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52442

Sigma-Aldrich

Monascin

≥97.0% (HPLC)

Synonym(s):

(3S,3aR,9aR)-3-Hexanoyl-9a-methyl-6-((E)-propenyl)-3a,4,8,9a-tetrahydro-3H-furo[3,2-g]isochromene-2,9-dione, (3S,3aR,9aR)-3a,4,8,9a-Tetrahydro-9a-methyl-3-(1-oxohexyl)-6-(1E)-1-propenyl-2H-furo[3,2-g][2]benzopyran-2,9(3H)-dione, Monascoflavin

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About This Item

Empirical Formula (Hill Notation):
C21H26O5
CAS Number:
21516-68-7
Molecular Weight:
358.43
Beilstein:
51355
MDL number:
MFCD09260177
UNSPSC Code:
12352200
PubChem Substance ID:
329757837
NACRES:
NA.47

Assay

≥97.0% (HPLC)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

CCCCCC(=O)[C@@H]1[C@H]2CC3=C(COC(\C=C\C)=C3)C(=O)[C@]2(C)OC1=O

InChI

1S/C21H26O5/c1-4-6-7-9-17(22)18-16-11-13-10-14(8-5-2)25-12-15(13)19(23)21(16,3)26-20(18)24/h5,8,10,16,18H,4,6-7,9,11-12H2,1-3H3/b8-5+/t16-,18+,21-/m1/s1

InChI key

XXKNHBAFFJINCK-RVEJDSBJSA-N

General description

Monascin is one of the major yellow pigments found in red mold rice. It is structurally similar to ankaflavin.

Application

Monascin has been used to treat 4T1 breast cancer cells and to test its effects on tumor cells anoikis and growth prevention.

Biochem/physiol Actions

Monascin (MS) exerts anti-diabetic and antioxidant properties and provides hyperglycemia control, tissue protection, and thermotolerance in diabetic rats and C. elegans, respectively. It also displays antitumor activity and inhibits Alzheimer′s disease-related tau protein aggregation. Monascin up-regulates high-density lipoprotein cholesterol (HDL-C) levels in hyperlipidemic hamsters model and possesses hypolipidemic properties. It may also possess hepatoprotective effects.
Monascin is one of the azaphilonoid pigments in extracts of Monascus pilosus-fermented rice (red-mold rice). It is a potent inhibitor of carcinogenesis measured against chemical or UV initiated, phorbol-promoted mouse skin tumors.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Malignant melanoma.
World journal of surgery, 16(2), 155-286 (1992-03-01)
S L Gartner et al.
Thymus, 19(2), 117-126 (1992-03-01)
We examined the effect of various carbohydrates on the proliferative response of murine thymocytes to cytokines. The monosaccharide, D-mannose (4-10 mM), significantly inhibited thymocyte proliferation induced by recombinant interleukin-1 (rIL-1). Mannose also inhibited the proliferation response to native, human IL-1.
Qiuyu Lin et al.
Neuroreport, 31(9), 637-643 (2020-05-20)
Increasing evidence verified that oxidative stress and neuroinflammatory response exacerbates motor deficits and increases neuronal loss in several rodent models of Parkinson's disease. In the present study, we explore the neuroprotective effects of monascin in a rotenone-induced Parkinson's disease model
Yeu-Ching Shi et al.
Free radical biology & medicine, 52(1), 109-117 (2011-11-02)
Monascin is a major yellow compound from red mold dioscorea. We investigated monascin to test whether this compound acts as an antidiabetic and antioxidative stress agent in diabetic rats and Caenorhabditis elegans. The mechanisms by which monascin exerts its action
[Symposium "Mechanisms of allergic inflammation". 2d Meeting of the Professional Society of the ADF: Immunologic mechanisms of inflammatory skin diseases. 21-23 February 1992, Freiburg i. Br].
W Czech
Der Hautarzt; Zeitschrift fur Dermatologie, Venerologie, und verwandte Gebiete, 43(11), 743-744 (1992-11-01)
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