Bullatacin

(+)-Bullatacin

Names
Other names Annonareticin; Rolliniastatin 2; Squamocin G
Identifiers
CAS Number	123123-32-0=
ChemSpider	9300122
Jmol interactive 3D	Image
PubChem	114749
InChI 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 Key: MBABCNBNDNGODA-LUVUIASKSA-N InChI=1/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 Key: MBABCNBNDNGODA-LUVUIASKBE
SMILES O=C\1O[C@H](/C=C/1C[C@H](O)CCCCCCCCCC[C@@H](O)[C@@H]3O[C@@H]([C@@H]2O[C@H](CC2)[C@@H](O)CCCCCCCCCC)CC3)C
Properties
Chemical formula	C37H66O7
Molar mass	622.93 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.^[1][2][3]

References

1. H. Naito; E. Kawahara; K. Maruta; M. Maeda; S. Sasaki (1995). "The First Total Synthesis of (+)-Bullatacin, a Potent Antitumor Annonaceous Acetogenin, and (+)-(15,24)-bis-epi-Bullatacin". Journal of Organic Chemistry 60 (14): 4419–4427. doi:10.1021/jo00119a019.
2. H.-W. Chih; H.-F. Chiu; K.-S. Tang; F.-R. Chang; Y.-C. Wu (2001). "Bullatacin, a potent antitumor annonaceous acetogenin, inhibits proliferation of human hepatocarcinoma cell line 2.2.15 by apoptosis induction". Life Sciences 69 (11): 1321–1331. doi:10.1016/S0024-3205(01)01209-7. PMID 11521756.
3. Y.-H. Hui; J. K. Rupprecht; Y. M. Liu; J. E. Anderson; D. L. Smith; C.-J. Chang; J. L. McLaughlin (1989). "Bullatacin and Bullatacinone: Two Highly Potent Bioactive Acetogenins from Annona bullata". Journal of Natural Products 52 (3): 463–477. doi:10.1021/np50063a002. PMID 2778448.