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SMB00088

Sigma-Aldrich

Oregonin

≥95% (LC/MS-ELSD)

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About This Item

Empirical Formula (Hill Notation):
C24H30O10
CAS Number:
55303-93-0
Molecular Weight:
478.49
MDL number:
MFCD24849303
UNSPSC Code:
12352205
PubChem Substance ID:
329824766
NACRES:
NA.25

assay

≥95% (LC/MS-ELSD)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

OC1=CC=C(CCC(C[C@H](CCC2=CC(O)=C(O)C=C2)O[C@H]3[C@H](O)[C@@H](O)[C@H](O)CO3)=O)C=C1O

InChI

1S/C24H30O10/c25-15(5-1-13-3-7-17(26)19(28)9-13)11-16(6-2-14-4-8-18(27)20(29)10-14)34-24-23(32)22(31)21(30)12-33-24/h3-4,7-10,16,21-24,26-32H,1-2,5-6,11-12H2/t16-,21+,22-,23+,24-/m0/s1

InChI key

AQRNEKDRSXYJIN-IRFILORWSA-N

Related Categories

General description

Natural product derived from plant source.

Biochem/physiol Actions

Oregonin is a diarylheptanoid with known antioxidant, anti-cancer, and anti-inflammatory properties.

Storage Class

11 - Combustible Solids

wgk_germany

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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Eun Joo Choi et al.
International immunopharmacology, 8(5), 748-755 (2008-04-05)
Antigen-presenting dendritic cells may play an important role in the pathogenesis of inflammatory skin diseases, including atopic dermatitis. Oregonin is demonstrated to have anti-inflammatory and anti-oxidant effects. The present study was designed to assess the effect of oregonin against stimulated
Sun Eun Choi et al.
Experimental dermatology, 19(8), e37-e43 (2009-10-24)
The diarylheptanoid, oregonin (ORE), which was isolated from the bark of Alnus japonica Steudel that grows natively in Korea, has been known to exert antioxidative, anti-inflammatory, anti-cancer and immune response inhibitory effects. The antioxidative effect of ORE was observed on
M W Lee et al.
Biological & pharmaceutical bulletin, 23(4), 517-518 (2000-04-28)
Two known diarylheptanoids, oregonin (1), (5S)-1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-one-5-O-beta-D-xylopyranosi de and hirsutanonol (2), (5S)-1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane-3-one isolated from the bark of Alnus hirsuta var. sibirica, showed significant inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced cyclooxygenase-2 (COX-2) expression in immortalized human breast epithelial MCF10A cells.
Seong-Soo Joo et al.
Archives of pharmacal research, 25(4), 493-499 (2002-09-07)
We investigated the antitumor activity of oregonin, a diarylheptanoid derivative purified from Alnus hirsuta Turcz, Betulaceae. Oregonin is a potential novel immunomodulator, which augments the activation of natural killer (NK) cells, and thereby leads to a powerful antitumor activity. To
K K Lee et al.
Journal of natural products, 61(11), 1407-1409 (1998-12-03)
Bioassay-guided fractionation of the CH2Cl2-MeOH extract of Pinus flexilis using an assay for protein kinase C (PKC) inhibitory activity led to the isolation of the two new bioactive diarylheptanoids (3R)-1,7-bis(3, 4-dihydroxyphenyl)-3-(beta-D-glucopyranosyl)heptan-3-ol (1) and its aglycon (3R)-1,7-bis(3,4-dihydroxyphenyl)heptan-3-ol (2), together with the
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