MONASCIN Chemical Properties

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

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

Safety Information

WGK Germany 

2

MONASCIN Usage And Synthesis

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

MONASCIN(21516-68-7)Related Product Information

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