Nudol

Nudol
Names

IUPAC name 3,4-dimethoxyphenanthrene-2,7-diol
Other names 2,7-dihydroxy-3,4-dimethoxyphenanthrene
Identifiers
CAS Registry Number	86630-46-8
ChemSpider	139835
InChI InChI=1S/C16H14O4/c1-19-15-13(18)8-10-4-3-9-7-11(17)5-6-12(9)14(10)16(15)20-2/h3-8,17-18H,1-2H3 Key: JZIYNZGPIKGKQC-UHFFFAOYSA-N InChI=1/C16H14O4/c1-19-15-13(18)8-10-4-3-9-7-11(17)5-6-12(9)14(10)16(15)20-2/h3-8,17-18H,1-2H3 Key: JZIYNZGPIKGKQC-UHFFFAOYAW
Jmol-3D images	Image
PubChem	158975
SMILES COC1=C(C=C2C=CC3=C(C2=C1OC)C=CC(=C3)O)O
Properties
Chemical formula	C₁₆H₁₄O₄
Molar mass	270.28 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Nudol is a phenanthrenoid of the orchids Eulophia nuda, Eria carinata, Eria stricta^[1] and Maxillaria densa.^[2]

References

↑ Nudol, a phenanthrene of the orchids Eulophia nuda, Eria carinata and Eria stricta. S Bhandari, Phytochemistry, January 1985, volume 24, issue 4, pages 801-804, doi:10.1016/S0031-9422(00)84898-0
↑ New Phenanthrene Derivatives from Maxillaria densa. Samuel Estrada, Rubén A. Toscanoand Rachel Mata, J. Nat. Prod., 1999, volume 62, issue 8, pages 1175–1178, doi:10.1021/np990061e

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