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Merck

06892

Sigma-Aldrich

(+)-ラリシレシノール

≥95.0% (HPLC)

別名:

(2S,3R,4R)-テトラヒドロ-2-(4-ヒドロキシ-3-メトキシフェニル)-4-[(4-ヒドロキシ-3-メトキシフェニル)メチル]-3-フランメタノール, 4-[(2S,3R,4R)-4-[(4-ヒドロキシ-3-メトキシフェニル)メチル]-3-(ヒドロキシメチル)オキソラン-2-イル]-2-メトキシフェノール, NSC 329247

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About This Item

実験式(ヒル表記法):
C20H24O6
CAS番号:
分子量:
360.40
Beilstein:
4560057
MDL番号:
UNSPSCコード:
12352005
PubChem Substance ID:
NACRES:
NA.25

品質水準

アッセイ

≥95.0% (HPLC)

フォーム

powder

アプリケーション

metabolomics
vitamins, nutraceuticals, and natural products

SMILES記法

COc1cc(C[C@H]2CO[C@@H]([C@H]2CO)c3ccc(O)c(OC)c3)ccc1O
COc1cc(C[C@H]2CO[C@@H]([C@H]2CO)c3ccc(O)c(OC)c3)ccc1O

InChI

1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m0/s1

InChI Key

MHXCIKYXNYCMHY-AUSJPIAWSA-N

詳細

Lariciresinol(LA) is a dietary phytoestrogen plant lignan. It is one of the main active phytochemicals in many traditional medicinal plants and cereals.

アプリケーション

Lariciresinol has been used as a reference standard:
  • in the purification, identification, and analysis of lignan phytoestrogens and lignan glycosides
  • for the determination of the enantiomeric composition of lariciresinol from the pinoresinol to lariciresinol reduction reaction using high-performance liquid chromatography (HPLC)
  • forqualitative and quantitative analysis of lignans in seven types of triticalegrain using ultra-performance liquid chromatography (UPLC)

生物化学的/生理学的作用

Lariciresinol is a potent dietary antioxidant and a radical scavenger by potentially chelating catalytic Fe2+ ions. It exerts antimicrobial effects against foodborne pathogens S. aureus and E. coli O157:H7. Lariciresinol is an effective anticancer agent that inhibits cell proliferation and induces apoptosis in human HepG2 cells in vitro. It also displays anti-inflammatory and anti-diabetic effects in vitro and in vivo studies respectively.

包装

底の開いたガラス瓶内容物は内部に挿入され接着された円錐部に入っています。

ピクトグラム

Environment

シグナルワード

Warning

危険有害性情報

注意書き

危険有害性の分類

Aquatic Acute 1

保管分類コード

11 - Combustible Solids

WGK

WGK 3

引火点(°F)

Not applicable

引火点(℃)

Not applicable


適用法令

試験研究用途を考慮した関連法令を主に挙げております。化学物質以外については、一部の情報のみ提供しています。 製品を安全かつ合法的に使用することは、使用者の義務です。最新情報により修正される場合があります。WEBの反映には時間を要することがあるため、適宜SDSをご参照ください。

Jan Code

06892-BULK:
06892-VAR:
06892-10MG:


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Slide 1 of 2

1 of 2

Hisashi Nishiwaki et al.
Journal of agricultural and food chemistry, 59(24), 13089-13095 (2011-11-10)
All stereoisomers of lariciresinol were synthesized to examine the effect of stereochemistry on plant growth. Configuration of benzylic 7-positions was constructed through S(N)1 or S(N)2 intramolecular etherification. 8- and 8'-position configurations were established from the starting material except for all
Bomi Hwang et al.
Biochemical and biophysical research communications, 410(3), 489-493 (2011-06-18)
Lariciresinol is an enterolignan precursor isolated from the herb Sambucus williamsii, a folk medicinal plant used for its therapeutic properties. In this study, the antifungal properties and mode of action of lariciresinol were investigated. Lariciresinol displays potent antifungal properties against
Niina M Saarinen et al.
International journal of cancer, 123(5), 1196-1204 (2008-06-06)
Lariciresinol is a dietary lignan that accounts for a significant portion of the total phytoestrogen intake from Western foods. Recent epidemiological studies suggest that high dietary intake of lignans and lariciresinol is associated with reduced breast cancer risk. However, no
Simone Angeloni et al.
Journal of mass spectrometry : JMS, 53(9), 842-848 (2018-06-21)
Lignans are polyphenolic compounds that are considered phytoestrogens for their plant origins, and they possess different biological activities. Three different extraction methods, ie, "dilute and shoot", acidic hydrolysis, and enzymatic digestion, have been compared for extracting lignans (secoisolariciresinol (SECO), matairesinol
Heidi Schwartz et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 838(2), 78-85 (2006-06-06)
The paper describes a method for the determination of selected lignans in plant foods. First, samples were submitted to methanolysis resulting in cleavage of ester bonds between lignan glycosides and organic acids. Glycosidic linkages were then broken by enzymatic hydrolysis

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