54297
(−)-α-Conidendrin
≥95.0% (HPLC)
Synonym(s):
(3aR,4S,9aR)-3a,4,9,9a-Tetrahydro-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxynaphtho[2,3-c]furan-1(3H)-one, (3aR,4S,9aR)-6-Hydroxy-4-(4-hydroxy-3-methoxy-phenyl)-7-methoxy-3a,4,9,9a-tetrahydro-3H-naphtho[2,3-c]furan-1-one, NSC 4586, Tsugalactone
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About This Item
Empirical Formula (Hill Notation):
C20H20O6
CAS Number:
Molecular Weight:
356.37
UNSPSC Code:
12352200
PubChem Substance ID:
MDL number:
assay
≥95.0% (HPLC)
SMILES string
COc1cc2C[C@@H]3[C@H](COC3=O)[C@@H](c4ccc(O)c(OC)c4)c2cc1O
InChI
1S/C20H20O6/c1-24-17-6-10(3-4-15(17)21)19-12-8-16(22)18(25-2)7-11(12)5-13-14(19)9-26-20(13)23/h3-4,6-8,13-14,19,21-22H,5,9H2,1-2H3/t13-,14+,19+/m1/s1
InChI key
CAYMSCGTKZIVTN-TYILLQQXSA-N
Application
α-conidendrin is a plant derived lignan that may be used as a source or reference compound to study bacteria that degrade plant lignans. α-conidendrin may be used as a starting material for the synthesis of sikkimotoxin derivatives and cytotoxic metabolites.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Robert T LaLonde et al.
Journal of natural products, 67(4), 697-699 (2004-04-24)
Oxidation of alpha-conidendrin (3) by Fremy's salt favored formation of an o-quinone (4) at the pendant aromatic ring as opposed to the fused aromatic ring. Quinone reduction and phenolic methylation, followed by lactone reduction, and subsequent oxidation by dichlorodicyanoquinone produced
Yimin Hu et al.
Chemistry, an Asian journal, 5(2), 309-314 (2009-12-31)
An efficient domino cyclization method for the construction of aza-podophyllotoxin/aza-conidendrin derivatives has been established. Reactions of different dienes with aryl halides in the presence of a palladium catalytic system produced different kinds of podophyllotoxin derivatives through a highly regioselective C-H
Annika I Smeds et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 816(1-2), 87-97 (2005-01-25)
Ten potential lignan metabolites were quantified in rat urine extracts using liquid chromatography-tandem mass spectrometry. The rats were orally administered with the plant lignans 7-hydroxymatairesinol, matairesinol, lariciresinol or secoisolariciresinol, or with the mammalian lignan enterolactone. The samples were enzymatically hydrolysed