Monascin - ≥98% , CAS No.21516-68-7

CAS: 21516-68-7 Cat. No.: M726486 Formula: C₂₁H₂₆O₅ Molecular Weight: 358.43

GRADE & PURITY ≥98%

Synonyms

Monascoflavin|(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

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Monascin is a kind of azaphilonoid pigments extracted from Monascus pilosus-fermented rice (red-mold rice). Monascin also exhibits anti-tumor-initiating activity and anti-inflammatory activity with oral administration. Monascin inhibits the activation of NOR 1 (an NO donor). Monascin is a Nrf2 activator and PPARγ agonist.

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

Specifications

Synonyms

Monascoflavin | (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

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

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-re

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

Pubchem Sid

528774541

Canonical Smiles

CCCCCC(=O)C1C2CC3=C(COC(=C3)C=CC)C(=O)C2(OC1=O)C

IUPAC Name

(3S,3aR,9aR)-3-hexanoyl-9a-methyl-6-[(E)-prop-1-enyl]-3,3a,4,8-tetrahydrofuro[3,2-g]isochromene-2,9-dione

InChIKey

XXKNHBAFFJINCK-RVEJDSBJSA-N

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

Isomeric SMILES

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

Alternate CAS

21516-68-7

MeSH Entry Terms

monascin

Molecular Weight

358.43

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbonyl compounds
        • Level5 Ketones
          • Level6 Cyclic ketones
            • Level7 Cyclohexenones

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbonyl compounds
• Intermediate Tree Nodes: Ketones - Cyclic ketones
• Direct Parent: Cyclohexenones
• Alternative Parents: Alpha-acyloxy ketones Pyrans Gamma butyrolactones 1,3-dicarbonyl compounds Tetrahydrofurans Carboxylic acid esters Oxacyclic compounds Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Cyclohexenone - Alpha-acyloxy ketone - 1,3-dicarbonyl compound - Pyran - Gamma butyrolactone - Tetrahydrofuran - Lactone - Carboxylic acid ester - Oxacycle - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxide - Hydrocarbon derivative - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as cyclohexenones. These are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
• External Descriptors: organic heterotricyclic compound - polyketide - gamma-lactone - alpha,beta-unsaturated ketone

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

A-431 (6446 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NCI-H460 (60772 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 358.400 g/mol
• XLogP3: 3.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 358.178 Da
• Monoisotopic Mass: 358.178 Da
• Topological Polar Surface Area: 69.700 Ų
• Heavy Atom Count: 26
• Formal Charge: 0
• Complexity: 727.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1