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Merck
CN

SML1519

Macelignan

≥98% (HPLC)

Synonym(s):

(+)-Anwulignan, 4-[(2S,3R)-4-(1,3-Benzodioxol-5-yl)-2,3-dimethylbutyl]-2-methoxy-phenol, Anwulignan

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About This Item

Empirical Formula (Hill Notation):
C20H24O4
CAS Number:
107534-93-0
Molecular Weight:
328.40
NACRES:
NA.77
PubChem Substance ID:
329825936
UNSPSC Code:
12352200
MDL number:
MFCD09953803

Key Documents

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InChI key

QDDILOVMGWUNGD-UONOGXRCSA-N

SMILES string

OC1=C(OC)C=C(C[C@H](C)[C@H](C)CC2=CC=C(OCO3)C3=C2)C=C1

InChI

1S/C20H24O4/c1-13(8-15-4-6-17(21)19(10-15)22-3)14(2)9-16-5-7-18-20(11-16)24-12-23-18/h4-7,10-11,13-14,21H,8-9,12H2,1-3H3/t13-,14+/m0/s1

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

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General description

Macelignan is a naturally occurring compound that has scavenging effects on free-radicals and inhibits prostaglandin. It also exhibits antioxidant and anti-inflammatory effects.

Biochem/physiol Actions

Macelignan is a neuroprotective lingan isolated from nutmeg (Myristica fragrans) that protects dopaminergic neurons from inflammatory degeneration. Apparently, the neuroprotective effect of macelignan is mediated by PPARγ activation and arginase-1 expression. Macelignan inhibits LPS induced production of NO as well and inflammatory cytokines including TNF and IL- 1β in primary cultures of microglia.
Macelignan is a neuroprotective lingan isolated from nutmeg.

Storage Class

11 - 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
0000278710
0000209095
0000209096
0000278710
0000209096

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Chun-Ai Cui et al.
Neuroscience letters, 448(1), 110-114 (2008-10-23)
Previous studies have shown that macelignan has anti-inflammatory and neuroprotective effects. Subsequently, in the current study, we demonstrate that oral administrations of macelignan reduce the hippocampal microglial activation induced by chronic infusions of lipopolysaccharide (LPS) into the fourth ventricle of

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