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SMB00182

Sigma-Aldrich

Eudesmine

≥95% (LC/MS-ELSD)

Synonym(s):

Eudesamin, Eudesmin

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About This Item

Empirical Formula (Hill Notation):
C22H26O6
CAS Number:
526-06-7
Molecular Weight:
386.44
MDL number:
MFCD00274496
UNSPSC Code:
12352205
PubChem Substance ID:
329824848
NACRES:
NA.25

Assay

≥95% (LC/MS-ELSD)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

COc1ccc(cc1OC)[C@@H]2OCC3C2CO[C@H]3c4ccc(OC)c(OC)c4

InChI

1S/C22H26O6/c1-23-17-7-5-13(9-19(17)25-3)21-15-11-28-22(16(15)12-27-21)14-6-8-18(24-2)20(10-14)26-4/h5-10,15-16,21-22H,11-12H2,1-4H3/t15-,16-,21+,22+/m1/s1

InChI key

PEUUVVGQIVMSAW-DJDZNOHASA-N

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General description

Natural product derived from plant source.

Biochem/physiol Actions

Eudesmin is a component of a Brazilian folk medicine that has been used for blood pressure reduction. Eudesmin also is an inhibitor of TNF-alpha production and T cell proliferation.
Found in the Rutaceae family that has estrogenic and sedative effects.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
122228152V
122228-152V

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Sigma-Aldrich

147524

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(R)-(+)-Limonene analytical standard

Supelco

62118

(R)-(+)-Limonene

(+)-Eudesmin phyproof® Reference Substance

PHL83851

(+)-Eudesmin

Ria Park et al.
Pharmaceutics, 13(2) (2021-02-05)
Eudesmin, fargesin, epimagnolin A, magnolin, and yangambin are tetrahydrofurofuranoid lignans with various pharmacological activities found in Magnoliae Flos. The inhibition potencies of eudesmin, fargesin, epimagnolin A, magnolin, and yangambin on six major human uridine 5'-diphospho-glucuronosyltransferase (UGT) activities in human liver
Yoo Jung Yang et al.
Archives of pharmacal research, 29(12), 1114-1118 (2007-01-18)
(+)-Eudesmin [4,8-bis(3,4-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane] was isolated from the stem bark of Magnolia kobus DC. var. borealis Sarg. and found to have neuritogenic activity. 50 microM (+)-eudesmin induced neurite outgrowth and enhanced nerve growth factor (NGF)-mediated neurite outgrowth from PC12 cells. At this
J Y Cho et al.
Archives of pharmacal research, 22(4), 348-353 (1999-09-18)
Possible antiinflammatory effects of eudesmin were examined by assessing the effects on tumor necrosis factor (TNF)-alpha production and lymphocyte proliferation as well as cytotoxicity against murine and human macrophages. The compound significantly inhibited TNF-alpha production by lipopolysaccharide (LPS)-stimulated murine macrophage
H Kasahara et al.
Phytochemistry, 44(8), 1479-1482 (1997-04-01)
Microbial transformation of (+/-)-eudesmin by Aspergillus niger was investigated. Enantioselective accumulation of (--)-pinoresinol was shown through O-demethylation of (+/-)-eudesmin. This fungus O- demethylated both enantiomers of eudesmin, but the conversion rates for each enantiomer were clearly different.
C L Cantrell et al.
Journal of agricultural and food chemistry, 53(20), 7741-7748 (2005-09-30)
Bioassay-guided fractionation of the hexane/ethyl acetate/water (H/EtOAc/H2O) crude extract of the aerial parts of Haplophyllum sieversii was performed because of preliminary screening data that indicated the presence of growth inhibitory components against Colletotrichum fragariae, Colletotrichum gloeosporioides, and Colletotrichum acutatum. Fractionation
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