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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

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Certificates of Analysis (COA)

Lot/Batch Number
122228354V
12222839V
122228-39V

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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
Jong-Min Han et al.
Journal of agricultural and food chemistry, 55(23), 9457-9464 (2007-10-13)
Atherosclerosis is a chronic inflammatory disease that is characterized by infiltration of mononuclear lymphocytes into the intima through the expression of adhesion molecules on the arterial wall. In the present study, we report the inhibitory effects of two diarylheptanoids, 5-O-methylhirsutanonol
Seong-Soo Joo et al.
Archives of pharmacal research, 25(4), 457-462 (2002-09-07)
Oregonin, a diarylheptanoid derivative from Alnus hirsuta Turcz, Betulaceae, was evaluated for its antitumor activity. Oregonin, known to have an antitumor function, and is a novel immunomodulator, which may augment macrophage activity. MTT assays and NO production tests were performed
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
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.
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