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Merck
CN

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:
518-55-8
Molecular Weight:
356.37
MDL number:
MFCD07784473
UNSPSC Code:
12352200
PubChem Substance ID:
329758026

Key Documents

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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 Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBT8143
BCBN0351V
BCBG3348V
BCBG3348

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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
A Dantzig et al.
Journal of medicinal chemistry, 44(2), 180-185 (2001-02-15)
Derivatives of alpha-conidendrin, podophyllotoxin, and sikkimotoxin were prepared to evaluate the cytotoxic contributions of C-4 configuration and pendant and fused arene substitutions. Dimethyl-alpha-conidendryl alcohol (5), 9-deoxypodophyllol (6), and 9-deoxysikkimol (17) were dehydrated to their respective oxolane derivatives 4, 3, and
Joshua Fischer et al.
Organic letters, 6(9), 1345-1348 (2004-04-23)
[reaction: see text] Total syntheses of seven biologically important lignan natural products, including (-)-arctigenin, (-)-matairesinol, and (-)-alpha-conidendrin, by way of a highly stereoselective domino radical sequence is presented. The reported stereochemistry of the natural product 7-hydroxyarctigenin is shown to be

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