82304-66-3

Usage

Health Benifits

7,9-Ditert-butyl-1-oxaspiro[4.5]deca-6,9-diene-2,8-dione belongs to flavonoid compound. It can be found in morels (Morchella spp.), which are among the most valuable and important mushrooms because of their taste and commercial value. It can be identified as one of bioactive compounds in whole plant extract of Euphorbia pulcherrima, which are used in folk medicine to treat skin diseases, gonorrhea, migraine, intestinal parasites, and warts. In addition, 7,9-ditert-butyl-1-oxaspiro[4.5]deca-6,9-diene-2,8-dione can also be found in marine algae, which have been highly acknowledged to possess noticeable pharmacological activities, including antineoplastic, antimicrobial and antiviral activities due to their specific functional compounds (which are not available in other plants).

Chemical Properties

7,9-Ditert-butyl-1-oxaspiro[4.5]deca-6,9-diene-2,8-dione (C17H24O3, CAS registry No. 82304-66-3) is an oxaspiro compound that is 1-oxaspiro[4.5]deca-6,9-diene-2,8-dione carrying two additional tert-butyl substituents at positions 7 and 9. It is an oxaspiro compound with a lactone, an enone and a cyclic ketone. Its melting point is 139-140 °C.

Uses

7,9-Di-tert-butyl-1-oxaspiro[4.5]deca-6,9-diene-2,8-dione is an antioxidant naturally found in aerial parts of Gmelina asiatica Linn (Verbenaceae). It is also found in essential oils of some Stachys species from Mediterranean area. It is an impurity of Irganox 1098 (A697523) used in the food packaging.

Upstream product

• 99591-64-7 3-(1-Amino-3,5-di-tert-butyl-4-oxo-cyclohexa-2,5-dienyl)-propionic acid 
• 26347-98-8 pentaerythritol ester of 4-hydroxy-3,5-di-tert-butylphenylpropionic acid 
• 75-05-8 acetonitrile 
• 6386-38-5 methyl 3-(4-hydroxy-3,5-di-tert-butyl)phenylpropanoate 
• 67-56-1 methanol 
• 20170-32-5 4-hydroxy-3,5-di-tert-butylphenylpropionic acid 
• 65849-91-4 methyl 3-(3,5-di-tert-butyl-1-hydroperoxy-4-oxocyclohexa-2,5-dien-1-yl)propanoate 

Downstream Products

• 50394-07-5 methyl ester of trans-4-hydroxy-3,5-di-tert-butylcinnamic acid 
• 99591-64-7 3-(1-Amino-3,5-di-tert-butyl-4-oxo-cyclohexa-2,5-dienyl)-propionic acid 
• 95602-92-9 3,5-di-tert-butyl-4-hydroxycinnamic acid 
• 20170-32-5 4-hydroxy-3,5-di-tert-butylphenylpropionic acid 
• 147167-96-2 ethyl ester of trans-4-hydroxy-3,5-di-tert-butylcinnamic acid 

Relevant academic research and scientific papers

CsOH catalyzed aerobic oxidative synthesis of p-quinols from multi-alkyl phenols under mild conditions

p-Quinols are ubiquitous structural motifs of various natural products and pharmaceutical compounds, and versatile building blocks in synthetic chemistry. The reported methods for the synthesis of p-quinol require stoichiometric amounts of oxidants. Molecular oxygen is considered as an ideal oxidant due to its natural, inexpensive, and environmentally friendly characteristics. During the ongoing research of C-H bond hydroxylation, we found that multi-alkyl phenols could react with molecular oxygen under mild conditions. Herein, we describe an efficient oxidative de-aromatization of multi-alkyl phenols to p-quinols. 1 atm of molecular oxygen was used as the oxidant. Many multi-alkyl phenols could react smoothly at room temperature. Isotopic labeling experiment was also performed, and the result proved that the oxygen atom in the produced hydroxyl group is from molecular oxygen.

A singlet oxygen approach to oxaspirocycles

A method for the preparation of oxygen containing spirocycles using singlet oxygen is reported. A series of phenols were converted into the corresponding peroxy-cyclohexadienone derivatives by irradiation with visible light in the presence of a sensitizer and oxygen. The resulting peroxides could be converted into ether and lactone spirocycles in one or two steps. The synthesis of the oxaspirocycles from the phenols can also be performed in a one-pot fashion, avoiding the isolation of the peroxide intermediates.

Electrochemical Oxidation, VII. Synthesis and Structure of 7-tert-Butyl-2-methylbenzoxazoles

Anodic oxidation of 15 tert-butylphenols 1a - o in absolute acetonitrile or acetonitrile/perchloric acid leads to the corresponding 7-tert-butyl-2-methylbenzoxazoles 3a - o.The proof of the structure was achieved by independent synthesis of 3k, and by 13C NMR spectroscopy as well as by X-ray analysis of 7-tert-butyl-2-methyl-5-benzoxazolecarbaldehyde (3j).The influence of the supporting electrolyte on the formation of the oxidation products is discussed.