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54298

Sigma-Aldrich

(−)-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
MDL number:
MFCD01725924
UNSPSC Code:
12352200
PubChem Substance ID:
329758027

Assay

≥95.0% (HPLC)

SMILES string

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

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

InChI key

ZITBJWXLODLDRH-XOBRGWDASA-N

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

Signal Word

Warning

Hazard Statements

H400

Precautionary Statements

P273

Hazard Classifications

Aquatic Acute 1

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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
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
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)
Xing-Qi Tan et al.
Planta medica, 71(1), 93-95 (2005-01-29)
Seven lignans having a diarylhydroxybutyrolactone skeleton were isolated from the leaves and stems of Trachelospermum jasminoides (Lindl.) Lem. Their structures were elucidated to be nortrachelogenin 8' -O-beta-D-glucopyranoside (1), nortrachelogenin 5'- C- beta-D-glucopyranoside (2), trachelogenin amide (3), nortracheloside, trachelogenin, tracheloside, and
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