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Merck
CN

54298

(−)-Nortrachelogenin

≥95.0% (HPLC)

Synonym(s):

(−)-Wikstromol, (3S)-4,5-Dihydro-4β-(4-hydroxy-3-methoxybenzyl)-3-(4-hydroxy-3-methoxybenzyl)-3β-hydroxyfuran-2(3H)-one, (3S,4S)-3-Hydroxy-3,4-bis(4-hydroxy-3-methoxybenzyl)dihydrofuran-2-one, (3S,4S)-Dihydro-3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone, NSC 271296, Pinopalustrin

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About This Item

Empirical Formula (Hill Notation):
C20H22O7
CAS Number:
34444-37-6
Molecular Weight:
374.38
UNSPSC Code:
12352200
PubChem Substance ID:
329758027
MDL number:
MFCD01725924

Key Documents

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InChI

1S/C20H22O7/c1-25-17-8-12(3-5-15(17)21)7-14-11-27-19(23)20(14,24)10-13-4-6-16(22)18(9-13)26-2/h3-6,8-9,14,21-22,24H,7,10-11H2,1-2H3/t14-,20-/m0/s1

SMILES string

COc1cc(C[C@H]2COC(=O)[C@]2(O)Cc3ccc(O)c(OC)c3)ccc1O

InChI key

ZITBJWXLODLDRH-XOBRGWDASA-N

assay

≥95.0% (HPLC)

Application

Nortrachelogenin [(−)-Wikstromol], a bioactive α-hydroxylated lactone, is a pharmacologically active lignan used to study its antitumor activities versus breast and lung cancer cells. Nortrachelogenin may be used as a reference compound during the isolation and identification of α-hydroxylated lactone type lignans.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Environment
GHS09

signalword

Warning

hcodes

H400

pcodes

P273

Hazard Classifications

Aquatic Acute 1

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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Certificates of Analysis (COA)

Lot/Batch Number
BCBN0350V
BCBG3352V
BCBG3352

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Wei-sheng Feng et al.
Yao xue xue bao = Acta pharmaceutica Sinica, 38(12), 927-930 (2004-03-26)
To study the chemical constituents from the water-extracts of pine needles of Pinus massoniana Lamb. Chromatographic techniques were used to separate and purify compounds. Their physico-chemical properties and spectral data (UV, IR, MS, 1H-1H, 13C-1H NMR, DEPT, HMBC etc.) were
Emilia Peuhu et al.
Biochemical pharmacology, 86(5), 571-583 (2013-06-12)
Prostate cancer cells frequently develop resistance toward androgen-deprivation and chemotherapy. To identify new approaches to treat androgen-dependent prostate cancer, we have performed a structure-activity analysis of lignan polyphenols for cancer cell specific sensitization to tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)
B S Sachin et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 862(1-2), 237-241 (2008-01-15)
A specific and sensitive high-performance liquid chromatographic (HPLC) method with photodiode-array (PDA) ultraviolet detection was developed for the simultaneous determination of three bioactive constituents of Cedrus deodara namely wikstromol, matairesinol and dibenzylbutyrolactol in mouse plasma. In solid-phase extraction (SPE) these
N M Saarinen et al.
The Journal of steroid biochemistry and molecular biology, 93(2-5), 209-219 (2005-04-30)
Low risk of breast cancer (BC) has been proposed to be associated with high intake of lignans. Some plant lignans are converted to mammalian lignans, e.g., enterolactone (ENL), suggested to be the biologically active lignan forms. Until now, little attention
J L Belletire et al.
Journal of natural products, 53(6), 1587-1592 (1990-11-01)
While the Davis oxaziridine reagent generally affords oxidation products based on simple steric considerations, this concept appears to have some limitations when used to design natural product synthetic strategies. Thus, an example has been found in which the observed stereoselectivity
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