24545-81-1

Basic information

• Product Name: Umbellulon
• Synonyms: Umbellulon;UMBELLULONE;2-Methyl-5-isopropyl-4-oxobicyclo[3.1.0]hexane-2-ene;4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hex-3-en-2-one
• CAS NO: 24545-81-1
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.2176
• Mol File: 24545-81-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 146-148 °C
• Boiling Point: 220°C (estimate)
• Flash Point: 85.2°C
• Appearance: /
• Density: 0.9572
• Vapor Pressure: 0.159mmHg at 25°C
• Refractive Index: 1.4833 (estimate)
• CAS DataBase Reference: Umbellulon(CAS DataBase Reference)
• NIST Chemistry Reference: Umbellulon(24545-81-1)
• EPA Substance Registry System: Umbellulon(24545-81-1)

Safety Data

• Hazardous Substances Data: 24545-81-1(Hazardous Substances Data)

Usage

General Description

Umbellulone is a bicyclic sesquiterpene ketone found in the essential oil of the plant, Sicilian fennel. This chemical compound is known for its strong odor and is used as a flavoring agent in the food industry. It has also been studied for its potential health benefits, including anti-inflammatory and antioxidant properties. Additionally, umbellulone has shown promise in the field of cancer research, with studies indicating its ability to inhibit the growth of cancer cells. However, further research is needed to fully understand the therapeutic potential and safety of umbellulone.

InChI:InChI=1/C10H14O/c1-6(2)10-5-8(10)7(3)4-9(10)11/h4,6,8H,5H2,1-3H3/t8-,10+/m0/s1

Upstream product

• 89-83-8 thymol 

Downstream Products

• 89-83-8 thymol 
• 5687-88-7 2-acetyl-1-isopropyl-cyclopropanecarboxylic acid 
• 15269-17-7 3,5-diisopropyl-4-methylphenol 
• 3228-03-3 3-isopropyl-5-methylphenol 
• 491-09-8 3-terpinolenone 
• 15269-16-6 2,5-Diisopropyl-4-methylphenol 
• 24760-21-2 methyl-4 bicyclo<3.1.0>hexen-3 one-2 
• 76138-70-0 2,5-diisopropyl-3-methylphenol 
• 108-39-4 3-methyl-phenol 
• 1125-12-8 thujone 

Relevant articles and documents

Photochemical Transformationos of Protonated Phenols. A One-Step Synthesis of Umbellulone from Thymol

UV irradiation of thymol (7) at 254 or 300 nm in trifluoromethanesulfonic acid affords ten products, eight of which have been isolated and characterized.Four competitive processes are suggested to be operating in the formation of the photoproducts: (i) regioselective type A rearrangement leading to umbellulone (8, about 10percent, (ii) formal C2->C3 migration by type A rearrangement and ring opening which affords the principal products, 3-isopropyl-5-methylphenol (12, 17percent), (iii) intermolecular transalkylation leading to diisopropylphenols 13-15 (17percent), and (iv) formation ofpiperitenone (10, 5percent) initiated by hydrogen abstraction.A mechanism for the formation of 10 is proposed.Both para- and ortho-protonated 7 are suggested to be involved in product formation.