| Identification | Back Directory | [Name]
MONASCIN | [CAS]
21516-68-7 | [Synonyms]
MONASCIN
Ccris 9138
Monascoflavin
Monascin >=97.0% (HPLC)
(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)-3aα,4,8,9a-Tetrahydro-9aβ-methyl-3-(1-oxohexyl)-6-[(E)-1-propenyl]-2H-furo[3,2-g][2]benzopyran-2,9(3H)-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
2H-Furo[3,2-g][2]benzopyran-2,9(3H)-dione, 3a,4,8,9a-tetrahydro-9a-methyl-3-(1-oxohexyl)-6-(1E)-1-propen-1-yl-, (3S,3aR,9aR)- | [Molecular Formula]
C21H26O5 | [MDL Number]
MFCD09260177 | [MOL File]
21516-68-7.mol | [Molecular Weight]
358.43 |
| Chemical Properties | Back Directory | [Melting point ]
145 °C | [Boiling point ]
574.6±50.0 °C(Predicted) | [density ]
1.18±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
Acetonitrile: Soluble
Chloroform: Soluble | [form ]
Solid | [pka]
10.59±0.60(Predicted) | [color ]
Light yellow to yellow | [BRN ]
51355 | [Major Application]
metabolomics
vitamins, nutraceuticals, and natural products | [InChI]
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 | [InChIKey]
XXKNHBAFFJINCK-RVEJDSBJSA-N | [SMILES]
C1(/C=C/C)OCC2C(=O)[C@]3(C)OC(=O)[C@H](C(=O)CCCCC)[C@@]3([H])CC=2C=1 |
| Hazard Information | Back Directory | [Uses]
Monascin is an azaphilonoid pigment extracted from Monascus pilosus-fermented rice (red-mold rice). Monascin also exhibits anti-tumor-initiating activity and anti-inflammatory activity with oral administration. | [Definition]
ChEBI: An organic heterotricyclic compound that is 3a,4,8,9a-tetrahydro-2H-furo[3,2-g][2]benzopyran-2,9(3H)-dione that is substituted at positions 3, 6, and 9a by hexanoyl, (1E)-prop-1-en-1-yl an
methyl groups, respectively (the 3S,3aR,9aR diastereoisomer). One of the azaphilonoid pigments in extracts of Monascus pilosus-fermented rice (red-mould rice), it is a potent inhibitor of car
inogenesis measured against chemical- or UV-initiated, phorbol-promoted mouse skin tumours. | [Biochem/physiol Actions]
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. | [References]
[1] WEI-HSUAN HSU . Monascin and ankaflavin act as natural AMPK activators with PPARα agonist activity to down-regulate nonalcoholic steatohepatitis in high-fat diet-fed C57BL/6 mice[J]. Food and Chemical Toxicology, 2014, 64: Pages 94-103. DOI: 10.1016/j.fct.2013.11.015
[2] TOSHIHIRO AKIHISA. Anti-Tumor-Initiating Effects of Monascin, an Azaphilonoid Pigment from the Extract of Monascus pilosus Fermented Rice (Red-Mold Rice)[J]. Chemistry & Biodiversity, 2005, 2 10: 1305-1309. DOI: 10.1002/cbdv.200590101
[3] YEU-CHING SHI Tzu M P Vivian Hsiu Chuan Liao. Monascin from red mold dioscorea as a novel antidiabetic and antioxidative stress agent in rats and Caenorhabditis elegans[J]. Free Radical Biology and Medicine, 2012, 52 1: Pages 109-117. DOI: 10.1016/j.freeradbiomed.2011.09.034 |
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