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Merck
CN

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

Key Documents

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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 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
BCBP6729V
BCBN2012V
BCBL5007V
BCBG3350V
BCBG3350

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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
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
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.
J Y Cho et al.
Planta medica, 67(4), 312-316 (2001-07-19)
Coptis japonica Makino (Ranunculaceae) is known to possess several biological activities such as anti-inflammatory effects. In this study, five lignans, isolariciresinol (1), lariciresinol glycoside (2), pinoresinol (3), pinoresinol glycoside (4) and syringaresinol glycoside (5), isolated from the rhizomes of C.
L P Meagher et al.
Journal of agricultural and food chemistry, 47(8), 3173-3180 (1999-12-20)
The isolation and characterization of the lignans, isolariciresinol, pinoresinol, secoisolariciresinol, and matairesinol, potent phytoestrogens, from flaxseed meal are described. This is the first report of isolariciresinol and pinoresinol being detected in a food. The extraction method selected combined the removal
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