Coicenal

Coicenal
Names
	Preferred IUPAC name (2Z)-2-[(1R,2R,3S,5R,6R,7S,8S)-8-butan-2-yl-2-hydroxy-3,5,7-trimethyl-11-oxatricyclo[5.3.2.01,6]dodec-9-en-12-ylidene]acetaldehyde
Identifiers
3D model (JSmol)	Interactive image; A: Interactive image; B: Interactive image; C: Interactive image; D: Interactive image;
PubChem CID	102527066; A: 102527063; B: 102527064; C: 102527065; D: 102527066;
	InChI InChI=1S/C20H30O3/c1-6-12(2)15-7-9-20-17(13(3)11-14(4)18(20)22)19(15,5)16(23-20)8-10-21/h7-10,12-15,17-18,22H,6,11H2,1-5H3/b16-8-/t12?,13-,14+,15-,17-,18-,19-,20-/m1/s1 Key: IHGAEHWJSSLSRR-CFBDQFINSA-N; A: InChI=1S/C20H30O3/c1-6-11(2)18-15-10-14-17(12(3)9-13(4)19(14)22)20(18,5)16(23-15)7-8-21/h7-8,10-13,15,17-19,22H,6,9H2,1-5H3/b16-7-/t11?,12-,13+,15+,17+,18+,19-,20+/m1/s1 Key: VLVIMVZGQOTSGT-PVOILIQDSA-N; B: InChI=1S/C24H34O6/c1-6-13(2)22-17-12-16-21(24(22,5)18(29-17)9-10-25)14(3)11-15(4)23(16)30-20(28)8-7-19(26)27/h9-10,12-15,17,21-23H,6-8,11H2,1-5H3,(H,26,27)/b18-9-/t13?,14-,15+,17+,21+,22+,23-,24+/m1/s1 Key: WZRUTTFXDCERSK-PXMPJTSQSA-N; C: InChI=1S/C25H36O6/c1-7-14(2)23-18-13-17-22(25(23,5)19(30-18)10-11-26)15(3)12-16(4)24(17)31-21(28)9-8-20(27)29-6/h10-11,13-16,18,22-24H,7-9,12H2,1-6H3/b19-10-/t14?,15-,16+,18+,22+,23+,24-,25+/m1/s1 Key: CETRZRNQBVTCKB-UXPXVMCKSA-N; D: InChI=1S/C20H30O3/c1-6-12(2)15-7-9-20-17(13(3)11-14(4)18(20)22)19(15,5)16(23-20)8-10-21/h7-10,12-15,17-18,22H,6,11H2,1-5H3/b16-8-/t12?,13-,14+,15-,17-,18-,19-,20-/m1/s1 Key: IHGAEHWJSSLSRR-CFBDQFINSA-N;
	SMILES CCC(C)C1C=CC23C(C1(C(=CC=O)O2)C)C(CC(C3O)C)C; A: CCC(C)[C@H]1[C@@H]2C=C3[C@@H]([C@@]1(/C(=C/C=O)/O2)C)[C@@H](C[C@@H]([C@H]3O)C)C; B: CCC(C)[C@H]1[C@@H]2C=C3[C@@H]([C@@]1(/C(=C/C=O)/O2)C)[C@@H](C[C@@H]([C@H]3OC(=O)CCC(=O)O)C)C; C: CCC(C)[C@H]1[C@@H]2C=C3[C@@H]([C@@]1(/C(=C/C=O)/O2)C)[C@@H](C[C@@H]([C@H]3OC(=O)CCC(=O)OC)C)C; D: CCC(C)[C@H]1C=C[C@]23[C@@H]([C@]1(/C(=C/C=O)/O2)C)[C@@H](C[C@@H]([C@H]3O)C)C;
Properties
Chemical formula	A: C20H30O3, B: C24H34O6, C: C25H36O6, D: C20H30O3
Molar mass	318.4 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Coicenals are a class of naturally occurring diterpenes extracted from the pathogenic fungus Bipolaris coicis. The four derivatives are named coicenal A-D. These molecules have an underlying bridged-ring structure with an acetaldehyde group. Biosynthetic pathways have been determined for these molecules, but total syntheses have not yet been published.