Confusarin

Confusarin
Names
Chemical structure of confusarin
IUPAC name 1,5,6-trimethoxyphenanthrene-2,7-diol
Other names 2,7-dihydroxy-3,4,8-trimethoxyphenanthrene
Identifiers
ChemSpider	10155793
InChI InChI=1S/C17H16O5/c1-20-15-11-5-4-9-8-13(19)16(21-2)17(22-3)14(9)10(11)6-7-12(15)18/h4-8,18-19H,1-3H3 Key: JHNVCKNCEVZGGC-UHFFFAOYSA-N InChI=1/C17H16O5/c1-20-15-11-5-4-9-8-13(19)16(21-2)17(22-3)14(9)10(11)6-7-12(15)18/h4-8,18-19H,1-3H3 Key: JHNVCKNCEVZGGC-UHFFFAOYAW
Jmol-3D images	Image
PubChem	11983285
SMILES COc3c2c(ccc1c(OC)c(O)ccc12)cc(O)c3OC
Properties
Chemical formula	C₁₇H₁₆O₅
Molar mass	300.30 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Confusarin is a phrenathrenoid found in the orchids Eria confusa^[1] and Bulbophyllum reptans.^[2] It can also be synthetized.^[3]

References

↑ Confusarin and confusaridin two phenanthrene derivatives of the orchid Eria Confusa. P.L. Majumder and Amita Kar, Phytochemistry, 1987, Volume 26, Issue 4, Pages 1127–1129, doi:10.1016/S0031-9422(00)82363-8
↑ Dimeric phenanthrenes from the orchid Bulbophyllum reptans. P.L Majumder, S Pal and S Majumder, Phytochemistry, Volume 50, Issue 5, 10 March 1999, Pages 891–897, doi:10.1016/S0031-9422(98)00609-8
↑ Total synthesis of two natural phenanthrenes: confusarin and a regioisomer. Sylvie Radix and Roland Barret, Tetrahedron, 10 December 2007, Volume 63, Issue 50, Pages 12379–12387, doi:10.1016/j.tet.2007.09.052

Phenanthrenoids and their glycosides (molecules with a C6-C2-C6 backbone)

Phenanthrols

polyhydroxylated phenanthrenes

coeloginanthrin (3,5,7-trihydroxy-1,2-dimethoxyphenanthrene)
confusaridin (2,6-dihydroxy-3,4,7,8-tetramethoxyphenanthrene)
confusarin (2,7-dihydroxy-3,4,8-trimethoxyphenanthrene)
dehydroeffusol
dehydrojuncusol (1,6-dimethyl-5-vinyl-8-phenanthrene-2,7-diol)
flavanthrinin (2,7-dihydroxy-4-methoxyphenanthrene)
gymnopusin (2,7-dihydroxy-3,4,9-trimethoxyphenanthrene)
Nudol (2,7-dihydroxy-3,4-dimethoxyphenanthrene)
Perakensol (7-hydroxy-2,3,6-trimethoxyphenanthrene)
plicatol A (2,5-dihydroxy-4,9,10-trimethoxyphenanthrene)
Plicatol B (2,5-dihydroxy-4-methoxyphenanthrene)

9,10-dihydrophenanthrene derivatives

coelogin (2,6-Dihydroxy-7,8-dimethoxy-9,10-dihydro-5H-phenanthro[4,5-bcd]pyran)
coeloginin (2,6-Dihydroxy-7,8-dimethoxy-9,1O-dihydro-5H-phenanthro[4,5-bcd]pyran-5-one)
coeloginanthridin (3,5,7-trihydroxy-1,2-dimethoxy-9,10-dihydrophenanthrene)
coelonin (9,10-dihydro-2,7-dihydroxy-4-methoxyphenanthrene)
effusol (5-ethenyl-1-methyl-9,10-dihydrophenanthrene-2,7-diol)
hircinol (9,10-dihydro-4-methoxyphenanthrene-2,5-diol)
juncusol (1,6-Dimethyl-5-vinyl-9,10-dihydro-2,7-phenanthrenediol)
loroglossol (5-hydroxy-2,4-dimethyoxy-9,10-dihydrophenanthrene)
orchinol (9,10-Dihydro-5,7-dimethoxyphenanthren-2-ol)
Plicatol C (2,5,9-trihydroxy-4-methoxy-9,10-dihydrophenanthrene)
4-methoxy-9,10-dihydrophenanthrene-2,3,7-triol
4,6-dimethoxy-9,10-dihydrophenanthrene-2,3,7-triol
9,10-dihydro-2,7-dihydroxy-3,4-dimethoxyphenanthrene
9,10-dihydro-2,7-dihydroxy-3,4,6-trimethoxyphenanthrene
9,10-Dihydro-2,5-dimethoxyphenanthrene-1,7-diol
9,10-dihydro-2,5-dihydroxy-3,4-dimethoxyphenanthrene

glycosides

Phenanthrene glycosides	denneanoside A, B, C, D and E

9,10-dihydrophenanthrene glycoside	denneanoside F

dimeric phenanthrenes

cirrhopetalanthrin (2,2′,7,7′-tetrahydroxy-4,4′-dimethoxy-1,1′-biphenanthryl)
flavanthrin (9,9′,10,10′-tetrahydro-2,2′,7,7′-tetrahydroxy-4,4′-dimethoxy-1,1′-biphenanthryl)
reptanthrin
isoreptanthrin
8,8'-bidehydrojuncusol (1,1',6,6'-tetramethyl-5,5'-divinyl-8,8'-biphenanthrene-2,2',7,7'-tetraol)

Cyclic bibenzyl-dihydrophenanthrene derivative