4444-74-0

Basic information

• Product Name: crenulatin
• Synonyms: crenulatin
• CAS NO: 4444-74-0
• Molecular Formula: C₁₁H₈O₄
• Molecular Weight: 204.17882
• Mol File: 4444-74-0.mol

Chemical Properties

• Boiling Point: 425.9°Cat760mmHg
• Flash Point: 195.2°C
• Appearance: /
• Density: 1.336g/cm³
• Vapor Pressure: 1.84E-07mmHg at 25°C
• Refractive Index: 1.613
• CAS DataBase Reference: crenulatin(CAS DataBase Reference)
• NIST Chemistry Reference: crenulatin(4444-74-0)
• EPA Substance Registry System: crenulatin(4444-74-0)

Safety Data

• Hazardous Substances Data: 4444-74-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Crenulatin is used as an anti-inflammatory agent for its capacity to inhibit the activity of COX-2, thereby reducing the production of inflammatory prostaglandins in the body.
Used in Oncology Research and Development:
Crenulatin is used as a potential anti-cancer drug candidate due to its observed inhibitory effects on the growth of cancer cells, making it a subject of interest for further research and development in oncology.
Used in Drug Discovery:
Crenulatin is utilized as a lead compound in drug discovery for its unique chemical structure and biological activities, which may contribute to the creation of new therapeutic agents for various medical conditions.

InChI:InChI=1/C11H8O4/c1-14-9-5-10-7(4-8(9)6-12)2-3-11(13)15-10/h2-6H,1H3

Upstream product

• 53811-57-7 7-methoxy-6-methylchromen-2-one 
• 496-73-1 4-methyl resorcinol 
• 53811-56-6 7-hydroxy-6-methylcoumarin 
• 15085-71-9 Micromelumin 
• 581-31-7 suberosin 

Downstream Products

• 106167-65-1 5-formyl-2,4-dimethoxy-cinnamic acid 
• 107151-35-9 2,4-dimethoxy-5-methyl-cinnamic acid methyl ester 

Relevant articles and documents

Synthesis of Naturally Occurring 6-Acyl-7-methoxycoumarins

A convenient synthesis of 6-azyl-7-methoxy coymarins (2a-e) is described sterting from 6-alkyl-7-methoxycoumarins (1a-e), using cerium(IV) ammonium nitrate (CAN) as an oxidizing agent.

Studies on Rutaceae: Part VI - Reacrtions and Rearrangements of Coumarins

Interesting reactions and rearrangements of isoprenoid systems have been observed in naturally occuring compounds like 6-(3',4'-epoxy-3'-methyl-γ-butyrolactonyl)-7-methoxycoumarin (micromelumin) (1), 7-methoxy-8-(1',2'-epoxy-3'-methylbut-3'-enyl)coumarin (phebalosin) (2), 7-methoxy-8-(2'-hydroxy-3'-methylbut-3'-enyl)coumarin (auraptenol) (3) and 7-methoxy-8-(3'-methylbut-2'-enyl)coumarin (osthol) (4).These reactions/rearrangements have led to the synthesis of coumarins already isolated from nature.Micromelumin (1) with pyridinium chloride affords the naturally occuring angelical (5), 6-(3'-methyl-3'-chloro-4'-hydroxy-γ-butyrolactonyl)- 7-methoxycoumarin (6b), 7-methoxycoumarinyl-6-tetronic acid derivative (7) and 6-(1'-carboxy-2'-methyl-3',4'-dihydroxybutenyl)-7-methoxycoumarin (8).Phebalosin (2) has been used for the hemisynthesis of the two naturally occuring diastereoisomeric coumarins minumicrolin (9) and murrangatin (10).Osthol (4) and auraptenol (3) have been used for the synthesis of the naturally occuring arnottinin (14)

Studies on Rutaceae - Part III. Reactions and Rearrangements of Prenyl and Prenyloxy Coumarins

During our study on the reactions and rearrangements of prenyl and prenyloxy coumarins interesting reactions and rearrangements were observed. 7-Methoxy-8-(1',2'-epoxy-3'-methylbut-3'-enyl)coumarin (phebalosin) (II) on oxidation with osmium tetroxide afforded 7-methoxy-coumarin-8-yl-acetaldehyde (XXXII) while 7-methoxy-8-(2'-hydroxy-3'-methylbut 3'-enyl) coumarin (auraptenol) (III) with m-chloroperbenzoic acid underwent rearrangement to 7-methoxy-8-(3'-formyl-but-2'-enyl) coumarin (XXX).The epoxy-lactone system of 7-methoxy-coumarin-6-(3',4'-epoxy-3'-methyl)-γ-butyrolactone (micromelumin) (IV) opened up with boron tribromide to give 7-methoxy-coumarin-6-(3'-bromo-3'-methyl-4'-hydroxy)-γ-butyrolactone (XXXIII) while with 10percent oxalic acid ring opening was accompained by further degradation to give 6-formyl-7-methoxy coumarin (angelical) (XXXIV).Chromous chloride reduction of micromelumin (IV) afforded deoxymicromelumin (XXXVI) and oxidation with chromic acid/sulphuric acid degraded it to umbelliferone-methyl-ether-6-carboxylic acid (XXXVII).Dehydrogenation of dihydroseselin (VII) with DDQ resulted in an unusual product 3,6-dichloro-dihydroseselin (XXIV).

The Chemical Constituents of Australian Zanthoxylum Species. VII. Some Transformation Products of Suberosin

Photosensitized oxidation of suberosin yielded suberenol (2), isosuberenol (6), and under certain conditions, 6,6'-ethylenebis(7-methoxy-2H-1-benzopyran-2-one).The epoxy alcohol (7a), its methyl ether and aldehyde (3) were also obtained, but these are believed to be artefacts formed under the conditions of workup.Autoxidation of suberosin does not appear to occur readily.Other oxygenated derivatives of suberosin were prepared by chemical methods. Dehydration of suberenol and isosuberenol yielded the diene (5) which on treatment with acid gave in low yield a bis-coumarin, isomeric with cyclobisuberodiene, for which structure (24) is suggested