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11219

Sigma-Aldrich

(+)-Isolariciresinol

≥95.0% (HPLC)

Synonym(s):

(1S,2R,3R)-1,2,3,4-Tetrahydro-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-6-methoxy-2,3-naphthalenedimethanol, (6R,7R,8S)-8-(4-Hydroxy-3-methoxyphenyl)-6,7-bis(hydroxymethyl)-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-ol

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About This Item

Empirical Formula (Hill Notation):
C20H24O6
CAS Number:
548-29-8
Molecular Weight:
360.40
MDL number:
MFCD07784475
UNSPSC Code:
12352200
PubChem Substance ID:
329749331

assay

≥95.0% (HPLC)

SMILES string

COc1cc2C[C@@H](CO)[C@H](CO)[C@@H](c3ccc(O)c(OC)c3)c2cc1O

InChI

1S/C20H24O6/c1-25-18-6-11(3-4-16(18)23)20-14-8-17(24)19(26-2)7-12(14)5-13(9-21)15(20)10-22/h3-4,6-8,13,15,20-24H,5,9-10H2,1-2H3/t13-,15-,20-/m0/s1

InChI key

OGFXBIXJCWAUCH-KPHUOKFYSA-N

Application

Isolariciresinol may be used as a reference compound in the purification, identification and analysis of lignan phytoestrogens and lignan glycosides.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Shuichi Yamamoto et al.
Journal of mass spectrometry : JMS, 39(11), 1337-1347 (2004-11-09)
Total extract of resin from Araucaria angustifolia was analyzed by gas chromatography/mass spectrometry and 32 lignans were identified. Lignan acetates are present in the resin and consist of four secoisolariciresinol acetates, six lariciresinol acetates, two 7'-hydroxylariciresinol acetates and an isolariciresinol
C Bannwart et al.
Clinica chimica acta; international journal of clinical chemistry, 180(3), 293-301 (1989-04-14)
The mammalian lignans enterolactone and enterodiol are regular constituents of human urine and are excreted daily in mumol amounts. They are produced by metabolic action of intestinal bacteria from natural plant lignan precursors which are constituents of various food plants.
Nikolas Fokialakis et al.
Planta medica, 69(6), 566-568 (2003-07-17)
Bioassay-guided fractionation of the neutral extract of the bark of Sarcomelicope megistophylla resulted in the isolation of the new nor-neolignan sarcomeginal ( 1), together with the known ailanthoidol ( 2) and (+/-)-seco-isolariciresinol ( 3). The structure of 1 was determined
Yuan Zhou et al.
Journal of natural medicines, 63(1), 100-101 (2008-07-05)
A new compound named pinoresinol 4-O-alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranoside (1) together with six known compounds, isolariciresinol 9-O-beta-D-glucopyranoside (2), apigenin 6,8-di-C-beta-D-glucopyranoside (3), luteolin 7-O-neohesperidoside (4), luteolin 7-O-beta-D-glucopyranoside (5), 5-methoxyluteolin 7-O-beta-D-glucopyranoside (6), and rutin (7), were isolated from the aerial parts of Urtica laetevirens
Nurgun Kucukboyaci et al.
Zeitschrift fur Naturforschung. C, Journal of biosciences, 65(3-4), 187-194 (2010-05-18)
Phytochemical investigations of Taxus baccata L. by successive chromatographic methods resulted in the isolation of the lignans lariciresinol (1), taxiresinol (2), 3'-demethylisolariciresinol-9'-hydroxyisopropylether (3), isolariciresinol (4), and 3-demethylisolariciresinol (5) as well as taxoids. Compounds 1-5 were evaluated for their acetylcholinesterase (AChE)
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