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
• Article Data: 4

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

General Description

Crenulatin is a natural chemical compound found in the Crenulate leadwort plant, a member of the Plumbaginaceae family. It has been identified as a potent oxime derivative with strong anti-inflammatory and anti-proliferative properties. Studies have shown that crenulatin can inhibit the activity of the enzyme cyclooxygenase-2 (COX-2), which is responsible for producing inflammatory prostaglandins in the body. Additionally, crenulatin has been found to inhibit the growth of cancer cells, making it a potential candidate for the development of new anti-cancer drugs. Its unique chemical structure and promising biological activities make crenulatin an interesting target for further research and potential medical applications.

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

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

Downstream Products

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

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 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).