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60372

Sigma-Aldrich

Secoisolariciresinol

≥95.0% (HPLC)

Synonym(s):

(2R,3R)-2,3-Bis(4-hydroxy-3-methoxybenzyl)-1,4-butanediol

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About This Item

Empirical Formula (Hill Notation):
C20H26O6
Molecular Weight:
362.42
Beilstein:
6611290
EC Number:
249-599-2
MDL number:
MFCD01075136
UNSPSC Code:
41116105
PubChem Substance ID:
329758917
NACRES:
NA.21
Pricing and availability is not currently available.

Quality Level

100

Assay

≥95.0% (HPLC)

form

solid

SMILES string

OC[C@@H]([C@H](CO)CC1=CC=C(O)C(OC)=C1)CC2=CC(OC)=C(O)C=C2

InChI

1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16-/m0/s1

InChI key

PUETUDUXMCLALY-HOTGVXAUSA-N

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trans,trans-Farnesyl bromide

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trans,trans-Farnesyl chloride 97%

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trans,trans-Farnesyl acetate 95%

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Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

bp

100-110 °C/15 mmHg (lit.)

bp

149 °C/4 mmHg (lit.)

bp

59-60 °C/2.4 mmHg (lit.)

bp

115-125 °C/0.3 mmHg (lit.)

refractive index

n20/D 1.509 (lit.)

refractive index

n20/D 1.489 (lit.)

refractive index

n20/D 1.493 (lit.)

refractive index

n20/D 1.477 (lit.)

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

-

form

liquid

form

liquid

form

liquid

form

liquid

Application

Secoisolariciresinol is a metabolite of secoisolariciresinol diglucoside (SDG), an antioxidant present in flaxseed.[1]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Physical form

mixture of enantiomers of the (R*,R*)-diastereoisomer

Other Notes

Component of functional food. Flaxseed lignan with antioxidant activity[2]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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    Certificates of Analysis (COA)

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    BCCH0033
    BCCB5794
    BCBR1232V

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    Carol J Fabian et al.
    Cancer prevention research (Philadelphia, Pa.), 3(10), 1342-1350 (2010-08-21)
    Preclinical and correlative studies suggest reduced breast cancer with higher lignan intake or blood levels. We conducted a pilot study of modulation of risk biomarkers for breast cancer in premenopausal women after administration of the plant lignan secoisolariciresinol given as
    Shiori Tominaga et al.
    Food & function, 3(1), 76-82 (2011-10-28)
    Flaxseed lignan, secoisolariciresinol has been reported to possess health benefits. We previously synthesized each stereoisomer of secoisolariciresinol and found that (-)-secoisolariciresinol reduces lipid accumulation and induces adiponectin production in 3T3-L1 adipocytes. Here we show the effects of (-)-secoisolariciresinol on high-fat
    Cheng-Zhi Wang et al.
    BMC microbiology, 10, 115-115 (2010-04-20)
    The effects of enterolignans, e.g., enterodiol (END) and particularly its oxidation product, enterolactone (ENL), on prevention of hormone-dependent diseases, such as osteoporosis, cardiovascular diseases, hyperlipemia, breast cancer, colon cancer, prostate cancer and menopausal syndrome, have attracted much attention. To date
    D D Kitts et al.
    Molecular and cellular biochemistry, 202(1-2), 91-100 (2000-03-08)
    The antioxidant activities of the flaxseed lignan secoisolariciresinol diglycoside (SDG) and its mammalian lignan metabolites, enterodiol (ED) and enterolactone (EL), were evaluated in both lipid and aqueous in vitro model systems. All three lignans significantly (p < or = 0.05)
    Hisashi Nishiwaki et al.
    Bioscience, biotechnology, and biochemistry, 75(9), 1735-1739 (2011-09-08)
    The larvicidal activity against Culex pipiens of all stereoisomers of dihydroguaiaretic acid (DGA) and secoisolariciresinol was measured, and these DGAs were found to be potent. Sixteen (-)-DGA derivatives were then newly synthesized to analyze their structure-activity relationship. Two derivatives monohydroxylated
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