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SML1519

Sigma-Aldrich

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
MDL number:
MFCD09953803
UNSPSC Code:
12352200
PubChem Substance ID:
329825936
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

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

InChI key

QDDILOVMGWUNGD-UONOGXRCSA-N

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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.

Storage Class Code

11 - Combustible Solids

WGK

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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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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