Mangal M, Khan MI, Agarwal SM. Acetogenins as Potential Anticancer Agents. Anticancer Agents Med Chem. 2015;16(2):138-59. Review. PubMed PMID: 26118710. 9: Oberlies NH, Croy VL, Harrison ML, McLaughlin JL. The Annonaceous acetogenin bullatacin is cytotoxic against multidrug-resistant human mammary adenocarcinoma cells. Cancer Lett. 1997 May 1;115(1):73-9. PubMed PMID: 9097981. 10: Chen Y, Chen JW, Zhai JH, Wang Y, Wang SL, Li X. Antitumor activity and toxicity relationship of annonaceous acetogenins. Food Chem Toxicol. 2013 Aug;58:394-400. doi: 10.1016/j.fct.2013.05.028. Epub 2013 May 24. PubMed PMID: 23712095. 11: Holschneider CH, Johnson MT, Knox RM, Rezai A, Ryan WJ, Montz FJ. Bullatacin--in vivo and in vitro experience in an ovarian cancer model. Cancer Chemother Pharmacol. 1994;34(2):166-70. PubMed PMID: 8194168. 12: Ahammadsahib KI, Hollingworth RM, McGovren JP, Hui YH, McLaughlin JL. Mode of action of bullatacin: a potent antitumor and pesticidal annonaceous acetogenin. Life Sci. 1993;53(14):1113-20. PubMed PMID: 8371627. 13: Avedissian H, Sinha SC, Yazbak A, Sinha A, Neogi P, Sinha SC, Keinan E. Total synthesis of asimicin and bullatacin. J Org Chem. 2000 Sep 22;65(19):6035-51. PubMed PMID: 10987938. 14: Li XH, Hui YH, Rupprecht JK, Liu YM, Wood KV, Smith DL, Chang CJ, McLaughlin JL. Bullatacin, bullatacinone, and squamone, a new bioactive acetogenin, from the bark of Annona squamosa. J Nat Prod. 1990 Jan-Feb;53(1):81-6. PubMed PMID: 2348205. 15: Tinsley JM, Mertz E, Chong PY, Rarig RA, Roush WR. Synthesis of (+)-bullatacin via the highly diastereoselective [3+2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane. Org Lett. 2005 Sep 15;7(19):4245-8. PubMed PMID: 16146398; PubMed Central PMCID: PMC2507730. 16: Zhao H, Gorman JS, Pagenkopf BL. Advances in Lewis acid controlled carbon-carbon bond-forming reactions enable a concise and convergent total synthesis of bullatacin. Org Lett. 2006 Sep 14;8(19):4379-82. PubMed PMID: 16956231. 17: Masuya T, Murai M, Morisaka H, Miyoshi H. Pinpoint chemical modification of Asp160 in the 49 kDa subunit of bovine mitochondrial complex I via a combination of ligand-directed tosyl chemistry and click chemistry. Biochemistry. 2014 Dec 16;53(49):7816-23. doi: 10.1021/bi501342w. Epub 2014 Dec 2. PubMed PMID: 25419630. 18: Rodrigues dos Santos Lima LA, Santos Pimenta LP, Diamantino Boaventura MA. Two new adjacent bis-tetrahydrofuran annonaceous acetogenins from seeds of Annona cornifolia. Planta Med. 2009 Jan;75(1):80-3. doi: 10.1055/s-0028-1088359. Epub 2008 Nov 27. PubMed PMID: 19039734. 19: Fu LW, Pan QC, Liang YJ, Huang HB. Circumvention of tumor multidrug resistance by a new annonaceous acetogenin: atemoyacin-B. Zhongguo Yao Li Xue Bao. 1999 May;20(5):435-9. PubMed PMID: 10678092. 20: Chen Y, Xu SS, Chen JW, Wang Y, Xu HQ, Fan NB, Li X. Anti-tumor activity of Annona squamosa seeds extract containing annonaceous acetogenin compounds. J Ethnopharmacol. 2012 Jul 13;142(2):462-6. doi: 10.1016/j.jep.2012.05.019. Epub 2012 May 17. PubMed PMID: 22609808.